Synthesis and Cytotoxicity of 1,4‐Dihydropyridines and an Unexpected 1,3‐Oxazin‐6‐one

Abstract

Eight heterocycles have been prepared in a one-pot reaction manner based on the Hantzsch dihydropyridine synthesis. The synthesis afforded seven dihydropyridines (DHP) and one unexpected 1,3-oxazin-6-one. Their structures were confirmed based on NMR spectroscopy and mass spectrometry. The obtained products have been evaluated for their cytotoxicity against eight cancer cell lines and one normal cell line. Two halogenated DHPs (7 and 8) displayed cytotoxicity toward all the nine tested cancer cell lines with IC 50 values from 4.10 to 58.90 lM, while others showed selective activities. DHPs (7 and 8) bearing a Me group at C(2) and C(6) as well as a halogenated substituent at C(4 0 ) were more antiproliferative than the others.

Green synthesis of polyhydroquinolines via MCR using Fe3O4/SiO2-OSO3H nanostructure catalyst and prediction of their pharmacological and biological activities by PASS

“…The isolated yields were 97, 95, 94, 92, 91 and 90% for the fresh catalyst and five subsequent recycled runs, respectively. As a result, the catalytic performance and recyclability of Fe 3 O 4 /SiO 2 -OSO 3 H were better than catalysts previously reported in the literature [8][9][10][11][12] and also our earlier works [13,20].…”

“…Therefore, several synthetic methods have been reported in the literature for their synthesis [8][9][10][11][12][13]. Although these various methods have some advantages for the synthesis of polyhydroquinolines, they have some drawbacks such as harsh reaction conditions, use of expensive catalysts or reagents, tedious workup procedures, sensitivity to water and toxicity.…”

Search for Antimicrobial Activity Among Fifty-Two Natural and Synthetic Compounds Identifies Anthraquinone and Polyacetylene Classes That Inhibit Mycobacterium tuberculosis

“…Bismuth chloride was used to promote the reaction, which was carried out in tetrahydrofuran under reflux conditions and was stirred for 6 h to synthesize compounds C29–C33 ( Sandjo et al, 2016a ). C34–C41 were obtained from the same reaction conditions replacing ethyl benzoylacetate with ethyl acetylacetate in reflux and free catalyst conditions to prepare these dihydropyridine analogs.…”

“… Structures of the compounds tested for anti -M. tuberculosis activity: Dihydropyridines C29–C44 ( Sandjo et al, 2016a ; Pollo et al, 2017 ). …”

“… Structures of the compounds tested for anti -M. tuberculosis activity: Dihydropyridines C45–C49, coumarin C50, and polyacetylenes C51–C55 ( Sandjo et al, 2016a ; Pollo et al, 2017 ; Machado et al, 2018 ; Martin et al, 2018 ). …”