20583-78-2Relevant academic research and scientific papers
Electrochemical reduction of a bromo propargyloxy ester at silver cathodes in dimethylformamide
Henderson, Robert J.,Buehler, Nathan R.,Pasciak, Erick M.,Mubarak, Mohammad S.,Peters, Dennis G.
, p. G128 - G132 (2014)
Cyclic voltammograms for the reduction of ethyl 2-bromo-3-(3',4'-dimethoxyphenyl)-3-(propargyloxy)propanoate (1) at a silver cathode in dimethylformamide (DMF) containing 0.10 M tetraethylammonium tetrafluoroborate (TEABF4) exhibit several cathodic peaks,
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.
In silico design and synthesis of N-arylalkanyl 2-naphthamides as a new class of non-purine xanthine oxidase inhibitors
Ho, Sheau Ling,Lin, Ching-Ting,Lee, Shoei-Sheng
, p. 789 - 801 (2021/01/12)
A series of N-arylalkanyl 2-naphthamides (Xa~e), which were predicted from virtual molecular docking on a built xanthine oxidase template as potential inhibitors, were synthesized. Their inhibitory activity against xanthine oxidase was assayed. Among these prepared, compounds Xb (IC50 13.6?μM), Xc (IC50 13.1?μM), and Xd (IC50 12.5?μM) showed comparable inhibitory activity to allopurinol (IC50 22.1?μM). The in vitro assay result correlated well with molecular docking scores, ΔG?=??16.99, ?17.66, and ?17.13 Kcal/mol, respectively. On the potassium oxonate-induced hyperuricemic mice model, oral administration of Xc-Ac (40 mg/ Kg), the per-O-acetylated Xc, could reduce the blood uric acid level by 60% in comparison to the normal control group and is statistically significant (p .01) while compared with the hyperuricemic mice group.
S,O-Ligand-Promoted Pd-Catalyzed C?H Olefination of Anisole Derivatives
Fernández-Ibá?ez, M. ángeles,Jia, Wen-Liang,Sukowski, Verena,van Borselen, Manuela,van Diest, Rianne
supporting information, p. 4132 - 4135 (2021/08/24)
The C?H olefination of substituted anisole derivatives by a Pd/S,O-ligand catalyst is reported. The reaction proceeds under mild conditions with a broad range of substituted aryl ethers bearing both electron donating and withdrawing substituents at ortho,
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.
Synthesis of Bidentate Nitrogen Ligands by Rh-Catalyzed C-H Annulation and Their Application to Pd-Catalyzed Aerobic C-H Alkenylation
Kim, Hyun Tae,Kang, Eunsu,Kim, Minkyu,Joo, Jung Min
supporting information, p. 3657 - 3662 (2021/05/10)
A new class of bidentate ligands was prepared by a modular approach involving Rh-catalyzed C-H annulation reactions. The resulting conformationally constrained ligands enabled the Pd-catalyzed C-H alkenylation at electron-rich and sterically less hindered positions of electron-rich arenes while promoting the facile oxidation of Pd(0) intermediates by oxygen. This newly introduced ligand class is complementary to the ligands developed for Pd-catalyzed oxidative reactions and may find broad application in transition-metal-catalyzed reactions.
Regioselective Br?nsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with N′-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2- a]quinazolin-5(1 H)ones
Banerjee, Prabal,Kaur, Navpreet,Singh, Priyanka
, p. 3393 - 3406 (2020/03/23)
A highly regioselective synthesis of tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one derivatives was achieved by reacting cyclopropane aldehydes with N′-aryl anthranil hydrazides in the presence of p-toluene sulfonic acid (PTSA). The transformation involves domino imine formation and intramolecular cyclization to form 2-arylcyclopropyl-2,3-dihydroquinolin-4(1H)-one, followed by nucleophilic ring opening of the cyclopropyl ring to form desired tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one in good to excellent yield with complete regioselectivity. This protocol tolerates a great variety of functional groups and thus provides a simple and step-efficient method for pyrroloquinazolinone synthesis.
Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine
Banerjee, Prabal,Kumar, Pankaj,Kumar, Rakesh
supporting information, p. 6535 - 6550 (2020/06/09)
A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.
Br?nsted Acid Catalyzed Tandem Defunctionalization of Biorenewable Ferulic acid and Derivates into Bio-Catechol
Bal, Mathias,Bomon, Jeroen,Liao, Yuhe,Maes, Bert U. W.,Sels, Bert F.,Sergeyev, Sergey,Van Den Broeck, Elias,Van Speybroeck, Veronique
supporting information, p. 3063 - 3068 (2020/02/05)
An efficient conversion of biorenewable ferulic acid into bio-catechol has been developed. The transformation comprises two consecutive defunctionalizations of the substrate, that is, C?O (demethylation) and C?C (de-2-carboxyvinylation) bond cleavage, occurring in one step. The process only requires heating of ferulic acid with HCl (or H2SO4) as catalyst in pressurized hot water (250 °C, 50 bar N2). The versatility is shown on a variety of other (biorenewable) substrates yielding up to 84 % di- (catechol, resorcinol, hydroquinone) and trihydroxybenzenes (pyrogallol, hydroxyquinol), in most cases just requiring simple extraction as work-up.
Iron-Catalyzed Cross-Coupling of Bis-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and mechanistic investigations
Rousseau, Lidie,Desaintjean, Alexandre,Knochel, Paul,Lefèvre, Guillaume
supporting information, (2020/02/18)
Various substituted bis-(aryl)manganese species were prepared from aryl bromides by one-pot insertion of magnesium turnings in the presence of LiCl and in situ trans-metalation with MnCl2 in THF at ?5 ?C within 2 h. These bis-(aryl)manganese reagents undergo smooth iron-catalyzed cross-couplings using 10 mol% Fe(acac)3 with various functionalized alkenyl iodides and bromides in 1 h at 25 ?C. The aryl-alkenyl cross-coupling reaction mechanism was thoroughly investigated through paramagnetic 1H-NMR, which identified the key role of tris-coordinated ate-iron(II) species in the catalytic process.
