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Exploration of NMI-MsCl mediated amide bond formation for the synthesis of novel 3,5-substituted-1,2,4-oxadiazole derivatives: synthesis, evaluation of anti-inflammatory activity and molecular docking studies

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Abstract

We herein report the facile synthesis of a series of 3,5-substituted-1,2,4-oxadiazole derivatives 9a–e and 10a–e in good to excellent yields by employing NMI-MsCl mediated amide bond formation reaction. The anti-inflammatory potential of the newly synthesized compounds were evaluated by anti-denaturation assay using diclofenac sodium as the reference drug. The compounds 9a and 9d demonstrated promising activity profile when compared to the reference standard. The SAR and molecular docking studies were also carried out for obtaining more details about the profound activity profile of the synthesized molecules. The synthesized compounds were docked against two target proteins TGF-β and IL-1 by AutoDock vina and Auto Dock 4.2.

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References

  1. Khan KM, Ambreen N, Mughal UR, Jalil S, Perveen S, Choudhary MI (2010) Eur J Med Chem 45:4058–4064

    Article  CAS  PubMed  Google Scholar 

  2. Koksal M, Ozkan-Dagliyan I, Ozyazici T, Kadioglu B, Sipahi H, Bozkurt A, Bilge SS (2017) Arch Pharm 350:e1700153

    Article  Google Scholar 

  3. Bezerra NMM, De Oliveira SP, Srivastava RM, Da Silva JR (2005) Il Farmaco 60:955–960

    Article  CAS  PubMed  Google Scholar 

  4. Rho T, Jeong HW, Hong YD, Yoon K, Cho JY, Yoon KD (2020) J Ginseng Res 44:145–153

    Article  PubMed  Google Scholar 

  5. Blobaum AL, Marnett LJ (2007) J Med Chem 50:1425–1441

    Article  CAS  PubMed  Google Scholar 

  6. Srivastava RM, Lima AA, Viana OS, Silva MJC, Catanho MTJA, Morais JOF (2003) Bioorg Med Chem 11:1821–1827

    Article  CAS  PubMed  Google Scholar 

  7. Feng Y, Guo M, Jia X, Liu N, Li X, Li X, Song L, Wang X, Qiu L, Yu Y (2020) Bioresour Technol 309:123346

    Article  CAS  PubMed  Google Scholar 

  8. Glomb T, Wiatrak B, Gebczak K, Gebarowski T, Bodetko D, Czyznikowska Z, Swiatek P (2020) Int J Mol Sci 21:9122

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Ustabas R, Suleymanoglu N, Unver Y, Direkel S (2020) J Mol Struct 1214:128217

    Article  CAS  Google Scholar 

  10. Silva FC, Cardoso MFC, Ferreira PG, Ferreira VF (2015) Top Heterocycl Chem 40:117–165

    Article  Google Scholar 

  11. El-Helby AA, Sakr H, Eissa IH, Abulkhair H, Al-Karmalawy AA, Khaled El-Adl K (2019) Arch Pharm 352:1900113

    Article  CAS  Google Scholar 

  12. Watkinson M (2012) Top Heterocycl Chem 28:109–136

    Article  CAS  Google Scholar 

  13. Huo H, Li G, Shi B, Li J (2022) Bioorg Med Chem 69:116882

    Article  CAS  PubMed  Google Scholar 

  14. Akhtar J, Khan AA, Ali Z, Haider R, Yar MS (2017) Eur J Med Chem 125:143–189

    Article  CAS  PubMed  Google Scholar 

  15. Kaur T, Gautam RN, Sharma A (2016) Chem Asian J 11:2938–2945

    Article  CAS  PubMed  Google Scholar 

  16. Eid I, Elsebaei MM, Mohammad H, Hagras M, Peters CE, Hegazy YA, Cooper B, Pogliano J, Pogliano K, Abulkhair HS, Seleem MN, Mayhoub AS (2017) Eur J Med Chem 139:665–673

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Venepally V, Jala RCR (2017) Eur J Med Chem 141:113–137

    Article  CAS  PubMed  Google Scholar 

  18. Singh A, Malhotra D, Singh K, Chadha R, Bedi PMS (2022) J Mol Struct 1266:133479

    Article  CAS  Google Scholar 

  19. Abdolmohammadi S, Afsharpour M, Keshavarz-Fatideh S (2014) S Afr J Chem 67:203–210

    Google Scholar 

  20. Abdolmohammadi S (2018) Comb Chem High Throughput Screen 21:594–601

    Article  CAS  PubMed  Google Scholar 

  21. Khalilian S, Abdolmohammadi S, Nematolahi F (2017) Lett Org Chem 14:361–367

    Article  CAS  Google Scholar 

  22. Samani A, Abdolmohammadi S, Otaredi-Kashani A (2018) Comb Chem High Throughput Screen 21:111–116

    Article  CAS  PubMed  Google Scholar 

  23. Abdolmohammadi S (2013) Curr Catal 2:116–121

    Article  CAS  Google Scholar 

  24. Abdolmohammadi S, Hossaini Z (2019) Mol Divers 23:885–896

    Article  CAS  PubMed  Google Scholar 

  25. Fakheri-Vayeghan S, Abdolmohammadi S, Kia-Kojoori R (2018) Z Naturforsch B 73:545–551

    Article  CAS  Google Scholar 

  26. Chaghari-Farahani F, Abdolmohammadi S, Kia-Kojoori R (2020) RSC Adv 10:15614–15621

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. Abdolmohammadi S, Ghiasi R, Ahmadzadeh-Vatani S (2016) Z Naturforsch B 71:777–782

    Article  CAS  Google Scholar 

  28. Abdolmohammadi S, Aghaei-Meybodi Z (2015) Comb Chem High Throughput Screen 18:911–916

    Article  CAS  PubMed  Google Scholar 

  29. Pitasse-Santos P, Sueth-Santiago V, Lima MEF (2018) J Braz Chem Soc 29:435–456

    CAS  Google Scholar 

  30. Koksal M, Yarim M, Erdal A, Bozkurt A (2014) Drug Res 64:66–72

    CAS  Google Scholar 

  31. Ozyazici T, Gurdal EE, Orak D, Hande Sipahi H, Ercetin T, Gulcan HO, Koksal M (2020) Arch Pharm 353:e2000061

    Article  CAS  Google Scholar 

  32. Mihailović N, Marković V, Matić IZ, Stanisavljević NS, Jovanović ŽS, Trifunović S, Joksović L (2017) RSC Adv 7:8550–8560

    Article  Google Scholar 

  33. Zhang TT, Wang PY, Zhou J, Shao WB, Fang HS, Zhou X, Wu ZB (2017) J Heterocycl Chem 54:2319–2325

    Article  CAS  Google Scholar 

  34. Hannoun MH, Hagras M, Kotb A, El-Attar AMM, Abulkhair HS (2020) Bioorg Chem 94:103364

    Article  CAS  PubMed  Google Scholar 

  35. Gan X, Hu D, Chen Z, Wang Y, Song B (2017) Bioorg Med Chem Lett 27:4298–4301

    Article  CAS  PubMed  Google Scholar 

  36. Benmansour F, Trist I, Coutard B, Decroly E, Querat G, Brancale A, Barral K (2017) Eur J Med Chem 125:865–880

    Article  CAS  PubMed  Google Scholar 

  37. Rathore A, Sudhakar R, Ahsan MJ, Ali A, Subbarao N, Jadav SS, Umar S, Yar MS (2017) Bioorg Chem 70:107–117

    Article  CAS  PubMed  Google Scholar 

  38. Abd-Ellah HS, Abdel-Aziz M, Shoman ME, Beshr EA, Kaoud T, Ahmed ASF (2017) Bioorg Chem 74:15–29

    Article  CAS  PubMed  Google Scholar 

  39. Al-Wahaibi LM, Mohamed AAB, Tawfik SS, Hassan HM, El-Emam AA (2021) Molecules 26:2110

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. McDonald CM, Campbell C, Torricelli RE, Finkel RS, Flanigan KM, Goemans N, Heydemann P, Kaminska A, Kirschner J, Muntoni F et al (2017) Lancet 390:1489–1498

    Article  CAS  PubMed  Google Scholar 

  41. Biernacki K, Dasko M, Ciupak O, Kubinski K, Rachon J, Demkowicz S (2020) Pharmaceuticals 13:111

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. Sanna P, Carta A, Nikookar ME (2000) Eur J Med Chem 35:535–543

    Article  CAS  PubMed  Google Scholar 

  43. Joy MN, Bakulev VA, Bodke YD, Telkar S (2020) Pharm Chem J 54:604–621

    Article  CAS  Google Scholar 

  44. Kulkarni B, Manjunatha K, Joy MN, Sajith AM, Prashantha CN, Pakkath R, Alshammari MB (2021). Mol Divers. https://doi.org/10.1007/s11030-021-10340-1

    Article  PubMed  Google Scholar 

  45. Manjunatha K, Poojary B, Lobo PL, Fernandes J, Kumari NS (2010) Eur J Med Chem 45:5225–5233

    Article  CAS  PubMed  Google Scholar 

  46. Shetty P, Praveen BM, Raghavendra M, Manjunath K, Cheruku S (2016) Mol Divers 20:391–398

    Article  CAS  PubMed  Google Scholar 

  47. Sajith AM, Khader KKA, Joshi N, Reddy MN, Padusha MSA, Nagaswarupa HP, Joy MN, Bodke YD, Karuvalam RP, Banerjee R, Muralidharan A, Rajendra P (2015) Eur J Med Chem 89:21–31

    Article  CAS  PubMed  Google Scholar 

  48. Rajendra MA, Sunil K, Sajith AM, Joy MN, Bakulev VA, Haridas KR (2020) Synlett 31:1629–1633

    Article  CAS  Google Scholar 

  49. Rajendra MA, Naseem M, Joy MN, Sunil K, Sajith AM, Howari F, Nazzal Y, Xavier C, Alshammari MB, Haridas KR (2022) Mol Divers 26:1761–1767

    Article  CAS  PubMed  Google Scholar 

  50. Naveena CS, Poojary B, Kumsi M, Thangavel A, Der SS (2011) Pharma Chem 3:247–257

    CAS  Google Scholar 

  51. Gokhale N, Panathur N, Dalimba U, Kumsi M (2015) Aust J Chem 68:1603–1613

    Article  CAS  Google Scholar 

  52. Savitha B, Reddy EK, Kumar CSA, Karuvalam RP, Padusha MSA, Bakulev VA, Narasimhamurthy KH, Sajith AM, Joy MN (2019) Tetrahedron Lett 60:151332

    Article  CAS  Google Scholar 

  53. Priya MGR, Girija K, Ravichandran N (2011) Rasayan J Chem 4:418–424

    CAS  Google Scholar 

  54. Prashantha CN, Gouthami K, Lavanya L, Bhavanam S, Jakhar A, Shakthiraju RG, Suraj V, Sahana KV, Sujana HS, Guruprasad NM, Ramachandra R (2020) J Mol Graph Model 102:107769

    Article  PubMed  PubMed Central  Google Scholar 

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Acknowledgements

The authors are thankful to Bharathiar University, Coimbatore, and Nagarjuna College of Engineering & Technology, Bengaluru, for providing all the facilities to carry out the research work. The authors are also thankful to Indian Institute of Science, Bengaluru, for providing the analytical data and spectra. Grigory V. Zyryanov is thankful to Ministry of Science and Higher Education of the Russian Federation (Grant # 075-15-2020-777) for the financial support. Sougata Santra is thankful to Russian Science Foundation (Grant # 20-73-10205) and Grants Council of the President of the Russian Federation (# NSh-1223.2022.1.3). Muthipeedika Nibin Joy is thankful to Russian Science Foundation (Grants ## 22-23-20189 and 21-13-00304). The detailed experimental procedure and characterization data including spectra are available in the Supporting Information uploaded along with the manuscript.

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Authors and Affiliations

  1. Research and Development Centre, Bharathiar University, Coimbatore, Tamilnadu, 641046, India

    B. Kulkarni & K. Manjunatha

  2. Department of Chemistry, Nagarjuna College of Engineering and Technology, Devanahalli, Bengaluru, Karnataka, 562164, India

    K. Manjunatha

  3. Institute of Chemical Technology, Ural Federal University, 19 Mira Street, Yekaterinburg, Russia, 620002

    Muthipeedika Nibin Joy, Sougata Santra & Grigory V. Zyryanov

  4. Department of Chemistry, SSIT, Sri Siddhartha Academy of Higher Education, Tumkur, Karnataka, 572107, India

    Ayyiliath Meleveetil Sajith & K. Sunil

  5. I. Ya. Postovskiy Institute of Organic Synthesis, Ural Division of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, Yekaterinburg, Russia, 620219

    Grigory V. Zyryanov

  6. Department of Biotechnology, School of Applied Sciences, Reva University, Bengaluru, Karnataka, 560064, India

    C. N. Prashantha

  7. Chemistry Department, College of Science and Humanities, Prince Sattam Bin Abdulaziz University, P.O. Box 83, Al-Kharj, 11942, Saudi Arabia

    Mohammed B. Alshammari

Authors
  1. B. Kulkarni
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  2. K. Manjunatha
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  6. Grigory V. Zyryanov
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  7. C. N. Prashantha
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  8. Mohammed B. Alshammari
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  9. K. Sunil
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Contributions

BK and AMS conducted the synthesis and purification of the compounds. MNJ, SS and GVZ carried out the anti-inflammatory activity studies. PCN and MBA evaluated the docking studies. KS and MK wrote the manuscript and reviewed it.

Corresponding author

Correspondence to K. Manjunatha.

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Kulkarni, B., Manjunatha, K., Joy, M.N. et al. Exploration of NMI-MsCl mediated amide bond formation for the synthesis of novel 3,5-substituted-1,2,4-oxadiazole derivatives: synthesis, evaluation of anti-inflammatory activity and molecular docking studies. Mol Divers 27, 1867–1878 (2023). https://doi.org/10.1007/s11030-022-10536-z

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