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SYNTHESIS AND BIOLOGICAL EVALUATION OF 1H-(INDOLE-5-YL)-3-SUBSTITUTED-1,2,4-OXADIAZOLES AS NOVEL 5-LOX INHIBITORS

Year 2024, , 11 - 18, 04.02.2024
https://doi.org/10.18596/jotcsa.1334005

Abstract

: A series of indolyloxadiazoles were synthesized from amidoxime and indole 3-carboxaldehyde using CAN as a catalyst and PEG as a solvent. In vitro, a 5-LOX inhibitory assay has been performed for all the synthesized compounds. Among the tested compounds, 4bf showed the highest potency (IC50 18.78 µg/ml). The synthesized compound carried out docking on the 5-LOX enzyme protein crystal structure. Compound (4bf) docked snugly into the receptor site with a score of -9.1 Kcal/mol, and it showed strong hydrogen bond interactions with two key amino acids, His368 and Asn555.

Supporting Institution

Aksum University and Ministry of Education, Ethiopia for financial support

Thanks

The authors thank Aksum University and Ministry of Education, Ethiopia for financial support

References

  • 1. Knölker HJ, Reddy KR. Isolation and synthesis of biologically active carbazole alkaloids. Chemical reviews. 2002 Nov 13;102(11):4303-428. Available from: <URL>
  • 2. Tale RH, Rodge AH, Keche AP, Hatnapure GD, Padole PR, Gaikwad GS, Turkar SS. Synthesis and antibacterial, antifungal activity of novel 1, 2, 4-oxadiazole. Journal of Chemical and Pharmaceutical Research. 2011;3(2):496-505. Available from: <URL>
  • 3. Pace A, Pierro P. The new era of 1, 2, 4-oxadiazoles. Organic & biomolecular chemistry. 2009;7(21):4337-48. Available from: <URL>
  • 4. Borg S, Luthman K, Nyberg F, Terenius L, Hacksell U. 1, 2, 4-Oxadiazole derivatives of phenyl-alanine: potential inhibitors of substance P endopepti-dase. European Journal of Medicinal Chemistry. 1993 Jan 1;28(10):801-10. Available from: <URL>
  • 5. Behalo MS, Aly AA, Wasfy AF, Rizk MM. Syn-thesis of some novel 1, 2, 4-triazole derivatives as potential antimicrobial agents. European Journal of Chemistry. 2013 Jun 30;4(2):92-7. Available from: <URL>
  • 6. Haugwitz RD, Martinez AJ, Venslavsky J, An-gel RG, Maurer BV, Jacobs GA, Narayanan VL, Cruthers LR, Szanto J. Antiparasitic agents. 6. Synthe-sis and anthelmintic activities of novel isothiocya-natophenyl-1, 2, 4-oxadiazoles. Journal of Medicinal Chemistry. 1985 Sep;28(9):1234-41. Available from: <URL>
  • 7. Dahlgren SE, Dalhamn T. The Anti‐Inflammatory Action of Phenyl‐Methyl‐Oxadiazole (PMO): An Experimental Study on the Guinea‐Pig Tra-chea. Acta Pharmacologica et Toxicologica. 1972 Jul;31(3):193-202. Available from: <URL>
  • 8. Manfredini S, Lampronti I, Vertuani S, Solaroli N, Recanatini M, Bryan D, McKinney M. Design, syn-thesis and binding at cloned muscarinic receptors of N-[5-(1′-substituted-acetoxymethyl)-3-oxadiazolyl] and N-[4-(1′-substituted-acetoxymethyl)-2-dioxolanyl] dialkyl amines. Bioorganic & medicinal chemistry. 2000 Jul 1;8(7):1559-66. Available from: <URL>
  • 9. Kumar D, Patel G, Chavers AK, Chang KH, Shah K. Synthesis of novel 1, 2, 4-oxadiazoles and analogues as potential anticancer agents. European Journal of Medicinal chemistry. 2011 Jul 1;46(7):3085-92. Available from: <URL>
  • 10. Kode NR, Vanden Eynde JJ, Mayence A, Wang G, Huang TL. Design and synthesis of N 1, N 5-bis [4-(5-alkyl-1, 2, 4-oxadiazol-3-yl) phenyl] glutaramides as potential antifungal prodrugs. Molecules. 2013 Sep 12;18(9):11250-63. Available from: <URL>
  • 11. Fortuna CG, Berardozzi R, Bonaccorso C, Caltabiano G, Di Bari L, Goracci L, Guarcello A, Pace A, Piccionello AP, Pescitelli G, Pierro P. New potent antibacterials against Gram-positive multiresistant pathogens: Effects of side chain modification and chi-rality in Linezolid-like 1, 2, 4-oxadiazoles. Bioorganic & Medicinal Chemistry. 2014 Dec 15;22(24):6814-25. Available from: <URL>
  • 12. Maftei CV, Fodor E, Jones PG, Daniliuc CG, Franz MH, Kelter G, Fiebig HH, Tamm M, Neda I. Novel 1, 2, 4-oxadiazoles and trifluoromethylpyridines relat-ed to natural products: Synthesis, structural analysis and investigation of their antitumor activity. Tetrahe-dron. 2016 Mar 3;72(9):1185-99. Available from: <URL>
  • 13. Clitherow JW, Beswick P, Irving WJ, Scopes DI, Barnes JC, Clapham J, Brown JD, Evans DJ, Hayes AG. Novel 1, 2, 4-oxadiazoles as potent and selective histamine H3 receptor antagonists. Bioorganic & Me-dicinal Chemistry Letters. 1996 Apr 9;6(7):833-8. Available from: <URL>
  • 14. Vu CB, Corpuz EG, Merry TJ, Pradeepan SG, Bartlett C, Bohacek RS, Botfield MC, Eyermann CJ, Lynch BA, MacNeil IA, Ram MK. Discovery of potent and selective SH2 inhibitors of the tyrosine kinase ZAP-70. Journal of Medicinal Chemistry. 1999 Oct 7;42(20):4088-98. Available from: <URL>
  • 15. Wright AE, Pomponi SA, Cross SS, McCarthy P. A new bis-(indole) alkaloid from a deep-water ma-rine sponge of the genus Spongosorites. The Journal of Organic Chemistry. 1992 Aug;57(17):4772-5. Available from: <URL>
  • 16. Bhambi D, Salvi VK, Jat JL, Ojha S, Talesara GL. Synthesis and antimicrobial activity of some new indole containing isoxazolines and phthalimidoxy de-rivatives of thiazolidinone and thiohydantoin. Journal of Sulfur Chemistry. 2007 Apr 1;28(2):155-63. Avail-able from: <URL>
  • 17. Mumuni M, Attama AA, Kunle OO. Formulation in vitro and in vivo evaluation of SRMS-based hetero-lipid-templated homolipid delivery system for diclo-fenac sodium. Drug Delivery. 2016 Mar 23;23(3):907-15. Available from: <URL>
  • 18. Tohid SF, Ziedan NI, Stefanelli F, Fogli S, Westwell AD. Synthesis and evaluation of indole-containing 3, 5-diarylisoxazoles as potential pro-apoptotic antitumour agents. European Journal of Medicinal Chemistry. 2012 Oct 1; 56:263-70. Available from: <URL>
  • 19. Nguyen CH, Lhoste JM, Lavelle F, Bissery MC, Bisagni E. Synthesis and antitumor activity of 1-[[(dialkylamino) alkyl] amino]-4-methyl-5H-pyrido [4, 3-b] benzo [e]-and-benzo [g]) indoles. A new class of antineoplastic agents. Journal of Medicinal Chemistry. 1990 May;33(5):1519-28. Available from: <URL>
  • 20. Safdy ME, Kurchacova E, Schut RN, Vidrio H, Hong E. Tryptophan analogs. 1. Synthesis and antihy-pertensive activity of positional isomers. Journal of Medicinal Chemistry. 1982 Jun;25(6):723-30. Availa-ble from: <URL>
  • 21. Williams JD, Chen JJ, Drach JC, Townsend LB. Synthesis and antiviral activity of 3-formyl-and 3-cyano-2, 5, 6-trichloroindole nucleoside derivatives. Journal of Medicinal Chemistry. 2004 Nov 4;47(23):5766-72. Available from: <URL>
  • 22. Saundane AR, Halu A, Kirankumar NM. Syn-thesis and biological evaluation of some novel indole analogues containing triazolopyrimidine moiety. Monatshefte für Chemie-Chemical Monthly. 2017 Aug; 148:1497-511. Available from: <URL>
  • 23. Wakchaure ND, Shejwal SS, Deshmukh VK, Chaudhari SR. Review on Common Methods to Syn-thesize Substituted1H-Indole-2, 3-Dione (Isatin) De-rivatives and Their Medicinal Significance. American J. PharmTech Res. 2012;2(4):288-310.
  • 24. Wang P, Liu J, Xing H, Liu Y, Xie W, Zhao G. Synthesis and anticancer activity of novel 5-(indole-2-yl)-3-substituted 1, 2, 4-oxadiazoles. Drug Discover-ies & Therapeutics. 2012 Jun 30;6(3):133-9. Available from: <URL>
  • 25. Swain CJ, Baker R, Kneen C, Moseley J, Saunders J, Seward EM, Stevenson G, Beer M, Stan-ton J, Watling K. Novel 5-HT3 antagonists. Indole oxadiazoles. Journal of Medicinal Chemistry. 1991 Jan;34(1):140-51. Available from: <URL>
  • 26. Carbone M, Li Y, Irace C, Mollo E, Castelluccio F, Di Pascale A, Cimino G, Santamaria R, Guo YW, Gavagnin M. Structure and cytotoxicity of phidiani-dines A and B: first finding of 1, 2, 4-oxadiazole sys-tem in a marine natural product. Organic Letters. 2011 May 20;13(10):2516-9. Available from: <URL>
  • 27. Peters-Golden M, Henderson Jr WR. Leukotri-enes. New England Journal of Medicine. 2007 Nov 1;357(18):1841-54.
  • 28. Young RN. Inhibitors of 5-lipoxygenase: a therapeutic potential yet to be fully realized. European Journal of Medicinal Chemistry. 1999 Sep 1;34(9):671-85. Available from: <URL>
  • 29. Helgadottir A, Manolescu A, Thorleifsson G, Gretarsdottir S, Jonsdottir H, Thorsteinsdottir U, Sa-mani NJ, Gudmundsson G, Grant SF, Thorgeirsson G, Sveinbjornsdottir S. The gene encoding 5-lipoxygenase activating protein confers risk of myo-cardial infarction and stroke. Nature Genetics. 2004 Mar 1;36(3):233-9. Available from: <URL>
  • 30. Rådmark O, Samuelsson B. Microsomal pros-taglandin E synthase‐1 and 5‐lipoxygenase: potential drug targets in cancer. Journal of Internal Medicine. 2010 Jul;268(1):5-14. Available from: <URL>
  • 31. Xiong WN, Yang CG, Jiang B. Synthesis of novel analogues of marine indole alkaloids: Mono (indolyl)-4-trifluoromethylpyridines and bis (indolyl)-4-trifluoromethylpyridines as potential anticancer agents. Bioorganic & Medicinal Chemistry. 2001 Jul 1;9(7):1773-80. Available from: <URL>
  • 32. Chandra T, Garg N, Kumar A. Synthesis and anti-inflammatory activity of indole derivatives. Inter-national Journal of ChemTech Research. 2010 Apr;2(2):762-3. Available from: <URL>
  • 33. Tohid SF, Ziedan NI, Stefanelli F, Fogli S, Westwell AD. Synthesis and evaluation of indole-containing 3, 5-diarylisoxazoles as potential pro-apoptotic antitumour agents. European Journal of Medicinal Chemistry. 2012 Oct 1; 56:263-70. Available from: <URL>
  • 34. Nguyen CH, Lhoste JM, Lavelle F, Bissery MC, Bisagni E. Synthesis and antitumor activity of 1-[[(dialkylamino) alkyl] amino]-4-methyl-5H-pyrido [4, 3-b] benzo [e]-and-benzo [g]) indoles. A new class of antineoplastic agents. Journal of Medicinal Chemistry. 1990 May;33(5):1519-28. Available from: <URL>
  • 35. Gupta PK, Hussain MK, Asad M, Kant R, Mahar R, Shukla SK, Hajela K. A metal-free tandem ap-proach to prepare structurally diverse N-heterocycles: synthesis of 1, 2, 4-oxadiazoles and pyrimidinones. New Journal of Chemistry. 2014;38(7):3062-70. Available from: <URL>
  • 36. Ziedan NI, Stefanelli F, Fogli S, Westwell AD. Design, synthesis and pro-apoptotic antitumour prop-erties of indole-based 3, 5-disubstituted oxadiazoles. European Journal of Medicinal Chemistry. 2010 Oct 1;45(10):4523-30. Available from: <URL>
Year 2024, , 11 - 18, 04.02.2024
https://doi.org/10.18596/jotcsa.1334005

Abstract

References

  • 1. Knölker HJ, Reddy KR. Isolation and synthesis of biologically active carbazole alkaloids. Chemical reviews. 2002 Nov 13;102(11):4303-428. Available from: <URL>
  • 2. Tale RH, Rodge AH, Keche AP, Hatnapure GD, Padole PR, Gaikwad GS, Turkar SS. Synthesis and antibacterial, antifungal activity of novel 1, 2, 4-oxadiazole. Journal of Chemical and Pharmaceutical Research. 2011;3(2):496-505. Available from: <URL>
  • 3. Pace A, Pierro P. The new era of 1, 2, 4-oxadiazoles. Organic & biomolecular chemistry. 2009;7(21):4337-48. Available from: <URL>
  • 4. Borg S, Luthman K, Nyberg F, Terenius L, Hacksell U. 1, 2, 4-Oxadiazole derivatives of phenyl-alanine: potential inhibitors of substance P endopepti-dase. European Journal of Medicinal Chemistry. 1993 Jan 1;28(10):801-10. Available from: <URL>
  • 5. Behalo MS, Aly AA, Wasfy AF, Rizk MM. Syn-thesis of some novel 1, 2, 4-triazole derivatives as potential antimicrobial agents. European Journal of Chemistry. 2013 Jun 30;4(2):92-7. Available from: <URL>
  • 6. Haugwitz RD, Martinez AJ, Venslavsky J, An-gel RG, Maurer BV, Jacobs GA, Narayanan VL, Cruthers LR, Szanto J. Antiparasitic agents. 6. Synthe-sis and anthelmintic activities of novel isothiocya-natophenyl-1, 2, 4-oxadiazoles. Journal of Medicinal Chemistry. 1985 Sep;28(9):1234-41. Available from: <URL>
  • 7. Dahlgren SE, Dalhamn T. The Anti‐Inflammatory Action of Phenyl‐Methyl‐Oxadiazole (PMO): An Experimental Study on the Guinea‐Pig Tra-chea. Acta Pharmacologica et Toxicologica. 1972 Jul;31(3):193-202. Available from: <URL>
  • 8. Manfredini S, Lampronti I, Vertuani S, Solaroli N, Recanatini M, Bryan D, McKinney M. Design, syn-thesis and binding at cloned muscarinic receptors of N-[5-(1′-substituted-acetoxymethyl)-3-oxadiazolyl] and N-[4-(1′-substituted-acetoxymethyl)-2-dioxolanyl] dialkyl amines. Bioorganic & medicinal chemistry. 2000 Jul 1;8(7):1559-66. Available from: <URL>
  • 9. Kumar D, Patel G, Chavers AK, Chang KH, Shah K. Synthesis of novel 1, 2, 4-oxadiazoles and analogues as potential anticancer agents. European Journal of Medicinal chemistry. 2011 Jul 1;46(7):3085-92. Available from: <URL>
  • 10. Kode NR, Vanden Eynde JJ, Mayence A, Wang G, Huang TL. Design and synthesis of N 1, N 5-bis [4-(5-alkyl-1, 2, 4-oxadiazol-3-yl) phenyl] glutaramides as potential antifungal prodrugs. Molecules. 2013 Sep 12;18(9):11250-63. Available from: <URL>
  • 11. Fortuna CG, Berardozzi R, Bonaccorso C, Caltabiano G, Di Bari L, Goracci L, Guarcello A, Pace A, Piccionello AP, Pescitelli G, Pierro P. New potent antibacterials against Gram-positive multiresistant pathogens: Effects of side chain modification and chi-rality in Linezolid-like 1, 2, 4-oxadiazoles. Bioorganic & Medicinal Chemistry. 2014 Dec 15;22(24):6814-25. Available from: <URL>
  • 12. Maftei CV, Fodor E, Jones PG, Daniliuc CG, Franz MH, Kelter G, Fiebig HH, Tamm M, Neda I. Novel 1, 2, 4-oxadiazoles and trifluoromethylpyridines relat-ed to natural products: Synthesis, structural analysis and investigation of their antitumor activity. Tetrahe-dron. 2016 Mar 3;72(9):1185-99. Available from: <URL>
  • 13. Clitherow JW, Beswick P, Irving WJ, Scopes DI, Barnes JC, Clapham J, Brown JD, Evans DJ, Hayes AG. Novel 1, 2, 4-oxadiazoles as potent and selective histamine H3 receptor antagonists. Bioorganic & Me-dicinal Chemistry Letters. 1996 Apr 9;6(7):833-8. Available from: <URL>
  • 14. Vu CB, Corpuz EG, Merry TJ, Pradeepan SG, Bartlett C, Bohacek RS, Botfield MC, Eyermann CJ, Lynch BA, MacNeil IA, Ram MK. Discovery of potent and selective SH2 inhibitors of the tyrosine kinase ZAP-70. Journal of Medicinal Chemistry. 1999 Oct 7;42(20):4088-98. Available from: <URL>
  • 15. Wright AE, Pomponi SA, Cross SS, McCarthy P. A new bis-(indole) alkaloid from a deep-water ma-rine sponge of the genus Spongosorites. The Journal of Organic Chemistry. 1992 Aug;57(17):4772-5. Available from: <URL>
  • 16. Bhambi D, Salvi VK, Jat JL, Ojha S, Talesara GL. Synthesis and antimicrobial activity of some new indole containing isoxazolines and phthalimidoxy de-rivatives of thiazolidinone and thiohydantoin. Journal of Sulfur Chemistry. 2007 Apr 1;28(2):155-63. Avail-able from: <URL>
  • 17. Mumuni M, Attama AA, Kunle OO. Formulation in vitro and in vivo evaluation of SRMS-based hetero-lipid-templated homolipid delivery system for diclo-fenac sodium. Drug Delivery. 2016 Mar 23;23(3):907-15. Available from: <URL>
  • 18. Tohid SF, Ziedan NI, Stefanelli F, Fogli S, Westwell AD. Synthesis and evaluation of indole-containing 3, 5-diarylisoxazoles as potential pro-apoptotic antitumour agents. European Journal of Medicinal Chemistry. 2012 Oct 1; 56:263-70. Available from: <URL>
  • 19. Nguyen CH, Lhoste JM, Lavelle F, Bissery MC, Bisagni E. Synthesis and antitumor activity of 1-[[(dialkylamino) alkyl] amino]-4-methyl-5H-pyrido [4, 3-b] benzo [e]-and-benzo [g]) indoles. A new class of antineoplastic agents. Journal of Medicinal Chemistry. 1990 May;33(5):1519-28. Available from: <URL>
  • 20. Safdy ME, Kurchacova E, Schut RN, Vidrio H, Hong E. Tryptophan analogs. 1. Synthesis and antihy-pertensive activity of positional isomers. Journal of Medicinal Chemistry. 1982 Jun;25(6):723-30. Availa-ble from: <URL>
  • 21. Williams JD, Chen JJ, Drach JC, Townsend LB. Synthesis and antiviral activity of 3-formyl-and 3-cyano-2, 5, 6-trichloroindole nucleoside derivatives. Journal of Medicinal Chemistry. 2004 Nov 4;47(23):5766-72. Available from: <URL>
  • 22. Saundane AR, Halu A, Kirankumar NM. Syn-thesis and biological evaluation of some novel indole analogues containing triazolopyrimidine moiety. Monatshefte für Chemie-Chemical Monthly. 2017 Aug; 148:1497-511. Available from: <URL>
  • 23. Wakchaure ND, Shejwal SS, Deshmukh VK, Chaudhari SR. Review on Common Methods to Syn-thesize Substituted1H-Indole-2, 3-Dione (Isatin) De-rivatives and Their Medicinal Significance. American J. PharmTech Res. 2012;2(4):288-310.
  • 24. Wang P, Liu J, Xing H, Liu Y, Xie W, Zhao G. Synthesis and anticancer activity of novel 5-(indole-2-yl)-3-substituted 1, 2, 4-oxadiazoles. Drug Discover-ies & Therapeutics. 2012 Jun 30;6(3):133-9. Available from: <URL>
  • 25. Swain CJ, Baker R, Kneen C, Moseley J, Saunders J, Seward EM, Stevenson G, Beer M, Stan-ton J, Watling K. Novel 5-HT3 antagonists. Indole oxadiazoles. Journal of Medicinal Chemistry. 1991 Jan;34(1):140-51. Available from: <URL>
  • 26. Carbone M, Li Y, Irace C, Mollo E, Castelluccio F, Di Pascale A, Cimino G, Santamaria R, Guo YW, Gavagnin M. Structure and cytotoxicity of phidiani-dines A and B: first finding of 1, 2, 4-oxadiazole sys-tem in a marine natural product. Organic Letters. 2011 May 20;13(10):2516-9. Available from: <URL>
  • 27. Peters-Golden M, Henderson Jr WR. Leukotri-enes. New England Journal of Medicine. 2007 Nov 1;357(18):1841-54.
  • 28. Young RN. Inhibitors of 5-lipoxygenase: a therapeutic potential yet to be fully realized. European Journal of Medicinal Chemistry. 1999 Sep 1;34(9):671-85. Available from: <URL>
  • 29. Helgadottir A, Manolescu A, Thorleifsson G, Gretarsdottir S, Jonsdottir H, Thorsteinsdottir U, Sa-mani NJ, Gudmundsson G, Grant SF, Thorgeirsson G, Sveinbjornsdottir S. The gene encoding 5-lipoxygenase activating protein confers risk of myo-cardial infarction and stroke. Nature Genetics. 2004 Mar 1;36(3):233-9. Available from: <URL>
  • 30. Rådmark O, Samuelsson B. Microsomal pros-taglandin E synthase‐1 and 5‐lipoxygenase: potential drug targets in cancer. Journal of Internal Medicine. 2010 Jul;268(1):5-14. Available from: <URL>
  • 31. Xiong WN, Yang CG, Jiang B. Synthesis of novel analogues of marine indole alkaloids: Mono (indolyl)-4-trifluoromethylpyridines and bis (indolyl)-4-trifluoromethylpyridines as potential anticancer agents. Bioorganic & Medicinal Chemistry. 2001 Jul 1;9(7):1773-80. Available from: <URL>
  • 32. Chandra T, Garg N, Kumar A. Synthesis and anti-inflammatory activity of indole derivatives. Inter-national Journal of ChemTech Research. 2010 Apr;2(2):762-3. Available from: <URL>
  • 33. Tohid SF, Ziedan NI, Stefanelli F, Fogli S, Westwell AD. Synthesis and evaluation of indole-containing 3, 5-diarylisoxazoles as potential pro-apoptotic antitumour agents. European Journal of Medicinal Chemistry. 2012 Oct 1; 56:263-70. Available from: <URL>
  • 34. Nguyen CH, Lhoste JM, Lavelle F, Bissery MC, Bisagni E. Synthesis and antitumor activity of 1-[[(dialkylamino) alkyl] amino]-4-methyl-5H-pyrido [4, 3-b] benzo [e]-and-benzo [g]) indoles. A new class of antineoplastic agents. Journal of Medicinal Chemistry. 1990 May;33(5):1519-28. Available from: <URL>
  • 35. Gupta PK, Hussain MK, Asad M, Kant R, Mahar R, Shukla SK, Hajela K. A metal-free tandem ap-proach to prepare structurally diverse N-heterocycles: synthesis of 1, 2, 4-oxadiazoles and pyrimidinones. New Journal of Chemistry. 2014;38(7):3062-70. Available from: <URL>
  • 36. Ziedan NI, Stefanelli F, Fogli S, Westwell AD. Design, synthesis and pro-apoptotic antitumour prop-erties of indole-based 3, 5-disubstituted oxadiazoles. European Journal of Medicinal Chemistry. 2010 Oct 1;45(10):4523-30. Available from: <URL>
There are 36 citations in total.

Details

Primary Language English
Subjects Organic Chemical Synthesis
Journal Section RESEARCH ARTICLES
Authors

Berihu Tekluu 0000-0001-9976-7209

Siddaiah Vidavalur 0000-0002-7190-7932

Sunanda Kumari Kadiri 0000-0003-0430-0476

Publication Date February 4, 2024
Submission Date July 31, 2023
Acceptance Date September 6, 2023
Published in Issue Year 2024

Cite

Vancouver Tekluu B, Vidavalur S, Kadiri SK. SYNTHESIS AND BIOLOGICAL EVALUATION OF 1H-(INDOLE-5-YL)-3-SUBSTITUTED-1,2,4-OXADIAZOLES AS NOVEL 5-LOX INHIBITORS. JOTCSA. 2024;11(1):11-8.