CAS: 865-21-4; Methyl (3Ar,3A1R,4R,5S,5Ar,10Br)-4-Acetoxy-3A-Ethyl-9-((5S,7R,9S)-5-Ethyl-5-Hydroxy-9-(Methoxycarbonyl)-1,4,5,6,7,8,9,10-Octahydro-2H-3,7-Methano[1]Azacycloundecino[5,4-B]Indol-9-yl)-5-Hydroxy-8-Methoxy-6-Methyl-3A,3A1,4,5,5A,6,11,12-Octahydro-1H-Indolizino[8,1-Cd]Carbazole-5-Carboxylate
该化合物是来自Pearwinkle工厂Catharanthus rosesus 的强力藻类,主要以其在癌症化疗中的应用而著称,特别是治疗各种白血病和淋巴瘤.通过抑制细胞分裂期间微囊形成,有效干扰线条并预防癌症细胞扩散的复合功能.Vinblastaine的特征是其复杂结构,包括一个甲状腺藻质藻质框架.它通常通过静脉注射进行,体内的半衰期相对较短,需要小心下药并监测副作用.常见的不良效应包括恶心,呕吐,发,发泡和乳房压,这可能导致感染的易感性增加.由于它的动作机制,Vinblastaine被归类为一种抑制剂,并经常与其他乳液化剂结合使用,以提高治疗功效.它的使用受到严格管制,并被归类为危险药物,需要在临床环境中适当处理和处置.
- 英文名称Methyl (3Ar,3A1R,4R,5S,5Ar,10Br)-4-Acetoxy-3A-Ethyl-9-((5S,7R,9S)-5-Ethyl-5-Hydroxy-9-(Methoxycarbonyl)-1,4,5,6,7,8,9,10-Octahydro-2H-3,7-Methano[1]Azacycloundecino[5,4-B]Indol-9-yl)-5-Hydroxy-8-Methoxy-6-Methyl-3A,3A1,4,5,5A,6,11,12-Octahydro-1H-Indolizino[8,1-Cd]Carbazole-5-Carboxylate
- 中文名称长春质碱
- IUPAC名称methyl (3aR,3a1R,4R,5S,5aR,10bR)-4-acetoxy-3a-ethyl-9-((5S,7R,9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-1,4,5,6,7,8,9,10-octahydro-2H-3,7-methano[1]azacycloundecino[5,4-b]indol-9-yl)-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate
- 其它别名Vinblastine 94% Bp98; Vinblastine; Vincristine Ep Impurity H; Vinblastine Sulfate(Rg); [3Ar-[3Aa,4B,5B,5Ab,9(3R*,5S*,7R*,9S*),10Br*,13Aa]]-Methyl 4-(Acetyloxy)-3A-Ethyl-9-[5-Ethyl-1,4,5,6,7,8,9,10-Octahydro-5-Hydroxy-9-(Methoxycarbonyl)-2H-3,7-Methanoazacycloundecino[5,4-B]Indol-9-Yl]-3A,4,5,5A,6,11,12,13A-Octahydro-5-Hydroxy-8-Methoxy-6-Methyl-1H-Indolizino[8,1-Cd]Carbazole-5-Carboxylate; 1H-Indolizino[8,1-Cd]Carbazole, Vincaleukoblastine Deriv.; 1H-Indolizino[8,1-Cd]Carbazole-5-Carboxylic Acid, 4-(Acetyloxy)-3A-Ethyl-9-[5-Ethyl-1,4,5,6,7,8,9,10-Octahydro-5-Hydroxy-9-(Methoxycarbonyl)-2H-3,7-Methanoazacycloundecino[5,4-B]Indol-9-Yl]-3A,4,5,5A,6,11,12,13A-Octahydro-5-Hydroxy-8-Methoxy-6-Methyl-, Methyl Ester, [3Ar-[3Aa,4B,5B,5Ab,9(3R*,5S*,7R*,9S*),10Br*,13Aa]]-; 2H-3,7-Methanoazacycloundecino[5,4-B]Indole, Vincaleukoblastine Deriv.
- CAS编号865-21-4
- MFCD编号:MFCD05662370
- EINECS号:212-734-0
- 分子式:C46H58N4O9
- 分子量:810.99
- 产品CID: 1867530
- 同类组份化合物CAS865-21-4 (free base)143-67-9 (sulfate)
- 产品分类分析化学 → 标准品
物理性质
MSDS等安全信息
上下游产品
20-21-anhydrovinblastineΔ20-21-anhydrovinblastinedeacetylvinblastine monohydrazide deactylvinblastine monohydrazide合成工艺路线路线简述
- 129895-95-0 = 865-21-4
反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
标题:Nonoxidative Coupling Methodology For The Synthesis Of The Antitumor Bisindole Alkaloid Vinblastine And A Lower-Half Analog: Solvent Effect On The Stereochemistry Of The Crucial C-15/c-18' Bond
作者:Magnus,Philip; Et Al
参考文献:Journal Of The American Chemical Society 日期:1992 卷标:114(26) 页码:10232-45]
= 865-21-4
反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol; 45 Min,Rt
标题:Synthesis Of (+)-Vinblastine And Its Analogues
作者:Miyazaki,Tohru; Et Al
参考文献:Organic Letters 日期:2007 卷标:9(23) 页码:4737-4740]
548774-92-1 = 865-21-4
反应条件:1.1 Reagents: Sodium Bicarbonate Solvents: Isopropanol,Water; Rt
标题:Stereocontrolled Total Synthesis Of (+)-Vinblastine
作者:Yokoshima,Satoshi; Et Al
参考文献:Pure And Applied Chemistry 日期:2003 卷标:75(1) 页码:29-38]
= 865-21-4
反应条件:1.1 Reagents: 2-Mercaptoethanol,1,8-Diazabicyclo[5.4.0]Undec-7-Ene Solvents: Acetone1.2 Reagents: Sodium Bicarbonate Solvents: Isopropanol,Water
标题:Stereocontrolled Total Synthesis Of (+)-Vinblastine
作者:Yokoshima,Satoshi; Et Al
参考文献:Journal Of The American Chemical Society 日期:2002 卷标:124(10) 页码:2137-2139]
2182-14-1 = 865-21-4
反应条件:1.1 Reagents: Hydrochloric Acid,Iron Chloride (Fecl3) Solvents: 2,2,2-Trifluoroethanol,Water; 2 H,23 °C1.2 Reagents: Ferric Oxalate Solvents: Water; 23 °C -> 0 °C1.3 Reagents: Oxygen; 20 Min,0 °C1.4 Reagents: Sodium Borohydride Solvents: Water; 30 Min,0 °C1.5 Reagents: Ammonium Hydroxide Solvents: Water
标题:Enantioselective Synthesis Of Iboga Alkaloids And Vinblastine Via Rearrangements Of Quaternary Ammoniums
作者:Zhang,Yun; Et Al
参考文献:Chemical Science 日期:2016 卷标:7(8) 页码:5530-5536]
2182-14-1 + 2468-21-5 = 865-21-4
反应条件:1.1 Reagents: Citric Acid,Hydrochloric Acid,Sodium Hypochlorite,Hydrogen Peroxide,Sodium Borohydride Solvents: Methanol,Dichloromethane,Water; Ph 2.2; 4.5 H,Ph 2.2 -> Ph 8.3,-5 - 0 °C
标题:A Simplified Procedure For Indole Alkaloid Extraction From Catharanthus Roseus Combined With A Semi-Synthetic Production Process For Vinblastine
作者:Verma,Arvind; Et Al
参考文献:Molecules 日期:2007 卷标:12(7) 页码:1307-1315]
= 865-21-4
反应条件:1.1 Reagents: Maleic Acid,Ammonium Oxalate Monohydrate,Ammonia,Ferric Chloride Hexahydrate Solvents: Water; 0 °C; 2 H,0 °C1.2 Reagents: Sodium Borohydride Solvents: Water; 30 Min,Rt
标题:Study On Synthesis Of Vinblastine From Catharanthine And Vindoline Isolated From Cantharanthus Roseus
作者:Nguyen,Le Tuan; Et Al
参考文献:Tap Chi Hoa Hoc 日期:2012 卷标:50(2) 页码:211-215]
= 865-21-4 [标题:Reaction Conditions
标题:Synthesis Of The Antitumor Bisindole Alkaloid Vinblastine: Diastereoselectivity And Solvent Effect On The Stereochemistry Of The Crucial C-15-C-18' Bond
作者:Magnus,Philip; Et Al
参考文献:Journal Of The American Chemical Society 日期:1990 卷标:112(22) 页码:8210-12]
= 865-21-4
反应条件:1.1 Reagents: Tetrabutylammonium Fluoride Solvents: Tetrahydrofuran2.1 Solvents: Methanol2.2 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
标题:Enantioselective Syntheses Of Vinblastine,Leurosidine,Vincovaline And 20'-Epi-Vincovaline
作者:Kuehne,Martin E.; Et Al
参考文献:Journal Of Organic Chemistry 日期:1991 卷标:56(2) 页码:513-28]
2182-14-1 + 4457-32-3 = 865-21-4
反应条件:1.1 Reagents: 2,6-Di-Tert-Butyl-4-Methylpyridine Solvents: Nitromethane2.1 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran3.1 Reagents: Triethylamine,Sulfur Trioxide-Pyridine Complex Solvents: Dimethyl Sulfoxide4.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
标题:Nonoxidative Coupling Methodology For The Synthesis Of The Antitumor Bisindole Alkaloid Vinblastine And A Lower-Half Analog: Solvent Effect On The Stereochemistry Of The Crucial C-15/c-18' Bond
作者:Magnus,Philip; Et Al
参考文献:Journal Of The American Chemical Society 日期:1992 卷标:114(26) 页码:10232-45]
38390-45-3 = 865-21-4
反应条件:1.1 Reagents: Ferric Oxalate,Oxygen Solvents: Water; 10 Min,0 °C1.2 Reagents: Hydrochloric Acid,Sodium Borohydride Solvents: 2,2,2-Trifluoroethanol,Water; 30 Min,0 °C1.3 Reagents: Ammonium Hydroxide Solvents: Water
标题:10'-Fluorovinblastine And 10'-Fluorovincristine: Synthesis Of A Key Series Of Modified Vinca Alkaloids
作者:Gotoh,Hiroaki; Et Al
参考文献:Acs Medicinal Chemistry Letters 日期:2011 卷标:2(12) 页码:948-952]
= 865-21-4
反应条件:1.1 Solvents: Methanol1.2 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
标题:Enantioselective Syntheses Of Vinblastine,Leurosidine,Vincovaline And 20'-Epi-Vincovaline
作者:Kuehne,Martin E.; Et Al
参考文献:Journal Of Organic Chemistry 日期:1991 卷标:56(2) 页码:513-28]
548774-92-1 = 865-21-4
反应条件:1.1 Reagents: Sodium Bicarbonate Solvents: Acetone,Water; Rt
标题:Total Synthesis Of (+)-Vinblastine
作者:Yokoshima,Satoshi; Et Al
参考文献:Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 日期:2001 卷标:43 页码:163-168]
= 865-21-4
反应条件:1.1 Reagents: 2-Mercaptoethanol,1,8-Diazabicyclo[5.4.0]Undec-7-Ene Solvents: Acetonitrile; Rt2.1 Reagents: Sodium Bicarbonate Solvents: Acetone,Water; Rt
标题:Total Synthesis Of (+)-Vinblastine
作者:Yokoshima,Satoshi; Et Al
参考文献:Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 日期:2001 卷标:43 页码:163-168]
= 865-21-4
反应条件:1.1 Reagents: Triethylamine Solvents: Methanol1.2 Reagents: 2-Mercaptoethanol,1,8-Diazabicyclo[5.4.0]Undec-7-Ene1.3 Reagents: Sodium Bicarbonate Solvents: Isopropanol
标题:First De Novo Synthesis Of The Bisindole Alkaloid Vinblastine
作者:Schneider,Christoph
参考文献:Angewandte Chemie 日期:2002 卷标:41(22) 页码:4217-4219]
= 865-21-4
反应条件:1.1 Reagents: Triethylamine Solvents: Methanol1.2 Reagents: 2-Mercaptoethanol,1,8-Diazabicyclo[5.4.0]Undec-7-Ene Solvents: Acetone2.1 Reagents: Sodium Bicarbonate Solvents: Isopropanol,Water; Rt
标题:Stereocontrolled Total Synthesis Of (+)-Vinblastine
作者:Yokoshima,Satoshi; Et Al
参考文献:Pure And Applied Chemistry 日期:2003 卷标:75(1) 页码:29-38]
2182-14-1 + 2468-21-5 = 865-21-4
反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Water
标题:Photochemical One-Pot Synthesis Of Vinblastine And Vincristine
作者:Pennanen,S.; Et Al
参考文献:Photochemistry And Photobiology 日期:1990 卷标:51(5) 页码:515-18]
= 865-21-4
反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran2.1 Reagents: Triethylamine,Sulfur Trioxide-Pyridine Complex Solvents: Dimethyl Sulfoxide3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
标题:Nonoxidative Coupling Methodology For The Synthesis Of The Antitumor Bisindole Alkaloid Vinblastine And A Lower-Half Analog: Solvent Effect On The Stereochemistry Of The Crucial C-15/c-18' Bond
作者:Magnus,Philip; Et Al
参考文献:Journal Of The American Chemical Society 日期:1992 卷标:114(26) 页码:10232-45]
2182-14-1 + 4457-32-3 = 865-21-4
反应条件:1.1 Reagents: 2,6-Di-Tert-Butyl-4-Methylpyridine Solvents: Nitromethane2.1 -
标题:Synthesis Of The Antitumor Bisindole Alkaloid Vinblastine: Diastereoselectivity And Solvent Effect On The Stereochemistry Of The Crucial C-15-C-18' Bond
作者:Magnus,Philip; Et Al
参考文献:Journal Of The American Chemical Society 日期:1990 卷标:112(22) 页码:8210-12]
= 865-21-4
反应条件:1.1 Reagents: Triethylamine,Sulfur Trioxide-Pyridine Complex Solvents: Dimethyl Sulfoxide2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
标题:Nonoxidative Coupling Methodology For The Synthesis Of The Antitumor Bisindole Alkaloid Vinblastine And A Lower-Half Analog: Solvent Effect On The Stereochemistry Of The Crucial C-15/c-18' Bond
作者:Magnus,Philip; Et Al
参考文献:Journal Of The American Chemical Society 日期:1992 卷标:114(26) 页码:10232-45]
1530-32-1 = 865-21-4
反应条件:1.1 Reagents: Potassium Tert-Butoxide Solvents: Tetrahydrofuran; 1 H,Rt1.2 Solvents: Tetrahydrofuran; 2 H,Rt1.3 Solvents: Water; Rt2.1 Reagents: Hydrochloric Acid,Iron Chloride (Fecl3) Solvents: 2,2,2-Trifluoroethanol,Water; 2 H,23 °C2.2 Reagents: Ferric Oxalate Solvents: Water; 23 °C -> 0 °C2.3 Reagents: Oxygen; 20 Min,0 °C2.4 Reagents: Sodium Borohydride Solvents: Water; 30 Min,0 °C2.5 Reagents: Ammonium Hydroxide Solvents: Water
标题:Enantioselective Synthesis Of Iboga Alkaloids And Vinblastine Via Rearrangements Of Quaternary Ammoniums
作者:Zhang,Yun; Et Al
参考文献:Chemical Science 日期:2016 卷标:7(8) 页码:5530-5536
Methyl (1R,9R,10S,11R,12R,19R)-11-Acetyloxy-12-Ethyl-10-Hydroxy-4-[(5S,7S)-5-[(2S)-2-Hydroxy-2-(Hydroxymethyl)Butyl]-7-Methoxycarbonyl-2,3,4,5,6,8-Hexahydro-1H-Azonino[5,4-B]Indol-7-Yl]-5-Methoxy-8-Methyl-8,16-Diazapentacyclo[10.6.1.01,9.02,7.016,19]Nonadeca-2,4,6,13-Tetraene-10-Carboxylate 反应生成 长春花碱
参考文献:Magnus,Philip;Stamford,Andrew;Ladlow,Mark,J. Amer. Chem. Soc.,112,(1990) N2,C. 8210-8212
标题:Magnus,Philip;Stamford,Andrew;Ladlow,Mark,J. Amer. Chem. Soc.,112,(1990) N2,C. 8210-8212
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专利信息
专利号:US-4841045-A
优先权日:1985-03-12
标 题 :Synthesis of vinblastine and vincristine type compounds
发明人：KUEHNE MARTIN
权利人:UNIV VERMONT
摘要:A new process for the stereospecific synthesis of alkaloids of the vinblastine and vincristine type including the synthesis of vinblastine and vincristine as well novel alkaloids which are active as anti-tumor agents.
专利号:US-4897477-A
优先权日:1985-03-12
标题:Synthesis of vinblastine and vincristine type compounds
发明人：KUEHNE MARTIN
权利人:UNIV VERMONT
摘要:A new process for the stereospecific synthesis of alkaloids of the vinblastine and vincristine type including the synthesis of vinblastine and vincristine as well novel alkaloids which are active as anti-tumor agents.
专利号:US-RE37449-E
优先权日:1987-02-06
标题:Process of synthesis of 3′,4′-anhydrovinblastine, vinblastine and vincristine
发明人：KUTNEY JAMES P; CHOI LEWIS S L; NAKANO JUN; TSUKAMOTO HIROKI; BOULET CAMILLE A; MCHUGH MICHAEL
权利人:UNIV BRITISH COLUMBIA
摘要:The present invention relates to the synthesis of dimer alkaloid compounds, particularly those of the Catharantus (Vinca) family, from an indole unit, such as cantharanthine, and a dihydroindole unit, such as vindoline. A multi-step process is disclosed including the steps of (1) of 1,4-reduction of a first dimeric iminium intermediate to an enamine compound by reaction with a 1,4-dihydropyridine compound; (2) oxidative transformation of the resulting enamine to a second iminium intermediate under controlled aeration; (3) reduction of the second iminium intermediate to form the target dimer alkaloid compounds. The entire process can be conducted in a one-pot operation to obtain the target compounds without isolation of the intermediates.
专利号:US-5047528-A
优先权日:1987-01-22
标题 :Process of synthesis of vinblastine and vincristine
发明人：KUTNEY JAMES P; CHOI LEWIS S L; NAKANO JUN; TSUKAMOTO HIROKI; BOULET CAMILLE A; MCHUGH MICHAEL
权利人:UNIV BRISTISH COLUMBIA
摘要:The present invention relates to the synthesis of dimer alkaloid compounds, particularly those of the Catharantus (Vinca) family, from an indole unit, such as cantharanthine, and a dihydroindole unit, such as vindoline. A multi-step process is disclosed including the steps of (1) of 1,4-reduction of a first dimeric iminium intermediate to an enamine compound by reaction with a 1,4-dihydropyridine compound; (2) oxidative transformation of the resulting enamine to a second iminium intermediate under controlled aeration; (3) reduction of the second iminium intermediate to form the target dimer alkaloid compounds. The entire process can be conducted in a one-pot operation to obtain the target compounds without isolation of the intermediates.
专利号:US-2025009786-A1
优先权日:2021-09-30
标 题 :Automated synthesis of polymeric dual drugs
发明人：MATRAY TRACY; VANBRUNT MICHAEL; MCCUTCHEON JOHN MICHAEL
权利人:SONY GROUP CORP
摘要:Compounds useful as biologically active compounds with or without fluorescent or colored dyes are disclosed. In some embodiments, the compounds have the following structure (I): (I) or a stereoisomer, tautomer or salt thereof, wherein R1, R2, R3, R4, R5, R6, R7, L1, L2, L3, L4, L5, L6, L7, L8, L9, L10, L11, M1, M2, M3, l, m, n, p, and q are as defined herein. Additional compound, methods of preparation, pharmaceutical compositions, and methods of treatment related to compounds of Structure (I) are also provided.
专利号:US-4279817-A
优先权日:1975-05-30
标 题:Method for producing dimer alkaloids
发明人：KUTNEY JAMES P
权利人:US DEPARTMENT OF HEALTH & HUMA
摘要:A concerted process for the synthesis of a dimer consisting of an indole unit and a dihydroindole unit possessing natural stereochemistry which comprises: n (a) forming an N-oxide intermediate from said indole unit; n (b) treating said N-oxide indole intermediate in the presence of acetic anhydride or halogenated derivative thereof to effect a Polonovski-type fragmentation reaction; n (c) without isolating the N-oxide indole intermediate and at a temperature of about -10° C. to +10° C., coupling said reaction product with a dihydroindole unit in the presence of acetic anhydride or a halogenated derivative thereof at a low temperature of about -10° C. to +10° C. under inert conditions; and n (d) subsequently reducing the immonium nitrogen on the indole unit by reacting with aqueous alkali metal borohydride to produce a dimer.
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主要参考文献
1: Haque A, Rahman MA, Faizi MSH, Khan MS. Next Generation Antineoplastic Agents: A Review on Structurally Modified Vinblastine (VBL) Analogues. Curr Med Chem. 2018;25(14):1650-1662. doi: 10.2174/0929867324666170502123639. 29(11):1370-1374. doi: 10.1016/j.bmcl.2019.03.036. Epub 2019 Mar 26.
3: Parthasarathy R, Shanmuganathan R, Pugazhendhi A. Vinblastine production by the endophytic fungus Curvularia verruculosa from the leaves of Catharanthus roseus and its in vitro cytotoxicity against HeLa cell line. Anal Biochem. 2020 Mar 15;593:113530. doi: 10.1016/j.ab.2019.113530. Epub 2019 Nov 30. 10(2):101-18. doi: 10.1002/tcr.201090001. 17(5):5893-914. doi: 10.3390/molecules17055893.
6: Sears JE, Boger DL. Total synthesis of vinblastine, related natural products, and key analogues and development of inspired methodology suitable for the systematic study of their structure-function properties. Acc Chem Res. 2015 Mar 17;48(3):653-62. doi: 10.1021/ar500400w. Epub 2015 Jan 14.
合成参考文献
参考文献:10.1016/j.ejmech.2018.04.042
摘要:La Regina G, Bai R, Coluccia A, Naccarato V, Famiglini V, Nalli M, Masci D, Verrico A, Rovella P, Mazzoccoli C, Da Pozzo E, Cavallini C, Martini C, Vultaggio S, Dondio G, Varasi M, Mercurio C, Hamel E, Lavia P, Silvestri R. New 6- and 7-heterocyclyl-1H-indole derivatives as potent tubulin assembly and cancer cell growth inhibitors. European Journal of Medicinal Chemistry. 2018 May;152():283–97. doi: 10.1016/j.ejmech.2018.04.042.
📝 需求与反馈
尽可能描述清楚需求与问题信息
