37059-18-0

Basic information

• Product Name: 1H-Pyrrole-3-carboxylicacid,5-formyl-2,4-dimethyl-,phenylmethylester(9CI)
• Synonyms: 1H-Pyrrole-3-carboxylicacid,5-formyl-2,4-dimethyl-,phenylmethylester(9CI)
• CAS NO: 37059-18-0
• Molecular Formula: C₁₅H₁₅NO₃
• Molecular Weight: 257.28
• Product Categories: HANTZSCH
• Mol File: 37059-18-0.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Pyrrole-3-carboxylicacid,5-formyl-2,4-dimethyl-,phenylmethylester(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-3-carboxylicacid,5-formyl-2,4-dimethyl-,phenylmethylester(9CI)(37059-18-0)
• EPA Substance Registry System: 1H-Pyrrole-3-carboxylicacid,5-formyl-2,4-dimethyl-,phenylmethylester(9CI)(37059-18-0)

Safety Data

• Hazardous Substances Data: 37059-18-0(Hazardous Substances Data)

Upstream product

• 89909-48-8 3,5-dimethyl-1H-pyrrole-2, 4-dicarboxylic acid 2-tert-butyl ester 4-benzyl ester 
• 37059-10-2 benzyl 2,4-dimethyl-1H-pyrrole-3-carboxylate 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1259400-49-1 (Z)-benzyl 5-((3-methoxy-5-oxo-1H-pyrrol-2(5H)-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate 
• 253870-02-9 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid 
• 1632147-04-6 1,3,7,9-tetramethyl-2,8-dibenzyloxycarbonyl-4,6-dipyrrin hydrobromide 

Relevant articles and documents

Synthetic prodigiosenes and the influence of C-ring substitution on DNA cleavage, transmembrane chloride transport and basicity

Analogues of the tripyrrolic natural product prodigiosin bearing an additional methyl and a carbonyl group at the C-ring were synthesised and evaluated. In vitro anticancer activity screening (NCI) and the study of modes of action (copper-mediated cleavage of double-stranded DNA and transmembrane transport of chloride anions) showed that the presence of the methyl group is not detrimental to activity. Furthermore, although the presence of an ester conjugated to the prodigiosene C-ring seems to decrease both pKa and chloride transport efficiency compared to the natural product, these analogues still exhibit a high rate of chloride transport. All analogues exhibit good in vitro anticancer activity and reduced toxicity compared to the natural product: compare an acute systemic toxicity of 100 mg kg-1 in mice vs. 4 mg kg-1 for prodigiosin, pointing towards a larger therapeutic window than for the natural product. This journal is The Royal Society of Chemistry 2013.