Chemical & Pharmaceutical Bulletin 2013-01-01

Synthesis of novel phosphorylated guanidine derivatives from cyanamide and their anti-inflammatory activity.

Venkata Ramana Katla, Rasheed Syed, Chandra Sekhar Kuruva, Hema Kumar Kuntrapakam, Naga Raju Chamarthi

Index: Chem. Pharm. Bull. 61(1) , 25-32, (2013)

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Abstract

A series of novel guanidine derivatives were synthesized in three steps and their anti-inflammatory activities in vitro and in vivo evaluated. 2-Aminopyridin-3-ol (1) was reacted with thiophosphoryl chloride (2) to give a monochloride (3). It was further reacted with cyanamide to afford the corresponding cyanamine (4), which was subsequently reacted with different heterocyclic amines to form the title compounds (5a-l). The substituent in the guanidine function affected the potency of anti-inflammatory activity. The compounds having benzothiazole, fluorophenyl, and piperazinyl moieties enhanced the anti-inflammatory activity.