54396-25-7Relevant academic research and scientific papers
Design, synthesis and in vitro evaluation of 2-oxo-n-substituted phenyl-2h-chromene-3-carboxamide derivatives as HIV integrase strand transfer inhibitors
Jadhav, Hemant R.,Jain, Priti,Wadhwa, Pankaj
, p. 416 - 425 (2020/04/17)
Background: A series of eighteen 2-Oxo-N-substituted phenyl-2H-chromene-3-carboxamide analogues has been evaluated for HIV-1 integrase (IN) inhibition. Methods: The derivatives were synthesized via a two-step pathway commencing with 2-hydroxybenzaldehyde and diethyl malonate followed by hydrolysis of ester and coupling with various aromatic amines. The HIV-1 IN inhibitory potential of these compounds has been studied relative to dolutegravir, a known HIV-1 IN inhibitor using a standard available kit. Results: Six molecules (compounds 13h, 13i, 13l, 13p to 13r) showed significant inhibition of HIV-1 integrase 3′-strand transfer with IC50 values less than 1.7 μM. The presence of chromene-3-carboxamide motif was shown to be crucial for the enzymatic activity. In addition, molecular modelling studies were also done to justify the IN inhibition and in vitro-in silico correlation was drawn. Conclusion: However, these compounds did not show HIV-1 and HIV-2 inhibition below their cytotoxic concentration indicating that these compounds cannot be taken further for anti-HIV activity as such and require structural modification.
A Primary Amide-Functionalized Heterogeneous Catalyst for the Synthesis of Coumarin-3-carboxylic Acids via a Tandem Reaction
Khullar, Sadhika,Mandal, Sanjay K.,Markad, Datta
supporting information, (2020/08/24)
A crystalline primary amide-based bifunctional heterogeneous catalyst, {[Cd2(2-BPXG)(Fum)2(H2O)2]·2H2O}n (1) (where, 2-BPXG = 2,2′-((1,4-phenylenebis(methylene))bis((pyridin-2-ylmethyl)azanediyl)) diacetamide and Fum = fumarate), has been developed for the one-pot synthesis of a series of potentially biologically active coumarin-3-carboxylic acids at room temperature via a Knoevenagel-intramolecular cyclization tandem reaction. Catalyst 1 is prepared at room temperature from a one-pot self-assembly process in 81% yield and high purity within a few hours and has a ladder-like polymeric architecture based on single-crystal X-ray diffraction. Additional characterization of 1 includes elemental analysis, infrared spectroscopy, thermogravimetric analysis, and powder X-ray diffraction. Based on the optimized conditions, it is determined that 1 is highly efficient (conditions: 2 mol % catalyst, 3 h, and 26-28 °C in methanol) for this reaction. Its recyclability up to five cycles without significant loss of activity and structural integrity is also demonstrated. Using both electron-donating and electron-withdrawing substituents on the salicylaldehyde substrate, seven different derivatives of coumarin-3-carboxylic acid were made. Additionally, the monoamine oxidase (MAO) inhibitor, coumarin-3-phenylcarboxamide, has also been synthesized from coumarin-3-carboxylic acid obtained in the catalysis process. A detailed mechanism of action is also provided.
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.
Synthesis of Multifunctionalized 2,3-Dihydro-4-pyridones and 4-Pyridones via the Reaction of Carbamoylated Enaminones with Aldehydes
Obydennov, Dmitrii L.,El-Tantawy, Asmaa I.,Sosnovskikh, Vyacheslav Y.
, p. 13776 - 13786 (2018/11/21)
The novel and effective diastereoselective synthesis of multifunctionalized dihydropyridones, including CF3-substituted derivatives, has been developed on the basis of the piperidine-promoted domino reaction of carbamoylated enaminones with ald
1,1'-carbonyldiimidazole (cdi) mediated facile synthesis, structural characterization, antimicrobial activity, and in-silico studies of coumarin- 3-carboxamide derivatives
Salar, Uzma,Khan, Khalid M.,Fakhri, Muhammad I.,Hussain, Shafqat,Tauseef, Saima,Ameer, Shagufta,Wadood, Abdul,Khan, Huma,Perveen, Shahnaz
, p. 86 - 101 (2018/02/14)
Background: Despite the availability of a variety of antibacterial agents, re-emergence of pathogenic bacteria is still a serious medical concern. So, identification of new, safer, and selective antibacterial agents is the key interest in the medicinal chemistry research. Method: To explore the antimicrobial activity of coumarin-3-carboxamides for a range of bacterial and fungal strains, twenty eight derivatives were synthesized by the reaction of coumarin-3-carboxylic acid with a variety of aniline derivatives in the presence of 1,1'-carbonyldiimidazole (CDI). All compounds were structurally characterized by different spectroscopic techniques EI-MS, HREI-MS, 1H-NMR, 13C-NMR, and evaluated for antimicrobial activities (antibacterial and antifungal). Results: A number of compounds showed good to weak antibacterial activity against various strains of Gram-positive and Gram-negative bacteria. Amongst them, compound 28 displayed noticeable inhibition against five strains of Gram-positive (Bacillus subtilis, Corynebacterium xerosis, Staphylococcus aureus, Streptococcus faecalis, and MRSA) and four strains of Gram-negative bacteria (Klebsiella pneumoniae, Pseudomonas aeruginosa, Enterobacter aerogene, and Shigella dysenteria). However, none of the compounds showed antifungal activity against tested fungi. MIC values were determined for most of the active compounds 2, 15, and 28 against particular bacterial cultures. In silico studies were performed on the most active compound 28 in order to specify and verify the target for antibacterial activity of synthetic coumarin-3-carboxamide derivatives. The cytotoxicity of these compounds on mammalian cells is unknown yet but we are planning to carry out research on the cytotoxic aspect of these compounds in future. Conclusion: The newly identified compounds may serve as lead molecules for the future research regarding the identification of new antibacterial agents.
Synthesis of novel 3-substitued coumarin carboxamides with biological interest and their spectral studies
Das, Asish R.,Medda, Arunima,Singha, Raghunath,Samanta, Anuva,Guchhait, Nikhil
experimental part, p. 1124 - 1129 (2010/03/03)
The 3-substitued coumarin carboxamides are prepared by a highly efficient one-pot procedure. The coupling reaction of coumarin carboxylic acids and its acid chlorides with different amines affodred amide derivatives of coumarin in moderate to high yields
Novel 3-carboxamide-coumarins as potent and selective FXIIa inhibitors
Robert, Séverine,Bertolla, Carine,Masereel, Bernard,Dogné, Jean-Michel,Pochet, Lionel
supporting information; experimental part, p. 3077 - 3080 (2009/04/07)
Recently, FXIIa was highlighted as an original attractive target for the development of new anticoagulant drugs with low rates of therapy-related hemorrhages. In this work, we describe the development of a new series of 3-carboxamide-coumarins that are the first potent and selective nonpeptidic inhibitors of FXIIa.
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
Coumarin congeners as antidepressants
Singh,Srivastava,Palit,Shanker
, p. 993 - 996 (2007/10/02)
3-Carboethyl coumarin (I) was converted to coumarin 3-acid hydrazide (II). This on reaction with appropriate aldehyde yielded 3-arylidino amino coumarin (III). Compound III on diazotisation and reaction with ferric chloride yielded the corresponding formazans viz. 3-substituted phenyl azoarylidino, amido coumarins (IVa1-a10) and oxadiazoles viz. 2-aryl-5-(3-coumarinyl)-1,3,4-oxadiazoles (Va1-a3), respectively. Simultaneously 3-carboethyl coumarin on hydrolysis gave 3-carboxy coumarin (VI) which on reaction with aryl amine in methylene chloride yielded 3-(N-aryl)amido coumarin (VIIa1-a3). The compounds were screened for their antidepressant activity against a tricyclic antidepressant (imipramine). Compounds IVa4, IVa5 and IVa9 exhibited activity better than imipramine with no toxicity (ALD50 > 1000 mg/kg) but IVa5 showed some side effects.
