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Research Articles

Synthesis, molecular docking and ADME studies of thiazole-thiazolidinedione hybrids as antimicrobial agents

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Pages 6211-6227 | Received 13 Sep 2020, Accepted 19 Jan 2021, Published online: 04 Feb 2021

References

  • Abdelazeem, A. H., Gouda, A. M., Omar, H. A., & Tolba, M. F. (2014). Design, synthesis and biological evaluation of novel diphenylthiazole-based cyclooxygenase inhibitors as potential anticancer agents. Bioorganic Chemistry, 57, 132–141. https://doi.org/10.1016/j.bioorg.2014.10.001
  • Alzhrani, Z. M. M., Alam, M. M., Neamatallah, T., & Nazreen, S. (2020). Design, synthesis and in vitro antiproliferative activity of new thiazolidinedione-1,3,4-oxadiazole hybrids as thymidylate synthase inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry, 35(1), 1116–1123. https://doi.org/10.1080/14756366.2020.1759581
  • Ayati, A., Emami, S., Asadipour, A., Shafiee, A., & Foroumadi, A. (2015). Recent applications of 1,3-thiazole core structure in the identification of new lead compounds and drug discovery. European Journal of Medicinal Chemistry, 97, 699–718. https://doi.org/10.1016/j.ejmech.2015.04.015
  • Azizmohammadi, M., Khoobi, M., Ramazani, A., Emami, S., Zarrin, A., Firuzi, O., Miri, R., & Shafiee, A. (2014). 2H-chromene derivatives bearing thiazolidine-2,4-dione, rhodanine or hydantoin moieties as potential anticancer agents. European Journal of Medicinal Chemistry, 76, 170–181.
  • Benesi, H. A., & Hildebrand, J. H. (1949). A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. Journal of the American Chemical Society, 71(8), 2703–2707. https://doi.org/10.1021/ja01176a030
  • Bharti, S. K., Nath, G., Tilak, R., & Singh, S. K. (2010). Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring. European Journal of Medicinal Chemistry, 45(2), 651–660. https://doi.org/10.1016/j.ejmech.2009.11.008
  • Bordessa, A., Colin-Cassin, C., Grillier-Vuissoz, I., Kuntz, S., Mazerbourg, S., Husson, G., Vo, M., Flament, S., Martin, H., Chapleur, Y., & Boisbrun, M. (2013). Optimization of troglitazone derivatives as potent anti-proliferative agents: Towards more active and less toxic compounds. European Journal of Medicinal Chemistry, 59, 15–22.
  • Dawane, B. S., Konda, S. G., Mandawad, G. G., & Shaikh, B. M. (2010). Poly(ethylene glycol) (PEG-400) as an alternative reaction solvent for the synthesis of some new 1-(4-(4'-chlorophenyl)-2-thiazolyl)-3-aryl-5-(2-butyl-4-chloro-1H-imidazol-5yl)-2-pyrazolines and their in vitro antimicrobial evaluation. European Journal of Medicinal Chemistry, 45(1), 387–392. https://doi.org/10.1016/j.ejmech.2009.10.015
  • El-Sabbagh, O. I., Baraka, M. M., Ibrahim, S. M., Pannecouque, C., Andrei, G., Snoeck, R., Balzarini, J., & Rashad, A. A. (2009). Synthesis and antiviral activity of new pyrazole and thiazole derivatives. European Journal of Medicinal Chemistry, 44(9), 3746–3753. https://doi.org/10.1016/j.ejmech.2009.03.038
  • Ghannam, I. A. Y., Abd El-Meguid, E. A., Ali, I. H., Sheir, D. H., & El Kerdawy, A. M. (2019). Novel 2-arylbenzothiazole DNA gyrase inhibitors: Synthesis, antimicrobial evaluation, QSAR and molecular docking studies. Bioorganic Chemistry, 93, 103373. https://doi.org/10.1016/j.bioorg.2019.103373
  • Inoue, T., Morita, M., Tojo, T., Nagashima, A., Moritomo, A., Imai, K., & Miyake, H. (2013). Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema: part 2. 23Bioorganic & Medicinal Chemistry, 21(9), 2478–2498. https://doi.org/10.1016/j.bmc.2013.02.048
  • Knight, S. D., Adams, N. D., Burgess, J. L., Chaudhari, A. M., Darcy, M. G., Donatelli, C. A., Luengo, J. I., Newlander, K. A., Parrish, C. A., Ridgers, L. H., Sarpong, M. A., Schmidt, S. J., Van Aller, G. S., Carson, J. D., Diamond, M. A., Elkins, P. A., Gardiner, C. M., Garver, E., Gilbert, S. A., … Dhanak, D. (2010). Discovery of GSK2126458, a highly potent inhibitor of PI3K and the mammalian target of rapamycin. ACS Medicinal Chemistry Letters, 1(1), 39–43. https://doi.org/10.1021/ml900028r
  • Mayhoub, A. S., Khaliq, M., Botting, C., Li, Z., Kuhn, R. J., & Cushman, M. (2011). an investigation of phenylthiazole antiflaviviral agents. Bioorganic & Medicinal Chemistry, 19(12), 3845–3845. https://doi.org/10.1016/j.bmc.2011.04.041
  • Moldovan, C. M., Oniga, O., Pârvu, A., Tiperciuc, B., Verite, P., Pîrnău, A., Crişan, O., Bojiţă, M., & Pop, R. (2011). Synthesis and anti-inflammatory evaluation of some new acyl-hydrazones bearing 2-aryl-thiazole. European Journal of Medicinal Chemistry, 46(2), 526–534. https://doi.org/10.1016/j.ejmech.2010.11.032
  • Mosmann, T. (1983). Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65(1-2), 55–63. https://doi.org/10.1016/0022-1759(83)90303-4
  • Naim, M. J., Alam, M. J., Ahmad, S., Nawaz, F., Shrivastava, N., Sahu, M., & Alam, O. (2017). Therapeutic journey of 2,4-thiazolid inediones as a versatile scaffold: An insight into structure activity relationship. European Journal of Medicinal Chemistry, 129, 218–250. https://doi.org/10.1016/j.ejmech.2017.02.031
  • National Committee for Clinical Laboratory Standards. (2000). Method for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard document M-7: A5. National Committee for Clinical Laboratory Standards.
  • Omar, M. A., Masaret, G., S., Abbas, E. M. H., Abdel-Aziz, M. M., Harras, M. F., & Farghaly, T. A. (2020). Novel anti-tubercular and antibacterial based benzosuberone-thiazole moieties: Synthesis, molecular docking analysis, DNA gyrase supercoiling and ATPase activity. Bioorganic Chemistry, 104, 104316. https://doi.org/10.1016/j.bioorg.2020.104316
  • Pathania, S., Narang, R. K., & Rawal, R. K. (2019). Role of sulphur-heterocycles in medicinal chemistry: An update . European Journal of Medicinal Chemistry, 180, 486–508.https://doi.org/10.1016/j.ejmech.2019.07.043
  • Rostom, S. A. F., Faidallah, H. M., Radwan, M. F., & Badr, M. H. (2014). Bifunctional ethyl 2-amino-4-methylthiazole-5-carboxylate derivatives: Synthesis and in vitro biological evaluation as antimicrobial and anticancer agents. European Journal of Medicinal Chemistry, 83, 129–140.
  • Rouf, A., & Tanyeli, C. (2015). Bioactive thiazole and benzothiazole derivatives. European Journal of Medicinal Chemistry, 97, 911–927. https://doi.org/10.1016/j.ejmech.2014.10.058
  • Saralkar, P., & Geldenhuys, W. J. (2019). Screening for anticancer properties of thiazolidinedione compounds in a galactose media metastatic breast cancer cell model. Medicinal Chemistry Research, 28(12), 2165–2170. https://doi.org/10.1007/s00044-019-02444-z
  • Siddiqui, N., & Ahsan, W. (2010). Triazole incorporated thiazoles as a new class of anticonvulsants: Design, synthesis and in vivo screening. European Journal of Medicinal Chemistry, 45(4), 1536–1543. https://doi.org/10.1016/j.ejmech.2009.12.062
  • Shukla, K. S., Pandey, S., & Chawla, P. (2019). Synthesis of some 5-(substituted benzylidene-2, 4-dioxothiazolidin-3-yl) benzoic acid derivatives by conventional and microwave-assisted methods and evaluation of their potential as antimicrobial agents. Anti-Infective Agents, 17(2), 115–129.81024151213 https://doi.org/10.2174/22113525166661
  • Slachtova, V., Janovska, L., & Brulikova, L. (2019). Solid phase synthesis of new thiazolidinedione-pyrimidine conjugates and their antibacterial properties. Journal of Molecular Structure, 1183, 182–189.
  • Turan-Zitouni, G., Kaplancikli, Z. A., & Ozdemir, A. (2010). Synthesis and antituberculosis activity of some N-pyridyl-N'-thiazolylhydrazine derivatives. European Journal of Medicinal Chemistry, 45(5), 2085–2088. https://doi.org/10.1016/j.ejmech.2010.01.017
  • Vicini, P., Geronikaki, A., Anastasia, K., Incerti, M., & Zani, F. (2006). Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones. Bioorganic & Medicinal Chemistry, 14(11), 3859–3864. https://doi.org/10.1016/j.bmc.2006.01.043
  • Wang, T., Bing, G., Zhang, X., Qin, Z., Yu, H., Qin, X., Dai, H., Miao, W., Wu, S., & Fang, J. (2010). Synthesis and herbicidal activities of 2-cyano-3-benzylaminoacrylates containing thiazole moiety. Bioorganic & Medicinal Chemistry Letters, 20(11), 3348–3351. https://doi.org/10.1016/j.bmcl.2010.04.027

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