Discovery andw biological evaluation of novel 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives possessing 1,2,3-triazole-4-carboxamide moiety as c-Met kinase inhibitors

Quinoline-Based Molecules Targeting c-Met, EGF, and VEGF Receptors and the Proteins Involved in Related Carcinogenic Pathways

“…In the last few years, a lot of more active and selective quinoline derivatives have been synthesized and biologically evaluated by modifying lead compounds ( Table 1 ). The most representative modifications are: (1) at position C-7 of quinoline ring system, generally with the introduction of appropriate substituents to improve solubility, (2) at the linker portion [ 34 ], that has been modified by different cyclic/acyclic 5-atoms-analogues with similar electronic features: pyridazinone-3-carboxyamide 3 [ 35 ], 3-oxo-3,4-dihydroquinoxaline 4 [ 36 ], 1H-imidazole-4-carboxamide or (E)-3-hydrosulfonylacrylamide 5 , 6 [ 37 ], 1,2,3-triazole-4-carboxamide 7 , 8 [ 38 , 39 ], 2-imidazolone-4-carboxamide 9 [ 40 ], acylhydrazone moiety 10 [ 41 ], pyridine/pyrimidine-2-carboxyamide 11 [ 42 ], 2-phenylquinoline-4-carboxamide 12 [ 33 ], 4-oxo-1,4-dihydrocinnoline-3-carboxamide moiety 13 [ 43 ], acyclic semicarbazones 14 [ 44 , 45 ], acylthiourea moiety [ 46 ], l,2,4-triazine-3,5-dione 15 [ 47 ], 1,8-naphthyridin-2-one 16 [ 48 ], 2-oxo-1,2-dihydropiridine-3-carboxamide 17 [ 49 ], 4-oxo-1,4-dihydroquinoline-3-carboxamide 18 [ 50 ], 5-(aminomethylene)pyrimidine-2,4,6-trione moiety 19 [ 51 ], 4-oxo-3,4-dihydrophthalazine-1-carboxamide 20 [ 52 ], pyrazolone 21 [ 53 ], and (thio)semicarbazone 22 [ 54 ].…”

Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-chlorophenyl)-5-cyclopropyl-1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxamide

“…In our previous studies on the anticancer screening of various 1,2,3-triazoles, compounds based on 1,2,3-triazolyl-4carboxamide scaffolds possessed the highest antiproliferative activity (Shyyka et al, 2019;Pokhodylo et al, 2013Pokhodylo et al, , 2014. Furthermore, a series of 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives possessing the 1,2,3-triazole-4carboxamide moiety have been evaluated against c-Met kinase and five typical cancer cell lines (A549, H460, HT-29, MKN-45 and U87MG) and exhibited moderate to excellent ISSN 2056-9890 antiproliferative activity (Zhou et al, 2014). A library of 1-benzyl-N-(2-(phenylamino)pyridin-3-yl)-1H-1,2,3-triazole-4-carboxamides was screened for their antiproliferative activity and showed promising cytotoxicity against lung cancer cell line A549 (Prasad et al, 2019).…”

1,2,3-Triazole-fused spirochromenes as potential anti-tubercular agents: synthesis and biological evaluation

“…The strategy adopted for synthesis of 1,2,3-triazole-fused spirochromene scaffolds, is depicted in Scheme 1. In the rst step, Kabbe condensation of substituted acetophenones 1a-c with 1,4-dioxaspiro [4.5]decan-8-one 2, in the presence of pyrrolidine gave corresponding dispiro[chromane-2,1 0 -cyclohexane-4 0 ,2 00 - [1,3]dioxolan]-4-ones 3a-c. 36,37 Subsequently, these were subjected to reduction using sodium borohydride (NaBH 4 ) to afford the spirochromanols 4a-c. 38 The following spirochromanols 4a- c on deprotection and dehydration with excess 6 N HCl provided the corresponding spirochromene 5a-c. 39,40 Thus obtained spirochromenes 5a-c on [3 + 2] Huisgen cycloaddition using a catalytic amount of pyrrolidine, with various aryl azides 6a-e, 41 furnished 1,2,3-triazole-fused spirochromene scaffolds 7a-o in low to moderate yields (Scheme 1 & Fig. 5).…”