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CAS 118292-34-5

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Duocarmycin A

Description:
Duocarmycin A is a potent antitumor agent belonging to the class of DNA minor groove binders. It is derived from the fermentation of the bacterium *Micromonospora* and exhibits a unique mechanism of action by forming covalent bonds with DNA, leading to the disruption of cellular replication and transcription processes. This compound is characterized by its complex structure, which includes a bicyclic core and a reactive electrophilic moiety that facilitates its interaction with DNA. Duocarmycin A is known for its high cytotoxicity against a variety of cancer cell lines, making it a subject of interest in cancer research and drug development. Its selectivity for cancer cells over normal cells is attributed to the differential expression of certain cellular components that facilitate its uptake and action. However, due to its potent nature, the development of Duocarmycin A into a therapeutic agent requires careful consideration of its pharmacokinetics and potential side effects. Overall, Duocarmycin A represents a promising avenue for targeted cancer therapy.
Formula:C26H25N3O8
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
InChI key:InChIKey=AZVARJHZBXHUSO-DZQVEHCYSA-N
SMILES:O=C1C=2[C@]34[C@](C3)(CN(C(=O)C=5NC=6C(C5)=CC(OC)=C(OC)C6OC)C4=CC(=O)C2N[C@]1(C(OC)=O)C)[H]
Synonyms:
  • Cyclopropa[c]pyrrolo[3,2-e]indole-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)-
  • Cyclopropa[c]pyrrolo[3,2-e]indole-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-(6α,7bR*,8aα)]-
  • 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)-
  • Dc 88A
  • Methyl (6R,7bR,8aS)-1,2,4,5,6,7,8,8a-octahydro-6-methyl-4,7-dioxo-2-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]cyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylate
  • methyl 2-methyl-3,8-dioxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,4,4a,5,6,8-octahydrocyclopropa[c]pyrrolo[3,2-e]indole-2-carboxylate
  • Duocarmycin A
  • (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
  • (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
  • DC-88-A
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