1878-29-1Relevant articles and documents
Synergistic Cooperative Effect of L-Arginine-[bmim]Br in Cascade Decarboxylative Knoevenagel-Thia-Michael Addition Reactions: Green Approach Towards C?S Bond Formation with In Situ Generated Unactivated α,β-Unsaturated Ester
Singh, Richa,Thopate, Yogesh,Equbal, Danish,Sinha, Arun K.
, p. 4412 - 4421 (2018)
In this report, a synergistic combination of L-arginine and [bmim]Br has been realized for the first time towards step-economical synthesis of β-aryl-β-sulfanyl esters from aromatic aldehyde, malonate and thiol via cascade thia-Michael addition reaction on in situ formed unactivated β-aryl-α,β-unsaturated esters (via decarboxylative Knoevenagel reaction) under metal-and acid/base-free conditions. Furthermore, the gram scalability and recyclability of the catalytic system (up to 5 cycles) makes our one-pot two-step protocol more economically efficient and synthetically attractive for cascade C?C and C?S bond formation than traditional two-step methods. The synergistic interaction of the catalytic system i. e. L-arginine with [bmim]Br has been probed by NMR (1H and 13C) studies. (Figure presented.).
Synthesis, in vitro cytotoxicity, and molecular docking study of novel 3,4-dihydroisoquinolin-1(2H)-one based piperlongumine analogues
Kulkarni, Mahesh R.,Lad, Nitin P.,Khedkar, Vijay M.,Gaikwad, Nitin D.
, p. 1359 - 1370 (2021/04/09)
With the aim of expanding the scope of SAR on piperlongumine (PL), a naturally occurring anticancer molecule, we have designed a novel hybrid molecule bearing 3,4-dihydroisoquinolin-1(2H)-one and trans-cinnamic acids. The structure, based on hybridization strategy, is used for hybridization of naturally occurring scaffolds. We have synthesized 14 hybrid molecules by coupling 3,4-dihydroisoquinolin-1(2H)-one core with cinnamic acids using the mix anhydride approach. The newly synthesized inhibitors were evaluated for cell viability against breast cancer MCF-7 and cervical cancer HeLa cell lines. Furthermore, the active compounds were screened for their potential in breast cancer MDA-MB-231, cervical cancer C33A cell lines, prostate cancer DU-145, PC-3, and normal VERO cells. From the series, compound 10g was seen to inhibit MCF-7 cell growth significantly with GI50 50 = 20 μM) and C33A (GI50 = 3.2 μM). While the inhibitor 10i inhibits MCF-7 breast cancer cell growth GI50 = 3.42 μM along with inhibition of cell growth in MDA-MB-231 (GI50 = 30 μM), HeLa (GI50 = 7.67 μM), C33A (GI50 = 13 μM), DU-145 (GI50 = 6.45 μM), PC-3 (GI50 = 8.68 μM), and VERO (GI50 = 2.93 μM), respectively. Furthermore, molecular docking study demonstrated these compounds could bind tightly to the colchicine domain of tubulin through a network of favorable steric and electrostatic interactions and thus act as a tubulin polymerization inhibitor.
Hypervalent iodine(iii) induced oxidative olefination of benzylamines using Wittig reagents
Ramavath, Vijayalakshmi,Rupanawar, Bapurao D.,More, Satish G.,Bansode, Ajay H.,Suryavanshi, Gurunath
, p. 8806 - 8813 (2021/05/26)
We have developed hypervalent iodine(iii) induced oxidative olefination of primary and secondary benzylamines using 2C-Wittig reagents, which provides easy access to α,β-unsaturated esters. Mild reaction conditions, good to excellent yields with high (E) selectivity, and a broad substrate scope are the key features of this reaction. We have successfully carried out the gram-scale synthesis of α,β-unsaturated esters.
A de novo peroxidase is also a promiscuous yet stereoselective carbene transferase
Stenner, Richard,Steventon, Jack W.,Seddon, Annela,Anderson, J.L. Ross
, p. 1419 - 1428 (2020/01/28)
By constructing an in vivo-assembled, catalytically proficient peroxidase, C45, we have recently demonstrated the catalytic potential of simple, de novo-designed heme proteins. Here, we show that C45's enzymatic activity extends to the efficient and stereoselective intermolecular transfer of carbenes to olefins, heterocycles, aldehydes, and amines. Not only is this a report of carbene transferase activity in a completely de novo protein, but also of enzyme-catalyzed ring expansion of aromatic heterocycles via carbene transfer by any enzyme.
