Intramolecular Ring Transformation of Bis‐oxadiazoles to Bis‐thiadiazoles and Investigation of Their Anticancer Activities

Abstract

A new series of 2,6‐dimethyl‐4‐phenyl‐N′3,N′5‐bis(3‐phenyl‐1,3,4‐thiadiazol‐2(3H)‐ylidene)‐1,4‐dihydropyridine‐3,5‐dicarbohydrazides were synthesized from reaction of 5,5′‐(2,6‐dimethyl‐4‐phenyl‐1,4‐dihydropyridine‐3,5‐diyl)bis(1,3,4‐oxadiazole‐2‐thiol) or diethyl 2,2′‐(2,6‐dimethyl‐4‐phenyl‐1,4‐dihydropyridine‐3,5‐dicarbonyl)bis(hydrazine‐1‐carbodithioate) with various hydrazonoyl chlorides. The structures of new compounds were established on the basis of their elemental analysis and IR, 1H NMR, and mass spectral data. The anticancer activities of the synthesized compounds were screened for their activity against human hepatocellular carcinoma (HepG2) cell lines, and the results showed that compounds 6l, 6k, and 6e were the most active (IC50 = 7.68 ± 9.8, 8.72 ± 9.7, and 9.78 ± 9.1 μM, respectively), compared with Cisplatin reference drug (IC50 value of 1.40 ± 1.1 μM).

Synthesis and In Silico Study of Some New bis-[1,3,4]thiadiazolimines and bis-Thiazolimines as Potential Inhibitors for SARS-CoV-2 Main Protease

“…Thus, many researchers orchestrated their efforts to formulate and construct novel bioactive bis -heterocycles as antiviral agents and other therapeutic effects. It has been reported in the literature that compounds containing bis -thiadiazole cores have attracted considerable interest in the area of drug discovery due to their potential as antihypertensive α -blocking [ 5 ], antimicrobial [ 6 , 7 , 8 ], and anticancer [ 9 , 10 ] agents. In addition, bis -thiazole pharmacophores were reported to reveal various biological activities such as anti-inflammatory, analgesic, anti-ulcerogenic [ 11 ], antiviral [ 12 ], antimicrobial [ 13 , 14 ], antioxidant [ 15 ], and anticancer activities [ 16 , 17 , 18 , 19 ].…”

Cross-Linked Chitosan/Multi-Walled Carbon Nanotubes Composite as Ecofriendly Biocatalyst for Synthesis of Some Novel Benzil Bis-Thiazoles

“…On the other hand, bis-thiazoles are known for their remarkable biological activities, having anticancerous, antibiotic, antimicrobial, antifungal, antibacterial, tuberculostatic, antiamoebial and anti-inflammatory activities [ 21 , 22 , 23 , 24 , 25 , 26 , 27 ].…”

Green synthesis, molecular docking and anticancer activity of novel 1,4-dihydropyridine-3,5-Dicarbohydrazones under grind-stone chemistry

“…1,4-Dihydropyridines are important class of compounds in the field of pharmaceuticals and drugs. Researches on dihydropyridine and its synthetic analogs has revealed that they possess many biological activities such as vasodilates, antihypertensive, antiinflammatory, anti-ischemic agents, antianginal, antithrombotic, anticonvulsant, antimicrobial activities (11)(12)(13)(14)(15)(16)(17)(18). Moreover, many heterocyclic hydrazones represents an interesting class of hetero compounds with a broad spectrum of biological activities, analgesic, anti-inflammatory, antimicrobial, antitubercular, antiplatelet, anticonvulsant, antimalarial and antiviral activities (19)(20)(21)(22)(23).…”