Design and synthesis of coumarin substituted oxathiadiazolone derivatives having anti-inflammatory activity possibly through p38 MAP kinase inhibition

Abstract

Compounds containing oxathiadiazolone nucleus bearing substituted coumarin ring were designed and synthesized while retaining the pharmacophores required for binding with p38 MAP kinase. A four-step synthetic scheme was employed for the synthesis of 7-methoxy-4-(3ǯ-substituted-2ǯ-oxo-1ǯ,2ǯ,3ǯ,5ǯ-oxathiadiazol-4ǯ-yl)-coumarin. The reactions were monitored by TLC and structures of the intermediates and the target compounds were ascertained by IR, NMR, Mass spectral data. The compounds were found to possess anti-inflammatory activity comparable to indomethacin. Superimposition studies of the target compounds with the lead p38 kinase inhibitors suggested that anti-inflammatory activity of the target compounds may be due to p38 MAP kinase inhibition. It was also suggested that methoxy group on coumarin nucleus may improve the binding profile with p38 MAP kinase.

Complete assignment of the 1H and 13C NMR spectra of antimicrobial 4‐arylamino‐ 3‐nitrocoumarin derivatives

“…The structural elucidation of these coumarin derivatives, which is important in the area of organic and medicinal chemistry, is heavily reliant on 1 H and 13 C NMR spectroscopy. However, many of the reported studies of these derivatives either do not provide NMR spectral data at all, or provide only limited, and often unassigned, NMR data 14–17. This situation is further complicated by the fact that full NMR assignments are often not performed due to a partial or complete overlap of the proton signals of the coumarinic moiety and also of the aryl side group.…”

Design, Synthesis, and Evaluation of the Kinase Inhibition Potential of Pyridylpyrimidinylaminophenyl Derivatives

“…1) [26] conserved in its structure; the drug is efficacious in imatinib resistant cases [27]. On the basis of above and considering the literature reports discussing Abl-imatinib structural interactions [16,[26][27][28][29][30][31][32], we decided to conjugate the scaffolds based on 2-pyridone [21,33,34], benzopyran-2-one [35], benzopyran-4-one [22,36], indole acetic acid, iso-nicotinic acid, hippuric acid, piperic acid, 2-oxoquinolinacetic acid, 3-oxobenzooxazinacetic acid [37], and trimethoxyphenyl acrylic acid [38], with PPAP moiety to form the amide/cyclic amide derivatives.…”

Pentafluorophenylammonium triflate (PFPAT) catalyzed facile construction of substituted chromeno[2,3-d]pyrimidinone derivatives and their antimicrobial activity

“…A new series of 4-(3-coumarinyl)-3-benzyl-4-thiazolin-2-one benzylidenehydrazones were synthesized, and they were evaluated for anti-tuberculosis activity against M. tuberculosis H37Rv in BACTEC 12B medium using the BACTEC 460 radiometric system [5] . Coumarin derivatives also used as anti-HIV [6] , antioxidant [7] , dyslipidemic [8] , anti-inflammatory agents [9] , and antimicrobial agents [10] .…”