2-Substituted thiazole-4-carboxamide derivatives as tiazofurin mimics: synthesis and in vitro antitumour activity

Popsavin, Mirjana; Kojić, Vesna; Spaić, Saša; Svirčev, Miloš; Bogdanovic, Gordana; Jakimov, Dimitar; Aleksić, Lidija D.; Popsavin, Velimir

doi:10.1016/j.tet.2014.02.035

Cited by 15 publications

(6 citation statements)

References 41 publications

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“…12 Thiazole containing marketed drugs Numbers of formulations are available in the market with international brand name that contains thiazole moiety having different pharmacological activities as described as below in Table 2. [13][14][15][16][17][18][19][20][21]…”

Section: Physical Propertiesmentioning

confidence: 99%

Thiazoles: A Retrospective Study on Synthesis, Structure-activity Relationship and Therapeutic Significance

Sharma¹,

Devgun²,

Narang³

et al. 2022

IJPER

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Thiazole or 1,3-thiazole is a distinct heterocyclic compound which incorporates sulphur and nitrogen atoms. It is a vital framework present in numerous pharmacologically active compounds, be it of natural origin or of synthetic nature. Many thiazoles having antitumor and antiviral activities, originate from microbes and marine organisms. A variety of synthetic drugs, having thiazole group, like antimicrobial sulfathiazole, antibiotic penicillin, antidepressant pramipexole, antineoplastic agent bleomycin, antiretroviral drug ritonavir, histamine H 2 receptor antagonist nizatidine, anti-inflammatory drug meloxicam, antifungal stilbene derivatives have been in the markets for quite some time. Hofmann and Hantzsch laid the groundwork for further development in the field of thiazole chemistry. The interaction of α-haloketones or α-halogenaldehyde and thioamide to obtain thiazoles is beautifully described by Hantzsch. Various studies have reported methods for the synthesis of the thiazoles; thioforamide, thiourea, α-thiocyanotoketones, and vinyl bromide have been extensively employed to synthesize thiazoles. The thiazoles have immense potential and this study tries to enlighten the crucial role of thiazoles for the betterment of society. The review provides different directions in the synthesis of novel thiazoles and also reveals diverse targets for augmentation in the field of designing of novel thiazoles.

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Section: Physical Propertiesmentioning

confidence: 99%

Thiazoles: A Retrospective Study on Synthesis, Structure-activity Relationship and Therapeutic Significance

Sharma¹,

Devgun²,

Narang³

et al. 2022

IJPER

View full text Add to dashboard Cite

show abstract

“…There are many compounds bearing this fragment which are used in therapy, for treating inflammation [16], oxidative stress [17,18], bacterial infections [19][20][21], hyperglycemia, hyperlipidemia [22], cancer [23][24][25], schizophrenia, hypertension, HIV infection, hypnotics, allergy, etc.…”

Section: Open Accessmentioning

confidence: 99%

New Hydrazones Bearing Thiazole Scaffold: Synthesis, Characterization, Antimicrobial, and Antioxidant Investigation

et al. 2015

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New series of hydrazones 5-18 were synthesized, in good yields, by reacting 4-methyl-2-(4-(trifluoromethyl)phenyl)thiazole-5-carbohydrazide with differently substituted benzaldehyde. The resulting compounds were characterized via elemental analysis, physico-chemical and spectral data. An antimicrobial screening was done, using Gram (+), Gram (−) bacteria and one fungal strain. Tested molecules displayed moderate-to-good growth inhibition activity. 2,2-Diphenyl-1-picrylhydrazide assay was used to test the antioxidant properties of the compounds. Monohydroxy (14-16), para-fluorine (13) and 2,4-dichlorine (17) derivatives exhibited better free-radical scavenging ability than the other investigated molecules.

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“…The myriad spectrum of therapeutic applications associated with thiazoles has encouraged medicinal chemists to design and synthesize a large number of new thiazole-based therapeutic agents. Several thiazole derivatives have been reported to show significant antimicrobial, antitumor, antiviral, antimalarial, anthelmintic, antidiabetic, antioxidant, anticonvulsant, antiasthmatic, analgesic, anti-inflammatory, and other activities [ 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. In particular, the clinical efficacy of tiazofurin, bleomycins (BLMs), and dasatinib has pointed out the medicinal significance of thiazole scaffold for the treatment of cancer [ 14 , 15 , 16 ].…”

Section: Introductionmentioning

confidence: 99%

“…Several thiazole derivatives have been reported to show significant antimicrobial, antitumor, antiviral, antimalarial, anthelmintic, antidiabetic, antioxidant, anticonvulsant, antiasthmatic, analgesic, anti-inflammatory, and other activities [ 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. In particular, the clinical efficacy of tiazofurin, bleomycins (BLMs), and dasatinib has pointed out the medicinal significance of thiazole scaffold for the treatment of cancer [ 14 , 15 , 16 ]. Recent studies have indicated that thiazole derivatives show significant antitumor activity against different cancer cell lines through the inhibition of histone deacetylases (HDACs), pro-matrix metalloproteinase activation, signal transducer and activator of transcription 3 (STAT3), Bcl-2 family, and kinases including Akt isoforms, aurora kinases, and cyclin-dependent kinases (CDKs) [ 17 , 18 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Evaluation of a New Series of Thiazole-Based Anticancer Agents as Potent Akt Inhibitors

et al. 2018

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In an attempt to develop potent anticancer agents targeting Akt, new thiazole derivatives (1–10) were synthesized and investigated for their cytotoxic effects on A549 human lung adenocarcinoma, C6 rat glioma, and NIH/3T3 (healthy) mouse embryonic fibroblast cell lines. The most potent compounds were also investigated for their effects on apoptosis and Akt pathway. The most promising anticancer agent was found to be 2-[2-((4-(4-cyanophenoxy)phenyl)methylene)hydrazinyl]-4-(4-cyanophenyl)thiazole (6), due to its selective inhibitory effects on A549 and C6 cells with IC50 values of 12.0 ± 1.73 µg/mL and 3.83 ± 0.76 µg/mL, respectively. Furthermore, compound 6 increased early and late apoptotic cell population (32.8%) in C6 cell line more than cisplatin (28.8%) and significantly inhibited the Akt enzyme. The molecular docking study was performed to predict the possible binding modes of compounds A, 6, and 8 inside the active site of Akt (PDB code: 4EJN). Molecular docking simulations were found to be in accordance with in vitro studies and, hence, supported the biological activity. A computational study for the prediction of absorption, distribution, metabolism and excretion (ADME) properties of all compounds was also performed. On the basis of Lipinski’s rule of five, the compounds were expected to be potential orally bioavailable agents.

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2-Substituted thiazole-4-carboxamide derivatives as tiazofurin mimics: synthesis and in vitro antitumour activity

Cited by 15 publications

References 41 publications

Thiazoles: A Retrospective Study on Synthesis, Structure-activity Relationship and Therapeutic Significance

Thiazoles: A Retrospective Study on Synthesis, Structure-activity Relationship and Therapeutic Significance

New Hydrazones Bearing Thiazole Scaffold: Synthesis, Characterization, Antimicrobial, and Antioxidant Investigation

Design, Synthesis, and Evaluation of a New Series of Thiazole-Based Anticancer Agents as Potent Akt Inhibitors

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