134106-68-6

Basic information

• Product Name: methyl 2-methyl-8-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,4,4a,5,6,8-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-3-carboxylate
• CAS NO: 134106-68-6
• Molecular Formula: C₂₆H₂₅N₃O₇
• Molecular Weight: 491.4926
• Mol File: 134106-68-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 815.5°C at 760 mmHg
• Flash Point: 447°C
• Density: 1.5g/cm³
• Vapor Pressure: 1.12E-26mmHg at 25°C
• Refractive Index: 1.7
• CAS DataBase Reference: methyl 2-methyl-8-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,4,4a,5,6,8-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-methyl-8-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,4,4a,5,6,8-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-3-carboxylate(134106-68-6)
• EPA Substance Registry System: methyl 2-methyl-8-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,4,4a,5,6,8-hexahydrocyclopropa[c]pyrrolo[3,2-e]indole-3-carboxylate(134106-68-6)

Safety Data

• Hazardous Substances Data: 134106-68-6(Hazardous Substances Data)

Upstream product

• 129953-15-7 8-O-tert-butyldimethylsilylduocarmycin B₂ 
• 124325-94-6 duocarmycin B₂ 
• 105-45-3 acetoacetic acid methyl ester 
• 128781-07-7 5,6,7-trimethoxy-1H-indole-2-carboxylic acid 
• 148778-32-9 methyl (1S)-1-(bromomethyl)-7-methyl-5-[(4-methylpiperazinyl)carbonyloxy]-3-[(5,6,7-trimethoxy-2-indolyl)-carbonyl]-1,2-dihydro-3H-pyrrolo[3,2-e]indole-8-carboxylatehydrobromide 
• 205652-13-7 (S)-8-Chloromethyl-4-hydroxy-2-methyl-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-1-carboxylic acid methyl ester 
• 177958-19-9 8-O-tert-butyldimethylsilyl-3-methoxycarbonyl-2-methylduocarmycin B₂ 
• 129953-17-9 8-O-tert-butyldimethylsilyl-3α-hydroxyduocarmycin B2 
• 156295-30-6 (S)-3-Acetoxymethyl-6-benzyloxy-5-((E)-2-methoxycarbonyl-1-methyl-vinylamino)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 
• 156295-31-7 (S)-8-Acetoxymethyl-4-benzyloxy-2-methyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester 
• 156295-32-8 (S)-4-Benzyloxy-8-hydroxymethyl-2-methyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester 
• 156295-33-9 (S)-4-Benzyloxy-8-chloromethyl-2-methyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester 
• 179693-97-1 (S)-8-Chloromethyl-4-hydroxy-2-methyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester 

Downstream Products

• 154889-68-6 3-methoxycarbonyl-2-methyl-8-O-(4-methyl-1-piperazinylcarbonyl)duocarmycin B2 
• 177958-20-2 3-methoxycarbonyl-2-methyl-8-O-N,N-dimethylcarbamoylduocarmycin B2 
• 134106-76-6 3-methoxycarbonyl-2-methyl-8-O-piperidinylcarbonylduocarmycin B2 
• 134106-77-7 3-methoxycarbonyl-2-methyl-8-O-pyrrolidinylcarbonylduocarmycin B2 
• 221549-90-2 C₂₂H₂₀N₄O₅ 
• 118292-37-8 5,6,7-trimethoxy-1H-indole-2-carboxylic acid methyl ester 
• 186760-22-5 CPI 

Relevant articles and documents

Synthesis and antitumor activity of duocarmycin derivatives: Modification at C-8 position of A-ring pyrrole compounds bearing the simplified DNA-binding groups

A series of the 8-O-substituted A-ring pyrrole derivatives of duocarmycin bearing the simplified DNA-binding moieties such as cinnamoyl or heteroarylacryloyl groups were synthesized, and evaluated for in vitro anticellular activity against HeLa S3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. In addition, the stability of the 8-O- substituted analogues in aqueous solution and the conversion to their active form (cyclopropane compound) from the 8-O-substituted analogues in mice or human serum were examined. The 8-O-substituted A-ring pyrrole derivatives bearing the simplified DNA-binding moieties showed remarkably potent in vivo antitumor activity and low peripheral blood toxicity compared with the 8-O- substituted A-ring pyrrole derivatives having the trimethoxyindole skeleton in segment-B (Seg-B), which were equal to 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxycinnamates and 4'-methoxy-β-heteroarylacrylates. Moreover, among 8-O-substituted analogues, several compounds can be chemically or enzymatically converted to their active form in human serum. This result indicated that new 8-O-substituted derivatives were different prodrugs from KW-2189 and 8-O-substituted analogues being the same type of prodrug as KW-2189. (C) 2000 Elsevier Science Ltd.

Novel syntheses of optically active CC-1065, U-73,975(adozelesin), U-80,244(carzelesin), U-77,779(bizelesin), KW-2189, and DU-86

The title syntheses were achieved by the method featuring oxidative cyclization of the enamino esters [(S)-13 and (S)-24] derived from the 5-aminoindoline [(5)-12], acylation with various structural types of indole-2-carboxylic acids, and formation of cyclopropapyrroloindole moieties.

Synthesis and antitumor activity of duocarmycin derivatives: Modification of segment A of duocarmycin B2

Several A-ring pyrrole derivatives of duocarmycin B2 were synthesized effectively from the 3-hydroxy compounds by utilizing an interesting acid- catalyzed rearrangement, their anticellular activity was preliminarily evaluated by assays of growth inhibition of HeLa S3 cells (in vitro) and antitumor activity against murine sarcoma 180 (in vivo). The 8-O-N,N- dialkylcarbamoyl derivatives of the A-ring pyrrole compound showed remarkably potent in vivo antitumor activity, superior to that of duocarmycin B2. These derivatives were subjected to further biological evaluation. They exhibited potent antitumor activity toward murine solid tumors including M5076 sarcoma, B-16 melanoma and Colon 26 adenocarcinoma. Their most noteworthy feature was their efficacy against various human xenografts including LC-6 (lung), St-4 (stomach), and Co-3 (colon).