Synthesis of thiazole clubbed pyrazole derivatives as apoptosis inducers and anti-infective agents

Bansal, Kushal Kumar; Bhardwaj, Jitender Kumar; Saraf, Priyanka; Thakur, Vijay Kumar; Sharma, Prateek

doi:10.1016/j.mtchem.2020.100335

Cited by 19 publications

(13 citation statements)

References 23 publications

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“…Bansal et al [ 113 ] synthesized several bisthiazole derivatives containing a pyrazole moiety and investigated their antimalarial activity against Plasmodium falciparum . Compounds 49 and 50 ( Figure 11 ) with 4-fluoro and 2,6-dichloro substitution, respectively, exhibited excellent activity against P. falciparum , with IC 50 values equal to 0.23 and 0.31 µg/mL, respectively.…”

Section: Biological Activity Of Bisthiazole Derivativesmentioning

confidence: 99%

An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives

et al. 2021

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Thiazole, a five-membered heteroaromatic ring, is an important scaffold of a large number of synthetic compounds. Its diverse pharmacological activity is reflected in many clinically approved thiazole-containing molecules, with an extensive range of biological activities, such as antibacterial, antifungal, antiviral, antihelmintic, antitumor, and anti-inflammatory effects. Due to its significance in the field of medicinal chemistry, numerous biologically active thiazole and bisthiazole derivatives have been reported in the scientific literature. The current review provides an overview of different methods for the synthesis of thiazole and bisthiazole derivatives and describes various compounds bearing a thiazole and bisthiazole moiety possessing antibacterial, antifungal, antiprotozoal, and antitumor activity, encouraging further research on the discovery of thiazole-containing drugs.

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Section: Biological Activity Of Bisthiazole Derivativesmentioning

confidence: 99%

An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives

et al. 2021

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“…Under the present conditions selected, the products are stable and the reactions gave reasonably good yields. The chosen synthetic routes of the reported compounds in this study are straightforward with limited steps and readily accessible, cheap starting materials, and yields are reasonably high (Nayak et al, 2013;Bansal et al, 2020). The biological activities of few of the related triaryl-substituted (thiazol-2yl)pyrazole compounds have been reported in the literature, such as Salian et al (2017) have demonstrated radical scavenging capacity owing to the destabilization of the radical formed during oxidation.…”

Section: Chemical Contextmentioning

confidence: 91%

“…Pyrazole derivatives are an important class of N-heterocyclic compounds with a wide spectrum of biological activities including antibacterial (Song et al, 2013;Yan et al, 2015), antifungal (Gondru et al, 2015), anti-inflammatory (El-Sayed et al, 2012;Kadambar et al, 2021), antimicrobial and antitumor (Insuasty et al, 2010;Alam et al, 2016) activities. Thiazole derivatives similarly also exhibit a broad spectrum of biological activity, including anticancer (Bansal et al, 2020), anti-inflammatory (Sharma et al, 1998) and antimicrobial (Kalluraya et al, 2001) activity. Accordingly, we have sought to combine pyrazole and thiazole pharmacophores in a single molecular skeleton and synthesized triaryl-substituted (thiazol-2-yl)pyrazole compounds (C3,C5-aryl substitutions on the pyrazole ring and C4-aryl substitution on the thiazole ring).…”

Section: Chemical Contextmentioning

confidence: 99%

Formation of 1-(thiazol-2-yl)-4,5-dihydropyrazoles from simple precursors: synthesis, spectroscopic characterization and the structures of an intermediate and two products

Mahesha¹,

Yathirajan²,

Banu³

et al. 2021

Acta Cryst E

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Two new 1-(thiazol-2-yl)-4,5-dihydropyrazoles have been synthesized from simple precursors, and characterized both spectroscopically and structurally. In addition, two intermediates in the reaction pathway have been isolated and characterized, one of them structurally. The molecules of the intermediate (E)-1-(4-methoxyphenyl)-3-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one, C19H16O3 (I), are linked by a combination of C—H...O and C—H...π(arene) hydrogen bonds to form ribbons. The products (RS)-5-(4-methoxyphenyl)-1-(4-phenythiazol-2-yl)-3-[4-(prop-2-ynyloxy)phenyl]-4,5-dihydro-1H-pyrazole, C28H23N3O2S (II), and (RS)-5-(4-methoxyphenyl)-1-[4-(4-methylphenyl)thiazol-2-yl]-3-[4-(prop-2-ynyloxy)phenyl]-4,5-dihydro-1H-pyrazole, C29H25N3O2S (III), are closely related – differing only by presence or absence of a methyl group at the arylthiazolyl substituent – and crystallize in an isomorphous setting. Both molecules contain an effectively planar dihydro-pyrazole ring, and possess an overall T-shaped structure, which is a characteristic of triaryl-substituted 4,5-dihydro-1-(thiazol-2-yl)pyrazole compounds. The crystal packing is characterized by intermolecular C—H...S and C—H...π (aryl/alkyne) interactions. A combination of two C—H...π(arene) hydrogen bonds links the product molecules into sheets.

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“…Compounds containing thiazole rings play an important role in biological activities, organic synthesis, agrochemicals, and pharmaceuticals [3]. Thiazole derivatives have a broad spectrum of activities, namely, antidiabetic [4], antibacterial [5], antiviral [6], antifungal [7], anticancer [8], anti‐inflammatory [4], antimalarial [9], antitubercular [10], anthelmintic [11], antioxidant [12], anticonvulsant [13], cardiovascular [2], and analgesic and antipyretic [14]. Pioglitazone and rosiglitazone [15], meloxicam, cefotaxime, thiamin (vitamin B12), dasatinib, dabrafenib, pramipexole, nizatidine, and so forth [2, 16, 17] are the most known examples of drugs containing thiazole ring (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, molecular docking, and biological evaluation of 5‐alkyl(aryl)‐2‐isobutylthiazole derivatives: As α‐amylase, α‐glucosidase, and protein kinase inhibitors

Khan

Buğday

Rehman

et al. 2022

Applied Organom Chemis

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A series of 18 biologically active C5‐arylated‐2‐isobutylthiazole derivatives that were synthesized by Pd‐NHC complexes [Pd(μ‐Cl)Cl (NHC)]2, NHC = SIXyl, 2), (LCl2Pd‐NHC, L = PPh3, 3), (LCl2Pd‐NHC, L = Py, 4), (LCl2Pd‐NHC, L = 3‐CHO‐Py, 5) catalyzed C‐H bond activation reactions. The catalytic activity of Pd‐NHC complexes was examined on the C‐H bond activation reaction of 2‐isobutylthiazole. All Pd‐NHC complexes were characterized by 1H nuclear magnetic resonance specroscopy (NMR), 13C NMR, fouirer transform infrared spektroscopy (FTIR), quadrupole‐time of flying‐liquit cromotagraphy/mass spektroscopy (Q‐TOF‐LC/MS), gas chromatography–mass spectrometry (GCMS), and melting point detection technique. The physicochemical properties, pharmacokinetics, and drug‐likeness were calculated by SwissADME. PkCSM database was used to calculate toxicities profile. All the products (6a–6s) were additionally assessed in vitro for their antidiabetic potential using α‐amylase and α‐glucosidase inhibitory activities. The protein kinase activity was performed to evaluate their anticancer activities. All the compounds possess drug‐like characters as they followed Lipinski's rule of five (RO5). Almost all the compounds showed no to fewer toxicities. In addition, other than the compounds, that is, 6a, 6b, 6c, 6m, 6n, 6p, and 6s, the rest of the compounds showed good α‐glucosidase inhibitory potential (IC50 7.17 ± 0.201 to 74.08 ± 0.244 μg/ml) when compared with acarbose standard (IC50 16.59 ± 0.135 μg/ml). All compounds had moderate to good inhibitory potential against the α‐amylase enzyme, with IC50 values ranging from 12.00 ± 0.289 to 76.15 ± 0.477 μg/ml. Eleven analogs (6e, 6f, 6g, 6h, 6j, 6k, 6l, 6n, 6o, 6p, and 6r) showed good to moderate activity. Seven analogs (6a, 6b, 6c, 6d, 6i, 6m, and 6s) showed no α‐amylase inhibitory activity. The protein kinase inhibition potential was determined for the first time, and the compounds 6d, 6e, 6f, 6h, 6k, 6p, and 6r depicted activity with the zone of inhibition in the range of 9 ± 1.3 to 19 ± 1.5 mm. The ligands and active site binding interactions of α‐glucosidase, α‐amylase, and protein kinase enzymes were also studied using molecular modeling.

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Synthesis of thiazole clubbed pyrazole derivatives as apoptosis inducers and anti-infective agents

Cited by 19 publications

References 23 publications

An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives

An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives

Formation of 1-(thiazol-2-yl)-4,5-dihydropyrazoles from simple precursors: synthesis, spectroscopic characterization and the structures of an intermediate and two products

Synthesis, molecular docking, and biological evaluation of 5‐alkyl(aryl)‐2‐isobutylthiazole derivatives: As α‐amylase, α‐glucosidase, and protein kinase inhibitors

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