One-pot synthesis of substituted pyrrole–imidazole derivatives with anticancer activity
A facile and efficient method to synthesize pyrrole–imidazole was developed via a post-Ugi cascade reaction followed by one purification procedure. Synthesized pyrrole–imidazole was collected by performing a mild reaction and a simple procedure, which could be applicable to a broad scope of functionalized anilines. The screening results demonstrated that compound 7e exhibited a high potency of anticancer activity in human pancreatic cancer cell lines PANC and ASPC-1. Our work shed light on the potential of post-Ugi cascade reaction in combinatorial and medicinal chemistry.
KeywordsPyrrole–imidazole MCRs Microwave irradiation One pot Anticancer activity
The authors would like to thank the Sichuan Provincial Science and Technology (2017fz0084), the Sichuan Province medical association (s15074), Chongqing Research Program of Basic Research and Frontier Technology (cstc2016jcyjA0534 and cstc2018jcyjAX0219) and the Scientific Research Foundation of the Chongqing University of Arts and Sciences (R2013XY01, R2015BX03, 2017ZBX05 and 2017ZBX10). We would also like to thank Ms H.Z. Liu for obtaining the LC/MS and NMR data.
Compliance with ethical standards
Conflict of interest
The authors have declared no conflict of interest.
- 5.Voss ME, Carter PH, Tebben AJ, Scherle PA, Brown GD, Thompson LA, Xu M, Lo YC, Yang G, Liu R-Q, Strzemienski P, Gerry Everlof J, Trzaskos JM, Decicco CP (2003) Both 5-arylidene-2-thioxodihydropyrimidine-4,6(1H,5H)-diones and 3-thioxo-2,3-dihydro-1H-imidazo[1,5-α]indol-1-ones are light-dependent tumor necrosis factor-α antagonists. Bioorg Med Chem Lett 13:533–538. https://doi.org/10.1016/S0960-894X(02)00941-1 CrossRefGoogle Scholar
- 8.Van-Gelder JM, Klein JY, Basel Y, Reizelman A, Tchilibon S, Mouallem O (2006) Preparation of rhodanine derivatives and analogs thereof as rigidified compounds for modulating heparanase activity. WO2006072953 A2Google Scholar
- 10.Sharp PP, Banwell MG, Renner J, Lohmann K, Willis AC (2013) Consecutive gold(I)-catalyzed cyclization reactions of o-(Buta-1,3-diyn-1-yl-)-substituted N-Aryl ureas: a one-pot synthesis of pyrimido[1,6-α]indol-1(2H)-ones and related systems. Org Lett 15:2616–2619. https://doi.org/10.1021/ol4007986 CrossRefGoogle Scholar