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.
Synthesis method of beta-chloro acid ester and alpha, beta-unsaturated acid ester compound
-
Paragraph 0103-0107, (2021/08/11)
The invention belongs to the technical field of organic chemistry, and particularly relates to a synthesis method of beta-chloro acid ester and an alpha, beta-unsaturated acid ester compound. The structure of the compound is characterized by 1H NMR and 13C NMR and is confirmed. The method comprises the steps of by taking acetonitrile as a solvent, carrying out fragmentation on olefin, chlorooxalic acid monoester and 2, 6-dimethyl pyridine under a photocatalytic condition to generate an alkoxyacyl free radical intermediate, carrying out free radical addition reaction on the alkoxyacyl free radical intermediate and the olefin to generate carbon free radicals, then carrying out chlorination reaction to obtain the beta-chloro acid ester compound, and carrying out dehydrochlorination reaction under a DBU condition to generate the alpha, beta-unsaturated acid ester compound. The preparation method of the compound disclosed by the invention has the advantages of starting from olefin, being mild in condition, simple and efficient, strong in functional group compatibility and wide in substrate application range, and various beta-chloro acid ester and alpha, beta-unsaturated acid ester compounds can be synthesized from highly commercialized raw materials. On the basis of photoreaction of fluid chemistry, a target product can also be obtained with a relatively good yield, and the method has very good industrial and medicinal chemistry application values.
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.
