FI119988B - Sykliset heksapeptidit, joilla on antibioottinen aktiivisuus - Google Patents

Info

Publication number

FI119988B

FI119988B FI971397A FI971397A FI119988B FI 119988 B FI119988 B FI 119988B FI 971397 A FI971397 A FI 971397A FI 971397 A FI971397 A FI 971397A FI 119988 B FI119988 B FI 119988B

Authority

FI

Finland

Prior art keywords

phenyl

alkoxy

substituted

nmr

alkyl

Prior art date

1994-10-07

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• 230000003115 biocidal effect Effects 0.000 title description 3
• 125000004122 cyclic group Chemical group 0.000 title description 2
• 238000002360 preparation method Methods 0.000 claims description 409
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 192
• 150000001875 compounds Chemical class 0.000 claims description 148
• -1 indolylcarbonyl Chemical group 0.000 claims description 104
• 125000003545 alkoxy group Chemical group 0.000 claims description 90
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 70
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 69
• 125000001424 substituent group Chemical group 0.000 claims description 39
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 28
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 27
• 229920001184 polypeptide Polymers 0.000 claims description 26
• 102000004196 processed proteins & peptides Human genes 0.000 claims description 26
• 125000001589 carboacyl group Chemical group 0.000 claims description 19
• 125000006530 (C4-C6) alkyl group Chemical group 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 125000004193 piperazinyl group Chemical group 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 12
• 125000005936 piperidyl group Chemical group 0.000 claims description 12
• 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 11
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 9
• 238000000034 method Methods 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 5
• 125000003277 amino group Chemical group 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 208000035473 Communicable disease Diseases 0.000 claims description 3
• 239000000654 additive Substances 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 230000000996 additive effect Effects 0.000 claims description 2
• 125000005872 benzooxazolyl group Chemical group 0.000 claims description 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 2
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
• 125000000335 thiazolyl group Chemical group 0.000 claims description 2
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
• 238000011321 prophylaxis Methods 0.000 claims 1
• 238000005481 NMR spectroscopy Methods 0.000 description 439
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 201
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 170
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 150
• 238000000921 elemental analysis Methods 0.000 description 119
• 239000011734 sodium Substances 0.000 description 113
• 239000000203 mixture Substances 0.000 description 97
• 230000002829 reductive effect Effects 0.000 description 88
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 85
• 235000019341 magnesium sulphate Nutrition 0.000 description 85
• 229910001868 water Inorganic materials 0.000 description 84
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 82
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 79
• 239000000243 solution Substances 0.000 description 78
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 55
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 52
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 51
• 239000012044 organic layer Substances 0.000 description 51
• 239000011541 reaction mixture Substances 0.000 description 49
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 42
• 239000012267 brine Substances 0.000 description 40
• 239000000706 filtrate Substances 0.000 description 38
• 238000001914 filtration Methods 0.000 description 36
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 31
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
• 239000000725 suspension Substances 0.000 description 28
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
• 239000002244 precipitate Substances 0.000 description 23
• 239000002904 solvent Substances 0.000 description 22
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
• UCGKVWNBKILEDM-UHFFFAOYSA-N C1=CC=C2[N+]([O-])=NNC2=C1 Chemical compound C1=CC=C2[N+]([O-])=NNC2=C1 UCGKVWNBKILEDM-UHFFFAOYSA-N 0.000 description 18
• 239000008188 pellet Substances 0.000 description 17
• 229910052739 hydrogen Inorganic materials 0.000 description 14
• 239000000843 powder Substances 0.000 description 13
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 12
• 238000004440 column chromatography Methods 0.000 description 12
• 239000000741 silica gel Substances 0.000 description 12
• 229910002027 silica gel Inorganic materials 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
• 238000001816 cooling Methods 0.000 description 10
• 229910052757 nitrogen Inorganic materials 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
• 229960000583 acetic acid Drugs 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 6
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 6
• 239000005711 Benzoic acid Substances 0.000 description 6
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 230000000845 anti-microbial effect Effects 0.000 description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
• 239000006227 byproduct Substances 0.000 description 6
• 239000005457 ice water Substances 0.000 description 6
• 239000003456 ion exchange resin Substances 0.000 description 6
• 229920003303 ion-exchange polymer Polymers 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
• 235000010233 benzoic acid Nutrition 0.000 description 5
• 238000001704 evaporation Methods 0.000 description 5
• 230000008020 evaporation Effects 0.000 description 5
• 150000004702 methyl esters Chemical class 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 238000010898 silica gel chromatography Methods 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
• 239000000443 aerosol Substances 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• 239000001257 hydrogen Substances 0.000 description 4
• 150000002923 oximes Chemical class 0.000 description 4
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 4
• 238000000746 purification Methods 0.000 description 4
• 239000012312 sodium hydride Substances 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• 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 4
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
• VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 3
• 238000005160 1H NMR spectroscopy Methods 0.000 description 3
• IEPCABVQANKPNT-UHFFFAOYSA-N 4-[4-(8-bromooctoxy)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(OCCCCCCCCBr)C=C1 IEPCABVQANKPNT-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
• 206010035660 Pneumocystis Infections Diseases 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 150000008065 acid anhydrides Chemical class 0.000 description 3
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 3
• 230000000843 anti-fungal effect Effects 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 230000037396 body weight Effects 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
• 239000000460 chlorine Substances 0.000 description 3
• 238000001990 intravenous administration Methods 0.000 description 3
• RUTXRPSNXSBXSF-UHFFFAOYSA-N methyl 4-[[(4-hexoxybenzoyl)amino]carbamoyl]benzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)NNC(=O)C1=CC=C(C(=O)OC)C=C1 RUTXRPSNXSBXSF-UHFFFAOYSA-N 0.000 description 3
• 239000012299 nitrogen atmosphere Substances 0.000 description 3
• 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
• 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 3
• 239000000126 substance Substances 0.000 description 3
• 229910052720 vanadium Inorganic materials 0.000 description 3
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• QHLVAKZJUURIQO-UHFFFAOYSA-N 1-(4-octoxyphenyl)piperazine Chemical compound C1=CC(OCCCCCCCC)=CC=C1N1CCNCC1 QHLVAKZJUURIQO-UHFFFAOYSA-N 0.000 description 2
• QQQSUVSRXPLWAH-UHFFFAOYSA-N 1-[4-(4-heptylphenyl)phenyl]ethanone Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=C(C(C)=O)C=C1 QQQSUVSRXPLWAH-UHFFFAOYSA-N 0.000 description 2
• PVRFWXFHUOIQLV-UHFFFAOYSA-N 1-amino-3-(4-octylphenyl)urea Chemical compound CCCCCCCCC1=CC=C(NC(=O)NN)C=C1 PVRFWXFHUOIQLV-UHFFFAOYSA-N 0.000 description 2
• RJQRJLCQHIMUQO-UHFFFAOYSA-N 1-bromo-4-(4-heptylphenyl)benzene Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=C(Br)C=C1 RJQRJLCQHIMUQO-UHFFFAOYSA-N 0.000 description 2
• VXJTWTJULLKDPY-UHFFFAOYSA-N 1-bromo-4-(4-pentylphenyl)benzene Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(Br)C=C1 VXJTWTJULLKDPY-UHFFFAOYSA-N 0.000 description 2
• UXQBXLHGTWIYNR-UHFFFAOYSA-N 1-bromo-4-[4-(7-bromoheptoxy)phenyl]benzene Chemical compound C1=CC(OCCCCCCCBr)=CC=C1C1=CC=C(Br)C=C1 UXQBXLHGTWIYNR-UHFFFAOYSA-N 0.000 description 2
• SNKZHWDUNHXAMY-UHFFFAOYSA-N 1-bromo-4-[4-(8-bromooctoxy)phenyl]benzene Chemical compound C1=CC(OCCCCCCCCBr)=CC=C1C1=CC=C(Br)C=C1 SNKZHWDUNHXAMY-UHFFFAOYSA-N 0.000 description 2
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
• MKSWQHOPSDCVMS-UHFFFAOYSA-N 1-ethynyl-4-pentoxybenzene Chemical group CCCCCOC1=CC=C(C#C)C=C1 MKSWQHOPSDCVMS-UHFFFAOYSA-N 0.000 description 2
• IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 2
• QIPBUORAZAUNLL-UHFFFAOYSA-N 2-hydroxy-4-octoxybenzaldehyde Chemical compound CCCCCCCCOC1=CC=C(C=O)C(O)=C1 QIPBUORAZAUNLL-UHFFFAOYSA-N 0.000 description 2
• ILWROKQKEDTIKB-UHFFFAOYSA-N 2-pentan-2-yloxy-1-phenylethanone Chemical compound CCCC(C)OCC(=O)C1=CC=CC=C1 ILWROKQKEDTIKB-UHFFFAOYSA-N 0.000 description 2
• DVFWRZHZHULTLX-UHFFFAOYSA-N 3-(4-bromophenyl)-5-(4-pentoxyphenyl)-1,2-oxazole Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC(C=2C=CC(Br)=CC=2)=NO1 DVFWRZHZHULTLX-UHFFFAOYSA-N 0.000 description 2
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
• OFUJQNIYHRBBFU-UHFFFAOYSA-N 3-[4-(4-heptylphenyl)phenyl]propanoic acid Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(CCC(O)=O)C=C1 OFUJQNIYHRBBFU-UHFFFAOYSA-N 0.000 description 2
• MWIWHZXYIFPWQF-UHFFFAOYSA-N 3-[4-(4-pentylphenyl)phenyl]prop-2-enoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C=CC(O)=O)C=C1 MWIWHZXYIFPWQF-UHFFFAOYSA-N 0.000 description 2
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
• PDTXSIGPZDVVIX-UHFFFAOYSA-N 4-[5-(4-pentoxyphenyl)-1,2-oxazol-3-yl]benzoic acid Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(O)=O)=NO1 PDTXSIGPZDVVIX-UHFFFAOYSA-N 0.000 description 2
• ZKSQOKZGDNEDJQ-UHFFFAOYSA-N 4-hexoxybenzohydrazide Chemical compound CCCCCCOC1=CC=C(C(=O)NN)C=C1 ZKSQOKZGDNEDJQ-UHFFFAOYSA-N 0.000 description 2
• DQQOONVCLQZWOY-UHFFFAOYSA-N 4-hexoxybenzoyl chloride Chemical compound CCCCCCOC1=CC=C(C(Cl)=O)C=C1 DQQOONVCLQZWOY-UHFFFAOYSA-N 0.000 description 2
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• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
• 230000037304 dermatophytes Effects 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
• IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
• 238000003113 dilution method Methods 0.000 description 1
• BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
• HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
• FOBPTJZYDGNHLR-UHFFFAOYSA-N diphosphorus Chemical compound P#P FOBPTJZYDGNHLR-UHFFFAOYSA-N 0.000 description 1
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 239000000428 dust Substances 0.000 description 1
• 210000005069 ears Anatomy 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 150000002169 ethanolamines Chemical class 0.000 description 1
• CAMDZZUCCKSMPS-FMQUCBEESA-N ethyl (e)-3-[4-(4-heptylphenyl)phenyl]but-2-enoate Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(C(\C)=C\C(=O)OCC)C=C1 CAMDZZUCCKSMPS-FMQUCBEESA-N 0.000 description 1
• RILLRPWNMMZZBV-UHFFFAOYSA-N ethyl 1-(4-hexoxyphenyl)-4-oxopiperidine-3-carboxylate Chemical compound C1=CC(OCCCCCC)=CC=C1N1CC(C(=O)OCC)C(=O)CC1 RILLRPWNMMZZBV-UHFFFAOYSA-N 0.000 description 1
• GIZQNAYESPVBRM-UHFFFAOYSA-N ethyl 1-(6-heptoxynaphthalene-2-carbonyl)piperidine-4-carboxylate Chemical compound C1=CC2=CC(OCCCCCCC)=CC=C2C=C1C(=O)N1CCC(C(=O)OCC)CC1 GIZQNAYESPVBRM-UHFFFAOYSA-N 0.000 description 1
• ODQSOTBFWCNPKF-UHFFFAOYSA-N ethyl 2-(4-hexoxyphenyl)-1,3-benzoxazole-5-carboxylate Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC2=CC(C(=O)OCC)=CC=C2O1 ODQSOTBFWCNPKF-UHFFFAOYSA-N 0.000 description 1
• OSLQGOBYIDZZTD-UHFFFAOYSA-N ethyl 2-(6-octoxypyridin-3-yl)-1,3-benzoxazole-5-carboxylate Chemical compound C1=NC(OCCCCCCCC)=CC=C1C1=NC2=CC(C(=O)OCC)=CC=C2O1 OSLQGOBYIDZZTD-UHFFFAOYSA-N 0.000 description 1
• RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 1
• FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
• UAHNKLUBOMFHKE-UHFFFAOYSA-N ethyl 4-[3-(4-pentoxyphenyl)prop-2-enoyl]benzoate Chemical compound C1=CC(OCCCCC)=CC=C1C=CC(=O)C1=CC=C(C(=O)OCC)C=C1 UAHNKLUBOMFHKE-UHFFFAOYSA-N 0.000 description 1
• PWLIDNJVLQJKIS-UHFFFAOYSA-N ethyl 4-[3-(dimethylamino)prop-2-enoyl]benzoate Chemical group CCOC(=O)C1=CC=C(C(=O)C=CN(C)C)C=C1 PWLIDNJVLQJKIS-UHFFFAOYSA-N 0.000 description 1
• WNJCQFLYGMSUJW-UHFFFAOYSA-N ethyl 4-[4-[1-(4-hexoxyphenyl)piperidin-4-yl]piperazin-1-yl]benzoate Chemical compound C1=CC(OCCCCCC)=CC=C1N1CCC(N2CCN(CC2)C=2C=CC(=CC=2)C(=O)OCC)CC1 WNJCQFLYGMSUJW-UHFFFAOYSA-N 0.000 description 1
• GHMHKOHJAFFUCP-UHFFFAOYSA-N ethyl 4-[5-(4-pentoxyphenyl)-1,2-oxazol-3-yl]benzoate Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(=O)OCC)=NO1 GHMHKOHJAFFUCP-UHFFFAOYSA-N 0.000 description 1
• GLOAPLPTWAXAIG-UHFFFAOYSA-N ethyl 4-acetylbenzoate Chemical compound CCOC(=O)C1=CC=C(C(C)=O)C=C1 GLOAPLPTWAXAIG-UHFFFAOYSA-N 0.000 description 1
• OQEHTFFLOHTFSB-UHFFFAOYSA-N ethyl 4-piperazin-1-ylbenzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1CCNCC1 OQEHTFFLOHTFSB-UHFFFAOYSA-N 0.000 description 1
• IXJHHMIKLJPXMW-UHFFFAOYSA-N ethyl 6-[4-(4-hexoxyphenyl)piperazin-1-yl]pyridazine-3-carboxylate Chemical compound C1=CC(OCCCCCC)=CC=C1N1CCN(C=2N=NC(=CC=2)C(=O)OCC)CC1 IXJHHMIKLJPXMW-UHFFFAOYSA-N 0.000 description 1
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
• WMYNMYVRWWCRPS-UHFFFAOYSA-N ethynoxyethane Chemical group CCOC#C WMYNMYVRWWCRPS-UHFFFAOYSA-N 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 239000003889 eye drop Substances 0.000 description 1
• 229940012356 eye drops Drugs 0.000 description 1
• 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• 238000000227 grinding Methods 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 238000004128 high performance liquid chromatography Methods 0.000 description 1
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• DCPMPXBYPZGNDC-UHFFFAOYSA-N hydron;methanediimine;chloride Chemical compound Cl.N=C=N DCPMPXBYPZGNDC-UHFFFAOYSA-N 0.000 description 1
• 150000003949 imides Chemical class 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 238000002329 infrared spectrum Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 238000005342 ion exchange Methods 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• JNODQFNWMXFMEV-UHFFFAOYSA-N latrepirdine Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1 JNODQFNWMXFMEV-UHFFFAOYSA-N 0.000 description 1
• 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• KNFPLMFTXFVFPA-UHFFFAOYSA-N lithium;bis(2-methylpropyl)azanide Chemical compound CC(C)CN([Li])CC(C)C KNFPLMFTXFVFPA-UHFFFAOYSA-N 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 125000000628 margaroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
• DFBUWLMRJBPCTJ-UHFFFAOYSA-N methyl 1-methyl-5-(4-octoxyphenyl)pyrazole-3-carboxylate Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC(C(=O)OC)=NN1C DFBUWLMRJBPCTJ-UHFFFAOYSA-N 0.000 description 1
• OQNUTBBRDVILAY-UHFFFAOYSA-N methyl 2-nonyl-3h-benzimidazole-5-carboxylate Chemical compound C1=C(C(=O)OC)C=C2NC(CCCCCCCCC)=NC2=C1 OQNUTBBRDVILAY-UHFFFAOYSA-N 0.000 description 1
• VURTXDMCDUXUKM-UHFFFAOYSA-N methyl 3,4-dipentoxybenzoate Chemical compound CCCCCOC1=CC=C(C(=O)OC)C=C1OCCCCC VURTXDMCDUXUKM-UHFFFAOYSA-N 0.000 description 1
• JZUXUPZONYEBIP-UHFFFAOYSA-N methyl 3-(6-heptoxynaphthalen-2-yl)propanoate Chemical compound C1=C(CCC(=O)OC)C=CC2=CC(OCCCCCCC)=CC=C21 JZUXUPZONYEBIP-UHFFFAOYSA-N 0.000 description 1
• DXHQGPCTERBXME-UHFFFAOYSA-N methyl 3-[4-(4-heptylphenyl)phenyl]prop-2-enoate Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(C=CC(=O)OC)C=C1 DXHQGPCTERBXME-UHFFFAOYSA-N 0.000 description 1
• KSQITGOTJMYVHT-UHFFFAOYSA-N methyl 3-[4-(4-heptylphenyl)phenyl]propanoate Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(CCC(=O)OC)C=C1 KSQITGOTJMYVHT-UHFFFAOYSA-N 0.000 description 1
• PKWJLGJNZNVUBD-UHFFFAOYSA-N methyl 3-[4-(4-pentoxyphenyl)phenyl]propanoate Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(CCC(=O)OC)C=C1 PKWJLGJNZNVUBD-UHFFFAOYSA-N 0.000 description 1
• UIEPULRPIPFXGJ-UHFFFAOYSA-N methyl 3-[4-(4-pentylphenyl)phenyl]propanoate Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(CCC(=O)OC)C=C1 UIEPULRPIPFXGJ-UHFFFAOYSA-N 0.000 description 1
• SSKROZKPITVKMK-UHFFFAOYSA-N methyl 4-(1-heptylpyrazol-4-yl)benzoate Chemical compound C1=NN(CCCCCCC)C=C1C1=CC=C(C(=O)OC)C=C1 SSKROZKPITVKMK-UHFFFAOYSA-N 0.000 description 1
• OSEDFBIVKALVNN-UHFFFAOYSA-N methyl 4-(c-chloro-n-hydroxycarbonimidoyl)benzoate Chemical compound COC(=O)C1=CC=C(C(Cl)=NO)C=C1 OSEDFBIVKALVNN-UHFFFAOYSA-N 0.000 description 1
• HGVBEQHEDXPHBI-UHFFFAOYSA-N methyl 4-(hydrazinecarbonyl)benzoate Chemical compound COC(=O)C1=CC=C(C(=O)NN)C=C1 HGVBEQHEDXPHBI-UHFFFAOYSA-N 0.000 description 1
• RJZGFGGJJGEFFT-UHFFFAOYSA-N methyl 4-[2-(4-hexoxyphenyl)pyrimidin-4-yl]benzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC=CC(C=2C=CC(=CC=2)C(=O)OC)=N1 RJZGFGGJJGEFFT-UHFFFAOYSA-N 0.000 description 1
• DDWVXFQATJTOFS-UHFFFAOYSA-N methyl 4-[3-(4-hexoxyphenyl)-3-oxopropanoyl]benzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)CC(=O)C1=CC=C(C(=O)OC)C=C1 DDWVXFQATJTOFS-UHFFFAOYSA-N 0.000 description 1
• GMNUNXQGSOGPAT-UHFFFAOYSA-N methyl 4-[3-(4-pentoxyphenyl)-1,2-oxazol-5-yl]benzoate Chemical compound C1=CC(OCCCCC)=CC=C1C1=NOC(C=2C=CC(=CC=2)C(=O)OC)=C1 GMNUNXQGSOGPAT-UHFFFAOYSA-N 0.000 description 1
• ZOBQOLMFGUPNTI-UHFFFAOYSA-N methyl 4-[4-(8-bromooctoxy)phenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OCCCCCCCCBr)C=C1 ZOBQOLMFGUPNTI-UHFFFAOYSA-N 0.000 description 1
• FUOKUWFZMCWRSJ-UHFFFAOYSA-N methyl 4-[4-(8-hydroxyoctoxy)phenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OCCCCCCCCO)C=C1 FUOKUWFZMCWRSJ-UHFFFAOYSA-N 0.000 description 1
• CIXYXCKHJMKPKG-UHFFFAOYSA-N methyl 4-[4-(8-oxo-8-piperidin-1-yloctoxy)phenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(C=C1)=CC=C1OCCCCCCCC(=O)N1CCCCC1 CIXYXCKHJMKPKG-UHFFFAOYSA-N 0.000 description 1
• DTJVUYGCIUXMOY-UHFFFAOYSA-N methyl 4-[5-(4-cyclohexylphenyl)-1,3,4-thiadiazol-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C2CCCCC2)S1 DTJVUYGCIUXMOY-UHFFFAOYSA-N 0.000 description 1
• WKFFUASNNKROGV-UHFFFAOYSA-N methyl 4-[[(4-cyclohexylbenzoyl)amino]carbamoyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)NNC(=O)C1=CC=C(C2CCCCC2)C=C1 WKFFUASNNKROGV-UHFFFAOYSA-N 0.000 description 1
• YQYAPGKIASWFPE-UHFFFAOYSA-N methyl 4-[[(4-pentoxybenzoyl)amino]carbamoyl]benzoate Chemical compound C1=CC(OCCCCC)=CC=C1C(=O)NNC(=O)C1=CC=C(C(=O)OC)C=C1 YQYAPGKIASWFPE-UHFFFAOYSA-N 0.000 description 1
• AGQJCMQLKCDQEL-UHFFFAOYSA-N methyl 4-[[(4-piperidin-1-ylbenzoyl)amino]carbamoyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)NNC(=O)C1=CC=C(N2CCCCC2)C=C1 AGQJCMQLKCDQEL-UHFFFAOYSA-N 0.000 description 1
• IKBJLIDFRQEDNL-UHFFFAOYSA-N methyl 4-[[[4-(4-propoxyphenyl)benzoyl]amino]carbamoyl]benzoate Chemical compound C1=CC(OCCC)=CC=C1C1=CC=C(C(=O)NNC(=O)C=2C=CC(=CC=2)C(=O)OC)C=C1 IKBJLIDFRQEDNL-UHFFFAOYSA-N 0.000 description 1
• INYNLXVGLZOULC-UHFFFAOYSA-N methyl 4-[[[4-(8-methoxyoctoxy)benzoyl]amino]carbamoyl]benzoate Chemical compound C1=CC(OCCCCCCCCOC)=CC=C1C(=O)NNC(=O)C1=CC=C(C(=O)OC)C=C1 INYNLXVGLZOULC-UHFFFAOYSA-N 0.000 description 1
• IVYQLXCACCEQHM-UHFFFAOYSA-N methyl 4-hexoxybenzoate Chemical compound CCCCCCOC1=CC=C(C(=O)OC)C=C1 IVYQLXCACCEQHM-UHFFFAOYSA-N 0.000 description 1
• MPUYLLIQJZUWBZ-UHFFFAOYSA-N methyl 6-(8-bromooctoxy)naphthalene-2-carboxylate Chemical compound C1=C(OCCCCCCCCBr)C=CC2=CC(C(=O)OC)=CC=C21 MPUYLLIQJZUWBZ-UHFFFAOYSA-N 0.000 description 1
• WPRSDVPSRCCIEQ-UHFFFAOYSA-N methyl 6-(8-methoxyoctoxy)naphthalene-2-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(OCCCCCCCCOC)=CC=C21 WPRSDVPSRCCIEQ-UHFFFAOYSA-N 0.000 description 1
• PZDVVVLVCQRQSV-UHFFFAOYSA-N methyl 6-[4-[4-(8-bromooctoxy)phenyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1N1CCN(C=2C=CC(OCCCCCCCCBr)=CC=2)CC1 PZDVVVLVCQRQSV-UHFFFAOYSA-N 0.000 description 1
• OMKOCPWIXVQHHX-UHFFFAOYSA-N methyl 6-hept-1-ynylnaphthalene-2-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C#CCCCCC)=CC=C21 OMKOCPWIXVQHHX-UHFFFAOYSA-N 0.000 description 1
• MKSIUKCSAHIELM-UHFFFAOYSA-N methyl 6-heptylnaphthalene-2-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(CCCCCCC)=CC=C21 MKSIUKCSAHIELM-UHFFFAOYSA-N 0.000 description 1
• HYWOJVCLXAQCPV-UHFFFAOYSA-N methyl 6-hexylnaphthalene-2-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(CCCCCC)=CC=C21 HYWOJVCLXAQCPV-UHFFFAOYSA-N 0.000 description 1
• PXKNNGRTOQEZFY-UHFFFAOYSA-N methyl 7-octoxy-2-oxochromene-3-carboxylate Chemical compound C1=C(C(=O)OC)C(=O)OC2=CC(OCCCCCCCC)=CC=C21 PXKNNGRTOQEZFY-UHFFFAOYSA-N 0.000 description 1
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
• XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
• 244000005700 microbiome Species 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• XPIHNCHVIZFNFJ-UHFFFAOYSA-N n'-hydroxy-4-octoxybenzenecarboximidamide Chemical compound CCCCCCCCOC1=CC=C(C(=N)NO)C=C1 XPIHNCHVIZFNFJ-UHFFFAOYSA-N 0.000 description 1
• UHAAFJWANJYDIS-UHFFFAOYSA-N n,n'-diethylmethanediimine Chemical compound CCN=C=NCC UHAAFJWANJYDIS-UHFFFAOYSA-N 0.000 description 1
• VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
• NJGRNRAXMBFJJY-UHFFFAOYSA-N n-(2-azaniumylethyl)carbamodithioate Chemical compound NCCNC(S)=S NJGRNRAXMBFJJY-UHFFFAOYSA-N 0.000 description 1
• FTNFEHXDETWERN-UHFFFAOYSA-N n-[bis(aziridin-1-yl)phosphoryl]-2,6-dimethyl-5-[(4-propan-2-yloxyphenyl)methyl]pyrimidin-4-amine Chemical compound C1=CC(OC(C)C)=CC=C1CC1=C(C)N=C(C)N=C1NP(=O)(N1CC1)N1CC1 FTNFEHXDETWERN-UHFFFAOYSA-N 0.000 description 1
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