Approaches towards the stabilization of hemiaminal function at ornithine unit of mulundocandin.
Semisynthetic modifications at position-12 (ornithine-5-position, hemiaminal function) of mulundocandin were carried out to improve its chemical stability. New carbon-carbon (C-C) and carbon-hydrogen (C-H) linkage at hemiaminal function -12 has been achieved. Lewis acid catalyzed introduction of electron rich aryl group at position-12 of mulundocandin is developed. Synthesized mulundocandin analogues were evaluated for their chemical stability and antifungal activity against C. albicans and A. fumigatus.
Quest Institute of LifeScience, Nicholas Piramal India Limited, and Hoechst Research Center, Mulund, Mumbai-400080, Maharashtra, India. bansilal@nicholaspiramal.co.in
Bansi
B
Lal
Vitthal Genbhau
VG
Gund
D000588:Amines / Q000737:chemistry; D000818:Animals; D000935:Antifungal Agents / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects / Q000254:growth & development; D002177:Candidiasis / Q000188:drug therapy; D004355:Drug Stability; D054714:Echinocandins; D007274:Injections, Intraperitoneal; D051379:Mice; D009952:Ornithine / Q000737:chemistry / Q000494:pharmacology*; D010456:Peptides, Cyclic / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology*
D000588:Amines; D000935:Antifungal Agents; D054714:Echinocandins; D010456:Peptides, Cyclic; D009952:Ornithine; C052098:mulundocandin