37059-18-0

Upstream product

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

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 academic research and scientific papers

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.

Improved synthetic route to C-ring ester-functionalized prodigiosenes

An efficient, optimized, and scalable process for the synthesis of C-ring ester-functionalized prodigiosenes has been developed by (i) exploiting a silylative Mukaiyama aldol strategy for the condensation of alkyl 5-formyl-2,4-dimethylpyrrole-3-carboxylate and 4-methoxy-3-pyrrolin-2-one to form the corresponding ester-functionalized dipyrrinone analogues, and (ii) developing a facile synthesis of stable bromodipyrrin analogues for the use in formal Suzuki coupling reactions. The process was applied to the synthesis of three C-ring ester-functionalized prodigiosenes in multigram scales (up to 6.5 g prodigiosene free-base) with useful yields (35-56% overall yields over three steps starting from the 2-formyl pyrroles). Georg Thieme Verlag Stuttgart New York.