24689-27-8Relevant articles and documents
Coumarin-derived azolyl ethanols: synthesis, antimicrobial evaluation and preliminary action mechanism
Peng, Xin-Mei,Kumar, Kannekanti Vijaya,Damu, Guri L.V.,Zhou, Cheng-He
, p. 878 - 894 (2016)
A series of coumarin-derived azolyl ethanols including imidazolyl, triazolyl, tetrazolyl, benzotriazolyl, thiol-imidazolyl and thiol-triazolyl ones were conveniently synthesized and characterized by IR, 1H NMR, 13C NMR and high-resolution mass spectra (HRMS) spectra. Some of the prepared compounds showed appropriate logPow values and effective antibacterial and antifungal activities. Noticeably, compound 14 with bis-triazolyl ethanol group exhibited low minimal inhibitory concentration (MIC) value of 8 mg/mL against MRSA, which was comparable or even superior to reference drugs Norfloxacin (MIC=8 mg/mL) and Chloramphenicol (MIC=16 mg/mL). It could also effectively inhibit the growth of the tested fungal strains compared to Fluconazole. Further binding studies of coumarin 14 with calf thymus DNA were investigated by UV-Vis absorption and fluorescence spectroscopy. It was found that compound 14 could interact with calf thymus DNA by groove binding to form 14-DNA complex via both hydrogen bonds and van der Waals force, which might be the factor to exert the powerful antimicrobial activity.
Resolution, absolute configuration and antifilarial activity of coumarinyl amino alcohols
Priyanka,Misra, Sweta,Misra-Bhattacharya, Shailja,Butcher, Ray J.,Katiyar, Diksha
, p. 734 - 743 (2017)
The resolution of racemic coumarinyl amino alcohols 5–10 was achieved by using the inexpensive and readily accessible chiral resolving agent N-carbethoxy-L-proline (S)-11. Direct esterification of rac-5–10 with (S)-11 furnished diastereomeric esters, which were easily separated by column chromatography. The obtained diastereomers yielded the desired enantiopure coumarinyl amino alcohols (S)-(+)-5–10 and (R)-(?)-5–10 in good yields with high enantiomeric excess on saponification. The absolute configurations were determined by X-ray crystal analysis and/or by comparison of the specific rotations. Furthermore, in in vitro antifilarial motility inhibition assays, enantiopure coumarins (S)-(+)-9, (R)-(?)-9 and (S)-(+)-10, (R)-(?)-10 were found to be less efficient in affecting the viability of macrofilariae of Brugia malayi than their racemic forms 9 and 10, respectively, indicating the synergistic effect of the enantiomers in evoking antifilarial action.
Synthesis and evaluation of cytotoxicity of novel coumarin peptide alcohol derivatives
Adhav, Pravin B.,Chabukswar, Anurudhha,Chabukswar, Vasant V.,Dallavalle, Sabrina,Diwate, Balasaheb B.,Gawali, Sunita S.,Jagdale, Swati C.,Kodam, Kisan M.,Pawar, Digamber S.,Tapase, Savita R.
, p. 926 - 936 (2021/10/21)
Background: Coumarins are naturally occurring biologically active heterocyclic molecules endowed with a wide range of biological properties, including antibacterial, antifungal, and antitumor activities. Objective: The present work was aimed to synthesize new coumarin-containing compounds and to investigate their cytotoxic activity. Methods: Coumarin peptide and coumarin amino alcohols were prepared by treating epoxide-containing coumarin derivatives with suitable aromatic amines and peptides in trifluoroethanol as a solvent at 50°C. These derivatives were evaluated for their cytotoxic activity on three different cell lines: HeLa, MDA-MB-231 and L-132. Cell viability was determined by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Results: A new protocol was developed for the synthesis of thirteen novel coumarin peptide and coumarin amino alcohol derivatives. Among the tested compounds, three derivatives showed significant activity against all the tested cell lines. Docking studies indicated favorable interactions of the disubstituted peptide coumarin derivatives with the Asp 351 and Thr 347 amino acids at the active site of the human estrogen receptor. Conclusions: The results suggest that the synthesized compounds may be promising candidates in the research of new antitumor compounds.
