216985-29-4Relevant 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.
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, molecular modeling, and selective inhibitory activity against human monoamine oxidases of 3-carboxamido-7-substituted coumarins
Chimenti, Franco,Secci, Daniela,Bolasco, Adriana,Chimenti, Paola,Bizzarri, Bruna,Granese, Arianna,Carradori, Simone,Yá?ez, Matilde,Orallo, Francisco,Ortuso, Francesco,Alcaro, Stefano
experimental part, p. 1935 - 1942 (2009/12/07)
A large series of 3-carboxamido-7-substituted coumarins have been synthesized and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Taking into account all the relevant structural information on MAOs reported in the literature, we made some changes in the coumarin nucleus and examined with particular attention the effect on activity and selectivity of substituting at position 3 with N-aryl or N-alkyl carboxamide and at position 7 with a benzyloxy or a 4'-F-benzyloxy group. Some of the assayed compounds proved to be potent, selective inhibitors of hMAO-B with IC50 values in the micromolar range. To better understand the enzyme-inhibitor interaction and to explain the selectivity of the most active compounds toward hMAOs, molecular modeling studies were carried out on new, high resolution, hMAO-A and hMAO-B crystallographic structures. ?2009 American Chemical Society.
