Abstract
An efficient method for trapping isocyanate 4, generated from the Curtius rearrangement, with ethyl alcohol to afford the carbamate 5 is reported. 5-Nitrobenzo[b]thiophene-2-carboxylic acid 1 is converted to the corresponding hydrazide 2 by the reaction with hydrazine hydrate and then to the azide 3 with nitrous acid, followed by thermal rearrangement, cooling, and trapping in one pot reaction. The carbamate 5 is treated with hydrazine hydrate to afford the desired, Zileuton analogue, 4-(5-nitrobenzo[b]thiophene-2-yl)semicarbazide 6. Also the reactivity of hydrazide 2 towards some carboxyaldehydes and phenylisothiocyanate afforded the corresponding carbohydrazides 7, 8 and phenylthiosemicarbazide 9, respectively. Compounds 9, 2 and 6, respectively, were more potent as anti-inflammatory and anti-nociceptive agents.
Citations
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Francisco J B Mendonça JuniorCarlos A de Simone
Jul 4, 2012·Acta Pharmaceutica : a Quarterly Journal of Croatian Pharmaceutical Society and Slovenian Pharmaceutical Society, Dealing with All Branches of Pharmacy and Allied Sciences·Beatriz C C SouzaFrancisco J B Mendonça
Feb 5, 2014·Expert Opinion on Drug Discovery·Thomas DuflotJeremy Bellien
Feb 12, 2014·Drug Delivery·Mahasen A RadwanDalia A El-Maraghy
Sep 10, 2014·Journal of Enzyme Inhibition and Medicinal Chemistry·Khaled R A AbdellatifHany A Omar
Apr 25, 2014·Drug Delivery·Amal El Sayeh F Abou el ElaEhsan H Ibrahim
Mar 16, 2017·Chemical Biology & Drug Design·Lavanya MalluIndira Viswambaran Asharani
Aug 10, 2017·Parasitology·Alvaro Martin-MontesSilvia Pérez-Silanes
Jul 25, 2018·Mini Reviews in Medicinal Chemistry·Zeinab A MuhammadMahmuod M Elaasser
Nov 21, 2017·Acta Crystallographica. Section E, Crystallographic Communications·Linh Nguyen NgocLuc Van Meervelt
Jan 16, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mohamed A A RadwanHanem M Awad
Oct 18, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Audrey Isabel ChiassonMohamed Touaibia
Sep 8, 2019·Bioorganic Chemistry· ZabiullaShaukath Ara Khanum
Jan 29, 2020·Bioorganic Chemistry·Mohamed A A RadwanDina S El-Kady
Aug 29, 2019·ACS Omega·Christopher WalterTanay Kesharwani
Feb 16, 2018·Organic Letters·Parul Garg, Anand Singh
Mar 14, 2019·Journal of Agricultural and Food Chemistry·Yawen DongLi Zhang
Jul 22, 2018·Experimental Parasitology·Sâmia Sousa DuartePatricia Mirella da Silva
Aug 29, 2021·Medicinal Research Reviews·Kritika LaxmikeshavNagula Shankaraiah