118292-37-8

Basic information

• Product Name: METHYL 5,6,7-TRIMETHOXY-1H-INDOLE-2-CARBOXYLATE
• Synonyms: SALOR-INT L308501-1EA;METHYL 5,6,7-TRIMETHOXY-1H-INDOLE-2-CARBOXYLATE;5,6,7-TRIMETHOXY-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER;AKOS JY2083248;ZSXHVDGSRITZMF-UHFFFAOYSA-N
• CAS NO: 118292-37-8
• Molecular Formula: C₁₃H₁₅NO₅
• Molecular Weight: 265.26
• Mol File: 118292-37-8.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL 5,6,7-TRIMETHOXY-1H-INDOLE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 5,6,7-TRIMETHOXY-1H-INDOLE-2-CARBOXYLATE(118292-37-8)
• EPA Substance Registry System: METHYL 5,6,7-TRIMETHOXY-1H-INDOLE-2-CARBOXYLATE(118292-37-8)

Safety Data

• Hazardous Substances Data: 118292-37-8(Hazardous Substances Data)

Upstream product

• 28059-24-7 methyl 5,6-dimethoxy-1H-indole-2-carboxylate 
• 4305-32-2 5-hydroxy-6-methoxy-indole-2-carboxylic acid methyl ester 
• 77-78-1 dimethyl sulfate 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 556038-53-0 2-benzyloxycarbonylamino-3-(2-bromo-3,4,5-trimethoxyphenyl)acrylic acid methyl ester 
• 35274-53-4 2-bromo-3,4,5-tri-methoxybenzaldehyde 
• 556038-54-1 1-benzyloxycarbonyl-5,6,7-trimethoxy-1H-indole-2-carboxylic acid methyl ester 
• 124-41-4 sodium methylate 
• 153925-97-4 3-methoxycarbonyl-2-methylduocarmycin A 
• 118292-35-6 duocarmycin C1 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 169181-35-5 duocarmycin D 
• 157485-07-9 methyl (Z)-2-azido-3-(3,4,5-trimethoxyphenyl)acrylate 

Downstream Products

• 128781-07-7 5,6,7-trimethoxy-1H-indole-2-carboxylic acid 
• 118292-34-5 dl-Duocarmycin A 
• 118292-34-5 dl-2-Epiduocarmycin A 
• 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 
• 132628-71-8 methyl (2S*,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 
• 132628-70-7 methyl (2S*,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 
• 297137-20-3 (E)-p-nitrophenyl 3-(5,6,7-trimethoxy-2-indolyl)acrylate 
• 556038-65-4 (2R,8S)-4-benzyloxy-8-(tert-butyldimethylsilanyloxymethyl)-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester 
• 556038-67-6 (2R,8S)-4-benzyloxy-8-methanesulfonyloxymethyl-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester 
• 556038-66-5 (2R,8S)-4-benzyloxy-8-hydroxymethyl-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester 
• 130288-24-3 (+)-duocarmycin SA 
• 118292-34-5 duocarmycin A 
• 853134-00-6 methyl 3-formyl-5,6,7-trimethoxy-N-methylindole-2-carboxylate 

Relevant articles and documents

Duocarmycin-pyrindamycin DNA alkylation properties and identification, synthesis, and evaluation of agents incorporating the pharmacophore of the duocarmycin-pyrindamycin alkylation subunit. Identification of the CC-1065-duocarmycin common pharmacophore

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Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer

Inspired by the natural product evodiamine, a novel antitumor indolopyrazinoquinazolinone scaffold was designed by scaffold hopping. Structure-activity relationship studies led to the discovery of compound 15j, which shows low nanomolar inhibitory activity against the HCT116 cell line. Further antitumor mechanism studies indicated that compound 15j acted by the dual inhibition of topoisomerase 1 and tubulin and induced apoptosis with G2 cell-cycle arrest. The quaternary ammonium salt of compound 15j (compound 15js) exhibited excellent in vivo antitumor activity (TGI = 66.6%) in the HCT116 xenograft model with low toxicity. Indolopyrazinoquinazolinone derivatives represent promising multitargeting antitumor leads for the development of novel antitumor agents.

Regioselective reactivity of some 5,7-dimethoxyindoles

The reactivity of some 5,7-dimethoxyindoles with respect to electrophiles has been investigated. The favoured sites for reaction are C3 and C4 and regioselectivity can be controlled by the judicious arrangement of electron-withdrawing substituents. Results of formylation, acylation, the Mannich reaction, bromination and nitration are described.

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