62291-38-7

Upstream product

• 3128-15-2 cyclopent-1-ene-1,2-dicarboxylic acid 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 122539-74-6 2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester 
• 141340-72-9 N-benzyloxymethyl-7,9-dioxo-8-azatricyclo<4.3.3.0>dodec-3-ene 
• 13861-05-7 7,9-dioxo-8-azatricyclo<4.3.3.0>dodec-3-ene 

Relevant academic research and scientific papers

Iso-maleimycin, a Constitutional Isomer of Maleimycin, from Streptomyces sp. QL37

Iso-maleimycin, a previously unknown constitutional isomer of the antibiotic maleimycin, has been detected in an extract of Streptomyces sp. QL37. Chemical synthesis of both maleimycin (20 % yield over seven steps) and iso-maleimycin, (15 % yield over six steps) allowed access to reference materials for identification. Gas Chromatography coupled Mass Spectrometry (GC-MS) analysis demonstrated that of the two isomers, only iso-maleimycin was present in the extract. This finding supports our hypothesis that iso-maleimycin is a biosynthetic intermediate of lugdunomycin. Iso-maleimycin displays low antibiotic activity, with a Minimum Inhibitory Concentration (MIC) value on both E. coli and B. subtilis of 250 μg/mL.

Identification of new anti-inflammatory agents based on nitrosporeusine natural products of marine origin

Nitrosporeusines A and B are two recently isolated marine natural products with novel skeleton and exceptional biological profile. Interesting antiviral activity of nitrosporeusines and promising potential in curing various diseases, evident from positive data from various animal models, led us to investigate their anti-inflammatory potential. Accordingly, we planned and synthesized nitrosporeusines A and B in racemic as well as enantiopure forms. The natural product synthesis was followed by preparation of several analogues, and all the synthesized compounds were evaluated for in vitro and in vivo anti-inflammatory potential. Among them, compounds 25, 29 and 40 significantly reduced levels of nitric oxide (NO), reactive oxygen species (ROS) and pro-inflammatory cytokines. In addition, these compounds suppressed several pro-inflammatory mediators including inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), nuclear factor-κB (NF-κB), and thereby can be emerged as potent anti-inflammatory compounds. Furthermore, all possible isomers of lead compound 25 were synthesized, characterized and profiled in same set of assays and found that one of the enantiomer (?)-25a was superior among them.

Formal synthesis of maleimycin

A formal synthesis of meleimycin is reported. A key feature includes formation of a tricyclic intermediate that undergoes flash vacuum thermolysis to afford the required skeletal framework of the target molecule.