DE602004010680T2 - Substituierte imidazopyrimidine zur prävention und behandlung von krebs - Google Patents

Info

Publication number

DE602004010680T2

DE602004010680T2 DE602004010680T DE602004010680T DE602004010680T2 DE 602004010680 T2 DE602004010680 T2 DE 602004010680T2 DE 602004010680 T DE602004010680 T DE 602004010680T DE 602004010680 T DE602004010680 T DE 602004010680T DE 602004010680 T2 DE602004010680 T2 DE 602004010680T2

Authority

DE

Germany

Prior art keywords

pyrimidine

imidazo

nmr

methylsulfanylphenyl

methoxyphenyl

Prior art date

2003-07-30

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

Links

• Espacenet
• Global Dossier
• DPMA
• Discuss

• 238000011282 treatment Methods 0.000 title claims abstract description 14
• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 13
• 201000011510 cancer Diseases 0.000 title claims abstract description 12
• 230000002265 prevention Effects 0.000 title description 3
• 150000005237 imidazopyrimidines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 53
• 230000002113 chemopreventative effect Effects 0.000 claims abstract description 10
• 230000003902 lesion Effects 0.000 claims abstract description 8
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
• -1 3- (3-Chloro-4-methylsulfanylphenyl) -2- (4-methoxyphenyl) -7-methylimidazo pyrimidine Chemical compound 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 239000000203 mixture Substances 0.000 claims description 16
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
• 206010009944 Colon cancer Diseases 0.000 claims description 12
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 11
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 229910052698 phosphorus Inorganic materials 0.000 claims description 10
• 208000009621 actinic keratosis Diseases 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 7
• 208000029664 classic familial adenomatous polyposis Diseases 0.000 claims description 7
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
• 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 claims description 6
• 101100519284 Cercospora nicotianae PDX1 gene Proteins 0.000 claims description 6
• 201000006107 Familial adenomatous polyposis Diseases 0.000 claims description 6
• 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 claims description 6
• 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 claims description 6
• 101100277598 Sorghum bicolor DES3 gene Proteins 0.000 claims description 6
• 101150111293 cor-1 gene Proteins 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 201000000849 skin cancer Diseases 0.000 claims description 6
• 101150073238 sor1 gene Proteins 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 150000003839 salts Chemical class 0.000 claims description 4
• QNEGJEZWIOXARM-UHFFFAOYSA-N 2-(4-bromophenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(Br)=CC=2)N=C2N1C=CC=N2 QNEGJEZWIOXARM-UHFFFAOYSA-N 0.000 claims description 3
• MKOZDXHSRDZEPA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(3-methyl-4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(C)C(SC)=CC=2)N2C=CC=NC2=N1 MKOZDXHSRDZEPA-UHFFFAOYSA-N 0.000 claims description 3
• BNIUKULMJGZVCF-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC=NC2=N1 BNIUKULMJGZVCF-UHFFFAOYSA-N 0.000 claims description 3
• CQGADDAMYKKHBF-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-propan-2-ylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC(C)C)=CC=2)N2C=CC=NC2=N1 CQGADDAMYKKHBF-UHFFFAOYSA-N 0.000 claims description 3
• JKDLHBFPHMCREW-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC(C)=NC2=N1 JKDLHBFPHMCREW-UHFFFAOYSA-N 0.000 claims description 3
• NWHHTSQOKQTUBY-UHFFFAOYSA-N 3-(3-bromo-4-methylsulfanylphenyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Br)C(SC)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N=C2N1C=CC=N2 NWHHTSQOKQTUBY-UHFFFAOYSA-N 0.000 claims description 3
• IRMVAYWYPYRLQU-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfanylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(SC)=CC=2)N2C=CC=NC2=N1 IRMVAYWYPYRLQU-UHFFFAOYSA-N 0.000 claims description 3
• YXZQHTDRNOAXGO-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfanylphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(Cl)C(SC)=CC=2)N2C=CC=NC2=N1 YXZQHTDRNOAXGO-UHFFFAOYSA-N 0.000 claims description 3
• VZVRDRXCBUFAEG-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-ylsulfanylphenyl)-2-(4-methylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SC(C)C)=CC=C1C1=C(C=2C=CC(C)=CC=2)N=C2N1C=CC=N2 VZVRDRXCBUFAEG-UHFFFAOYSA-N 0.000 claims description 3
• JEVNUDGHTSWDIL-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-ylsulfanylphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(Cl)C(SC(C)C)=CC=2)N2C=CC=NC2=N1 JEVNUDGHTSWDIL-UHFFFAOYSA-N 0.000 claims description 3
• WQBLNMCUYHVYKT-UHFFFAOYSA-N 3-(3-chloro-4-propylsulfanylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SCCC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N=C2N1C=CC=N2 WQBLNMCUYHVYKT-UHFFFAOYSA-N 0.000 claims description 3
• IKTHOCNOZUJIQV-UHFFFAOYSA-N 3-(3-methyl-4-methylsulfanylphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(C)C(SC)=CC=2)N2C=CC=NC2=N1 IKTHOCNOZUJIQV-UHFFFAOYSA-N 0.000 claims description 3
• MTHXCZAWVDJHQH-UHFFFAOYSA-N 7-methyl-3-(4-methylphenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N=C2N1C=CC(C)=N2 MTHXCZAWVDJHQH-UHFFFAOYSA-N 0.000 claims description 3
• 206010005003 Bladder cancer Diseases 0.000 claims description 3
• 206010006187 Breast cancer Diseases 0.000 claims description 3
• 208000026310 Breast neoplasm Diseases 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
• 210000000481 breast Anatomy 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 210000002307 prostate Anatomy 0.000 claims description 3
• 210000003932 urinary bladder Anatomy 0.000 claims description 3
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• 239000004480 active ingredient Substances 0.000 claims description 2
• 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
• 229940079593 drug Drugs 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims 1
• 239000012453 solvate Substances 0.000 claims 1
• 230000000153 supplemental effect Effects 0.000 claims 1
• 125000000217 alkyl group Chemical group 0.000 abstract description 3
• 229910052736 halogen Inorganic materials 0.000 abstract 2
• 150000002367 halogens Chemical class 0.000 abstract 2
• 150000003463 sulfur Chemical class 0.000 abstract 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 222
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
• 239000000243 solution Substances 0.000 description 20
• 238000005481 NMR spectroscopy Methods 0.000 description 18
• 235000019439 ethyl acetate Nutrition 0.000 description 17
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 238000000034 method Methods 0.000 description 13
• 210000004027 cell Anatomy 0.000 description 12
• 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 11
• 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 11
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 0 *c1ccc(-c2c(-c(cc3)ccc3S(*)(=O)=O)[n](cc(*)c(*)n3)c3n2)c(*)c1* Chemical compound *c1ccc(-c2c(-c(cc3)ccc3S(*)(=O)=O)[n](cc(*)c(*)n3)c3n2)c(*)c1* 0.000 description 8
• 238000006243 chemical reaction Methods 0.000 description 8
• 238000004440 column chromatography Methods 0.000 description 8
• 239000000741 silica gel Substances 0.000 description 8
• 229910002027 silica gel Inorganic materials 0.000 description 8
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
• 239000000460 chlorine Substances 0.000 description 7
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
• 235000017557 sodium bicarbonate Nutrition 0.000 description 7
• 150000003456 sulfonamides Chemical class 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• 230000006907 apoptotic process Effects 0.000 description 6
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
• 239000003480 eluent Substances 0.000 description 6
• 230000005764 inhibitory process Effects 0.000 description 6
• 239000012074 organic phase Substances 0.000 description 6
• 239000002904 solvent Substances 0.000 description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
• OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 5
• ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 5
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 229910052938 sodium sulfate Inorganic materials 0.000 description 5
• 235000011152 sodium sulphate Nutrition 0.000 description 5
• 229940124530 sulfonamide Drugs 0.000 description 5
• 230000001028 anti-proliverative effect Effects 0.000 description 4
• 229960000590 celecoxib Drugs 0.000 description 4
• RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 4
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 4
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 150000003462 sulfoxides Chemical class 0.000 description 4
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 description 3
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 230000031709 bromination Effects 0.000 description 3
• 238000005893 bromination reaction Methods 0.000 description 3
• 229940111134 coxibs Drugs 0.000 description 3
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 3
• 201000010099 disease Diseases 0.000 description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
• FODOUIXGKGNSMR-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate;hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O FODOUIXGKGNSMR-UHFFFAOYSA-L 0.000 description 3
• LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 3
• 230000008569 process Effects 0.000 description 3
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 3
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
• JFMNZQHBFKGUOR-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OCC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC=NC2=N1 JFMNZQHBFKGUOR-UHFFFAOYSA-N 0.000 description 2
• RJRLKJIMLXIKDJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5,7-dimethyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C(C)=CC(C)=NC2=N1 RJRLKJIMLXIKDJ-UHFFFAOYSA-N 0.000 description 2
• GHTQJGGOVFRPMG-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)-2-(4-methylsulfanylphenyl)ethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C(Br)C1=CC=C(SC)C=C1 GHTQJGGOVFRPMG-UHFFFAOYSA-N 0.000 description 2
• ONYRUSCZUWEZDP-UHFFFAOYSA-N 2-phenylimidazo[1,2-a]pyrimidine Chemical class N1=C2N=CC=CN2C=C1C1=CC=CC=C1 ONYRUSCZUWEZDP-UHFFFAOYSA-N 0.000 description 2
• HGHKJDLMPVJKEP-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfinylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(=CC=2)S(C)=O)N2C=CC=NC2=N1 HGHKJDLMPVJKEP-UHFFFAOYSA-N 0.000 description 2
• XGUHIICFHCTGHN-UHFFFAOYSA-N 3-(4-ethoxyphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OCC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C=CC=N2 XGUHIICFHCTGHN-UHFFFAOYSA-N 0.000 description 2
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
• AZPYKULCINXGPF-UHFFFAOYSA-N 5-methoxy-2-(4-methoxyphenyl)-3-(4-methylsulfanylphenyl)-1h-imidazo[1,2-a]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C(OC)=CC(=O)N=C2N1 AZPYKULCINXGPF-UHFFFAOYSA-N 0.000 description 2
• NZSDNHFYMNVQPO-UHFFFAOYSA-N 7-chloro-3-(4-methoxyphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C=CC(Cl)=N2 NZSDNHFYMNVQPO-UHFFFAOYSA-N 0.000 description 2
• YPDSIEMYVQERLJ-UHFFFAOYSA-N 8-Hydroxypurine Chemical compound C1=NC=C2NC(O)=NC2=N1 YPDSIEMYVQERLJ-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
• 201000009030 Carcinoma Diseases 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• 108010033040 Histones Proteins 0.000 description 2
• 108010047956 Nucleosomes Proteins 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 239000000908 ammonium hydroxide Substances 0.000 description 2
• 150000001450 anions Chemical class 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• 230000008901 benefit Effects 0.000 description 2
• 239000012267 brine Substances 0.000 description 2
• 230000000711 cancerogenic effect Effects 0.000 description 2
• 150000001768 cations Chemical class 0.000 description 2
• 230000004663 cell proliferation Effects 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
• 238000004042 decolorization Methods 0.000 description 2
• 238000000354 decomposition reaction Methods 0.000 description 2
• 230000000694 effects Effects 0.000 description 2
• 230000002255 enzymatic effect Effects 0.000 description 2
• 230000002401 inhibitory effect Effects 0.000 description 2
• 150000007529 inorganic bases Chemical class 0.000 description 2
• 230000000670 limiting effect Effects 0.000 description 2
• 230000007246 mechanism Effects 0.000 description 2
• 230000010534 mechanism of action Effects 0.000 description 2
• LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
• 230000035772 mutation Effects 0.000 description 2
• 210000001623 nucleosome Anatomy 0.000 description 2
• 150000007530 organic bases Chemical class 0.000 description 2
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
• 230000007170 pathology Effects 0.000 description 2
• 239000012071 phase Substances 0.000 description 2
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
• 235000011056 potassium acetate Nutrition 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• 230000035755 proliferation Effects 0.000 description 2
• 238000011084 recovery Methods 0.000 description 2
• 230000009467 reduction Effects 0.000 description 2
• 230000002829 reductive effect Effects 0.000 description 2
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• 231100000419 toxicity Toxicity 0.000 description 2
• 230000001988 toxicity Effects 0.000 description 2
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
• RVCBLEVSDTWFDW-UHFFFAOYSA-N 2,3-bis(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC=NC2=N1 RVCBLEVSDTWFDW-UHFFFAOYSA-N 0.000 description 1
• AIDQZGUOAMLZLS-UHFFFAOYSA-N 2-(2-fluoro-4-methoxyphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC=NC2=N1 AIDQZGUOAMLZLS-UHFFFAOYSA-N 0.000 description 1
• MALCNHPSJNUJCA-UHFFFAOYSA-N 2-(2-fluoro-4-methoxyphenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC(C)=NC2=N1 MALCNHPSJNUJCA-UHFFFAOYSA-N 0.000 description 1
• CGYSSSJIJPBNLO-UHFFFAOYSA-N 2-(3-bromo-4-methylsulfanylphenyl)-3-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Br)C(SC)=CC=2)N=C2N1C=CC=N2 CGYSSSJIJPBNLO-UHFFFAOYSA-N 0.000 description 1
• VHJGWVGGYSDGSD-UHFFFAOYSA-N 2-(3-chloro-4-ethylsulfanylphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SCC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC=NC2=N1 VHJGWVGGYSDGSD-UHFFFAOYSA-N 0.000 description 1
• SSNUMGSQQMAYEO-UHFFFAOYSA-N 2-(3-chloro-4-ethylsulfanylphenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SCC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC(C)=NC2=N1 SSNUMGSQQMAYEO-UHFFFAOYSA-N 0.000 description 1
• ZSCLTBRTVIPKQH-UHFFFAOYSA-N 2-(3-chloro-4-methoxyphenyl)-3-(3-chloro-4-methylsulfanylphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=C(Cl)C(SC)=CC=2)N2C=CC(C)=NC2=N1 ZSCLTBRTVIPKQH-UHFFFAOYSA-N 0.000 description 1
• KCKUTXBGXJWOBV-UHFFFAOYSA-N 2-(3-chloro-4-methoxyphenyl)-3-(3-chloro-4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=C(Cl)C(SC)=CC=2)N2C=CC=NC2=N1 KCKUTXBGXJWOBV-UHFFFAOYSA-N 0.000 description 1
• WYWQOROWDZZZPW-UHFFFAOYSA-N 2-(3-chloro-4-methoxyphenyl)-3-(3-chloro-4-methylsulfinylphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=C(Cl)C(=CC=2)S(C)=O)N2C=CC(C)=NC2=N1 WYWQOROWDZZZPW-UHFFFAOYSA-N 0.000 description 1
• NZBVAWAUDHJRJX-UHFFFAOYSA-N 2-(3-chloro-4-methoxyphenyl)-3-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(OC)=CC=2)N=C2N1C=CC=N2 NZBVAWAUDHJRJX-UHFFFAOYSA-N 0.000 description 1
• FEGXLUQNPKKHRA-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfinylphenyl)-3-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(=CC=2)S(C)=O)N=C2N1C=CC=N2 FEGXLUQNPKKHRA-UHFFFAOYSA-N 0.000 description 1
• SUAZSMWTIULMJY-UHFFFAOYSA-N 2-(3-chloro-4-propan-2-ylsulfanylphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(Cl)C(SC(C)C)=CC=2)N=C2N1C=CC=N2 SUAZSMWTIULMJY-UHFFFAOYSA-N 0.000 description 1
• GZSSRBKURJIEAD-UHFFFAOYSA-N 2-(3-chloro-4-propan-2-ylsulfanylphenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(Cl)C(SC(C)C)=CC=2)N=C2N1C=CC(C)=N2 GZSSRBKURJIEAD-UHFFFAOYSA-N 0.000 description 1
• LKQRJQIKBOOXIJ-UHFFFAOYSA-N 2-(3-chloro-4-propylsulfinylphenyl)-3-(4-methylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(S(=O)CCC)=CC=C1C1=C(C=2C=CC(C)=CC=2)N2C=CC=NC2=N1 LKQRJQIKBOOXIJ-UHFFFAOYSA-N 0.000 description 1
• USPYWZWDEPWHJB-UHFFFAOYSA-N 2-(3-chloro-4-propylsulfonylphenyl)-3-(4-methylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(S(=O)(=O)CCC)=CC=C1C1=C(C=2C=CC(C)=CC=2)N2C=CC=NC2=N1 USPYWZWDEPWHJB-UHFFFAOYSA-N 0.000 description 1
• HRRHATJAQQVRKY-UHFFFAOYSA-N 2-(3-chlorophenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(Cl)C=CC=2)N=C2N1C=CC=N2 HRRHATJAQQVRKY-UHFFFAOYSA-N 0.000 description 1
• JBKFROVVEWOFBA-UHFFFAOYSA-N 2-(3-chlorophenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(Cl)C=CC=2)N=C2N1C=CC(C)=N2 JBKFROVVEWOFBA-UHFFFAOYSA-N 0.000 description 1
• SVMBYWLRHSYIRQ-UHFFFAOYSA-N 2-(3-fluorophenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(F)C=CC=2)N=C2N1C=CC=N2 SVMBYWLRHSYIRQ-UHFFFAOYSA-N 0.000 description 1
• OQILVXKHBNUCKG-UHFFFAOYSA-N 2-(3-fluorophenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(F)C=CC=2)N=C2N1C=CC(C)=N2 OQILVXKHBNUCKG-UHFFFAOYSA-N 0.000 description 1
• WLPPSFSHXDEUKJ-UHFFFAOYSA-N 2-(3-methoxy-4-methylphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(C)C(OC)=CC(C2=C(N3C=CC=NC3=N2)C=2C=CC(SC)=CC=2)=C1 WLPPSFSHXDEUKJ-UHFFFAOYSA-N 0.000 description 1
• JYHHQYHEXYRMIW-UHFFFAOYSA-N 2-(3-methoxy-4-methylphenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(C)C(OC)=CC(C2=C(N3C=CC(C)=NC3=N2)C=2C=CC(SC)=CC=2)=C1 JYHHQYHEXYRMIW-UHFFFAOYSA-N 0.000 description 1
• UEOVWZPBXNEOPM-UHFFFAOYSA-N 2-(3-methoxyphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound COC1=CC=CC(C2=C(N3C=CC=NC3=N2)C=2C=CC(SC)=CC=2)=C1 UEOVWZPBXNEOPM-UHFFFAOYSA-N 0.000 description 1
• GSFYYUDFIUQNLL-UHFFFAOYSA-N 2-(3-methoxyphenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound COC1=CC=CC(C2=C(N3C=CC(C)=NC3=N2)C=2C=CC(SC)=CC=2)=C1 GSFYYUDFIUQNLL-UHFFFAOYSA-N 0.000 description 1
• NCFWUIPXERXKDM-UHFFFAOYSA-N 2-(3-tert-butyl-4-methoxyphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(C(C)(C)C)C(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC=NC2=N1 NCFWUIPXERXKDM-UHFFFAOYSA-N 0.000 description 1
• LWXNGJYOGJEHKZ-UHFFFAOYSA-N 2-(3-tert-butyl-4-methoxyphenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(C(C)(C)C)C(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC(C)=NC2=N1 LWXNGJYOGJEHKZ-UHFFFAOYSA-N 0.000 description 1
• UABUXPQJAJEFRK-UHFFFAOYSA-N 2-(3-tert-butyl-4-methoxyphenyl)-7-methyl-3-(4-methylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(C(C)(C)C)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)=O)N2C=CC(C)=NC2=N1 UABUXPQJAJEFRK-UHFFFAOYSA-N 0.000 description 1
• BAVXQSDMBPHFBG-UHFFFAOYSA-N 2-(4-cyclopropylsulfanylphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(SC3CC3)=CC=2)N=C2N1C=CC=N2 BAVXQSDMBPHFBG-UHFFFAOYSA-N 0.000 description 1
• WCCMMAMMQBOHBY-UHFFFAOYSA-N 2-(4-cyclopropylsulfanylphenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(SC3CC3)=CC=2)N=C2N1C=CC(C)=N2 WCCMMAMMQBOHBY-UHFFFAOYSA-N 0.000 description 1
• SQKBWJPGHZWAAG-UHFFFAOYSA-N 2-(4-ethoxy-3-fluorophenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(OCC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC=NC2=N1 SQKBWJPGHZWAAG-UHFFFAOYSA-N 0.000 description 1
• BPWJTZDPHXEJRR-UHFFFAOYSA-N 2-(4-ethoxy-3-fluorophenyl)-3-(4-methylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(OCC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)=O)N2C=CC=NC2=N1 BPWJTZDPHXEJRR-UHFFFAOYSA-N 0.000 description 1
• DNZXIMDNEHSLSU-UHFFFAOYSA-N 2-(4-ethoxy-3-fluorophenyl)-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(OCC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 DNZXIMDNEHSLSU-UHFFFAOYSA-N 0.000 description 1
• CMDCLKYHGOCFDX-UHFFFAOYSA-N 2-(4-ethoxy-3-fluorophenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(OCC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC(C)=NC2=N1 CMDCLKYHGOCFDX-UHFFFAOYSA-N 0.000 description 1
• PWMXSVUAZNNEAH-UHFFFAOYSA-N 2-(4-ethoxy-3-fluorophenyl)-7-methyl-3-(4-methylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(OCC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)=O)N2C=CC(C)=NC2=N1 PWMXSVUAZNNEAH-UHFFFAOYSA-N 0.000 description 1
• FDHVSNCBZVVYED-UHFFFAOYSA-N 2-(4-ethoxy-3-fluorophenyl)-7-methyl-3-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(OCC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N2C=CC(C)=NC2=N1 FDHVSNCBZVVYED-UHFFFAOYSA-N 0.000 description 1
• XYXDCWCBDJCCAH-UHFFFAOYSA-N 2-(4-ethoxy-3-fluorophenyl)-7-methyl-3-phenylimidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(OCC)=CC=C1C1=C(C=2C=CC=CC=2)N2C=CC(C)=NC2=N1 XYXDCWCBDJCCAH-UHFFFAOYSA-N 0.000 description 1
• OCPSSXOQEIMBFD-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C2N1C=CC=N2 OCPSSXOQEIMBFD-UHFFFAOYSA-N 0.000 description 1
• XYNQLPWIWSVEPT-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-(4-nitrophenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C2N1C=CC=N2 XYNQLPWIWSVEPT-UHFFFAOYSA-N 0.000 description 1
• ZYIISHKHQFWAEG-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-methyl-3-(4-methylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound N1=C2N=C(C)C=CN2C(C=2C=CC(=CC=2)S(C)=O)=C1C1=CC=C(F)C=C1 ZYIISHKHQFWAEG-UHFFFAOYSA-N 0.000 description 1
• GHNOEHVODAUDMU-UHFFFAOYSA-N 2-(4-methoxy-2-methylphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound CC1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC=NC2=N1 GHNOEHVODAUDMU-UHFFFAOYSA-N 0.000 description 1
• YXJWYKVLGYJGSI-UHFFFAOYSA-N 2-(4-methoxy-2-methylphenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound CC1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC(C)=NC2=N1 YXJWYKVLGYJGSI-UHFFFAOYSA-N 0.000 description 1
• GNIHLUUKCBOEMY-UHFFFAOYSA-N 2-(4-methoxy-3-methylphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(C)C(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC=NC2=N1 GNIHLUUKCBOEMY-UHFFFAOYSA-N 0.000 description 1
• FBQURQJQTITSDZ-UHFFFAOYSA-N 2-(4-methoxy-3-methylphenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(C)C(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC(C)=NC2=N1 FBQURQJQTITSDZ-UHFFFAOYSA-N 0.000 description 1
• LPDVGOJJELYNGW-UHFFFAOYSA-N 2-(4-methoxy-3-methylphenyl)-7-methyl-3-(4-methylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(C)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)=O)N2C=CC(C)=NC2=N1 LPDVGOJJELYNGW-UHFFFAOYSA-N 0.000 description 1
• LWGMNOKCEPLYGL-UHFFFAOYSA-N 2-(4-methoxy-3-phenylphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound COC1=CC=C(C2=C(N3C=CC=NC3=N2)C=2C=CC(SC)=CC=2)C=C1C1=CC=CC=C1 LWGMNOKCEPLYGL-UHFFFAOYSA-N 0.000 description 1
• GOKVFMJPICVUDX-UHFFFAOYSA-N 2-(4-methoxy-3-phenylphenyl)-3-(4-methylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound COC1=CC=C(C2=C(N3C=CC=NC3=N2)C=2C=CC(=CC=2)S(C)=O)C=C1C1=CC=CC=C1 GOKVFMJPICVUDX-UHFFFAOYSA-N 0.000 description 1
• DIRUKORTEVEAOL-UHFFFAOYSA-N 2-(4-methoxy-3-phenylphenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound COC1=CC=C(C2=C(N3C=CC(C)=NC3=N2)C=2C=CC(SC)=CC=2)C=C1C1=CC=CC=C1 DIRUKORTEVEAOL-UHFFFAOYSA-N 0.000 description 1
• XSEPSBJFQKLFEU-UHFFFAOYSA-N 2-(4-methoxy-3-phenylphenyl)-7-methyl-3-(4-methylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound COC1=CC=C(C2=C(N3C=CC(C)=NC3=N2)C=2C=CC(=CC=2)S(C)=O)C=C1C1=CC=CC=C1 XSEPSBJFQKLFEU-UHFFFAOYSA-N 0.000 description 1
• KKKKNFUQWUQEIY-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(3-nitrophenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(C=CC=2)[N+]([O-])=O)N2C=CC=NC2=N1 KKKKNFUQWUQEIY-UHFFFAOYSA-N 0.000 description 1
• DCOOFYIJUJRGKK-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-methylsulfanylphenyl)-1h-imidazo[1,2-a]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC(=O)N=C2N1 DCOOFYIJUJRGKK-UHFFFAOYSA-N 0.000 description 1
• JSZPVFGAXAPLHQ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-methylsulfanylphenyl)-6-nitroimidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=C([N+]([O-])=O)C=NC2=N1 JSZPVFGAXAPLHQ-UHFFFAOYSA-N 0.000 description 1
• IOARRYISHMUCGG-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC(N)=NC2=N1 IOARRYISHMUCGG-UHFFFAOYSA-N 0.000 description 1
• JZGGSDPBSYQKMW-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-nitrophenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)[N+]([O-])=O)N2C=CC=NC2=N1 JZGGSDPBSYQKMW-UHFFFAOYSA-N 0.000 description 1
• LJURUIPDUJKLIX-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-propan-2-ylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(=O)C(C)C)N2C=CC=NC2=N1 LJURUIPDUJKLIX-UHFFFAOYSA-N 0.000 description 1
• GUNOFMHEFJXARU-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-propan-2-ylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(=O)(=O)C(C)C)N2C=CC=NC2=N1 GUNOFMHEFJXARU-UHFFFAOYSA-N 0.000 description 1
• XBXYWLTXUKETPY-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(C=CC=2)C(F)(F)F)N2C=CC=NC2=N1 XBXYWLTXUKETPY-UHFFFAOYSA-N 0.000 description 1
• WXGYKYKVOYFMAD-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-methyl-3-(4-methylsulfanylphenyl)-1h-imidazo[1,2-a]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C(C)=CC(=O)N=C2N1 WXGYKYKVOYFMAD-UHFFFAOYSA-N 0.000 description 1
• VXIKANQMWXLXLF-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-methyl-3-(4-methylsulfanylphenyl)-1h-imidazo[1,2-a]pyrimidine-7-thione Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C(C)=CC(=S)N=C2N1 VXIKANQMWXLXLF-UHFFFAOYSA-N 0.000 description 1
• BYPDZUZQVUFZFN-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-n,5-n-dimethyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine-5,7-diamine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C(N(C)C)=CC(N)=NC2=N1 BYPDZUZQVUFZFN-UHFFFAOYSA-N 0.000 description 1
• TZHBXQUFPOYFLT-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7-methyl-3-(3-methyl-4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(C)C(SC)=CC=2)N2C=CC(C)=NC2=N1 TZHBXQUFPOYFLT-UHFFFAOYSA-N 0.000 description 1
• FTCGJRFYZIYGBE-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7-methyl-3-(4-methylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)=O)N2C=CC(C)=NC2=N1 FTCGJRFYZIYGBE-UHFFFAOYSA-N 0.000 description 1
• OLCFPDRWERDZAS-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7-methyl-3-(4-nitrophenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)[N+]([O-])=O)N2C=CC(C)=NC2=N1 OLCFPDRWERDZAS-UHFFFAOYSA-N 0.000 description 1
• LXHXZMCIHZMNKK-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7-methyl-3-(4-propan-2-ylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)C(C)C)N2C=CC(C)=NC2=N1 LXHXZMCIHZMNKK-UHFFFAOYSA-N 0.000 description 1
• CDNBCJILBRJCKM-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7-methyl-3-(4-propan-2-ylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC(C)C)=CC=2)N2C=CC(C)=NC2=N1 CDNBCJILBRJCKM-UHFFFAOYSA-N 0.000 description 1
• BGKGUGRDNKSDDE-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7-methyl-3-(4-propan-2-ylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(=O)C(C)C)N2C=CC(C)=NC2=N1 BGKGUGRDNKSDDE-UHFFFAOYSA-N 0.000 description 1
• GSPRWZMBXYZMCY-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7-methyl-3-(4-propan-2-ylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(=O)(=O)C(C)C)N2C=CC(C)=NC2=N1 GSPRWZMBXYZMCY-UHFFFAOYSA-N 0.000 description 1
• QNQXGRBNSIJBRI-UHFFFAOYSA-N 2-(4-methylsulfanylphenyl)-3-phenylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC=CC=2)N2C=CC=NC2=N1 QNQXGRBNSIJBRI-UHFFFAOYSA-N 0.000 description 1
• VAZMNSMLRNCAFG-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-3-phenylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)N2C=CC=NC2=N1 VAZMNSMLRNCAFG-UHFFFAOYSA-N 0.000 description 1
• IDQNBVFPZMCDDN-UHFFFAOYSA-N 2-Amino-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(N)=N1 IDQNBVFPZMCDDN-UHFFFAOYSA-N 0.000 description 1
• IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3h-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-UHFFFAOYSA-N 0.000 description 1
• 150000005006 2-aminopyrimidines Chemical class 0.000 description 1
• IVRKHWYQOYMJQX-UHFFFAOYSA-N 2-bromo-2-(4-ethoxyphenyl)-1-(4-methylsulfanylphenyl)ethanone Chemical compound C1=CC(OCC)=CC=C1C(Br)C(=O)C1=CC=C(SC)C=C1 IVRKHWYQOYMJQX-UHFFFAOYSA-N 0.000 description 1
• VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical class ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
• BTWFYGVYHJJDTR-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C3OCOC3=CC=2)N2C=CC=NC2=N1 BTWFYGVYHJJDTR-UHFFFAOYSA-N 0.000 description 1
• HGOMBTIYXMTGLE-UHFFFAOYSA-N 3-(2,3-dichloro-4-methylsulfanylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C(=C(Cl)C(SC)=CC=2)Cl)N2C=CC=NC2=N1 HGOMBTIYXMTGLE-UHFFFAOYSA-N 0.000 description 1
• GCNUWBSKSUGFJR-UHFFFAOYSA-N 3-(2-bromo-5-methoxyphenyl)-2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C(=CC=C(OC)C=2)Br)N2C=CC(C)=NC2=N1 GCNUWBSKSUGFJR-UHFFFAOYSA-N 0.000 description 1
• XAXOMNMBJOVTQA-UHFFFAOYSA-N 3-(2-bromo-5-methoxyphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C(=CC=C(OC)C=2)Br)N2C=CC=NC2=N1 XAXOMNMBJOVTQA-UHFFFAOYSA-N 0.000 description 1
• CTBNREXXSRULMQ-UHFFFAOYSA-N 3-(2-chloro-4-methylsulfanylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C(=CC(SC)=CC=2)Cl)N2C=CC=NC2=N1 CTBNREXXSRULMQ-UHFFFAOYSA-N 0.000 description 1
• BVHBTOFFOBIGEL-UHFFFAOYSA-N 3-(2-chloro-4-methylsulfonylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C(=CC(=CC=2)S(C)(=O)=O)Cl)N2C=CC=NC2=N1 BVHBTOFFOBIGEL-UHFFFAOYSA-N 0.000 description 1
• HPPZTFGXHDPKNP-UHFFFAOYSA-N 3-(2-fluoro-4-methoxyphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C=CC=N2 HPPZTFGXHDPKNP-UHFFFAOYSA-N 0.000 description 1
• LXWFPZKQJTZKSB-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C(F)=CC=2)N2C=CC=NC2=N1 LXWFPZKQJTZKSB-UHFFFAOYSA-N 0.000 description 1
• LVTURTVUJRGIBS-UHFFFAOYSA-N 3-(3-bromo-4-methylsulfanylphenyl)-2-(4-chlorophenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=C(Br)C(SC)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N=C2N1C=CC(C)=N2 LVTURTVUJRGIBS-UHFFFAOYSA-N 0.000 description 1
• UAVQNHRETASSCK-UHFFFAOYSA-N 3-(3-bromo-4-methylsulfanylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Br)C(SC)=CC=2)N2C=CC=NC2=N1 UAVQNHRETASSCK-UHFFFAOYSA-N 0.000 description 1
• QFHMXTDMAHGMSM-UHFFFAOYSA-N 3-(3-bromo-4-methylsulfanylphenyl)-7-methyl-2-(3-methylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Br)C(SC)=CC=C1C1=C(C=2C=C(C)C=CC=2)N=C2N1C=CC(C)=N2 QFHMXTDMAHGMSM-UHFFFAOYSA-N 0.000 description 1
• PGLXAHSRZDYYQV-UHFFFAOYSA-N 3-(3-chloro-4-ethylsulfanylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SCC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N=C2N1C=CC=N2 PGLXAHSRZDYYQV-UHFFFAOYSA-N 0.000 description 1
• PWPWIDQMTCGGHE-UHFFFAOYSA-N 3-(3-chloro-4-methoxyphenyl)-2-(2,4-dichloro-5-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C(=CC(Cl)=C(OC)C=2)Cl)N=C2N1C=CC(C)=N2 PWPWIDQMTCGGHE-UHFFFAOYSA-N 0.000 description 1
• SJKJRFPKZGYFHS-UHFFFAOYSA-N 3-(3-chloro-4-methoxyphenyl)-2-(2,4-dichloro-5-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C(=CC(Cl)=C(OC)C=2)Cl)N=C2N1C=CC=N2 SJKJRFPKZGYFHS-UHFFFAOYSA-N 0.000 description 1
• JCEJRMWHWRLNSP-UHFFFAOYSA-N 3-(3-chloro-4-methoxyphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C=CC=N2 JCEJRMWHWRLNSP-UHFFFAOYSA-N 0.000 description 1
• ZLFSKCVTSBNDAM-UHFFFAOYSA-N 3-(3-chloro-4-methoxyphenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N=C2N1C=CC=N2 ZLFSKCVTSBNDAM-UHFFFAOYSA-N 0.000 description 1
• MCDCPMKNBHUNTE-UHFFFAOYSA-N 3-(3-chloro-4-methoxyphenyl)-7-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C=CC(C)=N2 MCDCPMKNBHUNTE-UHFFFAOYSA-N 0.000 description 1
• ONQRWWOBPKMJBV-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfanylphenyl)-2-(2-fluoro-4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(SC)=CC=2)N2C=CC=NC2=N1 ONQRWWOBPKMJBV-UHFFFAOYSA-N 0.000 description 1
• ISPKSQZPSQVWPV-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfanylphenyl)-2-(3-fluoro-4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(OC)=CC=C1C1=C(C=2C=C(Cl)C(SC)=CC=2)N2C=CC(C)=NC2=N1 ISPKSQZPSQVWPV-UHFFFAOYSA-N 0.000 description 1
• SRIMXOBZTIOOPY-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfanylphenyl)-2-(3-fluoro-4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(OC)=CC=C1C1=C(C=2C=C(Cl)C(SC)=CC=2)N2C=CC=NC2=N1 SRIMXOBZTIOOPY-UHFFFAOYSA-N 0.000 description 1
• BOQSBJFDEWZLDG-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfanylphenyl)-2-(4-chlorophenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SC)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N=C2N1C=CC(C)=N2 BOQSBJFDEWZLDG-UHFFFAOYSA-N 0.000 description 1
• GUMLRAZFEVLWKZ-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfanylphenyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SC)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N=C2N1C=CC=N2 GUMLRAZFEVLWKZ-UHFFFAOYSA-N 0.000 description 1
• QXVYQLIMTOPJCT-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfanylphenyl)-2-(4-fluorophenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SC)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C2N1C=CC=N2 QXVYQLIMTOPJCT-UHFFFAOYSA-N 0.000 description 1
• USAPABZUMGIIQG-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfanylphenyl)-2-(4-methylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)=O)N=C2N1C=CC=N2 USAPABZUMGIIQG-UHFFFAOYSA-N 0.000 description 1
• KNSZOTZLVZATAR-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfanylphenyl)-7-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(Cl)C(SC)=CC=2)N2C=CC(C)=NC2=N1 KNSZOTZLVZATAR-UHFFFAOYSA-N 0.000 description 1
• JHTJNSJAOTVTJB-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfonylphenyl)-2-(3-fluoro-4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(OC)=CC=C1C1=C(C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 JHTJNSJAOTVTJB-UHFFFAOYSA-N 0.000 description 1
• OFXOYPBCBQHEGA-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfonylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)N2C=CC=NC2=N1 OFXOYPBCBQHEGA-UHFFFAOYSA-N 0.000 description 1
• DHZHDEGGWNCPEL-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-ylsulfanylphenyl)-2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(SC(C)C)=CC=2)N2C=CC(C)=NC2=N1 DHZHDEGGWNCPEL-UHFFFAOYSA-N 0.000 description 1
• POPHXVLUGRUSJW-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-ylsulfanylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(SC(C)C)=CC=2)N2C=CC=NC2=N1 POPHXVLUGRUSJW-UHFFFAOYSA-N 0.000 description 1
• ODZVUDZOUGCBNA-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-ylsulfanylphenyl)-7-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SC(C)C)=CC=C1C1=C(C=2C=CC(C)=CC=2)N=C2N1C=CC(C)=N2 ODZVUDZOUGCBNA-UHFFFAOYSA-N 0.000 description 1
• ZQTIMWTYNWOKEY-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-ylsulfanylphenyl)-7-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(Cl)C(SC(C)C)=CC=2)N2C=CC(C)=NC2=N1 ZQTIMWTYNWOKEY-UHFFFAOYSA-N 0.000 description 1
• ZMOOKFDSJHTSQR-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-ylsulfinylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(=CC=2)S(=O)C(C)C)N2C=CC=NC2=N1 ZMOOKFDSJHTSQR-UHFFFAOYSA-N 0.000 description 1
• DSVSXVFVWXXVCR-UHFFFAOYSA-N 3-(3-chloro-4-propylsulfanylphenyl)-2-(4-methylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SCCC)=CC=C1C1=C(C=2C=CC(C)=CC=2)N=C2N1C=CC=N2 DSVSXVFVWXXVCR-UHFFFAOYSA-N 0.000 description 1
• PNVIYJRQSFVDES-UHFFFAOYSA-N 3-(3-chloro-4-propylsulfanylphenyl)-7-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SCCC)=CC=C1C1=C(C=2C=CC(C)=CC=2)N=C2N1C=CC(C)=N2 PNVIYJRQSFVDES-UHFFFAOYSA-N 0.000 description 1
• OWMDFAXGIVNQFF-UHFFFAOYSA-N 3-(3-chloro-4-propylsulfanylphenyl)-7-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SCCC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C=CC(C)=N2 OWMDFAXGIVNQFF-UHFFFAOYSA-N 0.000 description 1
• NUGZGFQDQJNXDX-UHFFFAOYSA-N 3-(3-chloro-4-propylsulfinylphenyl)-2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(S(=O)CCC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N=C2N1C=CC(C)=N2 NUGZGFQDQJNXDX-UHFFFAOYSA-N 0.000 description 1
• ACOPUKRQXXWSDU-UHFFFAOYSA-N 3-(3-chloro-4-propylsulfinylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(S(=O)CCC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N=C2N1C=CC=N2 ACOPUKRQXXWSDU-UHFFFAOYSA-N 0.000 description 1
• ONINZYCJKHAEPP-UHFFFAOYSA-N 3-(3-chloro-4-propylsulfinylphenyl)-2-(4-methylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(S(=O)CCC)=CC=C1C1=C(C=2C=CC(C)=CC=2)N=C2N1C=CC=N2 ONINZYCJKHAEPP-UHFFFAOYSA-N 0.000 description 1
• NRDTYKDAIZWLHK-UHFFFAOYSA-N 3-(3-chloro-4-propylsulfonylphenyl)-2-(4-methylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(S(=O)(=O)CCC)=CC=C1C1=C(C=2C=CC(C)=CC=2)N=C2N1C=CC=N2 NRDTYKDAIZWLHK-UHFFFAOYSA-N 0.000 description 1
• SZSZENFVBSRTDF-UHFFFAOYSA-N 3-(3-chloro-5-methyl-4-methylsulfanylphenyl)-2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(SC)=C(C)C=2)N2C=CC(C)=NC2=N1 SZSZENFVBSRTDF-UHFFFAOYSA-N 0.000 description 1
• HFEDYHRCZSTDBH-UHFFFAOYSA-N 3-(3-chloro-5-methyl-4-methylsulfanylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(SC)=C(C)C=2)N2C=CC=NC2=N1 HFEDYHRCZSTDBH-UHFFFAOYSA-N 0.000 description 1
• RCIJYMHVNWQFME-UHFFFAOYSA-N 3-(3-chloro-5-methyl-4-methylsulfinylphenyl)-2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(=C(C)C=2)S(C)=O)N2C=CC(C)=NC2=N1 RCIJYMHVNWQFME-UHFFFAOYSA-N 0.000 description 1
• LGUWCSHNADITPN-UHFFFAOYSA-N 3-(3-chloro-5-methyl-4-methylsulfinylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(=C(C)C=2)S(C)=O)N2C=CC=NC2=N1 LGUWCSHNADITPN-UHFFFAOYSA-N 0.000 description 1
• HGHANVDKWIFXCE-UHFFFAOYSA-N 3-(3-chloro-5-methyl-4-methylsulfonylphenyl)-2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(=C(C)C=2)S(C)(=O)=O)N2C=CC(C)=NC2=N1 HGHANVDKWIFXCE-UHFFFAOYSA-N 0.000 description 1
• DYQVRTNMEGERHH-UHFFFAOYSA-N 3-(3-chloro-5-methyl-4-methylsulfonylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(=C(C)C=2)S(C)(=O)=O)N2C=CC=NC2=N1 DYQVRTNMEGERHH-UHFFFAOYSA-N 0.000 description 1
• UWZXEPMJSYLVML-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C=CC=2)N2C=CC=NC2=N1 UWZXEPMJSYLVML-UHFFFAOYSA-N 0.000 description 1
• LEYDHZVJQOMLRV-UHFFFAOYSA-N 3-(3-fluoro-4-methoxyphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C=CC=N2 LEYDHZVJQOMLRV-UHFFFAOYSA-N 0.000 description 1
• PTQQKGZRLHZTHR-UHFFFAOYSA-N 3-(3-fluoro-4-methoxyphenyl)-7-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C=CC(C)=N2 PTQQKGZRLHZTHR-UHFFFAOYSA-N 0.000 description 1
• SCDUDUDYZQNGTM-UHFFFAOYSA-N 3-(3-fluoro-4-methylsulfanylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(F)C(SC)=CC=2)N2C=CC=NC2=N1 SCDUDUDYZQNGTM-UHFFFAOYSA-N 0.000 description 1
• UFBZWJBKDHXBAE-UHFFFAOYSA-N 3-(3-fluoro-4-methylsulfanylphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(F)C(SC)=CC=2)N2C=CC=NC2=N1 UFBZWJBKDHXBAE-UHFFFAOYSA-N 0.000 description 1
• SBJNMNNSJRVMOG-UHFFFAOYSA-N 3-(3-fluoro-4-methylsulfanylphenyl)-2-(4-methylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(SC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)=O)N=C2N1C=CC=N2 SBJNMNNSJRVMOG-UHFFFAOYSA-N 0.000 description 1
• CNZUWOVKRBPFAJ-UHFFFAOYSA-N 3-(3-fluoro-4-methylsulfanylphenyl)-7-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(F)C(SC)=CC=2)N2C=CC(C)=NC2=N1 CNZUWOVKRBPFAJ-UHFFFAOYSA-N 0.000 description 1
• CCRAJBIWXOSKDD-UHFFFAOYSA-N 3-(3-fluoro-4-methylsulfinylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(F)C(=CC=2)S(C)=O)N2C=CC=NC2=N1 CCRAJBIWXOSKDD-UHFFFAOYSA-N 0.000 description 1
• ILXKLVIYLKWIND-UHFFFAOYSA-N 3-(3-fluorophenyl)-2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(F)C=CC=2)N2C=CC(C)=NC2=N1 ILXKLVIYLKWIND-UHFFFAOYSA-N 0.000 description 1
• KZUAAZZAJDJPJK-UHFFFAOYSA-N 3-(3-fluorophenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(F)C=CC=2)N2C=CC=NC2=N1 KZUAAZZAJDJPJK-UHFFFAOYSA-N 0.000 description 1
• IDQZYGJOOKJRMV-UHFFFAOYSA-N 3-(3-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C=CC=2)N2C=CC=NC2=N1 IDQZYGJOOKJRMV-UHFFFAOYSA-N 0.000 description 1
• LVBDVQMLJGCUAS-UHFFFAOYSA-N 3-(3-methoxyphenyl)-2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(OC)C=CC=2)N2C=CC(C)=NC2=N1 LVBDVQMLJGCUAS-UHFFFAOYSA-N 0.000 description 1
• TWQZFFRRJDFRFR-UHFFFAOYSA-N 3-(3-methoxyphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(OC)C=CC=2)N2C=CC=NC2=N1 TWQZFFRRJDFRFR-UHFFFAOYSA-N 0.000 description 1
• YHXANDFFHXUWMZ-UHFFFAOYSA-N 3-(3-methoxyphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound COC1=CC=CC(C=2N3C=CC=NC3=NC=2C=2C=CC(SC)=CC=2)=C1 YHXANDFFHXUWMZ-UHFFFAOYSA-N 0.000 description 1
• XWYLEPBCIOUXQN-UHFFFAOYSA-N 3-(3-methoxyphenyl)-7-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound COC1=CC=CC(C=2N3C=CC(C)=NC3=NC=2C=2C=CC(SC)=CC=2)=C1 XWYLEPBCIOUXQN-UHFFFAOYSA-N 0.000 description 1
• NMEHWGPMYYXQSP-UHFFFAOYSA-N 3-(3-tert-butyl-4-methylsulfanylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(C(SC)=CC=2)C(C)(C)C)N2C=CC=NC2=N1 NMEHWGPMYYXQSP-UHFFFAOYSA-N 0.000 description 1
• WTNHXFJKTIZIBW-UHFFFAOYSA-N 3-(3-tert-butyl-4-methylsulfinylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(C(=CC=2)S(C)=O)C(C)(C)C)N2C=CC=NC2=N1 WTNHXFJKTIZIBW-UHFFFAOYSA-N 0.000 description 1
• QKCJIKZPRFFWDQ-UHFFFAOYSA-N 3-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)-2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C3C(C)(C)CCSC3=CC=2)N2C=CC(C)=NC2=N1 QKCJIKZPRFFWDQ-UHFFFAOYSA-N 0.000 description 1
• APLWCLWCRZSWAO-UHFFFAOYSA-N 3-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C3C(C)(C)CCSC3=CC=2)N2C=CC=NC2=N1 APLWCLWCRZSWAO-UHFFFAOYSA-N 0.000 description 1
• HLJDIIHGYJHGFX-UHFFFAOYSA-N 3-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)-7-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C3C(C)(C)CCSC3=CC=2)N2C=CC(C)=NC2=N1 HLJDIIHGYJHGFX-UHFFFAOYSA-N 0.000 description 1
• ATYBPAVANHIQGB-UHFFFAOYSA-N 3-(4-bromophenyl)-2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(Br)=CC=2)N2C=CC(C)=NC2=N1 ATYBPAVANHIQGB-UHFFFAOYSA-N 0.000 description 1
• JYURDYWMAADWQP-UHFFFAOYSA-N 3-(4-bromophenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(Br)=CC=2)N2C=CC=NC2=N1 JYURDYWMAADWQP-UHFFFAOYSA-N 0.000 description 1
• BUGQNRDMXVTRNS-UHFFFAOYSA-N 3-(4-bromophenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(Br)=CC=2)N2C=CC=NC2=N1 BUGQNRDMXVTRNS-UHFFFAOYSA-N 0.000 description 1
• CRZIIGRROIHADK-UHFFFAOYSA-N 3-(4-bromophenyl)-7-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(Br)=CC=2)N2C=CC(C)=NC2=N1 CRZIIGRROIHADK-UHFFFAOYSA-N 0.000 description 1
• LOAXCGYVDGKQCI-UHFFFAOYSA-N 3-(4-bromophenyl)-7-methyl-2-(4-methylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound N1=C2N=C(C)C=CN2C(C=2C=CC(Br)=CC=2)=C1C1=CC=C(S(C)=O)C=C1 LOAXCGYVDGKQCI-UHFFFAOYSA-N 0.000 description 1
• PQWBUQKNGQXIRH-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N2C=CC=NC2=N1 PQWBUQKNGQXIRH-UHFFFAOYSA-N 0.000 description 1
• SQSXLZWUXLVPMF-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(4-methylsulfinylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(S(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N2C=CC=NC2=N1 SQSXLZWUXLVPMF-UHFFFAOYSA-N 0.000 description 1
• SGCQDYFCGKQPIV-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N2C=CC=NC2=N1 SGCQDYFCGKQPIV-UHFFFAOYSA-N 0.000 description 1
• JGJJLBMHNQXADH-UHFFFAOYSA-N 3-(4-chlorophenyl)-7-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N2C=CC(C)=NC2=N1 JGJJLBMHNQXADH-UHFFFAOYSA-N 0.000 description 1
• APNQJYQUVLLBGK-UHFFFAOYSA-N 3-(4-cyclopropylsulfanylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC3CC3)=CC=2)N2C=CC=NC2=N1 APNQJYQUVLLBGK-UHFFFAOYSA-N 0.000 description 1
• BSRPEEQZNLWXHX-UHFFFAOYSA-N 3-(4-ethoxyphenyl)-7-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OCC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C=CC(C)=N2 BSRPEEQZNLWXHX-UHFFFAOYSA-N 0.000 description 1
• RNXBNORLUTYBGK-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(4-methylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N2C=CC=NC2=N1 RNXBNORLUTYBGK-UHFFFAOYSA-N 0.000 description 1
• BSYCHEJOLVSCOI-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N2C=CC=NC2=N1 BSYCHEJOLVSCOI-UHFFFAOYSA-N 0.000 description 1
• UVFBDUJJOZFCNX-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(4-nitrophenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=C(C=2C=CC(F)=CC=2)N2C=CC=NC2=N1 UVFBDUJJOZFCNX-UHFFFAOYSA-N 0.000 description 1
• OJBKGFJNHFLPKS-UHFFFAOYSA-N 3-(4-fluorophenyl)-5,7-dimethyl-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound N1=C2N=C(C)C=C(C)N2C(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 OJBKGFJNHFLPKS-UHFFFAOYSA-N 0.000 description 1
• UHVVIILRXZWYTA-UHFFFAOYSA-N 3-(4-fluorophenyl)-7-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(F)=CC=2)N2C=CC(C)=NC2=N1 UHVVIILRXZWYTA-UHFFFAOYSA-N 0.000 description 1
• DTWFVYZPTMBBDV-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-(3-nitrophenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(C=CC=2)[N+]([O-])=O)N=C2N1C=CC=N2 DTWFVYZPTMBBDV-UHFFFAOYSA-N 0.000 description 1
• OINSTMREQNRIPJ-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-(4-methylsulfanylphenyl)-1h-imidazo[1,2-a]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)NC2=NC(=O)C=CN12 OINSTMREQNRIPJ-UHFFFAOYSA-N 0.000 description 1
• QOCSGKXJHVXJFF-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C=CC=N2 QOCSGKXJHVXJFF-UHFFFAOYSA-N 0.000 description 1
• ASWSGUVHXSVNFN-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(C=CC=2)C(F)(F)F)N=C2N1C=CC=N2 ASWSGUVHXSVNFN-UHFFFAOYSA-N 0.000 description 1
• ONWPQXQOGXJUJA-UHFFFAOYSA-N 3-(4-methoxyphenyl)-7-methyl-2-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(C=CC=2)C(F)(F)F)N=C2N1C=CC(C)=N2 ONWPQXQOGXJUJA-UHFFFAOYSA-N 0.000 description 1
• MZHLWZCKNQOXDC-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)C(C)(C)C)N2C=CC(C)=NC2=N1 MZHLWZCKNQOXDC-UHFFFAOYSA-N 0.000 description 1
• PYOURQGLBJKECH-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)C(C)(C)C)N2C=CC=NC2=N1 PYOURQGLBJKECH-UHFFFAOYSA-N 0.000 description 1
• SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
• BWVWMWLEKFZGTG-UHFFFAOYSA-N 3-[4-(cyclohexylmethylsulfanyl)phenyl]-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SCC3CCCCC3)=CC=2)N2C=CC=NC2=N1 BWVWMWLEKFZGTG-UHFFFAOYSA-N 0.000 description 1
• PYRSCINXZPIIHL-UHFFFAOYSA-N 3-[4-(cyclohexylmethylsulfanyl)phenyl]-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(SCC3CCCCC3)=CC=2)N2C=CC=NC2=N1 PYRSCINXZPIIHL-UHFFFAOYSA-N 0.000 description 1
• BMGWLEICRDVGAM-UHFFFAOYSA-N 3-[4-(cyclohexylmethylsulfanyl)phenyl]-7-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(SCC3CCCCC3)=CC=2)N2C=CC(C)=NC2=N1 BMGWLEICRDVGAM-UHFFFAOYSA-N 0.000 description 1
• QHUGBIDXOCJARL-UHFFFAOYSA-N 3-[4-(cyclohexylmethylsulfinyl)phenyl]-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(=O)CC2CCCCC2)N2C=CC=NC2=N1 QHUGBIDXOCJARL-UHFFFAOYSA-N 0.000 description 1
• UXRRHNOZVPRVNO-UHFFFAOYSA-N 3-[4-(cyclohexylmethylsulfonyl)phenyl]-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(=O)(=O)CC2CCCCC2)N2C=CC=NC2=N1 UXRRHNOZVPRVNO-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• ASYKOYNBRLHNSP-UHFFFAOYSA-N 3-bromo-2-(4-methylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(C)=CC=C1C1=C(Br)N2C=CC=NC2=N1 ASYKOYNBRLHNSP-UHFFFAOYSA-N 0.000 description 1
• ADGMBHUSGZGHTE-UHFFFAOYSA-N 3-bromo-2-phenylimidazo[1,2-a]pyrimidine Chemical compound N1=C2N=CC=CN2C(Br)=C1C1=CC=CC=C1 ADGMBHUSGZGHTE-UHFFFAOYSA-N 0.000 description 1
• YDENRMADTTVYCK-UHFFFAOYSA-N 3-phenyl-2-(4-propylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SCCC)=CC=C1C1=C(C=2C=CC=CC=2)N2C=CC=NC2=N1 YDENRMADTTVYCK-UHFFFAOYSA-N 0.000 description 1
• LVFRCHIUUKWBLR-UHFFFAOYSA-N 4,6-dimethoxypyrimidin-2-amine Chemical compound COC1=CC(OC)=NC(N)=N1 LVFRCHIUUKWBLR-UHFFFAOYSA-N 0.000 description 1
• YUPXYSYAQAONLY-UHFFFAOYSA-N 4-(7-methyl-3-phenylimidazo[1,2-a]pyrimidin-2-yl)benzenesulfinic acid Chemical compound N1=C2N=C(C)C=CN2C(C=2C=CC=CC=2)=C1C1=CC=C(S(O)=O)C=C1 YUPXYSYAQAONLY-UHFFFAOYSA-N 0.000 description 1
• VBRXDPMWKPAZBC-UHFFFAOYSA-N 4-(7-methyl-3-phenylimidazo[1,2-a]pyrimidin-2-yl)benzenesulfonamide Chemical compound N1=C2N=C(C)C=CN2C(C=2C=CC=CC=2)=C1C1=CC=C(S(N)(=O)=O)C=C1 VBRXDPMWKPAZBC-UHFFFAOYSA-N 0.000 description 1
• OAHNJOWFNIGCTA-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-3-yl]benzonitrile Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC(=CC=2)C#N)N2C=CC=NC2=N1 OAHNJOWFNIGCTA-UHFFFAOYSA-N 0.000 description 1
• SKNMMTHAZXUAIK-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-methylphenyl)-7-methylimidazo[1,2-a]pyrimidin-3-yl]benzenesulfonamide Chemical compound N1=C2N=C(C)C=CN2C(C=2C=CC(=CC=2)S(N)(=O)=O)=C1C1=CC=C(O)C(C)=C1 SKNMMTHAZXUAIK-UHFFFAOYSA-N 0.000 description 1
• GYWQIQPJQOPZMN-UHFFFAOYSA-N 4-[2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidin-3-yl]-2-methylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(C)C(=CC=2)S(N)(=O)=O)N2C=CC(C)=NC2=N1 GYWQIQPJQOPZMN-UHFFFAOYSA-N 0.000 description 1
• JWZXYLPTFUSMOE-UHFFFAOYSA-N 4-[2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidin-3-yl]aniline Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(N)=CC=2)N2C=CC(C)=NC2=N1 JWZXYLPTFUSMOE-UHFFFAOYSA-N 0.000 description 1
• LCJNOPDKXLZEKI-UHFFFAOYSA-N 4-[2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidin-3-yl]-2-methylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(C)C(=CC=2)S(N)(=O)=O)N2C=CC=NC2=N1 LCJNOPDKXLZEKI-UHFFFAOYSA-N 0.000 description 1
• LFKGBOULXZPTEV-UHFFFAOYSA-N 4-[2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidin-3-yl]aniline Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(N)=CC=2)N2C=CC=NC2=N1 LFKGBOULXZPTEV-UHFFFAOYSA-N 0.000 description 1
• ICOYNCNMVQLTNW-UHFFFAOYSA-N 4-[2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidin-3-yl]benzonitrile Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(=CC=2)C#N)N2C=CC=NC2=N1 ICOYNCNMVQLTNW-UHFFFAOYSA-N 0.000 description 1
• OZDQDRGUGMLUEB-UHFFFAOYSA-N 4-[3-(4-bromophenyl)imidazo[1,2-a]pyrimidin-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(Br)=CC=2)N2C=CC=NC2=N1 OZDQDRGUGMLUEB-UHFFFAOYSA-N 0.000 description 1
• PIHMMDBBWZHWQO-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC(=CC=2)C#N)N=C2N1C=CC=N2 PIHMMDBBWZHWQO-UHFFFAOYSA-N 0.000 description 1
• AXHVYUJBPKZVHK-UHFFFAOYSA-N 4-[3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(=CC=2)C#N)N=C2N1C=CC=N2 AXHVYUJBPKZVHK-UHFFFAOYSA-N 0.000 description 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
• RLYPDBLECVNQNR-UHFFFAOYSA-N 5,7-dichloro-3-(4-methoxyphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C(Cl)=CC(Cl)=N2 RLYPDBLECVNQNR-UHFFFAOYSA-N 0.000 description 1
• VINZDCKASJNXPZ-UHFFFAOYSA-N 5,7-dimethyl-2-(4-methylsulfonylphenyl)-3-phenylimidazo[1,2-a]pyrimidine Chemical compound N1=C2N=C(C)C=C(C)N2C(C=2C=CC=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 VINZDCKASJNXPZ-UHFFFAOYSA-N 0.000 description 1
• YMBGJQGAZXKMRF-UHFFFAOYSA-N 5-chloro-2-(4-methoxyphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C(Cl)=CC(N)=NC2=N1 YMBGJQGAZXKMRF-UHFFFAOYSA-N 0.000 description 1
• OSIXRGHZTYGLOO-UHFFFAOYSA-N 5-chloro-3-(4-methoxyphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C(Cl)=CC=N2 OSIXRGHZTYGLOO-UHFFFAOYSA-N 0.000 description 1
• XKQWPTBIRUAPOB-UHFFFAOYSA-N 6-bromo-2-(4-methoxyphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=C(Br)C=NC2=N1 XKQWPTBIRUAPOB-UHFFFAOYSA-N 0.000 description 1
• POQAKXJONYETKG-UHFFFAOYSA-N 6-bromo-3-(4-methoxyphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C=C(Br)C=N2 POQAKXJONYETKG-UHFFFAOYSA-N 0.000 description 1
• SQVFZZDKJCEBOZ-UHFFFAOYSA-N 7-chloro-2-(4-methoxyphenyl)-5-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C(C)=CC(Cl)=NC2=N1 SQVFZZDKJCEBOZ-UHFFFAOYSA-N 0.000 description 1
• LFOSGNOFSPNQBX-UHFFFAOYSA-N 7-chloro-5-methoxy-3-(4-methoxyphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C(OC)=CC(Cl)=N2 LFOSGNOFSPNQBX-UHFFFAOYSA-N 0.000 description 1
• VFKFFLQXUHCAPL-UHFFFAOYSA-N 7-methoxy-2-(4-methoxyphenyl)-5-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C(C)=CC(OC)=NC2=N1 VFKFFLQXUHCAPL-UHFFFAOYSA-N 0.000 description 1
• MTBHRWWKWXKLIS-UHFFFAOYSA-N 7-methoxy-3-(4-methoxyphenyl)-5-methyl-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N=C2N1C(C)=CC(OC)=N2 MTBHRWWKWXKLIS-UHFFFAOYSA-N 0.000 description 1
• JYXLGAPKWNKWJD-UHFFFAOYSA-N 7-methyl-2,3-bis(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC(C)=NC2=N1 JYXLGAPKWNKWJD-UHFFFAOYSA-N 0.000 description 1
• DGXRWFPPKYQANQ-UHFFFAOYSA-N 7-methyl-2-(4-methylsulfanylphenyl)-3-phenylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC=CC=2)N2C=CC(C)=NC2=N1 DGXRWFPPKYQANQ-UHFFFAOYSA-N 0.000 description 1
• KLJJBKVSEOQPOY-UHFFFAOYSA-N 7-methyl-2-(4-methylsulfinylphenyl)-3-phenylimidazo[1,2-a]pyrimidine Chemical compound N1=C2N=C(C)C=CN2C(C=2C=CC=CC=2)=C1C1=CC=C(S(C)=O)C=C1 KLJJBKVSEOQPOY-UHFFFAOYSA-N 0.000 description 1
• WTUCSNBNVYOISR-UHFFFAOYSA-N 7-methyl-2-(4-methylsulfonylphenyl)-3-phenylimidazo[1,2-a]pyrimidine Chemical compound N1=C2N=C(C)C=CN2C(C=2C=CC=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 WTUCSNBNVYOISR-UHFFFAOYSA-N 0.000 description 1
• JNYXNXZJOWGXAX-UHFFFAOYSA-N 7-methyl-3-(3-methyl-4-methylsulfanylphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(C)C(SC)=CC=2)N2C=CC(C)=NC2=N1 JNYXNXZJOWGXAX-UHFFFAOYSA-N 0.000 description 1
• ONRPPRYKEPJBIE-UHFFFAOYSA-N 7-methyl-3-(4-methylsulfinylphenyl)-2-phenylimidazo[1,2-a]pyrimidine Chemical compound N1=C2N=C(C)C=CN2C(C=2C=CC(=CC=2)S(C)=O)=C1C1=CC=CC=C1 ONRPPRYKEPJBIE-UHFFFAOYSA-N 0.000 description 1
• DVQYTZKQXAHJAZ-UHFFFAOYSA-N 7-methyl-3-phenyl-2-(4-propylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SCCC)=CC=C1C1=C(C=2C=CC=CC=2)N2C=CC(C)=NC2=N1 DVQYTZKQXAHJAZ-UHFFFAOYSA-N 0.000 description 1
• USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 description 1
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
• 208000003200 Adenoma Diseases 0.000 description 1
• 208000004804 Adenomatous Polyps Diseases 0.000 description 1
• 235000011437 Amygdalus communis Nutrition 0.000 description 1
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
• OPCXYECQGRTBFV-UHFFFAOYSA-O CC(N[S+](=O)=O)=O Chemical compound CC(N[S+](=O)=O)=O OPCXYECQGRTBFV-UHFFFAOYSA-O 0.000 description 1
• CXVHLHRDBQSUFG-UHFFFAOYSA-N COc(cc1)ccc1-c1c(-c(cc2)ccc2OC)nc2nccc[n]12 Chemical compound COc(cc1)ccc1-c1c(-c(cc2)ccc2OC)nc2nccc[n]12 CXVHLHRDBQSUFG-UHFFFAOYSA-N 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
• 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
• 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
• 230000005778 DNA damage Effects 0.000 description 1
• 231100000277 DNA damage Toxicity 0.000 description 1
• 238000002965 ELISA Methods 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
• 102000006947 Histones Human genes 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
• 206010020649 Hyperkeratosis Diseases 0.000 description 1
• 206010020751 Hypersensitivity Diseases 0.000 description 1
• 206010061218 Inflammation Diseases 0.000 description 1
• 108010044467 Isoenzymes Proteins 0.000 description 1
• 208000001126 Keratosis Diseases 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
• 241001529936 Murinae Species 0.000 description 1
• 206010029098 Neoplasm skin Diseases 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 1
• 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 1
• 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
• 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
• 241000220304 Prunus dulcis Species 0.000 description 1
• 238000006956 Pummerer reaction Methods 0.000 description 1
• 229940124639 Selective inhibitor Drugs 0.000 description 1
• 206010040914 Skin reaction Diseases 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• 238000006069 Suzuki reaction reaction Methods 0.000 description 1
• 239000007983 Tris buffer Substances 0.000 description 1
• 108700025716 Tumor Suppressor Genes Proteins 0.000 description 1
• 102000044209 Tumor Suppressor Genes Human genes 0.000 description 1
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
• 238000006640 acetylation reaction Methods 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 229910001413 alkali metal ion Inorganic materials 0.000 description 1
• 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
• 125000004414 alkyl thio group Chemical group 0.000 description 1
• 235000020224 almond Nutrition 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 238000005576 amination reaction Methods 0.000 description 1
• 150000005005 aminopyrimidines Chemical class 0.000 description 1
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 230000003110 anti-inflammatory effect Effects 0.000 description 1
• 230000000118 anti-neoplastic effect Effects 0.000 description 1
• 230000001640 apoptogenic effect Effects 0.000 description 1
• 150000001543 aryl boronic acids Chemical class 0.000 description 1
• 125000003118 aryl group Chemical group 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 230000008033 biological extinction Effects 0.000 description 1
• 230000036983 biotransformation Effects 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• NMRLGXWKUKATHC-UHFFFAOYSA-N c(cc1)ccc1-c([n]1c(-c2ccccc2)c2)c(-c3ccccc3)nc1nc2-c1ccccc1 Chemical compound c(cc1)ccc1-c([n]1c(-c2ccccc2)c2)c(-c3ccccc3)nc1nc2-c1ccccc1 NMRLGXWKUKATHC-UHFFFAOYSA-N 0.000 description 1
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
• 239000000920 calcium hydroxide Substances 0.000 description 1
• 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 231100000357 carcinogen Toxicity 0.000 description 1
• 231100000315 carcinogenic Toxicity 0.000 description 1
• 239000003183 carcinogenic agent Substances 0.000 description 1
• 230000030833 cell death Effects 0.000 description 1
• 230000025611 cell-substrate adhesion Effects 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 150000001793 charged compounds Chemical class 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 238000013375 chromatographic separation Methods 0.000 description 1
• 210000001072 colon Anatomy 0.000 description 1
• 201000010897 colon adenocarcinoma Diseases 0.000 description 1
• 208000029742 colonic neoplasm Diseases 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 238000009109 curative therapy Methods 0.000 description 1
• 210000000172 cytosol Anatomy 0.000 description 1
• 231100000433 cytotoxic Toxicity 0.000 description 1
• 230000001472 cytotoxic effect Effects 0.000 description 1
• 230000034994 death Effects 0.000 description 1
• 231100000517 death Toxicity 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• 230000002526 effect on cardiovascular system Effects 0.000 description 1
• 229950000484 exisulind Drugs 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• 210000002950 fibroblast Anatomy 0.000 description 1
• 238000001640 fractional crystallisation Methods 0.000 description 1
• 239000012634 fragment Substances 0.000 description 1
• 238000013467 fragmentation Methods 0.000 description 1
• 238000006062 fragmentation reaction Methods 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 230000002068 genetic effect Effects 0.000 description 1
• 210000004602 germ cell Anatomy 0.000 description 1
• 230000009036 growth inhibition Effects 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 230000003301 hydrolyzing effect Effects 0.000 description 1
• DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
• 238000003018 immunoassay Methods 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 231100001231 less toxic Toxicity 0.000 description 1
• 150000002689 maleic acids Chemical class 0.000 description 1
• 238000004949 mass spectrometry Methods 0.000 description 1
• 229910021645 metal ion Inorganic materials 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• VZILXIWIVFCOEH-UHFFFAOYSA-N n-[5-(dimethylamino)-2-(4-methoxyphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidin-7-yl]-2,2,2-trifluoroacetamide Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C(N(C)C)=CC(NC(=O)C(F)(F)F)=NC2=N1 VZILXIWIVFCOEH-UHFFFAOYSA-N 0.000 description 1
• 230000001338 necrotic effect Effects 0.000 description 1
• 230000035407 negative regulation of cell proliferation Effects 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 230000002018 overexpression Effects 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 239000002831 pharmacologic agent Substances 0.000 description 1
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
• 102000054765 polymorphisms of proteins Human genes 0.000 description 1
• 208000015768 polyposis Diseases 0.000 description 1
• 230000003449 preventive effect Effects 0.000 description 1
• 230000000861 pro-apoptotic effect Effects 0.000 description 1
• 230000000069 prophylactic effect Effects 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• 239000005297 pyrex Substances 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 230000005855 radiation Effects 0.000 description 1
• 239000000523 sample Substances 0.000 description 1
• 239000012047 saturated solution Substances 0.000 description 1
• 230000019491 signal transduction Effects 0.000 description 1
• 231100000430 skin reaction Toxicity 0.000 description 1
• 230000035483 skin reaction Effects 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 230000003637 steroidlike Effects 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 125000000565 sulfonamide group Chemical group 0.000 description 1
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
• MVGSNCBCUWPVDA-MFOYZWKCSA-N sulindac sulfone Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)(=O)=O)C=C1 MVGSNCBCUWPVDA-MFOYZWKCSA-N 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 230000009897 systematic effect Effects 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 210000004881 tumor cell Anatomy 0.000 description 1
• BIDDLDNGQCUOJQ-SDNWHVSQSA-N α-phenylcinnamic acid Chemical compound C=1C=CC=CC=1/C(C(=O)O)=C\C1=CC=CC=C1 BIDDLDNGQCUOJQ-SDNWHVSQSA-N 0.000 description 1