184
Views
1
CrossRef citations to date
0
Altmetric
Research Articles

Synthesis, characterization, anticancer and in silico studies of a pyrazole-tethered thiazolidine-2,4-dione derivative

, , , , & ORCID Icon
Pages 13075-13082 | Received 10 Jul 2021, Accepted 10 Sep 2021, Published online: 23 Sep 2021

References

  • Abdalha, A. A., & Hekal, M. H. (2021). An efficient synthesis and evaluation of some novel quinazolinone-pyrazole hybrids as potential antiproliferative agents. Synthetic Communications, 51(16), 2498–2509. https://doi.org/10.1080/00397911.2021.1939058
  • Abeed, A. A. O., Youssef, M. S. K., & Hegazy, R. (2017). Synthesis, anti-diabetic and renoprotective activity of some new benzazole, thiazolidin-4-one and azetidin-2-one derivatives. Journal of Brazilian Chemical Society, 28, 2054–2063.
  • Akhtar, W., Marella, A., Alam, M. M., Khan, M. F., Akhtar, M., Anwer, T., Khan, F., Naematullah, M., Azam, F., Rizvi, M. A., & Shaquiquzzaman, M. (2021). Design and synthesis of pyrazole–pyrazoline hybrids as cancer‐associated selective COX‐2 inhibitors. Archiv der Pharmazie, 354(1), 2000116. https://doi.org/10.1002/ardp.202000116
  • Ali, I., Haque, A., Saleem, K., & Hsieh, M. F. (2013). Curcumin-I knoevenagel’s condensates and their Schiff’s bases as anticancer agents: Synthesis, pharmacological and simulation studies. Bioorganic & Medicinal Chemistry, 21(13), 3808–3820. https://doi.org/10.1016/j.bmc.2013.04.018
  • Ansari, A., Ali, A., Asif, M., & Shamsuzzaman, S. (2017). Biologically active pyrazole derivatives. New Journal of Chemistry, 41(1), 16–41. https://doi.org/10.1039/C6NJ03181A
  • Bauer, M. R., & Mackey, M. D. (2019). Electrostatic complementarity as a fast and effective tool to optimize binding and selectivity of protein–ligand complexes. Journal of Medicinal Chemistry, 62(6), 3036–3050.
  • Cheeseright, T., Mackey, M., Rose, S., & Vinter, A. (2006). Molecular field extrema as descriptors of biological activity: Definition and validation. Journal of Chemical Information and Modeling, 46(2), 665–676.
  • Cheng, C.-Y., Haque, A., Hsieh, M.-F., Imran Hassan, S., Faizi, M., Haque, S., Dege, N., & Khan, M. S. (2020). 1, 4-disubstituted 1H-1, 2, 3-triazoles for renal diseases: Studies of viability, anti-inflammatory, and antioxidant activities. International Journal of Molecular Sciences, 21(11), 3823. https://doi.org/10.3390/ijms21113823
  • Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific Reports, 7, 42713–42717. https://doi.org/10.1038/srep42717
  • Daina, A., & Zoete, V. (2016). A boiled-egg to predict gastrointestinal absorption and brain penetration of small molecules. ChemMedChem, 11(11), 1117–1121. https://doi.org/10.1002/cmdc.201600182
  • Dalinger, I. L., Kormanov, A. V., Suponitsky, K. Y., Muravyev, N. V., & Sheremetev, A. B. (2018). Pyrazole–tetrazole hybrid with trinitromethyl, fluorodinitromethyl, or (difluoroamino) dinitromethyl groups: High‐performance energetic materials. Chemistry, An Asian Journal, 13(9), 1165–1172. https://doi.org/10.1002/asia.201800214
  • Desai, N. C., Vaja, D. V., Joshi, S. B., & Khedkar, V. M. (2021). Synthesis and molecular docking study of pyrazole clubbed oxazole as antibacterial agents. Research on Chemical Intermediates, 47(2), 573–587. https://doi.org/10.1007/s11164-020-04286-6
  • Fekri, L. Z., Hamidian, H., & Chekosarani, M. A. (2020). Urazolium diacetate as a new, efficient and reusable Brønsted acid ionic liquid for the synthesis of novel derivatives of thiazolidine-4-ones. RSC Advances, 10(1), 556–564. https://doi.org/10.1039/C9RA08649H
  • Fukui, K. (1982). Role of frontier orbitals in chemical reactions. Science (New York, N.Y.), 218(4574), 747–754. https://doi.org/10.1126/science.218.4574.747
  • Gondru, R., Sirisha, K., Raj, S., Gunda, S. K., Kumar, C. G., Pasupuleti, M., & Bavantula, R. (2018). Design, synthesis, in vitro evaluation and docking studies of pyrazole-thiazole hybrids as antimicrobial and antibiofilm agents. Chemistry Select, 3, 8270–8276.
  • Gupta, M. K., Neelakantan, T., Sanghamitra, M., Tyagi, R. K., Dinda, A., Maulik, S., Mukhopadhyay, C. K., & Goswami, S. K. (2006). An assessment of the role of reactive oxygen species and redox signaling in norepinephrine-induced apoptosis and hypertrophy of h9c2 cardiac myoblasts. Antioxidants & Redox Signaling, 8(5-6), 1081–1093. https://doi.org/10.1089/ars.2006.8.1081
  • Haque, A., Al-Balushi, R. A., Al-Busaidi, I. J., Khan, M. S., & Raithby, P. R. (2018). Rise of conjugated poly-ynes and poly(metalla-ynes): From design through synthesis to structure-property relationships and applications. Chemical Reviews, 118(18), 8474–8597. https://doi.org/10.1021/acs.chemrev.8b00022
  • Haque, A., Faizi, M. S. H., Rather, J. A., & Khan, M. S. (2017). Next generation NIR fluorophores for tumor imaging and fluorescence-guided surgery: A review. Bioorganic & Medicinal Chemistry, 25(7), 2017–2034. https://doi.org/10.1016/j.bmc.2017.02.061
  • Haque, A., Hsieh, M.-F., Hassan, S. I., Faizi, M. S. H., Saha, A., Dege, N., Rather, J. A., & Khan, M. S. (2017). Synthesis, characterization, and pharmacological studies of ferrocene-1h-1, 2, 3-triazole hybrids. Journal of Molecular Structure, 1146, 536–545. https://doi.org/10.1016/j.molstruc.2017.06.027
  • Ilmi, R., Haque, A., & Khan, M. S. (2018). High efficiency small molecule-based donor materials for organic solar cells. Organic Electronics, 58, 53–62. https://doi.org/10.1016/j.orgel.2018.03.048
  • Jain, A. K., Vaidya, A., Ravichandran, V., Kashaw, S. K., & Agrawal, R. K. (2012). Recent developments and biological activities of thiazolidinone derivatives: A review. Bioorganic & Medicinal Chemistry, 20(11), 3378–3395. https://doi.org/10.1016/j.bmc.2012.03.069
  • Jampilek, J. (2019). Heterocycles in medicinal chemistry. Molecules, 24, 3839. https://doi.org/10.3390/molecules24213839
  • Karrouchi, K., Fettach, S., Jotani, M. M., Sagaama, A., Radi, S., Ghabbour, H. A., Mabkhot, Y. N., Himmi, B., Faouzi, M. E. A., & Issaoui, N. (2020). Synthesis, crystal structure, Hirshfeld surface analysis, DFT calculations, anti-diabetic activity and molecular docking studies of (E)-N’-(5-bromo-2-hydroxybenzylidene) isonicotinohydrazide. Journal of Molecular Structure, 1221, 128800. https://doi.org/10.1016/j.molstruc.2020.128800
  • Karrouchi, K., Radi, S., Ramli, Y., Taoufik, J., Mabkhot, Y. N., Al-Aizari, F. A., & Ansar, M. (2018). Synthesis and pharmacological activities of pyrazole derivatives: A review. Molecules (Basel, Switzerland), 23(1), 134.
  • Khan, K. M., Rahim, F., Halim, S. A., Taha, M., Khan, M., Perveen, S., Mesaik, M. A., & Choudhary, M. I. (2011). Synthesis of novel inhibitors of β-glucuronidase based on benzothiazole skeleton and study of their binding affinity by molecular docking. Bioorganic & Medicinal Chemistry, 19, 4286–4294.
  • Kim, S. R., Park, M. J., Lee, M. K., Sung, S. H., Park, E. J., Kim, J., Kim, S. Y., Oh, T. H., Markelonis, G. J., & Kim, Y. C. (2002). Flavonoids of inula Britannica protect cultured cortical cells from necrotic cell death induced by glutamate. Free Radical Biology & Medicine, 32(7), 596–604.
  • Kumar, V., Kaur, K., Gupta, G. K., & Sharma, A. K. (2013). Pyrazole containing natural products: Synthetic preview and biological significance. European Journal of Medicinal Chemistry, 69, 735–753. https://doi.org/10.1016/j.ejmech.2013.08.053
  • Manjal, S. K., Kaur, R., Bhatia, R., Kumar, K., Singh, V., Shankar, R., Kaur, R., & Rawal, R. K. (2017). Synthetic and medicinal perspective of thiazolidinones: A review. Bioorganic Chemistry, 75, 406–423.
  • Mermer, A., Bayrak, H., Alyar, S., & Alagumuthu, M. (2020). Synthesis, DFT calculations, biological investigation, molecular docking studies of β-lactam derivatives. Journal of Molecular Structure, 1208 (1208)., 127891. https://doi.org/10.1016/j.molstruc.2020.127891
  • Michaelides, M. R. (2010). Kinase inhibitors with improved CYP safety profile. Google Patents.
  • Mushtaque, M., Ahamad, S., Jahan, M., Hussain, K., & Khan, M. S. (2016). Azole-based compounds as antiamoebic agents: A perspective using theoretical calculations. RSC Advances, 6(1), 815–824. https://doi.org/10.1039/C5RA20552B
  • Mushtaque, M., Avecilla, F., Haque, A., Perwez, A., Khan, M. S., & Rizvi, M. M. A. (2017). Experimental and theoretical studies of a pyrazole-thiazolidin-2, 4-di-one hybrid. Journal of Molecular Structure, 1141, 417–427. https://doi.org/10.1016/j.molstruc.2017.03.100
  • Mushtaque, M., Avecilla, F., Haque, A., Yab, Z., Rizvi, M. M. A., & Khan, M. S. (2019). Synthesis, structural and biological activity of N-substituted 2-methyl-4-/5-nitroimidazole derivatives. Journal of Molecular Structure, 1185, 440–449. https://doi.org/10.1016/j.molstruc.2019.02.101
  • Nikpassand, M., Fekri, L. Z., & Taherkhorsand, H. (2017). Green synthesis of novel 2-pyrazolyl-1, 3-thiazolidine-4-ones using 2-oxoimidazolidine-1, 3-disulfonic acid. Heterocyclic Communications, 23(6), 429–432. https://doi.org/10.1515/hc-2017-0124
  • Nirwan, S., Chahal, V., & Kakkar, R. (2019). Thiazolidinones: Synthesis, reactivity, and their biological applications. Journal of Heterocyclic Chemistry, 56(4), 1239–1253. https://doi.org/10.1002/jhet.3514
  • Parr, R. G., Szentpály, L. V., & Liu, S. (1999). Electrophilicity index. Journal of the American Chemical Society, 121(9), 1922–1924. https://doi.org/10.1021/ja983494x
  • Pires, D. E., Blundell, T. L., & Ascher, D. B. (2015). pkCSM: Predicting small-molecule pharmacokinetic and toxicity properties using graph-based signatures. Journal of Medicinal Chemistry, 58(9), 4066–4072.
  • Reddy, T. S., Kulhari, H., Reddy, V. G., Rao, A. S., Bansal, V., Kamal, A., & Shukla, R. (2015). Synthesis and biological evaluation of pyrazolo–triazole hybrids as cytotoxic and apoptosis inducing agents. Organic & Biomolecular Chemistry, 13(40), 10136–10149. https://doi.org/10.1039/C5OB00842E
  • Shafiei, M., Peyton, L., Hashemzadeh, M., & Foroumadi, A. (2020). History of the development of antifungal azoles: A review on structures, SAR, and mechanism of action. Bioorganic Chemistry, 104, 104240.
  • Shamim, F., Khan, F. A., Taha, M., & Khan, K. M. (2019). Synthesis and in vitro anti-proliferative capabilities of steroidal thiazole and indole derivatives. Journal of Saudi Chemical Society, 23, 775–780.
  • Taha, M., Shah, S. A. A., Afifi, M., Zulkeflee, M., Sultan, S., Wadood, A., Rahim, F., & Ismail, N. H. (2017). Morpholine hydrazone scaffold: Synthesis, anticancer activity and docking studies. Chinese Chemical Letters, 28(3), 607–611. https://doi.org/10.1016/j.cclet.2016.10.020
  • Taha, M., Sultan, S., Herizal, M., Fatmi, M. Q., Selvaraj, M., Ramasamy, K., Halim, S. A., Lim, S. M., Rahim, F., Ashraf, K., & Shehzad, A. (2019). Synthesis, anticancer, molecular docking and QSAR studies of benzoylhydrazone. Journal of Saudi Chemical Society, 23(8), 1168–1179. https://doi.org/10.1016/j.jscs.2019.07.007
  • Thom, S. M., Horobin, R., Seidler, E., & Barer, M. (1993). Factors affecting the selection and use of tetrazolium salts as cytochemical indicators of microbial viability and activity. Journal of Applied Bacteriology, 74(4), 433–443. https://doi.org/10.1111/j.1365-2672.1993.tb05151.x
  • Van Mourik, T., Bühl, M., & Gaigeot, M.-P. (2014). Density functional theory across chemistry, physics and biology. Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences, 372(2011), 20120488. https://doi.org/10.1098/rsta.2012.0488
  • Viegas-Junior, C., Danuello, A., da Silva Bolzani, V., Barreiro, E. J., & Fraga, C. A. M. (2007). Molecular hybridization: A useful tool in the design of new drug prototypes. Current Medicinal Chemistry, 14(17), 1829–1852. https://doi.org/10.2174/092986707781058805
  • Zhang, H.-Z., Gan, L.-L., Wang, H., & Zhou, C.-H. (2017). New progress in azole compounds as antimicrobial agents. Mini Reviews in Medicinal Chemistry, 17(2), 122–166.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.