Synthesis and antitumor evaluation of some new thiazolopyridine, nicotinonitrile, pyrazolopyridine, and polyhydroquinoline derivatives using ceric ammonium nitrate as a green catalyst

Abstract

A novel series of thiazolo[5,4‐b]pyridine, polysubstituted pyridines, pyrazolo [3,4‐b] pyridine‐5‐carbonitriles, and polyhydroquinoline were synthesized via one‐pot reaction of 2‐iminothiazolidin‐5‐one, acetyl pyridine, pyrazolone, and/or cyclohexanone with various aldehydes, some active methylene and ammonium acetate in the presence of ceric ammonium nitrate (CAN). The resulting compounds were generated in high yields in a short amount of time, and the structures of the novel compounds were confirmed using IR, 1H NMR, 13C‐NMR, and mass spectra. The cytotoxic activity of 15 substances was tested in vitro against HePG‐2 and Caco‐2 cell lines. The results of antitumor assay confirmed that quinoline 12d compounds possess higher cytotoxic activity against two cell lines closed to doxorubicin, which is used as a standard anticancer drug. Also, 12c compounds are more efficient antitumor against the 2‐cell lines. While compounds 1 showed moderate activity toward Caco‐2. On the other hand, most of the tested compounds exhibited moderate to low cytotoxic activity toward the two cell lines. Based on the results, some of the newly synthesized derivatives showed excellent antitumor activity that qualified them for biomedical applications.

Fused Pyridine Derivatives: Synthesis and Biological Activities

“…Antibacterial (against both gram-positive and gram-negative bacteria), antiviral, antifungal, antituberculose, and antiparasitic activity of compounds containing thiazolopyridine structure were reported [247][248][249][250][251]. Additionally, cytotoxic and anticancer activity of thiazolopyridine derivatives were investigated in many studies [252][253][254][255]. Moreover, there are many thiazolopyridine-bearing compounds with various bioactivity profile, such as histamine H3-receptor antagonistic activity, mGluR5metabotropic glutamate receptor subtype 5-antagonist, sphingosine-1-phosphate (S1P) agonist, DNA Gyrase B (GyrB) ATPase inhibitor, anti-inflammatory activity, phosphoinositide 3-kinase inhibitor, and allosteric inhibitor of MALT1 [129,[256][257][258][259][260][261].…”

Exploring Chemistry with Pyridine Derivatives

“…Antibacterial (against both gram-positive and gram-negative bacteria), antiviral, antifungal, antituberculose, and antiparasitic activity of compounds containing thiazolopyridine structure were reported [247][248][249][250][251]. Additionally, cytotoxic and anticancer activity of thiazolopyridine derivatives were investigated in many studies [252][253][254][255]. Exploring Chemistry with Pyridine Derivatives 132 Moreover, there are many thiazolopyridine-bearing compounds with various bioactivity profile, such as histamine H3-receptor antagonistic activity, mGluR5metabotropic glutamate receptor subtype 5-antagonist, sphingosine-1-phosphate (S1P) agonist, DNA Gyrase B (GyrB) ATPase inhibitor, anti-inflammatory activity, phosphoinositide 3-kinase inhibitor, and allosteric inhibitor of MALT1 [129,[256][257][258][259][260][261].…”

Design, green synthesis, and quorum sensing quenching potential of novel 2-oxo-pyridines containing a thiophene/furan scaffold and targeting a LasR gene on P. aeruginosa

“…As a result of their chemical and physical properties, chemical compounds exert their therapeutic effects on biomolecules in contact with them. 67,68 Our most active derivatives 2a, 2b, 3a, 3b, 6a, and 6b were evaluated to determine the molecular properties, drug likeness, and some medicinal chemistry prediction items as described in Table 6 compared with Doxycycline using SwissADME web tools as described previously. 69,70 All the 2-oxo-pyridine derivatives exhibited obeys to Lipinski rule of ve without any violation.…”