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Open accessJournal ArticleDOI: 10.1080/00397911.2020.1854787

Review of the synthesis and biological activity of thiazoles

04 Mar 2021-Synthetic Communications (Informa UK Limited)-Vol. 51, Iss: 5, pp 670-700
Abstract: This study covers the literature documents available on the chemistry of preparation of thiazoles. Additionally, we cover the biological activities of certain thiazoles. The information of several ...

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Open accessJournal ArticleDOI: 10.3390/MOLECULES26030624
25 Jan 2021-Molecules
Abstract: 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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Topics: Thiazole (58%)

15 Citations


Open accessPosted ContentDOI: 10.20944/PREPRINTS202105.0039.V1
05 May 2021-
Abstract: There is a need to search for new antifungals, especially for the treatment of the invasive Candida infections, caused mainly by C. albicans. These infections are steadily increasing at an alarming rate, mostly among immunocompromised patients. The newly synthesized compounds (3a-3k) were characterized by physico-chemical parameters and investigated for antimicrobial activity using the microdilution broth method to estimate minimal inhibitory concentration (MIC). Additionally, their antibiofilm activity and mode of action together with the effect on the membrane permeability in C. albicans were investigated. Biofilm biomass and its metabolic activity were quantitatively measured using crystal violet (CV) staining and tetrazolium salt (XTT) reduction assay. The cytotoxic effect on normal human lung fibroblasts and hemolytic effect were also evaluated. The results showed differential activity of the compounds against yeasts (MIC = 0.24-500 μg/mL) and bacteria (MIC = 125-1000 μg/mL). Most compounds possessed strong antifungal activity (MIC = 0.24-7.81 μg/mL). The compounds 3b, 3c, and 3e, showed no inhibitory (at 1/2 MIC) and eradication (at 8 x MIC) effect on C. albicans biofilm. Only slight decrease in the biofilm metabolic activity was observed for compound 3b. Moreover, the studied compounds increased the permeability of the membrane/cell wall of C. albicans and their mode of action may be related to action within the fungal cell wall structure and/or within the cell membrane. It is worth noting that the compounds had no cytotoxicity effect on pulmonary fibroblasts and erythrocytes at concentrations showing anticandidal activity. The present studies in vitro confirm that these derivatives appear to be a very promising group of antifungals for further preclinical studies.

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Topics: Thiazole (60%)

1 Citations


Journal ArticleDOI: 10.1021/JACS.1C07559
Kevin M. Wernke1, Alina Tirla1, Mengzhao Xue1, Yulia V. Surovtseva1  +2 moreInstitutions (1)
Abstract: Colibactin is a genotoxic metabolite produced by commensal-pathogenic members of the human microbiome that possess the clb (aka pks) biosynthetic gene cluster. clb+ bacteria induce tumorigenesis in models of intestinal inflammation and have been causally linked to oncogenesis in humans. While colibactin is believed underlie these effects, it has not been possible to study the molecule directly due to its instability. Herein, we report the synthesis and biological studies of colibactin 742 (4), a stable colibactin derivative. We show that colibactin 742 (4) induces DNA interstrand-cross-links, activation of the Fanconi Anemia DNA repair pathway, and G2/M arrest in a manner similar to clb+E. coli. The linear precursor 9, which mimics the biosynthetic precursor to colibactin, also recapitulates the bacterial phenotype. In the course of this work, we discovered a novel cyclization pathway that was previously undetected in MS-based studies of colibactin, suggesting a refinement to the natural product structure and its mode of DNA binding. Colibactin 742 (4) and its precursor 9 will allow researchers to study colibactin's genotoxic effects independent of the producing organism for the first time.

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1 Citations


Journal ArticleDOI: 10.1039/D1NJ00680K
Abstract: A new series of 2,3-thiazoline–coumarin hybrid compounds that contained D-glucose and D-galactose moieties (4a–g) were synthesized and their cytotoxic activity was evaluated against breast adenocarcinoma (MCF-7), human liver cancer (HepG2), human cervical cancer (HeLa), human melanoma cancer (SK-Mel-2), and human lung cancer (LU-1) cells. To reveal their selectivity toward cancer cells, the compounds were also tested against the human fibroblast cell line MRC-5. The synthesized compounds exhibited potent cytotoxic activity against the tested cell lines with IC50 values of 1.18–11.32, 1.91–9.81, 1.96–13.16, 1.35–16.12, and 2.12–15.92 μM (against MCF-7, HepG2, HeLa, SK-Mel-2, and LU-1 cells, respectively) compared with Sorafenib, doxorubicin, and 5-fluorouracil. Interestingly, compounds 4a–g displayed selectivity toward cancer cell lines over MRC-5 (IC50 3.97–25.75 μM). The most active compounds, including 4d, 4e, and 4f, also displayed potent inhibitory activity against EGFR and HER2 kinases (IC50 0.15–0.31 and 0.15–0.25 μM, respectively) compared with the standard drug Sorafenib (IC50 = 0.11 and 0.13 μM, respectively). Molecular docking also showed that the hydrogen binding interactions often occurred between the CO lactone of the coumarin ring and appropriate amino acid residues, which played a key role in enhancing its potency against both enzymes.

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Topics: HeLa (56%), Cancer cell (51%)

1 Citations


Journal ArticleDOI: 10.1016/J.MOLSTRUC.2021.131324
Abstract: In the present study, a simple and efficient protocol has been developed to synthesize a series of new (4-substituted-phenyl)-1,5-dihydro-2H-pyrimido[4,5-d][1,3]thiazolo[3,2a]-pyrimidine-2,4(3H)-dione derivatives (4a-g) through L -proline-catalyzed reaction of 2-amino-4-(4-substituted-phenyl)thiazole (1), substituted benzaldehyde (2), and barbituric/thiobarbituric acid (3) at a refluxed temperature in aqueous ethanol under mild and metal-free conditions. The obtained compounds were evaluated for in vitro cytotoxicity and anti-inflammatory effects. The in silico docking studies provided the probable interactions of synthesized compounds with P38 MAP kinase and MMP-9 proteins. The structures of all the synthesized compounds were confirmed using analytical and spectroscopic techniques. The in vitro cytotoxicity studies revealed the potential cytotoxic effects of the compounds 4f and 4g. The anti-inflammatory studies suggested the prominent anti-inflammatory effects of the compounds 4a and 4g. The SAR studies showed the importance of electron-withdrawing groups in enhancing the potency among the tested compounds. The results of in silico studies supported our findings from in vitro analysis in terms of drug-likeness of the synthesized compounds and their effective interactions with P38 MAP kinase and MMP-9 proteins envisaging their use as prominent therapeutic agents.

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Topics: Thiazole (52%)

1 Citations


References
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Journal ArticleDOI: 10.1016/J.EJMECH.2010.08.008
Abstract: Antitumor screening of several novel 4-thiazolidinones with benzothiazole moiety has been performed. Reactions of (benzothiazole-2-yl)hydrazine with trithiocarbonyl diglycolic acid or 6-methyl-2-aminobenzothiazole with 2-carbethoxymethylthio-2-thiazoline-4-one have yielded starting 3- (1) or 2-substituted (11) 4-thiazolidinones which have been subsequently utilized in a Knoevenagel condensation for obtaining a series of 5-arylidene derivatives 2-10, 12-16. Compound 11 has been obtained alternatively by a counter synthesis method based on the reaction of 2-chloro-N-(6-methylbenzothiazol-2-yl)-acetamide and ammonium thiocyanate. The structures of compounds have been determined by (1)H, (13)C NMR, IR and X-ray analysis. In vitro anticancer activity of the synthesized compounds was tested by the National Cancer Institute and two (6, 16) of them has revealed the anticancer activity on leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate and breast cancers cell lines. Among tested compounds, 2-{2-[3-(benzothiazol-2-ylamino)-4-oxo-2-thioxothiazolidin-5-ylidenemethyl]-4-chlorophenoxy}-N-(4-methoxyphenyl)-acetamide (6) was found to be the most active candidate with average logGI(50) and logTGI values -5.38 and -4.45 respectively.

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Topics: Benzothiazole (58%), Knoevenagel condensation (53%), Diglycolic acid (53%) ... show more

177 Citations


Journal ArticleDOI: 10.1016/J.EJMECH.2014.10.058
Abdul Rouf1, Cihangir Tanyeli1Institutions (1)
Abstract: The heterocycles are the versatile compounds existing in almost all natural products and synthetic organic compounds, usually associated with one or the other biological activity. Among the heterocycles the thiazoles and benzothiazoles occupy a prominent position. They possess a broad range of biological activities and are found in many potent biologically active molecules and drugs such as vitamin thiamine, sulfathiazol (antimicrobial drug), ritonavir (antiretroviral drug), abafungin (antifungal drug) and tiazofurin (antineoplastic drug). The thiazole moiety is abundantly found in natural products while benzothiazole moiety is rare. In this review we disclose the literature reports of thiazoles and benzothiazoles possessing different biological activities.

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Topics: Antifungal drug (60%), Thiazole (57%), Benzothiazole (57%)

169 Citations


Journal ArticleDOI: 10.1016/J.EJMECH.2009.12.062
Nadeem Siddiqui1, Waquar Ahsan1Institutions (1)
Abstract: Various 3-[4-(substituted phenyl)-1,3-thiazol-2-ylamino]-4-(substituted phenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thiones (7a–t) were designed keeping in view the structural requirements suggested in the pharmacophore model for anticonvulsant activity. Thiazole and triazole moieties being anticonvulsants were clubbed together to get the titled compounds and their in vivo anticonvulsant screening were performed by two most adopted seizure models, maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ). Two compounds 7d and 7f showed significant anticonvulsant activity in both the screens with ED50 values 23.9 mg/kg and 13.4 mg/kg respectively in MES screen and 178.6 mg/kg and 81.6 mg/kg respectively in scPTZ test. They displayed a wide margin of safety with Protective index (PI), median hypnotic dose (HD50) and median lethal dose (LD50) much higher than the standard drugs.

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Topics: Anticonvulsant (50%)

165 Citations


Journal ArticleDOI: 10.1016/J.EJMECH.2008.05.029
Abstract: A series of adamantane derivatives of thiazolyl-N-substituted amides were synthesized in a three-step reaction and tested for anti-inflammatory activity as well as lipoxygenase and cycloxygenase inhibitory actions. Theoretical calculation of their lipophilicity, as C log P was performed. The effect of the synthesized compounds on inflammation, using the carrageenin-induced mouse paw oedema model was studied and compared to indomethacin. In general, the studied compounds were found to be potent anti-inflammatory agents (29.6–81.5%). Anti-inflammatory activity was influenced by some structural characteristics of the synthesized compounds. The lipoxygenase inhibitory activity was tested by the conversion of sodium linoleate to 13-hydroperoxylinoleic acid. Low inhibitory activity was observed. Evaluation of COX-1 and COX-2 inhibitory activities of the compounds revealed a COX-1 inhibitory potential, comparable to that of naproxen for some of the compounds and a low to moderate COX-2 inhibitory potential. Comparison of the in vivo and in vitro results leads to the conclusion that most compounds of this series may be involved in other mechanisms of inflammation, too.

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Topics: Adamantane (52%)

86 Citations


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