1846-90-8Relevant academic research and scientific papers
KPF6-Mediated Esterification and Amidation of Carboxylic Acids
Kumar, Anil,Shinde, Vikki N.,Sonam
, (2022/02/07)
A novel KPF6-promoted green method has been developed for the synthesis of esters and amides. A wide range of carboxylic acids and alcohols or amines worked well under the developed reaction conditions, thus providing good to excellent (61-98%) yields of
Synthesis, antiproliferative activities, and DNA binding of coumarin-3-formamido derivatives
Shi, Jiuzhou,Lu, Wen,Chen, Jichao,Sun, Lu,Yang, Shilong,Zhou, Mengyi,Xu, Li,Ma, Ying,Yu, Long
, (2020/10/21)
Ten coumarin-3-formamido derivatives, N-benzyl-coumarin-3-carboxamide (2), N-fluorobenzyl-coumarin-3-carboxamide (3–5), N-methoxybenzyl-coumarin-3-carboxamide (6–8), N-((1-methyl-1H-imidazol-5-yl)methyl)-coumarin-3-carboxamide (9), N-(thiophen-2-ylmethyl)-coumarin-3-carboxamide (10), and N-(furan-2-ylmethyl)-coumarin-3-carboxamide (11), were synthesized and characterized. Compound 5 crystallizes in a monoclinic system P21/c space group with four chemical formulas in a unit cell; molecules of compound 5 are self-assembled into a two-dimensional supramolecular structure by intermolecular hydrogen bonds and C?C π stacking. The potential anticancer effects of these compounds on HeLa (cervical carcinoma), MCF-7 (breast), A549 (lung), HepG2 (liver), and human umbilical vein (HUVEC) cells were examined. Compared with compounds 1–8 and 10–11, compound 9 exhibits potent in vitro cytotoxicity against HeLa cells and lower cytotoxicity against normal cells. Therefore, further in-depth investigations of compound 9 were performed. Absorption titration experiments and fluorescence spectroscopy studies suggested that compound 9 binds to DNA through the intercalation mode.
Design, synthesis and antifungal activity evaluation of coumarin-3-carboxamide derivatives
Yu, Xiang,Teng, Peng,Zhang, Ya-Ling,Xu, Zhao-Jun,Zhang, Ming-Zhi,Zhang, Wei-Hua
, p. 387 - 395 (2018/04/19)
A series of coumarin-3-carboxamides/hydrazides have been designed and synthesized, all the target compounds were evaluated in vitro for their antifungal activity against Botrytis cinerea, Alternaria solani, Gibberella zeae, Rhizoctorzia solani, Cucumber anthrax and Alternaria leaf spot, some of the designed compounds 4a-4g exhibited potential activity in the primary assays, this highlighted by the compounds 4a, 4d, 4e and 4f, EC50 values of which against Rhizoctorzia solani were as low as 1.80 μg/mL, 2.50 μg/mL, 2.25 μg/mL and 2.10 μg/mL, respectively, exhibiting more effective control with that of the positive control than Boscalid. Furthermore, compounds 4a and 4e represented equivalent antifungal activity with Boscalid against Botrytis cinerea.
Lanthanum(III)-Catalyzed Three-Component Reaction of Coumarin-3-carboxylates for the Synthesis of Indolylmalonamides and Analysis of Their Photophysical Properties
Jennings, Julia J.,Bhatt, Chinmay P.,Franz, Annaliese K.
, p. 6211 - 6222 (2016/08/16)
New methodology has been developed for the Lewis acid catalyzed synthesis of malonamides. First, the scandium(III)-catalyzed addition of diverse nucleophiles (e.g., indoles, N,N-dimethyl-m-anisidine, 2-ethylpyrrole, and 2-methylallylsilane) to coumarin-3-carboxylates has been developed to afford chromanone-3-carboxylates in high yields as a single diastereomer. Upon investigating a subsequent lanthanum(III)-catalyzed amidation reaction, a new multicomponent reaction was designed by bringing together coumarin-3-carboxylates with indoles and amines to afford indolylmalonamides, which were identified to exhibit fluorescent properties. The photophysical properties for selected compounds have been analyzed, including quantum yield, molar absorptivity, and Stokes shift. Synthetic studies of several reaction byproducts involved in the network of reaction equilibria for the three-component reaction provide mechanistic insight for the development of this methodology.
Synthesis and research of benzylamides of some isocyclic and heterocyclic acids as potential anticonvulsants
Strupinska, Marzanna,Rostafinska-Suchar, Grazyna,Pirianowicz-Chaber, Elzbieta,Stables, James P.,Jiang, Jeff,Paruszewski, Ryszard
, p. 681 - 686 (2013/10/01)
A series of benzylamides of isocyclic and heterocyclic acids was synthesized and tested in Anticonvulsant Screening Project (ASP) of Antiepileptic Drug Development Program (ADDP) of NIH. Near all synthesized derivatives of heterocyclic acids showed activity. All obtained derivatives of mono- and bicyclic isocyclic acids were inactive. The power of action of heterocyclic acids derivatives seems does not depend upon kind of heteroatom (N, O or S). One of the compounds (2-furoic acid benzylamide (4)) appeared most promising. It showed in minimal clonic seizure (6Hz) test (ASP) in rats after i. p. administration: MES ED50 = 36.5 mg/kg, TOX TD50 = 269.75 mg/kg, and PI = 7.39.
Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives
Bonsignore,Loy,Secci,Calignano
, p. 517 - 520 (2007/10/02)
Continuing our research on the synthesis and biological activity of heterocyclic compounds synthesized by carbon suboxide, we prepared and screened some 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives. The results of pharmacological assays are reported
