56700-58-4Relevant academic research and scientific papers
Novel orally active analgesic and anti-inflammatory cyclohexyl-N-acylhydrazone derivatives
Da Silva, Tiago Fernandes,Jnior, Walfrido Bispo,Alexandre-Moreira, Magna Suzana,Costa, Fanny Nascimento,Da Silva Monteiro, Carlos Eduardo,Ferreira, Fabio Furlan,Barroso, Regina Cely Rodrigues,Nol, Francois,Sudo, Roberto Takashi,Zapata-Sudo, Gisele,Lima, Ldia Moreira,Barreiro, Eliezer J.
, p. 3067 - 3088 (2015/03/04)
The N-acylhydrazone (NAH) moiety is considered a privileged structure, being present in many compounds with diverse pharmacological activities. Among the activities attributed to NAH derivatives anti-inflammatory and analgesic ones are recurrent. As part of a research program aiming at the design of new analgesic and anti-inflammatory lead-candidates, a series of cyclohexyl-N-acylhydrazones 10-26 were structurally designed from molecular modification on the prototype LASSBio-294, representing a new class of cycloalkyl analogues. Compounds 10-26 and their conformationally restricted analogue 9 were synthetized and evaluated as analgesic and anti-inflammatory agents in classical pharmacologic protocols. The cyclohexyl-N-acylhydrazones 10-26 and the cyclohexenyl analogue 9 showed great anti-inflammatory and/or analgesic activities, but compound 13 stood out as a new prototype to treat acute and chronic painful states due to its important analgesic activity in a neuropathic pain model.
A new procedure for preparation of carboxylic acid hydrazides
Zhang, Xini,Breslav, Michael,Grimm, Jeffrey,Guan, Kailin,Huang, Aihua,Liu, Fuqiang,Maryanoff, Cynthia A.,Palmer, David,Patel, Mitul,Qian, Yun,Shaw, Charles,Sorgi, Kirk,Stefanick, Stephen,Xu, Dawei
, p. 9471 - 9474 (2007/10/03)
The standard method for preparing carboxylic acid hydrazides is hydrazinolysis of esters in alcoholic solutions. However, when applied to α,β-unsaturated esters, the main product typically is the pyrazolidinone resulting from an undesired Michael-type cyclization. Other alternative methodologies reported for direct preparation of hydrazides from acids are inefficient. We developed an efficient and general process, involving preforming activated esters and/or amides followed by reaction with hydrazine, for the preparation of hydrazides including those of α,β-unsaturated acids. This process gives the desired hydrazides in excellent yield and purity under mild conditions.
