118292-34-5

Basic information

• Product Name: Duocarmycin A
• Synonyms: Duocarmycin A;Cyclopropacpyrrolo3,2-eindole-6-carboxylic acid, 1,2,4,5,6,7,8,8a-octahydro-6-methyl-4,7-dioxo-2-(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl-, methyl ester, (6R,7bR,8aS)-;(6R,7bR,8aS)-1,2,4,5,6,7,8,8aβ-Octahydro-6-methyl-4,7-dioxo-2-(5,6,7-trimethoxy-1H-indol-2-ylcarbonyl)cyclopropa[c]pyrrolo[3,2-e]indole-6β-carboxylic acid methyl ester;(7bR,8aS)-2-[(5,6,7-Trimethoxy-1H-indole-2-yl)carbonyl]-1,2,4,5,8,8aβ-hexahydro-4,7-dioxo-6-methylcyclopropa[c]pyrrolo[3,2-e]indole-6β-carboxylic acid methyl ester;DC-88-A
• CAS NO: 118292-34-5
• Molecular Formula: C₂₆H₂₅N₃O₈
• Molecular Weight: 507.496
• Mol File: 118292-34-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 779.8°Cat760mmHg
• Flash Point: 425.4°C
• Appearance: /
• Density: 1.52g/cm³
• Vapor Pressure: 2.89E-24mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: Duocarmycin A(CAS DataBase Reference)
• NIST Chemistry Reference: Duocarmycin A(118292-34-5)
• EPA Substance Registry System: Duocarmycin A(118292-34-5)

Safety Data

• Hazardous Substances Data: 118292-34-5(Hazardous Substances Data)

Usage

General Description

Duocarmycin A is a potent anti-tumor antibiotic that works by causing DNA damage in cancer cells, ultimately leading to their death. It is a member of the duocarmycin family of compounds, which are known for their ability to selectively target and kill cancer cells while sparing healthy cells. Duocarmycin A works by binding to the minor groove of DNA and inducing alkylation, which disrupts the DNA structure and leads to cell death. It has shown promising results in preclinical studies and is being investigated as a potential treatment for various types of cancer. Its unique mechanism of action and high potency make it a promising candidate for the development of new cancer therapies.

InChI:InChI=1/C26H25N3O8/c1-25(24(33)37-5)22(31)17-19(28-25)14(30)8-16-26(17)9-12(26)10-29(16)23(32)13-6-11-7-15(34-2)20(35-3)21(36-4)18(11)27-13/h6-8,12,27-28H,9-10H2,1-5H3

Upstream product

• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 128781-06-6 methyl 2-azido-3-(3',4',5'-trimethoxyphenyl)-propenoate 
• 157485-07-9 methyl (Z)-2-azido-3-(3,4,5-trimethoxyphenyl)acrylate 
• 143874-45-7 3-acetoxymethyl-6-benzyloxy-2,3-dihydro-1H-indole 
• 132628-67-2 methyl (2R*,8S*)-4-benzyloxy-6-t-butoxycarbonyl-8-(t-butyldimethylsilyloxy)methyl-3-formyl-1,2,3,6,7,8-hexahydro-2-methyl-1-oxobenzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate 
• 132628-69-4 methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxobenzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate dihydrochloride 
• 132628-71-8 methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-(methanesulfonyloxy)methyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate 
• 132628-70-7 methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate 
• 149365-65-1 methyl 6-benzyloxy-1-t-butoxycarbonyl-3-(t-butyldimethylsilyloxy)methyl-2,3-dihydro-5-amino-1H-indole-4-carboxylate 
• 132628-65-0 methyl 6-benzyloxy-1-t-butoxycarbonyl-3-(t-butyldimethylsilyloxy)methyl-2,3-dihydro-5-(1-methoxycarbonylethyl)amino-1H-indole-4-carboxylate 
• 143874-47-9 5-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxymethyl)-1,3-dioxo-3,4,8,9-tetrahydro-1H-[1,3]oxazino[5,4-e]indole-7-carboxylic acid tert-butyl ester 
• 132628-61-6 8-acetoxymethyl-4-benzyloxy-6-t-butoxycarbonyl-1,2,3,6,7,8-hexahydro-1-methylthio-1,2-dioxobenzo<1,2-b;4,3-b'>dipyrrole 
• 132628-63-8 4-benzyloxy-6-t-butoxycarbonyl-8-(t-butyldimethylsilyloxy)methyl-1,2,3,6,7,8-hexahydro-1,2-dioxobenzo<1,2-b;4,3-b'>dipyrrole 
• 132628-62-7 8-acetoxymethyl-4-benzyloxy-6-t-butoxycarbonyl-1,2,3,6,7,8-hexahydro-1,2-dioxobenzo<1,2-b;4,3-b'>dipyrrole 

Downstream Products

• 124325-94-6 duocarmycin B₂ 
• 124325-93-5 duocarmycin B₁ 
• 118292-36-7 duocarmycin C₂ 
• 118292-35-6 duocarmycin C1 
• 128517-09-9 Duocarmycin C₂ 
• 118292-35-6 Duocarmycin C1 

Relevant articles and documents

Total synthesis of the duocarmycins

The total synthesis of (+)-duocarmycin A and SA through a common indoline intermediate is described. The key reactions include selective lithiation of a 2,6-dibromoiodobenzene derivative and diastereoselective addition to a chiral nitroalkene, copper-mediated aryl amination, and addition of aryllithium to azlactones. Copyright

Enantioselective total synthesis of (+)-duocarmycin A, epi-(+)-duocarmycin A, and their unnatural enantiomers

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Synthetic Studies on Duocarmycin. 1. Total Synthesis of dl-Duocarmycin A and Its 2-Epimer

The title synthesis was first achieved by employing novel methoxycarbonylation of the C4-position of the 5-aminoindoline by way of the isatin and subsequent Dieckmann cyclization to the methyl 2-methylindoxyl-2-carboxylate as key steps.In vitro cytotoxicity assay against P388 murine leukemia obviously disclosed that cytotoxicities of the synthesized compounds are comparable and almost half of that of natural (+)-duocarmycin A. - Key Words: dl-duocarmycin A, dl-2-epi-duocarmycin A, total synthesis, antitumor antibiotic, cytotoxicity