Azaprostaglandin analogs. Synthesis and biological properties of 11-azaprostaglandin derivatives

Abstract

New nitrogen analogues of prostaglandins (11, 11a, 12, and 12a) have been synthesized starting from a 4,5-disubstituted 2-pyrrolidinone nucleus (5 and 5a) containing one side chain and a suitable functionality for elaborating the second one. These analogues had no better activity than natural prostaglandins in vitro [guinea pig ileum and trachea, rat stomach fundus strip, uterus and portal vein, ADP-induced guinea pig platelet-rich plasma (PRP) aggregation]. They similarly lacked any interesting activity in vivo [anesthetized rat blood pressure, stress, and acetylsalycilic acid (ASA) induced gastric lesions in rat].

NaBH4−InCl3-Mediated One-Pot Chemo- and Stereoselective Decarboxylative Reduction of α-Aza gem-Dicarboxylic Esters to Monoalcohols

“…To the best of our knowledge, to date there is no report of single-step chemo- and stereoselective decarboxylative reduction of gem -dicarboxylic esters to monoalcohols in the presence of a lactam, though this one-pot transformation would be very useful for the synthesis of various bioactive compounds. ,, …”

Synthesis of cis-4-Trifluoromethyl- and cis-4-Difluoromethyl-l-pyroglutamic Acids

“…Pyroglutamic acid and its derivatives are important amino acids in many bioactive compounds such as Azaprostaglandin analogues, monocylic thienyl gamma lactam (high antibacterial activity), and thyroliberin (TRH)…”