CAS: 20267-87-2; Rel-(5Br,6R,12Bs)-13-Methyl-5B,6,7,12B,13,14-Hexahydro-[1,3]Dioxolo[4',5':4,5]Benzo[1,2-C][1,3]Dioxolo[4,5-I]Phenanthridin-6-Ol
- 英文名称Rel-(5Br,6R,12Bs)-13-Methyl-5B,6,7,12B,13,14-Hexahydro-[1,3]Dioxolo[4',5':4,5]Benzo[1,2-C][1,3]Dioxolo[4,5-I]Phenanthridin-6-Ol
- 中文名称白屈菜碱
- IUPAC名称(5bR,6S,12bS)-13-methyl-5b,6,7,12b,13,14-hexahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol
- 其它别名Chelidonine Monohydrate*; (+/-)-Chelidonine; [1,3]Benzodioxolo[5,6-C]-1,3-Dioxolo[4,5-I]Phenanthridin-6-Ol, 5B,6,7,12B,13,14-Hexahydro-13-Methyl-, (5Br,6S,12Bs)-Rel-; Chelidonine Monohydrate* Usp/ep/bp
- CAS编号20267-87-2
- MFCD编号:MFCD00150892
- EINECS号:243-662-8
- FDA UNII编号:4UDG3LY0GT
- 分子式:C20H19NO5分子量:353.37
- 产品CID: 1028966
- 产品分类原料药 → 解热镇痛药 → 镇痛药
物理性质
MSDS等安全信息
- 警示词Warning
- 危险描述H302 (90.5%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (90.5%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H332 (90.5%): Harmful if inhaled [Warning Acute toxicity, inhalation] - 防范说明P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501
- 安全声明Chelidonine is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen. Chelidonine has an acetylcholinesterase and butyrylcholinesterase inhibitory activity. (Wikipedia) Generally, some of the alkaloid extract from Chelidonium majus, which contains protoberberine and benzo[c]phenanthridine alkaloids such as chelidonine, intercalate DNA, and in consequence inhibit DNA and RNA polymerase, topoisomerase, telomerase, and even ribosomal protein biosynthesis or bind to tubulin/microtubules, thus acting as spindle poisons. Chelidonine has the ability to overcome multidrug resistance (MDR) of different cancer cell lines through interaction with ABC-transporters, CYP3A4 and GST, by induction of apoptosis, and cytotoxic effects. It induced apoptosis in MDR cells which was accompanied by an activation of caspase-3, -8,-6/9, and phosphatidyl serine (PS) exposure. (A15442) Chelidonine is known to cause mitotic arrest and to interact weakly with tubulin. Chelidonine has proven to be a weak inhibitor of cell growth in two normal (monkey kidney and Hs27), two transformed (Vero and Graham 293) and two malignant (WHCO5 and HeLa) cell lines. (A15443)
上下游产品
(+/-)-norchelidonine phenanthridinecis-N-methyl-1,2-(methylenedioxy)-5,11-dioxo-7,8-(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzophenanthridine *,10bS*)-5-benzyloxycarbonyl-2,3,7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzophenanthridin-11-one(4bR*,10bS*)-5-benzyloxycarbonyl-2,3,7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzophenanthridin-11-one *,10bS*,11R*)-5-benzyloxycarbonyl-2,3,7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzophenanthridin-11-ol(4bR*,10bS*,11R*)-5-benzyloxycarbonyl-2,3,7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzophenanthridin-11-ol合成工艺路线路线简述
📜2-(Ethoxycarbonyl)-3,4-(Methylenedioxy)Benzyl Cyanide置于氢氧化钾,Lithium Aluminium Tetrahydride,氯化亚砜,三乙胺,乙酰氯,三氟乙酸体系中,用 四氢呋喃,乙醚,水 用作溶剂,化学反应 29.33H,反应生成白屈菜碱
参考文献:总的化学合成的鹅油蛋白
标题:总的化学合成的鹅油蛋白
摘要:高纯邻苯二甲酸酐3与席夫碱4的缩合被用作苯并菲啶生物碱(+/-)-蛇毒碱(8)的全合成中的关键步骤.
Doi:10.1016/0040-4039(80)80196-1
海关参考信息
- 2902600000-乙苯
2902700000-异丙基苯
2905122000-异丙醇
2907210001-间苯二酚 - 💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
- 详情请参考：📖 海关编码查询和海关进出口税则
专利信息
专利号:US-2008287407-A1
优先权日:2003-12-10
标题 :Nitric Oxide Releasing Pyruvate Compounds, Compositions and Methods of Use
发明人：GARVEY DAVID S; FANG XINQIN; KHANAPURE SUBHASH P; RANATUNGA RAMANI R; WEY SHIOW-JYI
权利人:NITROMED INC
摘要:The invention describes novel nitrosated and/or nitrosylated pyruvate compounds and pharmaceutically acceptable salts thereof, and novel compositions comprising at least one nitrosated and/or nitrosylated pyruvate compound, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or at least one therapeutic agent. The invention also provides novel compositions comprising at least one pyruvate compound and at least one compound that donates, transfers or releases nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor, stimulates endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase and/or at least one therapeutic agent. The invention also provides novel kits comprising at least one pyruvate compound, that is optionally nitrosated and/or nitrosylated, and, optionally, at least one nitric oxide donor and/or at least one therapeutic agent. The invention also provides methods for treating diseases resulting from oxidative stress, diabetes, reperfusion injury following ischemia, preservation of tissues, organs, organ parts and/or limbs.
专利号:US-12180228-B2
优先权日:2019-06-05
标题:Compounds, conjugates, and compositions of epipolythiodiketopiperazines and polythiodiketopiperazines and uses thereof
发明人：MOVASSAGHI MOHAMMAD; OLSSON CHASE ROBERT; SCOTT TONY Z; CHEAH JAIME; PAYETTE JOSHUA NATHANIEL
权利人:MASSACHUSETTS INST TECHNOLOGY
摘要:The present disclosure provides, e.g., compounds, compositions, kits, methods of synthesis, and methods of use, involving epipolythiodiketopiperazines and polythiodiketopiperazines.
专利号:US-2021329919-A9
优先权日:2019-07-01
标 题:Synthesis and anti-cancer activity of communesin alkaloids
发明人：MOVASSAGHI MOHAMMAD; POMPEO MATTHEW M; CHEAH JAIME
权利人:MASSACHUSETTS INST TECHNOLOGY
摘要:Described herein are compounds of Formula (I):and salts, tautomers, and stereoisomers thereof. Methods of making the compounds, salts, tautomers, and stereoisomers are also described. Further described herein are composition, kits, methods, and uses involving the compounds, salts, tautomers, and stereoisomers. The methods include methods of treating and preventing diseases (e.g., cancers) in subjects (e.g., humans).
专利号:WO-2013001352-A3
优先权日:2011-06-30
标 题:Synthesis of cleistanthin a an derivatives thereof
专利号:WO-2013001352-A2
优先权日:2011-06-30
标 题 :Synthesis of cleistanthin a an derivatives thereof
专利号:EP-2726458-A2
优先权日:2011-06-30
标 题:Synthesis of cleistanthin a an derivatives thereof
供应商参考报价(招募中)
品牌试剂参考报价(招募中)
📌 第三方产品分析报告
合成参考文献
摘要:Herba Polonica., 25(209), 1979
摘要:W. Debska. Nature 182, 666 (1958).
摘要:S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198
摘要:Kuznetsova LP, Nikol'skaia EB, Sochilina EE, Faddeeva MD. [Inhibition by various alkaloids of acetylcholinesterase and butyrylcholinesterase from human blood]. Zh Evol Biokhim Fiziol. 2002 Jan;38(1):28–31.
参考文献:10.1038/182666a0
摘要:DEBSKA W. Separation and determination of the dissociation constants of chelidonine and protopine by paper chromatography. Nature. 1958 Sep 06;182(4636):666–7. doi: 10.1038/182666a0.
📝 需求与反馈
尽可能描述清楚需求与问题信息
