Pyridine- and Thiazole-Based Hydrazides with Promising Anti-inflammatory and Antimicrobial Activities along with Their In Silico Studies

Abstract

A new class of compounds formed by the linkage of −C(O)–NH– with pyridine and thiazole moieties was designed, synthesized, and characterized by various spectral approaches. The newly characterized compounds were evaluated for their antimicrobial as well as anti-inflammatory properties. The in vitro anti-inflammatory activity of these compounds was evaluated by denaturation of the bovine serum albumin method and showed inhibition in the range of IC 50 values—46.29–100.60 μg/mL. Among all the tested compounds, compound 5l has the highest IC 50 value and compound 5g has the least IC 50 value. On the other hand, antimicrobial results revealed that compound 5j showed the lowest MIC values and compound 5a has the highest MIC values. Furthermore, molecular docking of the active compounds demonstrated a better docking score and interacted well with the target protein. Physicochemical parameters of the titled compounds were found suitable in the reference range only. The in silico molecular docking study revealed their COX-inhibitory action. Compound 5j emerged as a significant bioactive molecule among the synthesized analogues.

Thiazole Ring—A Biologically Active Scaffold

“…Kamat et al [73] designed and synthesized a new class of compounds by the linkage of −C(O)−NH− between pyridine and thiazole moieties with the aim to study their antimicrobial as well as anti-inflammatory activity. All compounds were tested against antibacterial strains such as S. aureus (MTCC 9660), B. subtilis (MTCC 441), E. coli (MTCC 443), and P. aeruginosa (MTCC 424) as well as fungal strains, namely A. flavus (MTCC 1316), Trichoderma atroviridae (T. atroviridae, MTCC 28036), Penicillium citranum (P. citranum, MTCC9849), and C. albicans (MTCC 461).…”

“…The results revealed that compounds 159a (IC50 4.040 nΜ and 4.520 nM, respectively) and 159b (IC50 7.50 nΜ and 16.02 nM) were the most active COX-1/COX-2 inhibitors compared to celecoxib (IC50 15.00 μΜ and 40.00 nM) and naproxen (IC50 8.70 μΜ and 520.0 nΜ) with compound 159a being more than 10 times more active than celecoxib and 115 times more potent than naproxen. Kamat et al [73] synthesized thiazole-based hydrazide derivatives and evaluated their anti-inflammatory activity by inhibition of the protein (bovine albumin) denaturation method using diclofenac sodium as a standard drug. The inhibition was determined using concentrations varying from 20 to 100 μg/mL.…”

“…The most potent inhibitor among all compounds tested proved to be N,N-dimethyl-1-(6-(4-(methylsulfonyl)phenyl)imidazo[2,1-b]thiazol-5-yl)methanamine (161a) with IC50 Kamat et al [73] synthesized thiazole-based hydrazide derivatives and evaluated their anti-inflammatory activity by inhibition of the protein (bovine albumin) denaturation method using diclofenac sodium as a standard drug. The inhibition was determined using concentrations varying from 20 to 100 µg/mL.…”

Synthesis and Physicochemical Characterization of Novel Dicyclopropyl-Thiazole Compounds as Nontoxic and Promising Antifungals

“…Due to the nonlinear optical properties (NLO) of the thiazole system, it is used in optical devices such as photovoltaic detectors or light-emitting diodes [14]. However, its greatest advantage is that it exhibits a wide range of biological properties, such as antimicrobial [15][16][17][18], anticancer [19][20][21], anticonvulsant [22], antioxidant [23] and anti-SARS-CoV [24]. Numerous studies, including those carried out over the years by our group, show that thiazole derivatives have high antifungal activity [3,25].…”

New Substituted 5-Benzylideno-2-Adamantylthiazol[3,2-b][1,2,4]Triazol-6(5H)ones as Possible Anti-Inflammatory Agents

“…Thiazole ring is an important heterocyclic system possessing a wide range of pharmacological activities. Among them are bacteriostatics, antibiotics [ 8 , 9 , 10 ], local anesthetics [ 11 ], anti-inflammatory [ 12 , 13 , 14 , 15 ], analgesic and antipyretics [ 16 ], anti-HIV [ 17 , 18 ], antiallergic [ 19 ], antihypertensives [ 20 ] against schizophrenia [ 21 ] and hypnotics [ 22 ]. Furthermore, some drugs, such as meloxicam, a new NSAID [ 23 ], the sulfathiazole, simple sulfonamide antibacterial, as well as niridazole, stronger medicine drug against schistosomiasis [ 24 ] contain thiazole ring in its molecules.…”