Synthetic Communications p. 244 - 255 (2019)
Update date:2022-08-05
Topics:
Ramírez-Marroquín, Oscar Abelardo
Manzano-Pérez, Flavio
López-Torres, Adolfo
Hernández-López, Alejandro
Cortés-Pacheco, Abimelek
Reyes-González, Miguel Angel
Piperlotines are natural products characterized by an α,β-unsaturated amide moiety. These compounds found wide applications in Medicinal Chemistry like antibacterials, cytotoxic agents, anticoagulants, among others. To date, diverse methods of synthesis have been reported for piperlotines, but involving the use of catalysts, hazard reagents, anhydrous media or coupling reagents. Thus, in this work, we developed a greener method of synthesis of piperlotines A, C, and derivatives, through mechanochemical activation under solvent-free conditions. The reaction of a β-amidophosphonate, K2CO3, and an aromatic aldehyde afforded target compounds in moderate to good yields (46–77%), in an open atmosphere by grinding. It is worth to mention that this mechanochemical process was under thermodynamic control because just E isomer was isolated for every reaction. Moreover, synthesized piperlotines have been predicted by means of chemoinformatic analysis as potential therapeutic agents for the treatment of arthritis or cancer.
View Morejintan yufan Medicine Raw materials Co.,Ltd.
Contact:86-519-82808282
Address:6th,Jincheng Huangzhuang
Nantong Advance Chemical Co., Ltd
Contact:86-13818730908
Address:Fine Chemical Industry Garden,Beixin Town,Qidong
Guangzhou Reachin Chemical Co., Ltd
Contact:+86-20-37087379 ext.604
Address:A122C-1, Tianyuan Plaza, 401 Tianyuan Rd., Tianhe, Guangzhou, China
Yingkou Sanzheng New Technology Chemical Industry Co., Ltd.
Contact:+86-417-2927806
Address:yingkou
website:http://www.china-sinoway.com
Contact:+86-592-5853819
Address:16/F,Huicheng Comm,Complex,No839 XiaHe Rd, Xiamen,China
Doi:10.1016/S0040-4039(00)97150-8
(1990)Doi:10.1021/jacs.5b08103
(2015)Doi:10.1016/S0040-4039(01)80504-9
(1989)Doi:10.1016/j.tet.2010.12.052
(2011)Doi:10.1002/anie.201006021
(2011)Doi:10.1021/ol1028173
(2011)