Issue

Vol. 34 No. 8 (2022): Vol 34 Issue 8, 2022

Copyright (c) 2022 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Structural and Functional Insights of Thiazole Derivatives as Potential Anti-inflammatory Candidate: A New Contender on Chronic and Acute SARS-CoV-2 Inflammation and Inhibition of SARS-CoV-2 Proteins: A Review

https://doi.org/10.14233/ajchem.2022.23673
B.T. Harshitha
Department of Chemistry, SJCE, JSS Science and Technology University, Mysuru-570006, India
J. Jayashankar
Department of Chemistry, SJCE, JSS Science and Technology University, Mysuru-570006, India
A.P. Anand
Research and Development Centre, Bharathiar University, Coimbatore-641046, India
S. Sandeep
Department of Chemistry, SJCE, JSS Science and Technology University, Mysuru-570006, India
H.S. Jayanth
Department of Microbiology, Yuvaraja’s College, Mysuru-570005, India
C.S. Karthik
Department of Chemistry, SJCE, JSS Science and Technology University, Mysuru-570006, India
P. Mallu
Department of Chemistry, SJCE, JSS Science and Technology University, Mysuru-570006, India
N. Haraprasad
Department of Biotechnology, SJCE, JSS Science and Technology University, Mysuru-570006, India
N.B. Krishnamurthy
Research and Development Centre, Bharathiar University, Coimbatore-641046, India

Corresponding Author(s) : C.S. Karthik

csk@jssstuniv.in

Asian Journal of Chemistry, Vol. 34 No. 8 (2022): Vol 34 Issue 8, 2022

Abstract

Thiazoles are notable five-membered heterocyclic rings and their moieties can be found in several biologically active compounds of natural origin, as well as synthetic molecules that possess a wide range of pharmacological activities. Inflammation is the common cause that is associated with different disorders and diseases such as psoriasis, arthritis, infections, asthma, cancer, etc. In this article, the synthesis pattern of these novel molecules are discussed and their anti-inflammatory activities against cyclooxygenase-1 (COX-1), cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) were reviewed and documented. The potent 26 thiazole analogs were validated with molecular docking against main protease (6LU7) and spike binding domain ACE2 receptor (6M0J) to defeat from the COVID-19 infections. Among this, THI-9a showed excellent binding energy and affinity against deadly SAR CoV-2. The reviewed and theoretical study information strongly suggested that thiazole derivatives can be used for the development of futuristic target drugs against death-causing diseases like SAR-CoV-2.

Keywords

Anti-inflammatory COX-1 COX-2 PLA2 Thiazole SARS-CoV-2
Harshitha, B., Jayashankar, J., Anand, A., Sandeep, S., Jayanth, H., Karthik, C., … Krishnamurthy, N. (2022). Structural and Functional Insights of Thiazole Derivatives as Potential Anti-inflammatory Candidate: A New Contender on Chronic and Acute SARS-CoV-2 Inflammation and Inhibition of SARS-CoV-2 Proteins: A Review. Asian Journal of Chemistry, 34(8), 1893–1920. https://doi.org/10.14233/ajchem.2022.23673
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. M. Pal, G. Berhanu, C. Desalegn and V. Kandi, Cureus, 12, e7423 (2020); https://doi.org/10.7759/cureus.7423
  2. A.A.T. Naqvi, K. Fatima, T. Mohammad, U. Fatima, I.K. Singh, A. Singh, S.M. Atif, G. Hariprasad, G.M. Hasan and M.I. Hassan, Biochim. Biophys. Acta-Mol. basis Dis., 1866, 165878 (2020); https://doi.org/10.1016/j.bbadis.2020.165878
  3. L. Pang, C.Y. Liu, G.H. Gong and Z.S. Quan, Acta Pharm. Sin. B, 10, 628 (2020); https://doi.org/10.1016/j.apsb.2019.09.002
  4. P. Pathak, P.K. Shukla, V. Naumovich, M. Grishina, V. Potemkin and A. Verma, Synth. Commun., 49, 2725 (2019); https://doi.org/10.1080/00397911.2019.1643485
  5. S.M. Wang, G.F. Zha, K.P. Rakesh, N. Darshini, T. Shubhavathi, H.K. Vivek, N. Mallesha and H.L. Qin, MedChemComm, 8, 1173 (2017); https://doi.org/10.1039/C7MD00111H
  6. S. Sinha, M. Doble and S.L. Manju, Eur. J. Med. Chem., 158, 34 (2018); https://doi.org/10.1016/j.ejmech.2018.08.098
  7. Z. Chulovska, T. Chaban, I. Drapak, V. Matiychuk, I. Chaban and I. Nektegaev, Biointerface Res. Appl. Chem., 11, 8009 (2021); https://doi.org/10.33263/BRIAC111.80098017
  8. Y. Li, J. Geng, Y. Liu, S. Yu and G. Zhao, ChemMedChem, 8, 27 (2013); https://doi.org/10.1002/cmdc.201200355
  9. I.P. Singh, S. Gupta and S. Kumar, Med. Chem., 16, 4 (2020); https://doi.org/10.2174/1573406415666190614101253
  10. R. Mishra, P.K. Sharma, P.K. Verma, I. Tomer, G. Mathur and P.K. Dhakad, J. Heterocycl. Chem., 54, 2103 (2017); https://doi.org/10.1002/jhet.2827
  11. A. Chowdhury, S. Patel, A. Sharma, A. Das, P. Meshram and A. Shard, Chem. Heterocycl. Compd., 56, 455 (2020); https://doi.org/10.1007/s10593-020-02680-x
  12. A. Chawla, H. Kaur, P. Chawla and U.S. Baghel, J. Glob. Trends Pharm. Sci., 5, 1641 (2014).
  13. S. Jubie, B. Gowramma, K.M. Nitin, N. Jawahar, R. Kalirajan, S. Gomathy, S. Sankar and K. Elango, Int. J. Pharm. Sci., 1, 32 (2009).
  14. M. Gopal, B. Padmashali, Y.N. Manohara and B.M. Gurupadayya, Indian J. Pharm. Sci., 70, 572 (2008); https://doi.org/10.4103/0250-474X.45393
  15. K. Z. Laczkowski, A. Biernasiuk, A. Baranowska-Laczkowska, K. Misiura, A. Malm, T. Plech and A. Paneth, Med. Chem., 12, 553 (2016); https://doi.org/10.2174/1573406412666160201121310
  16. A. Bishayee, R. Karmakar, A. Mandal, S.N. Kundu and M. Chatterjee, Eur. J. Cancer Prev., 6, 58 (1997); https://doi.org/10.1097/00008469-199702000-00010
  17. K.D. Hargrave, F.K. Hess and J.T. Oliver, J. Med. Chem., 26, 1158 (1983); https://doi.org/10.1021/jm00362a014
  18. W.C. Patt, H.W. Hamilton, M.D. Taylor, M.J. Ryan, J.R. Taylor Jr.,.J.C. Connolly, A.M. Doherty, S.R. Klutchko and I. Sircar, J. Med. Chem., 35, 2562 (1992); https://doi.org/10.1021/jm00092a006
  19. Z. A. Muhammad, G. S. Masaret, M. M. Amin, M. A. Abdallah and T. A. Farghaly, Med. Chem., 13, 226 (2017); https://doi.org/10.2174/1573406412666160920091146
  20. H.N. Karade, B.N. Acharya, M. Sathe and M.P. Kaushik, Med. Chem. Res., 17, 19 (2008); https://doi.org/10.1007/s00044-008-9089-0
  21. S. Vengurlekar, S. Prachand, S. Jain and R. Gupta, Int. J. Pharm. Life Sci., 5, 3526 (2014).
  22. S.R. Pattan, N.S. Dighe, S.A. Nirmal, A.N. Merekar, R.B. Laware and H.V. Shinde, Asian J. Res. Chem., 2, 196 (2009).
  23. A. Leoni, A. Locatelli, R. Morigi and M. Rambaldi, Expert Opin. Ther. Pat., 24, 759 (2014); https://doi.org/10.1517/13543776.2014.910196
  24. A.A. Nadaf, D.A. Barretto, M.S. Najare, S. Mantur, M. Garbhagudi, S. Gaonkar, S. Joshi and I.A.M. Khazi, Med. Chem. Res., 29, 442 (2020); https://doi.org/10.1007/s00044-019-02495-2
  25. O.I. El-Sabbagh, M.M. Baraka, S.M. Ibrahim, C. Pannecouque, G. Andrei, R. Snoeck, J. Balzarini and A.A. Rashad, Eur. J. Med. Chem., 44, 3746 (2009); https://doi.org/10.1016/j.ejmech.2009.03.038
  26. K.M. Dawood, T.M. Eldebss, H.S. El-Zahabi and M.H. Yousef, Eur. J. Med. Chem., 102, 266 (2015); https://doi.org/10.1016/j.ejmech.2015.08.005
  27. J.V.J Silva Júnior T.R.R Lopes, P.S.B de Oliveira, R. Weiblen and E.F. Flores, Viral Immunol., 34, 358 (2020); https://doi.org/10.1089/vim.2020.0059
  28. D.S. Hui, E.I. Azhar, Y.J. Kim, Z.A. Memish, M.D. Oh and A. Zumla, Lancet Infect. Dis., 18, e217 (2018); https://doi.org/10.1016/S1473-3099(18)30127-0
  29. S. Anuradha, J. Int. Med. Sci. Acad., 27, 191 (2014).
  30. E. De Clercq, J. Pharmacol. Exp. Ther., 297, 1 (2001).
  31. F. Baldanti, M.R. Underwood, S.C. Stanat, K.K. Biron, S. Chou, A. Sarasini, E. Silini and G. Gerna, J. Virol., 70, 1390 (1996); https://doi.org/10.1128/jvi.70.3.1390-1395.1996
  32. M.G. Ghany and E.C. Doo, Hepatology, 49(S5), S174 (2009); https://doi.org/10.1002/hep.22900
  33. C. Marzolini, A. Telenti, L.A. Decosterd, G. Greub, J. Biollaz and T. Buclin, AIDS, 15, 71 (2001); https://doi.org/10.1097/00002030-200101050-00011
  34. A. Ammassari, R. Murri, P. Pezzotti, M.P. Trotta, L. Ravasio, P. De Longis, L. Caputo, P. Narciso, S. Pauluzzi, G. Carosi, S. Nappa, P. Piano, C.M. Izzo, M. Lichtner, G. Rezza, A.A. Monforte, G. Ippolito, M. Moroni, A.W. Wu and A. Antinori, J. Acquir. Immune Defic. Syndr., 28, 445 (2001); https://doi.org/10.1097/00042560-200112150-00006
  35. E. Ewers, S. Anisowicz, M. Washington, W. Agee, B. Swierczewski, T. Ferguson, M. Burnett, S. Seronello, M. Nahid, O. Serichantalergs, W. Lurchachaiwong, J. Barnhill and V. Ngauy, Open Forum Infect. Dis., 3(suppl_1), 1201 (2016); https://doi.org/10.1093/ofid/ofw172.904
  36. K.E. Hanson and S. Swaminathan, Future Microbiol., 10, 1545 (2015); https://doi.org/10.2217/fmb.15.82
  37. I. Astuti and Ysrafil, Diabetes Metab. Syndr., 14, 407 (2020); https://doi.org/10.1016/j.dsx.2020.04.020
  38. M.A. Shereen, S. Khan, A. Kazmi, N. Bashir and R. Siddique, J. Adv. Res., 24, 91 (2020); https://doi.org/10.1016/j.jare.2020.03.005
  39. M. Hoffmann, H. Kleine-Weber, S. Schroeder, N. Krüger, T. Herrler, S. Erichsen, T.S. Schiergens, G. Herrler, N.-H. Wu, A. Nitsche, M.A. Müller, C. Drosten and S. Pöhlmann, Cell, 181, 271 (2020); https://doi.org/10.1016/j.cell.2020.02.052
  40. Y. Wan, J. Shang and R. Graham, J. Virol., 94, e00127 (2020); https://doi.org/10.1128/JVI.00127-20
  41. W. Sungnak, N. Huang, C. Bécavin, M. Berg, M. Litvinukova, R. Queen, C. Talavera-López, H. Maatz, D. Reichart, F. Sampaziotis, K.B. Worlock, M. Yoshida and J.L. Barnes, Nat. Med., 26, 681 (2020); https://doi.org/10.1038/s41591-020-0868-6
  42. A. Reyfman, J.M. Walter, N. Joshi, K.R. Anekalla, A.C. McQuattiePimentel, S. Chiu, R. Fernandez, M. Akbarpour, C.-I. Chen, Z. Ren, R. Verma, H. Abdala-Valencia, K. Nam, M. Chi, S.H. Han, F.J. Gonzalez-Gonzalez, S. Soberanes, S. Watanabe, K.J.N. Williams, A.S. Flozak, T.T. Nicholson, V.K. Morgan, D.R. Winter, M. Hinchcliff, C.L. Hrusch, R.D. Guzy, C.A. Bonham, A.I. Sperling, R. Bag, R.B. Hamanaka, G.M. Mutlu, A.V. Yeldandi, S.A. Marshall, A. Shilatifard, L.A.N. Amaral, H. Perlman, J.I. Sznajder, A.C. Argento, C.T. Gillespie, J. Dematte, M. Jain, B.D. Singer, K.M. Ridge, A.P. Lam, A. Bharat, S.M. Bhorade, C.J. Gottardi, G.R.S. Budinger and A.V. Misharin, Am. J. Respir. Crit. Care Med., 199, 1517 (2019); https://doi.org/10.1164/rccm.201712-2410OC
  43. R.J. Mason, Eur. Respir. J., 55, 2000607 (2020); https://doi.org/10.1183/13993003.00607-2020
  44. A.S. Hancock, C.J. Stairiker, A.C. Boesteanu, E. Monzón-Casanova, S. Lukasiak, Y.M. Mueller, A.P. Stubbs, A. Garcia-Sastre, M. Turner and P.D. Katsikis, J. Virol., 92, e01325 (2018); https://doi.org/10.1128/JVI.01325-18
  45. N.L.-S. Tang, P.K.-S. Chan, C.-K. Wong, K.-F. To, A.K.-L. Wu, Y.-M.Sung, D.S.-C. Hui, J.J.-Y. Sung and C.W.-K. Lam, Clin. Chem., 51, 2333 (2005); https://doi.org/10.1373/clinchem.2005.054460
  46. M. Fagyas, A. Kertész, I.M. Siket, V. Bánhegyi, B. Kracskó, A. Szegedi, M. Szokol, G. Vajda, I. Rácz, H. Gulyás, N. Szkibák, V. Rácz, Z. Csanádi, Z. Papp, A. Tóth and S. Sipka, Geroscience, 43, 19 (2021); https://doi.org/10.1007/s11357-020-00300-2
  47. J. Braciale and Y.S. Hahn, Immunol. Rev., 255, 5 (2013); https://doi.org/10.1111/imr.12109
  48. M.R. Thompson, J.J. Kaminski, E.A. Kurt-Jones and K.A. Fitzgerald, Viruses, 3, 920 (2011); https://doi.org/10.3390/v3060920
  49. N. Chen, M. Zhou, X. Dong, J. Qu, F. Gong, Y. Han, Y. Qiu, J. Wang, Y. Liu, Y. Wei, J. Xia, T. Yu, X. Zhang and L. Zhang, Lancet, 395, 507 (2020); https://doi.org/10.1016/S0140-6736(20)30211-7
  50. C. Huang, Y. Wang, X. Li, L. Ren, J. Zhao, Y. Hu, L. Zhang, G. Fan, J. Xu, X. Gu, Z. Cheng, T. Yu, J. Xia, Y. Wei, W. Wu, X. Xie, W. Yin, H. Li, M. Liu, Y. Xiao, H. Gao, L. Guo, J. Xie, G. Wang, R. Jiang, Z. Gao, Q. Jin, J. Wang and B. Cao, Lancet, 395, 497 (2020); https://doi.org/10.1016/S0140-6736(20)30183-5
  51. C.C. Lai, T.P. Shih, W.C. Ko, H.J. Tang and P.R. Hsueh, Int. J. Antimicrob. Agents, 55, 105924 (2020); https://doi.org/10.1016/j.ijantimicag.2020.105924
  52. R.C. Langenbach, C. Loftin, C. Lee and H. Tiano, Biochem. Pharmacol., 58, 1237 (1999); https://doi.org/10.1016/S0006-2952(99)00158-6
  53. K. Gudis and C. Sakamoto, Dig. Dis. Sci., 50(Suppl. 1), S16 (2005); https://doi.org/10.1007/s10620-005-2802-7
  54. W.L. Smith, D.L. DeWitt and R.M. Garavito, Annu. Rev. Biochem., 69, 145 (2000); https://doi.org/10.1146/annurev.biochem.69.1.145
  55. W.A. van der Donk, A.L. Tsai and R.J. Kulmacz, Biochemistry, 41, 15451 (2002); https://doi.org/10.1021/bi026938h
  56. L.H. Heckmann, R.M. Sibly, M.J. Timmermans and A. Callaghan, Front. Zool., 5, 11 (2008); https://doi.org/10.1186/1742-9994-5-11
  57. H.A. Khamees, Y.H.E. Mohammed, S. Ananda, F.H. Al-Ostoot, Y. Sangappa, S. Alghamdi, S.A. Khanum and M. Madegowda, J. Mol. Struct., 1199, 127024 (2020); https://doi.org/10.1016/j.molstruc.2019.127024
  58. R.D. Kamble, R.J. Meshram, S.V. Hese, R.A. More, S.S. Kamble, R.N. Gacche and B.S. Dawane, Comput. Biol. Chem., 61, 86 (2016); https://doi.org/10.1016/j.compbiolchem.2016.01.007
  59. S.N. Thore, S.V. Gupta and K.G. Baheti, Med. Chem. Res., 22, 3802 (2013); https://doi.org/10.1007/s00044-012-0382-6
  60. V. Kamat, R. Santosh, B. Poojary, S.P. Nayak, M. Sankaranarayanan, S. Faheem, S. Khanapure, D.A. Barretto, B.K. Kumar and S.K. Vootla, ACS Omega, 5, 25228 (2020); https://doi.org/10.1021/acsomega.0c03386
  61. Y.M. Omar, H.H. Abdu-Allah and S.G. Abdel-Moty, Bioorg. Chem., 80, 461 (2018); https://doi.org/10.1016/j.bioorg.2018.06.036
  62. M. Thérien, C. Brideau, C.C. Chan, W.A. Cromlish, J.Y. Gauthier, R. Gordon, G. Greig, S. Kargman, C.K. Lau, Y. Leblanc, C.-S. Li, G.P. O’Neill, D. Riendeau, P. Roy, Z. Wang, L. Xu and P. Prasit, Bioorg. Med. Chem. Lett., 7, 47 (1997); https://doi.org/10.1016/S0960-894X(96)00580-X
  63. M.A. Abdelgawad, R.B. Bakr, A. El-Gendy, G.M. Kamel, A.A. Azouz and S.N.A. Bukhari, Future Med. Chem., 9, 1899 (2017); https://doi.org/10.4155/fmc-2017-0115
  64. L.Y. He, S.S. Zhang, D.X. Peng, L.P. Guan and S.H. Wang, Bioorg. Med. Chem. Lett., 30, 127376 (2020); https://doi.org/10.1016/j.bmcl.2020.127376
  65. M.S. Altowyan, A. Barakat, A.M. Al-Majid and H.A. Al-Ghulikah, Saudi J. Biol. Sci., 27, 1208 (2020); https://doi.org/10.1016/j.sjbs.2020.02.010
  66. O. Unsal-Tan, K. Ozadali, K. Piskin and A. Balkan, Eur. J. Med. Chem., 57, 59 (2012); https://doi.org/10.1016/j.ejmech.2012.08.046
  67. K. Liaras, M. Fesatidou and A. Geronikaki, Molecules, 23, 685 (2018); https://doi.org/10.3390/molecules23030685
  68. A. Zarghi and S. Arfaei, Iran. J. Pharm.. Res., 10, 665 (2011).
  69. P. J. Jacob and S.L. Manju, Med. Chem. Res., 30, 236 (2020); https://doi.org/10.1007/s00044-020-02655-9
  70. S. Yatam, S.S. Jadav, K.P. Gundla, K. Paidikondala, A.R. Ankireddy, B.N. Babu, M.J. Ahsan and R. Gundla, ChemistrySelect, 4, 11081 (2019); https://doi.org/10.1002/slct.201902972
  71. M. Shahrasbi, M.A. Movahed, O.G. Dadras, B. Daraei and A. Zarghi, Iran. J. Pharm. Res., 17, 1288 (2018).
  72. S. Sinha, S.L. Manju and M. Doble, ACS Med. Chem. Lett., 10, 1415 (2019); https://doi.org/10.1021/acsmedchemlett.9b00193
  73. M.T.E. Maghraby, O.M. Abou-Ghadir, S.G. Abdel-Moty, A.Y. Ali and O.I. Salem, Bioorg. Med. Chem., 28, 115403 (2020); https://doi.org/10.1016/j.bmc.2020.115403
  74. E.K. Abdelall and G.M. Kamel, Eur. J. Med. Chem., 118, 250 (2016); https://doi.org/10.1016/j.ejmech.2016.04.049
  75. A.A. Geronikaki, A.A. Lagunin, D.I. Hadjipavlou-Litina, P.T. Eleftheriou, D.A. Filimonov, V.V. Poroikov, I. Alam and A.K. Saxena, J. Med. Chem., 51, 1601 (2008); https://doi.org/10.1021/jm701496h
  76. I. Apostolidis, K. Liaras, A. Geronikaki, D. Hadjipavlou-Litina, A. Gavalas, M. Sokovic, J. Glamoèlija and A. Ciric, Bioorg. Med. Chem., 21, 532 (2013); https://doi.org/10.1016/j.bmc.2012.10.046
  77. P. Eleftheriou, A. Geronikaki, D. Hadjipavlou-Litina, P. Vicini, O. Filz, D. Filimonov, V. Poroikov, S.S. Chaudhaery, K.K. Roy and A.K. Saxena, Eur. J. Med. Chem., 47, 111 (2012); https://doi.org/10.1016/j.ejmech.2011.10.029
  78. T. Hanke, C. Lamers, R.C. Gomez, G. Schneider, O. Werz and M. Schubert-Zsilavecz, Bioorg. Med. Chem. Lett., 24, 3757 (2014); https://doi.org/10.1016/j.bmcl.2014.06.077
  79. O.S. Afifi, O.G. Shaaban, H.A. Abd El Razik, S.E.-D.A. Shams ElDine, F.A. Ashour, A.A. El-Tombary and M.M. Abu-Serie, Bioorg. Chem., 87, 821 (2019); https://doi.org/10.1016/j.bioorg.2019.03.076
  80. S.K. Sinha, S.K. Prasad, M.A. Islam, S.S. Gurav, R.B. Patil, N.A. AlFaris, T.S. Aldayel, N.M. AlKehayez, S.M. Wabaidur and A. Shakya, J. Biomol. Struct. Dyn., 39, 4686 (2020); https://doi.org/10.1080/07391102.2020.1779132
  81. Mahesha, H.M. Krishnegowda, C.S. Karthik, P.J. Kudigana, P. Mallu and L.K. Neratur, Polyhedron, 185, 114571 (2020); https://doi.org/10.1016/j.poly.2020.114571
  82. S. Mahanta, P. Chowdhury, N. Gogoi, N. Goswami, D. Borah, R. Kumar, D. Chetia, P. Borah, A.K. Buragohain and B. Gogoi, J. Biomol. Struct. Dyn., 39, 3802 (2020); https://doi.org/10.1080/07391102.2020.1768902
  83. R. Islam, M.R. Parves, A.S. Paul, N. Uddin, M.S. Rahman, A.A. Mamun, M.N. Hossain, M.A. Ali and M.A. Halim, J. Biomol. Struct. Dyn., 39, 3213 (2020); https://doi.org/10.1080/07391102.2020.1761883
  84. N.A. Al-Shar’i, E.K. Al-Rousan, L.I. Fakhouri, Q.A. Al-Balas and M.A. Hassan, Med. Chem. Res., 29, 356 (2020); https://doi.org/10.1007/s00044-019-02486-3
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 1 Download : 0