DE2642840A1 - Substituierte 2-nitro-3-phenylbenzofuranverbindungen - Google Patents
Substituierte 2-nitro-3-phenylbenzofuranverbindungenInfo
- Publication number
- DE2642840A1 DE2642840A1 DE19762642840 DE2642840A DE2642840A1 DE 2642840 A1 DE2642840 A1 DE 2642840A1 DE 19762642840 DE19762642840 DE 19762642840 DE 2642840 A DE2642840 A DE 2642840A DE 2642840 A1 DE2642840 A1 DE 2642840A1
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- acid
- phenyl
- mixture
- group
- Prior art date
- 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.)
- Pending
Links
- AROVMVPUPBWOAS-UHFFFAOYSA-N 2-nitro-3-phenyl-1-benzofuran Chemical class [O-][N+](=O)C=1OC2=CC=CC=C2C=1C1=CC=CC=C1 AROVMVPUPBWOAS-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 50
- -1 nitro, phenyl Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 34
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 21
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 10
- 244000005700 microbiome Species 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 241000894006 Bacteria Species 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052740 iodine Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- 150000001266 acyl halides Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- KHZXISCMFGRTFU-UHFFFAOYSA-N 2-nitro-3-phenyl-3h-1-benzofuran-2-carbaldehyde Chemical compound [O-][N+](=O)C1(C=O)OC2=CC=CC=C2C1C1=CC=CC=C1 KHZXISCMFGRTFU-UHFFFAOYSA-N 0.000 claims description 2
- UXOCJHANNJEISD-UHFFFAOYSA-N 3-(2-nitro-3-phenyl-3h-1-benzofuran-2-yl)prop-2-enoic acid Chemical compound OC(=O)C=CC1([N+]([O-])=O)OC2=CC=CC=C2C1C1=CC=CC=C1 UXOCJHANNJEISD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 241000224526 Trichomonas Species 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 82
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 75
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 74
- 239000000203 mixture Substances 0.000 description 68
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 53
- 239000002253 acid Substances 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 27
- 239000007787 solid Substances 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 235000011054 acetic acid Nutrition 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 24
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 17
- 238000010992 reflux Methods 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 13
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
- 230000000845 anti-microbial effect Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 235000010288 sodium nitrite Nutrition 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 238000006396 nitration reaction Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000031709 bromination Effects 0.000 description 6
- 238000005893 bromination reaction Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 229920000137 polyphosphoric acid Polymers 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- JAFHKQUFCVEPEY-UHFFFAOYSA-N 2-(2-nitro-3-phenyl-3h-cyclopenta[b]pyran-2-yl)acetic acid Chemical compound OC(=O)CC1([N+]([O-])=O)OC2=CC=CC2=CC1C1=CC=CC=C1 JAFHKQUFCVEPEY-UHFFFAOYSA-N 0.000 description 4
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- MJBZHKDQFMFYEI-UHFFFAOYSA-N 2-(2-bromo-3-phenyl-3h-cyclopenta[b]pyran-2-yl)acetic acid Chemical compound OC(=O)CC1(Br)OC2=CC=CC2=CC1C1=CC=CC=C1 MJBZHKDQFMFYEI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 150000008062 acetophenones Chemical class 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- VGSDHJAXIRBARN-UHFFFAOYSA-N 2-(2,7-dibromo-3-phenyl-1-benzofuran-5-yl)acetonitrile Chemical compound BrC=1OC2=C(Br)C=C(CC#N)C=C2C=1C1=CC=CC=C1 VGSDHJAXIRBARN-UHFFFAOYSA-N 0.000 description 2
- RFBIATJJCXJSTO-UHFFFAOYSA-N 2-(2-iodo-3-phenyl-3h-cyclopenta[b]pyran-2-yl)acetic acid Chemical compound OC(=O)CC1(I)OC2=CC=CC2=CC1C1=CC=CC=C1 RFBIATJJCXJSTO-UHFFFAOYSA-N 0.000 description 2
- SWORVQXZNIJIOP-UHFFFAOYSA-N 2-(2-nitro-3-phenyl-1-benzofuran-5-yl)acetic acid Chemical compound C12=CC(CC(=O)O)=CC=C2OC([N+]([O-])=O)=C1C1=CC=CC=C1 SWORVQXZNIJIOP-UHFFFAOYSA-N 0.000 description 2
- MKAQQWGYTYNWBT-UHFFFAOYSA-N 2-(3-phenylcyclopenta[b]pyran-2-yl)acetic acid Chemical compound OC(=O)CC=1OC2=CC=CC2=CC=1C1=CC=CC=C1 MKAQQWGYTYNWBT-UHFFFAOYSA-N 0.000 description 2
- IFLCHKZVHQMOTC-UHFFFAOYSA-N 2-[2-bromo-3-(2-fluorophenyl)-4-methoxy-1-benzofuran-7-yl]acetonitrile Chemical compound C1=2C(OC)=CC=C(CC#N)C=2OC(Br)=C1C1=CC=CC=C1F IFLCHKZVHQMOTC-UHFFFAOYSA-N 0.000 description 2
- BILXPNSGLNPLLM-UHFFFAOYSA-N 2-[3-(4-cyanophenyl)cyclopenta[c]pyran-1-yl]acetic acid Chemical compound C=1C2=CC=CC2=C(CC(=O)O)OC=1C1=CC=C(C#N)C=C1 BILXPNSGLNPLLM-UHFFFAOYSA-N 0.000 description 2
- SUNQAAGGQUMIFW-UHFFFAOYSA-N 2-[3-(4-phenylphenyl)cyclopenta[c]pyran-1-yl]acetic acid Chemical compound C=1C2=CC=CC2=C(CC(=O)O)OC=1C(C=C1)=CC=C1C1=CC=CC=C1 SUNQAAGGQUMIFW-UHFFFAOYSA-N 0.000 description 2
- HNZRVKGAUIDWRC-UHFFFAOYSA-N 2-bromo-4-methyl-3-phenyl-1-benzofuran Chemical compound C1=2C(C)=CC=CC=2OC(Br)=C1C1=CC=CC=C1 HNZRVKGAUIDWRC-UHFFFAOYSA-N 0.000 description 2
- SORAXUUZQGMHDC-UHFFFAOYSA-N 2-bromo-5-(bromomethyl)-3-phenyl-1-benzofuran Chemical compound C12=CC(CBr)=CC=C2OC(Br)=C1C1=CC=CC=C1 SORAXUUZQGMHDC-UHFFFAOYSA-N 0.000 description 2
- CCCGLIZAQCPMBD-UHFFFAOYSA-N 2-bromo-6-methyl-3-phenyl-1-benzofuran Chemical compound BrC=1OC2=CC(C)=CC=C2C=1C1=CC=CC=C1 CCCGLIZAQCPMBD-UHFFFAOYSA-N 0.000 description 2
- NBVNLJCSDNSGEY-UHFFFAOYSA-N 2-cyclopenta[c]pyran-1-ylacetic acid Chemical compound O1C=CC2=CC=CC2=C1CC(=O)O NBVNLJCSDNSGEY-UHFFFAOYSA-N 0.000 description 2
- SBRNQLHGSVPRLM-UHFFFAOYSA-N 2-nitro-3-phenyl-1-benzofuran-7-carbaldehyde Chemical compound [O-][N+](=O)C=1OC2=C(C=O)C=CC=C2C=1C1=CC=CC=C1 SBRNQLHGSVPRLM-UHFFFAOYSA-N 0.000 description 2
- SVXXDGOWGXUSLS-UHFFFAOYSA-N 3-(2-fluorophenyl)-4-methoxy-7-methyl-1-benzofuran Chemical compound C1=2C(OC)=CC=C(C)C=2OC=C1C1=CC=CC=C1F SVXXDGOWGXUSLS-UHFFFAOYSA-N 0.000 description 2
- WGVCJKNNOCSSTL-UHFFFAOYSA-N 3-phenyl-1-benzofuran-2-carbonitrile Chemical compound N#CC=1OC2=CC=CC=C2C=1C1=CC=CC=C1 WGVCJKNNOCSSTL-UHFFFAOYSA-N 0.000 description 2
- UBIJPTXXMGZTMG-UHFFFAOYSA-N 3-phenyl-1-benzofuran-7-carbonitrile Chemical compound C=1OC=2C(C#N)=CC=CC=2C=1C1=CC=CC=C1 UBIJPTXXMGZTMG-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- KKQTWMBJGFRJON-UHFFFAOYSA-N 5,7-dimethyl-3-phenyl-1-benzofuran Chemical compound C12=CC(C)=CC(C)=C2OC=C1C1=CC=CC=C1 KKQTWMBJGFRJON-UHFFFAOYSA-N 0.000 description 2
- SKINUFDEOOLFMT-UHFFFAOYSA-N 5-(bromomethyl)-2-nitro-3-phenyl-1-benzofuran Chemical compound [O-][N+](=O)C=1OC2=CC=C(CBr)C=C2C=1C1=CC=CC=C1 SKINUFDEOOLFMT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- VUSWCWPCANWBFG-UHFFFAOYSA-N cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC=CC1 VUSWCWPCANWBFG-UHFFFAOYSA-N 0.000 description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
- HYUPPKVFCGIMDB-UHFFFAOYSA-N ethyl 2-(4-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C=C1 HYUPPKVFCGIMDB-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000026045 iodination Effects 0.000 description 2
- 238000006192 iodination reaction Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
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- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61627775A | 1975-09-24 | 1975-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2642840A1 true DE2642840A1 (de) | 1977-04-07 |
Family
ID=24468746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762642840 Pending DE2642840A1 (de) | 1975-09-24 | 1976-09-23 | Substituierte 2-nitro-3-phenylbenzofuranverbindungen |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5239666A (enExample) |
| AR (1) | AR215598A1 (enExample) |
| AU (1) | AU1804276A (enExample) |
| BE (1) | BE846502A (enExample) |
| CS (1) | CS191319B2 (enExample) |
| DD (1) | DD130786A5 (enExample) |
| DE (1) | DE2642840A1 (enExample) |
| DK (1) | DK413676A (enExample) |
| EG (1) | EG12427A (enExample) |
| ES (1) | ES451542A1 (enExample) |
| FI (1) | FI762715A7 (enExample) |
| FR (1) | FR2325369A1 (enExample) |
| IL (1) | IL50543A0 (enExample) |
| IT (1) | IT1070556B (enExample) |
| NL (1) | NL7610166A (enExample) |
| NO (1) | NO763144L (enExample) |
| OA (1) | OA05441A (enExample) |
| PT (1) | PT65632B (enExample) |
| SE (1) | SE7610149L (enExample) |
| SU (1) | SU692561A3 (enExample) |
| ZA (1) | ZA765079B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128659A (en) | 1977-12-19 | 1978-12-05 | Riker Laboratories, Inc. | Antimicrobial polycyclic nitrofurans |
| US4153721A (en) | 1977-12-19 | 1979-05-08 | Riker Laboratories, Inc. | Derivatives of 2-nitrobenzofuran |
| US4143152A (en) | 1977-12-19 | 1979-03-06 | Riker Laboratories, Inc. | Anti-microbial (2-nitro-3-phenyl benzofuranyl)-phenylalkanoic acids and derivatives |
| US4174403A (en) | 1978-06-26 | 1979-11-13 | Riker Laboratories, Inc. | 5,6-Methylenedioxy-2-nitro-3-phenylbenzofurans |
| US4154847A (en) | 1978-06-26 | 1979-05-15 | Riker Laboratories, Inc. | Derivatives of 2-nitro-3-phenylbenzofurancarboxaldehydes |
| EP4031128A4 (en) | 2019-09-16 | 2023-12-13 | Koda Therapeutics, LLC | Antimicrobial agents and compositions and uses thereof |
-
1976
- 1976-08-24 ZA ZA765079A patent/ZA765079B/xx unknown
- 1976-09-14 NO NO763144A patent/NO763144L/no unknown
- 1976-09-14 SE SE7610149A patent/SE7610149L/xx unknown
- 1976-09-14 NL NL7610166A patent/NL7610166A/xx not_active Application Discontinuation
- 1976-09-14 DK DK413676A patent/DK413676A/da unknown
- 1976-09-15 ES ES451542A patent/ES451542A1/es not_active Expired
- 1976-09-23 AR AR264829A patent/AR215598A1/es active
- 1976-09-23 IL IL50543A patent/IL50543A0/xx unknown
- 1976-09-23 OA OA55942A patent/OA05441A/xx unknown
- 1976-09-23 DE DE19762642840 patent/DE2642840A1/de active Pending
- 1976-09-23 BE BE170876A patent/BE846502A/xx unknown
- 1976-09-23 DD DD7600194956A patent/DD130786A5/xx unknown
- 1976-09-23 IT IT27552/76A patent/IT1070556B/it active
- 1976-09-23 AU AU18042/76A patent/AU1804276A/en not_active Expired
- 1976-09-23 FI FI762715A patent/FI762715A7/fi not_active Application Discontinuation
- 1976-09-23 FR FR7628662A patent/FR2325369A1/fr active Granted
- 1976-09-23 SU SU762405875A patent/SU692561A3/ru active
- 1976-09-23 CS CS766174A patent/CS191319B2/cs unknown
- 1976-09-23 PT PT65632A patent/PT65632B/pt unknown
- 1976-09-24 JP JP51114551A patent/JPS5239666A/ja active Pending
- 1976-09-28 EG EG592/76A patent/EG12427A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| DD130786A5 (de) | 1978-05-03 |
| CS191319B2 (en) | 1979-06-29 |
| PT65632A (en) | 1976-10-01 |
| PT65632B (en) | 1978-04-05 |
| JPS5239666A (en) | 1977-03-28 |
| AR215598A1 (es) | 1979-10-31 |
| NO763144L (no) | 1977-03-25 |
| BE846502A (fr) | 1977-03-23 |
| SU692561A3 (ru) | 1979-10-15 |
| NL7610166A (nl) | 1977-03-28 |
| SE7610149L (sv) | 1977-03-25 |
| AU1804276A (en) | 1978-04-06 |
| ZA765079B (en) | 1977-08-31 |
| FR2325369B1 (enExample) | 1979-02-23 |
| ES451542A1 (es) | 1977-10-01 |
| IL50543A0 (en) | 1976-11-30 |
| EG12427A (en) | 1979-03-31 |
| IT1070556B (it) | 1985-03-29 |
| OA05441A (fr) | 1981-03-31 |
| DK413676A (da) | 1977-03-25 |
| FR2325369A1 (fr) | 1977-04-22 |
| FI762715A7 (enExample) | 1977-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |