DE2342709A1 - Neue berberinderivate - Google Patents
Neue berberinderivateInfo
- Publication number
- DE2342709A1 DE2342709A1 DE19732342709 DE2342709A DE2342709A1 DE 2342709 A1 DE2342709 A1 DE 2342709A1 DE 19732342709 DE19732342709 DE 19732342709 DE 2342709 A DE2342709 A DE 2342709A DE 2342709 A1 DE2342709 A1 DE 2342709A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- chloride ion
- rco
- radical
- chloride
- 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
- YBHILYKTIRIUTE-UHFFFAOYSA-N berberine Chemical class C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 YBHILYKTIRIUTE-UHFFFAOYSA-N 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
- -1 cinnamoyl group Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000010979 ruby Substances 0.000 claims description 8
- 229910001750 ruby Inorganic materials 0.000 claims description 8
- 150000003832 berberine derivatives Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 235000013985 cinnamic acid Nutrition 0.000 claims description 4
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229930016911 cinnamic acid Natural products 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VKJGBAJNNALVAV-UHFFFAOYSA-M Berberine chloride (TN) Chemical compound [Cl-].C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 VKJGBAJNNALVAV-UHFFFAOYSA-M 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 206010039491 Sarcoma Diseases 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- QFQYZMGOKIROEC-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=C2OCOC2=C1 QFQYZMGOKIROEC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IHKNVZISLLDMOR-UHFFFAOYSA-N O-Acetylferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1OC(C)=O IHKNVZISLLDMOR-UHFFFAOYSA-N 0.000 description 2
- IHKNVZISLLDMOR-GQCTYLIASA-N O-acetylferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1OC(C)=O IHKNVZISLLDMOR-GQCTYLIASA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- KPCPQHBDENMEIR-WEVVVXLNSA-N (2E)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-oxobutanoyl chloride Chemical compound COC1=CC(\C=C(/C(C)=O)C(Cl)=O)=CC=C1O KPCPQHBDENMEIR-WEVVVXLNSA-N 0.000 description 1
- HGDZRSNJGRIAKS-GQCTYLIASA-N (e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl chloride Chemical compound COC1=CC=C(\C=C\C(Cl)=O)C=C1OC HGDZRSNJGRIAKS-GQCTYLIASA-N 0.000 description 1
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- WBJQTHIVYWAEDD-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)prop-2-enoyl chloride Chemical compound ClC(=O)C=CC1=CC=C2OCOC2=C1 WBJQTHIVYWAEDD-UHFFFAOYSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- LFYJSSARVMHQJB-QIXNEVBVSA-N bakuchiol Chemical compound CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1 LFYJSSARVMHQJB-QIXNEVBVSA-N 0.000 description 1
- 229940093265 berberine Drugs 0.000 description 1
- QISXPYZVZJBNDM-UHFFFAOYSA-N berberine Natural products COc1ccc2C=C3N(Cc2c1OC)C=Cc4cc5OCOc5cc34 QISXPYZVZJBNDM-UHFFFAOYSA-N 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000004303 peritoneum Anatomy 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- OLTVTFUBQOLTND-UHFFFAOYSA-N tris(2-methoxyethoxy)-methylsilane Chemical compound COCCO[Si](C)(OCCOC)OCCOC OLTVTFUBQOLTND-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47085651A JPS4942700A (enExample) | 1972-08-25 | 1972-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2342709A1 true DE2342709A1 (de) | 1974-03-14 |
Family
ID=13864717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732342709 Pending DE2342709A1 (de) | 1972-08-25 | 1973-08-23 | Neue berberinderivate |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3884911A (enExample) |
| JP (1) | JPS4942700A (enExample) |
| CH (1) | CH595384A5 (enExample) |
| DE (1) | DE2342709A1 (enExample) |
| FR (1) | FR2197008B1 (enExample) |
| GB (1) | GB1393521A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000037468A1 (en) * | 1998-12-21 | 2000-06-29 | Hanwha Chemical Corporation | DIBENZO[a,g]QUINOLIZINIUM DERIVATIVES AND THE SALTS THEREOF |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4033966A (en) * | 1975-06-24 | 1977-07-05 | Kanebo, Ltd. | Novel berbine derivatives |
| US4749708A (en) * | 1982-05-14 | 1988-06-07 | Maroko Peter R | Composition for improving circulatory performance |
| US4980344A (en) * | 1982-05-14 | 1990-12-25 | Maroko Peter R | Compositions for improving circulatory performance |
| IE55519B1 (en) * | 1982-05-14 | 1990-10-10 | Maroko Peter R | Use of a protoberberine alkaloid and composition containing same |
| US5981541A (en) * | 1996-09-23 | 1999-11-09 | Rutgers, The State University Of New Jersey | Substituted heterocycles as anti-tumor agents |
| US6740650B2 (en) | 1999-10-29 | 2004-05-25 | Rutgers, The State University Of New Jersey | Heterocyclic cytotoxic agents |
| KR100383285B1 (ko) * | 2000-06-22 | 2003-05-09 | (주)뉴트리산업 | 항균 및 항진균 활성을 갖는 신규한 베르베루빈 유도체와이의 염 |
| PT1465625E (pt) * | 2001-11-14 | 2010-03-09 | Univ Rutgers | Venenos de topoisomerase solubilizados |
| AU2002365161B2 (en) * | 2001-11-14 | 2008-07-03 | Rutgers, The State University | Solubilized topoisomerase poison agents |
| AU2002364953A1 (en) * | 2001-11-14 | 2003-06-17 | Edmond J. Lavoie | Topoisomerase poison agents |
| EP1453812B1 (en) * | 2001-11-14 | 2008-08-20 | Rutgers, The State University | Cytotoxic agents |
| AU2003268075A1 (en) * | 2002-08-09 | 2004-02-25 | Edmond J. Lavoie | Nitro and amino substituted dibenzonaphthyridines as topoisomerase agents |
| AU2003265406A1 (en) * | 2002-08-09 | 2004-02-25 | Edmond J. Lavoie | Nitro and amino substituted topoisomerase agents |
| US6992088B2 (en) * | 2002-08-09 | 2006-01-31 | Rutgers, The State University Of New Jersey | Nitro and amino substituted heterocycles as topoisomerase I targeting agents |
| AU2003290818A1 (en) * | 2002-11-12 | 2004-06-03 | Edmond J. Lavoie | Topoisomerase-targeting agents |
| EP2403856B1 (en) | 2009-03-06 | 2012-12-19 | Rutgers, The State University of New Jersey | Methylenedioxybenzo [i]phenanthridine derivatives used to treat cancer |
| WO2010127363A1 (en) | 2009-05-01 | 2010-11-04 | Rutgers, The State University Of New Jersey | Toposiomerase inhibitors |
| JP2019515025A (ja) | 2016-04-04 | 2019-06-06 | ラトガース ザ ステイト ユニバーシティー オブ ニュージャージー | トポイソメラーゼ毒 |
| CN107722000A (zh) * | 2017-11-03 | 2018-02-23 | 中国药科大学 | 9位－取代的小檗碱衍生物的制备及其医药用途 |
| CN112062761B (zh) * | 2020-09-25 | 2023-03-21 | 常州大学 | 一种小檗红碱酯类物质的合成方法 |
-
1972
- 1972-08-25 JP JP47085651A patent/JPS4942700A/ja active Pending
-
1973
- 1973-08-22 US US390402A patent/US3884911A/en not_active Expired - Lifetime
- 1973-08-22 GB GB3982073A patent/GB1393521A/en not_active Expired
- 1973-08-22 CH CH1208973A patent/CH595384A5/xx not_active IP Right Cessation
- 1973-08-23 DE DE19732342709 patent/DE2342709A1/de active Pending
- 1973-08-23 FR FR7330528A patent/FR2197008B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000037468A1 (en) * | 1998-12-21 | 2000-06-29 | Hanwha Chemical Corporation | DIBENZO[a,g]QUINOLIZINIUM DERIVATIVES AND THE SALTS THEREOF |
Also Published As
| Publication number | Publication date |
|---|---|
| CH595384A5 (enExample) | 1978-02-15 |
| GB1393521A (en) | 1975-05-07 |
| FR2197008A1 (enExample) | 1974-03-22 |
| FR2197008B1 (enExample) | 1976-05-07 |
| US3884911A (en) | 1975-05-20 |
| JPS4942700A (enExample) | 1974-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |