We use cookies to improve your experience. By continuing to browse this site, you accept our cookie policy.×
Published Online:https://doi.org/10.4155/fmc-2020-0295

Tuberculosis is a deadly communicable disease caused by the bacillus Mycobacterium tuberculosis (MTB), and pulmonary tuberculosis accounts for over 80% of the total cases. The 1,2,4-triazole is a privileged structure in the discovery of new drugs, and its derivatives act on various targets in MTB. In particular, 1,2,4-triazole hybrids can not only exert dual or multiple antitubercular mechanisms of action but also have the potential to enhance efficacy and reduce side effects. The present work aims to summarize the current status of 1,2,4-triazole hybrids as potential antitubercular agents, covering articles published between 2010 and 2020, to aid the further rational design of novel potential drug candidates endowed with higher efficacy, better compliance and fewer side effects.

Papers of special note have been highlighted as: • of interest; •• of considerable interest

References

  • 1. Pai M, Behr MA, Dowdy D et al. Tuberculosis. Nat. Rev. Dis. Primers 2, e16076 (2016).
  • 2. Saleem A, Azher M. The next pandemic – tuberculosis: the oldest disease of mankind rising one more time. Br. J. Med. Pract. 6(1), a615 (2013).
  • 3. World Health Organization. Global tuberculosis report 2019. https://apps.who.int/iris/bitstream/handle/10665/329368/9789241565714-eng.pdf?ua=1
  • 4. Getahun H, Matteelli A, Chaisson RE, Raviglione M. Latent Mycobacterium tuberculosis infection. N. Engl. J. Med. 372, 2127–2135 (2015).
  • 5. Natarajan A, Beena PM, Devnikar AV, Mali S. A systemic review on tuberculosis. Indian J. Tuberc. 67(3), 295–311 (2020).
  • 6. Knight GM, McQuaid CF, Dodd PJ, Houben RMGJ. Global burden of latent multidrug-resistant tuberculosis: trends and estimates based on mathematical modelling. Lancet Infect. Dis. 19(8), 903–912 (2019). • The recent development of 1,2,4-triazoles with anti-TB potential was outlined to faciliate further rational design.
  • 7. Garcia-Basteiro AL, Jenkins HE, Rangaka M. The burden of latent multidrug-resistant tuberculosis. Lancet Infect. Dis. 19(8), 802–803 (2019). • The recent development of 1,2,4-triazoles with anti-TB potential was outlined to faciliate further rational design.
  • 8. Umumararungu T, Mukazayire MJ, Mpenda M et al. A review of recent advances in anti-tubercular drug development. Indian J. Tuberc. 67(4), 539–559 (2020).
  • 9. Tornheim JA, Dooley KE. The global landscape of tuberculosis therapeutics. Ann. Rev. Med. 70, 105–120 (2019).
  • 10. Gawad J, Bonde C. Current affairs, future perspectives of tuberculosis and antitubercular agents. Indian J. Tuberc. 65(1), 15–22 (2018).
  • 11. Dutta A, Sarma D. Recent advances in the synthesis of quinazoline analogues as anti-TB agents. Tuberculosis 124, 101986 (2020).
  • 12. Xu Z, Gao C, Ren QC et al. Recent advances of pyrazole-containing derivatives as anti-tubercular agents. Eur. J. Med. Chem. 139, 429–440 (2017).
  • 13. Bahuguna A, Rawat DS. An overview of new antitubercular drugs, drug candidates, and their targets. Med. Res. Rev. 40(1), 263–292 (2020). • The recent development of 1,2,4-triazoles with anti-TB potential was outlined to faciliate further rational design.
  • 14. Gatadi S, Nanduri S. New potential drug leads against MDR-MTB: a short review. Bioorg. Chem. 95, e103534 (2020). • The recent development of 1,2,4-triazoles with anti-TB potential was outlined to faciliate further rational design.
  • 15. Huszar S, Chibale K, Singh V. The quest for the holy grail: new antitubercular chemical entities, targets and strategies. Drug Discov. Today 25(4), 772–780 (2020). • The recent development of 1,2,4-triazoles with anti-TB potential was outlined to faciliate further rational design.
  • 16. Borisov SE, D'Ambrosio L, Centis R, Tiberi S, Dheda K, Alffenaar JW. Outcomes of patients with drug-resistant-tuberculosis treated with bedaquiline-containing regimens and undergoing adjunctive surgery. J. Infect. 78(1), 35–39 (2019).
  • 17. Park M, Satta G, Kon OM. An update on multidrug-resistant tuberculosis. Clin. Med. 19(2), 135–139 (2019).
  • 18. Ramirea LMN, Bargas KQ, Diaz G. Whole genome sequencing for the analysis of drug resistant strains of mycobacterium tuberculosis: a systematic review for bedaquiline and delamanid. Antibiotics 9(3), e133 (2020).
  • 19. Moulin A, Bibian A, Blayo AL et al. Synthesis of 3,4,5-Trisubstituted-1,2,4-triazoles. Chem. Rev. 110(4), 1809–1827 (2010).
  • 20. Suresh M, Ramakanth P, Sreekanth J. 1,2,4-Triazoles: a review of synthetic approaches and the biological activity. Lett. Org. Chem. 10, 693–714 (2013).
  • 21. Kuang J, Chen B, Ma S. Copper-mediated efficient three-component synthesis of 1,2,4-triazoles from amines and nitriles. Org. Chem. Front. 1, 186–189 (2014).
  • 22. Amin NH, El-Saadi MT, Ibrahim AA, Abdel-Rahman HM. Design, synthesis and mechanistic study of new 1,2,4-triazole derivatives as antimicrobial agents. Bioorg. Chem. 111, e104841 (2021).
  • 23. Emami S, Ghobadi E, Saednia S, Hashemi SM. Current advances of triazole alcohols derived from fluconazole: design, in vitro and in silico studies. Eur. J. Med. Chem. 170, 173–194 (2019).
  • 24. Kun S, Begum J, Kyriakis E et al. A multidisciplinary study of 3-(β-d-glucopyranosyl)-5-substituted-1,2,4-triazole derivatives as glycogen phosphorylase inhibitors: computation, synthesis, crystallography and kinetics reveal new potent inhibitors. Eur. J. Med. Chem. 147, 266–278 (2018).
  • 25. Gokalp M, Dede B, Tilki T, Atay CK. Triazole based azo molecules as potential antibacterial agents: synthesis, characterization, DFT, ADME and molecular docking studies. J. Mol. Struct. 1212, e128140 (2020).
  • 26. Aggarwal R, Sumran G. An insight on medicinal attributes of 1,2,4-triazoles. Eur. J. Med. Chem. 205, e112652 (2020). •• The recent development of 1,2,4-triazoles with anti-TB potential was outlined to faciliate further rational design.
  • 27. Sathyanarayana R, Poojary B. Exploring recent developments on 1,2,4-triazole: synthesis and biological applications. J. Chin. Chem. Soc. 67(4), 459–477 (2020). ••The recent development of 1,2,4-triazoles with anti-TB potential was outlined to faciliate further rational design.
  • 28. Kuar P, Chawla A. 1,2,4-Triazole: a review of pharmacological activities. Int. Res. J. Pharm. 8(7), 10–29 (2017).
  • 29. Sharma J, Ahmad S, Shamsher A. Bioactive triazoles: a potential review. J. Chem. Pharm. Res. 4(12), 5157–5164 (2012).
  • 30. Gao F, Wang T, Xiao J, Huang G. Antibacterial activity study of 1,2,4-triazole derivatives. Eur. J. Med. Chem. 173, 274–281 (2019).
  • 31. Zhang J, Wang S, Ba Y, Xu Z. 1,2,4-Triazole-quinoline/quinolone hybrids as potential anti-bacterial agents. Eur. J. Med. Chem. 174, 1–8 (2019).
  • 32. Wen X, Zhou Y, Zeng J, Liu X. Recent development of 1,2,4-triazole-containing compounds as anticancer agents. Curr. Top. Med. Chem. 20(16), 1441–1460 (2020).
  • 33. Kaur R, Dwivedi AR, Kumar B, Kumar V. Recent developments on 1,2,4-triazole nucleus in anticancer compounds: a review. Anti-Cancer Agents Med. Chem. 16(4), 465–489 (2016).
  • 34. Kamboj VK, Verma PK, Dhanda A, Ranjan S. 1,2,4-Triazole derivatives as potential scaffold for anticonvulsant activity. Cent. Nerv. Syst. Agents Med. Chem. 15(1), 17–22 (2015).
  • 35. Ayati A, Emami S, Foroumadi A. The importance of triazole scaffold in the development of anticonvulsant agents. Eur. J. Med. Chem. 109, 380–392 (2016).
  • 36. Emami S, Ghobadi E, Saednia S, Hashemi SM. Current advances of triazole alcohols derived from fluconazole: design, in vitro and in silico studies. Eur. J. Med. Chem. 170, 173–194 (2019).
  • 37. Peyton LR, Gallagher S, Hashemzadeh M. Triazole antifungals: a review. Drugs Today 51(12), 705–718 (2015).
  • 38. Chu XM, Wang C, Wang WL et al. Triazole derivatives and their antiplasmodial and antimalarial activities. Eur. J. Med. Chem. 166, 206–223 (2019).
  • 39. Thakkar SS, Thakor P, Doshi H, Ray A. 1,2,4-Triazole and 1,3,4-oxadiazole analogues: Synthesis, MO studies, in silico molecular docking studies, antimalarial as DHFR inhibitor and antimicrobial activities. Bioorg. Med. Chem. 25(15), 4064–4075 (2017).
  • 40. Zhang S, Xu Z, Gao C et al. Triazole derivatives and their anti-tubercular activity. Eur. J. Med. Chem. 138, 501–513 (2017).
  • 41. Keri RS, Patil SA, Budagumpi S, Nagaraja BM. Triazole: a promising antitubercular agent. Chem. Biol. Drug Des. 86(4), 410–423 (2015). •• The recent development of 1,2,4-triazoles with anti-TB potential was outlined to faciliate further rational design.
  • 42. Dasan N, Babu G, George S. Molecular docking studies and synthesis of 3,4-disubstituted triazoles as Mycobacterium tuberculosis enoyl-acp reductase and CYP-51 inhibitors. Int. J. Pharm. Pharma. Sci. 11(1), 85–91 (2019).
  • 43. Shcherbyna RO, Parchenko VV, Safonov AA et al. Synthesis and research of the impact of new derivatives of 4-R-3-(morpholinomethyl)-4H-1,2,4-triazole-5-thiol on cultural attributes of pathogenic M. Bovis. Res. J. Pharm. Biol. Chem. Sci. 9(2), 70–79 (2018).
  • 44. Ibrar A, Shejzadi SA, Saeed F, Khan I. Developing hybrid molecule therapeutics for diverse enzyme inhibitory action: active role of coumarin-based structural leads in drug discovery. Bioorg. Med. Chem. 26(13), 3731–3762 (2018).
  • 45. Shaveta S, Mishra S, Singh P. Hybrid molecules: the privileged scaffolds for various pharmaceuticals. Eur. J. Med. Chem. 124, 500–536 (2016).
  • 46. Kuar P, Kuar R, Goswami M. A review on methods of synthesis of 1,2,4-triazole derivatives. Int. Res. J. Pharm. 9(1), 1–35 (2018).
  • 47. Raval K, Patel K, Patel S, Patel R, Patel S. A review on 1,2,4-triazoles. J. Pharm. Res. 1(1), 1–4 (2012).
  • 48. Namratha P, Gaonkar SL. 1,2,4-Triazoles: synthetic strategies and pharmacological. Int. J. Pharm. Pharmaceut. Sci. 6(8), 73–80 (2014).
  • 49. Al-Masoudi JA, Al-Soud YA, Al-Salihi NJ, Al-Masoudi NA. 1,2,4-Triazoles: synthetic approaches and pharmacological importance. (Review). Chem. Heterocycl. Compd. 42(11), 1377–1403 (2006).
  • 50. Dhall E, Sain S, Jain S, Dwivedi J. Synthesis of triazole derivatives manifesting antimicrobial and anti-tubercular activities. Mini-Rev. Org. Chem. 15, 291–314 (2018).
  • 51. Gao Y, Na LX, Xu Z et al. Design, synthesis and antibacterial evaluation of 1-[(1R,2S)-2-fluorocyclopropyl]ciprofloxacin-1,2,4-triazole-5(4H)-thione hybrids. Chem. Biodiver. 15(10), E1800261 (2018).
  • 52. Riyadh SM, Gomha SM. Two decades of the synthesis of mono- and bis-aminomercapto[1,2,4]triazoles. RSC Adv. 10(42), 24994–25012 (2020).
  • 53. Das R, Asthana GS, Suri KA, Mehta D, Asthana A. Recent developments in azole compounds as antitubercular agent. Mini-Rev. Org. Chem. 16(3), 290–306 (2019).
  • 54. Bozorov K, Zhao J, Aisa HA. 1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: a recent overview. Bioorg. Med. Chem. 27(16), 142–163 (2019). •• The recent development of 1,2,4-triazoles with anti-TB potential was outlined to faciliate further rational design.
  • 55. Zhang HZ, Gan LL, Wang H, Zhou CH. New progress in azole compounds as antimicrobial agents. Mini-Rev. Med. Chem. 17(2), 122–166 (2017).
  • 56. Li Z, Liu Y, Bai X et al. SAR studies on 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazoles as inhibitors of Mtb shikimate dehydrogenase for the development of novel antitubercular agents. RSC Adv. 5, 97089–97101 (2015).
  • 57. Deng Q, Meng J, Liu Y, Guan Y, Xiao C. IMB-SD62, a triazolothiadiazoles derivative with promising action against tuberculosis. Tuberculosis 112, 37–44 (2018).
  • 58. Seelam N, Shrivastava SP, Prasanthi S, Gupta S. Synthesis and in vitro study of some fused 1,2,4-triazole derivatives as antimycobacterial agents. J. Saudi Chem. Soc. 20, 411–418 (2016).
  • 59. Udupi RH, Manjunath CJ. Synthesis and biological evaluation of certain N-bridged 1,2,4-triazole analogues. J. Pharm. Sci. Res. 10(2), 420–424 (2018).
  • 60. Udupi RH, Manjunath CJ. Synthesis and biological evaluation of certain N-bridged 1,2,4-triazole analogues. J. Pharm. Sci. Res. 11(1), 44–49 (2019).
  • 61. Kumar GVS, Prasad YR, Mallikarjuna BP, Chandrashekar SM. Synthesis and pharmacological evaluation of clubbed isopropylthiazole derived triazolothiadiazoles, triazolothiadiazines and mannich bases as potential antimicrobial and antitubercular agents. Eur. J. Med. Chem. 45, 5120–5129 (2010).
  • 62. Kumar GVS, Rajendraprasad Y, Mallikarjuna BP, Chandrashekar SM, Kistayya C. Synthesis of some novel 2-substituted-5-[isopropylthiazole] clubbed 1,2,4-triazole and 1,3,4-oxadiazoles as potential antimicrobial and antitubercular agents. Eur. J. Med. Chem. 45, 2063–2074 (2010).
  • 63. Kumar GVS, Prasad YR, Chandrashekar SM. Synthesis and pharmacological evaluation of some novel 4-isopropyl thiazole-based sulfonyl derivatives as potent antimicrobial and antitubercular agents. Med. Chem. Res. 22, 4239–4252 (2013).
  • 64. Kumar GVS, Prasad YR, Chandrashekar SM. Synthesis and pharmacological evaluation of novel 4-isopropylthiazole-4-phenyl-1,2,4-triazole derivatives as potential antimicrobial and antitubercular agents. Med. Chem. Res. 22, 938–948 (2013).
  • 65. Papadopoulou MV, Bloomer WD, Rosenzweig HS. The antitubercular activity of various nitro(triazole/imidazole)-based compounds. Bioorg. Med. Chem. 25, 6039–6048 (2017).
  • 66. Patel NB, Khan IH, Rajani SD. Pharmacological evaluation and characterizations of newly synthesized 1,2,4-triazoles. Eur. J. Med. Chem. 45, 4293–4299 (2010).
  • 67. Patel NB, Khan IH, Rajani SD. Antimycobacterial and antimicrobial study of new 1,2,4-triazoles with benzothiazoles. Arch. Pharm. Chem. Life Sci. 10, 692–699 (2010).
  • 68. Guzeldemirci NU, Kucukbasmaci O. Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety. Eur. J. Med. Chem. 45, 63–68 (2010).
  • 69. Eroglu B, Ozadali-Sari K, Unsal-Tan O, Sriram D, Yogeeswari P, Balkan A. Novel thiazolidinone-azole hybrids: design, synthesis and antimycobacterial activity studies. Iran J. Pharm. Res. 15(4), 783–790 (2016).
  • 70. Taban IM, Elshihawy AE, Torun B et al. Novel aryl substituted pyrazoles as small molecule inhibitors of cytochrome P450 CYP121A1: synthesis and antimycobacterial evaluation. J. Med. Chem. 60, 10257–10267 (2017).
  • 71. Kishk SM, MeLean KJ, Sood S et al. Design and synthesis of imidazole and triazole pyrazoles as Mycobacterium tuberculosis CYP121A1 inhibitors. ChemistryOpen 8, 995–1011 (2019).
  • 72. Nandha B, Nargund LVG, Nargund SL. Design and synthesis of some new imidazole and 1,2,4-triazole substituted fluorobenzimidazoles for antitubercular and antifungal activity. Der Pharm. Chem. 5, 317–327 (2013).
  • 73. Suresh A, Suresh N, Misra S, Kumar MMK, Sekhar KVGC. Design, synthesis and biological evaluation of new substituted sulfonamide tetrazole derivatives as antitubercular agents. ChemistrySelect 1, 1705–1710 (2016).
  • 74. Khanage S, Mohite P, Pandhare R, Raju A. Synthesis and pharmacological evaluation of isoxazole derivatives containing 1,2,4-triazole moiety. Marmara Pharm. J. 16, 134–140 (2012).
  • 75. Dixit PP, Dixit PP, Thore SN. Hybrid triazoles: design and synthesis as potential dual inhibitor of growth and efflux inhibition in tuberculosis. Eur. J. Med. Chem. 107, 38–47 (2016).
  • 76. Alshibl HM, Al-Abdullah ES, Alkahtani HM. Coumarin: a promising scaffold for design and development of bioactive agents. Curr. Bioact. Compd. 16(6), 837–852 (2020).
  • 77. Hu YQ, Xu Z, Zhang S et al. Recent developments of coumarin-containing derivatives and their anti-tubercular activity. Eur. J. Med. Chem. 136, 122–130 (2017).
  • 78. Feng D, Zhang A, Yang Y, Yang P. Coumarin-containing hybrids and their antibacterial activities. Arch. Pharm. 353(6), e1900380 (2020).
  • 79. Sudha BN, Sastry VG. Synthesis, antibacterial and antimycobacterial activity of some novel 3-(6-phenyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl)-2H-chromen-2-one. Int. J. Pharm. Sci. Res. 7(5), 1302–1307 (2016).
  • 80. Somagond SM, Kamble RR, Bayannavar PK et al. Click chemistry based regioselective one-pot synthesis of coumarin-3-yl-methyl-1,2,3-triazolyl-1,2,4-triazol-3(4H)-ones as newer potent antitubercular agents. Arch. Pharm. 352, e1900013 (2019).
  • 81. Chaudhari KS, Patel HM, Surana SJ. Pyridines: multidrug-resistant tuberculosis (MDR-TB) inhibitors. Indian J. Tuberc. 64(2), 119–128 (2017).
  • 82. Villamizar-Mogotocoro AF, Vargas-Méndez LY, Kouznetsov VV. Pyridine and quinoline molecules as crucial protagonists in the never-stopping discovery of new agents against tuberculosis. Eur. J. Pharm. Sci. 151, e105374 (2020).
  • 83. Vora D, Upahdhyay N, Tilekar K, Jain V, Ramaa CS. Development of 1,2,4-triazole-5-thione derivatives as potential inhibitors of enoyl acyl carrier protein reductase (InhA) in tuberculosis. Iran. J. Pharm. Res. 18, 1742–1758 (2019).
  • 84. Rajoriya V, Kashaw V, Kashaw SK. Design, synthesis, characterization and antitubercular screening of some new 1,2,4-triazoles derived from isonicotinic acid hydrazides. Lett. Drug Des. Discov. 15, 451–462 (2018).
  • 85. Patel VM, Patel NB, Chan-Bacab MJ, Rivera G. Synthesis, biological evaluation and molecular dynamics studies of 1,2,4-triazole clubbed Mannich bases. Comput. Biol. Chem. 76, 264–274 (2018).
  • 86. Bogdanowicz A, Foks H, Gobis K, Augustynowicz-Kopec E. Synthesis and tuberculostatic activity of novel N‘-methyl-4-(pyrrolidin-1-yl)picolinohydrazide and N'-methylpyrimidine-2-carbohydrazide derivatives. Heteroatom Chem. 23, 223–230 (2012).
  • 87. Bobis K, Foks H, Augustynowicz-Kopec E, Napiorkowska A. Synthesis and tuberculostatic activity of novel diverse heterocyclic compounds derived from heterocyclic carbohydrazides and methyl 2-heteroaroylhydraziecarbodithioates. Heterocycles 85(4), 871–885 (2012).
  • 88. Vijayaraghavan S, Shirodkar PY. Synthesis of some 1,2,4-triazoles as potent anti-tubercular agents. Indian J. Chem. 54B, 1149–1543 (2015).
  • 89. Somani RR, Shinde GK, Shirodkar PY, Sanap GJ. Synthesis of some 1,2,4-triazoles as potent anti-tubercular agents. Indian Drugs 51(1), 41–47 (2014).
  • 90. Rode ND, Sonawane AD, Nawale L et al. Synthesis, biological evaluation and molecular docking studies of novel 3-aryl-5-(alkyl-thio)-1H-1,2,4-triazoles derivatives targeting Mycobacterium tuberculosis. Chem. Biol. Drug. Des. 90, 1206–1214 (2017).
  • 91. Thomas B, Harindran J. Design, synthesis and evaluation of antitubercular activity of amino azetidinones from isoniazid. Int. J. Pharm. Sci. Res. 7, 2795–2804 (2016).
  • 92. Himaja M, Prathap KJ, Mali SV. Facile synthesis of 3,6-disubstituted-1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles via oxidative cyclization of n-heteroaryl-substituted hydrazones and their biological activity. J. Heterocycl. Chem. 49, 823–827 (2012).
  • 93. Oh T, Hayat F, Yoo E et al. Antitubercular activities of the novel synthesized 1,2,4-triazole derivatives. Bull. Korean Chem. Soc. 36, 43–51 (2015).
  • 94. Liu B, Li F, Zhou T, Tang XQ, Hu GW. Quinoline derivatives with potential activity against multidrug-resistant tuberculosis. J. Heterocyclic Chem. 55(8), 1863–1873 (2018).
  • 95. Fan YL, Wu JB, Cheng XW, Zhang FZ, Feng LS. Fluoroquinolone derivatives and their anti-tubercular activities. Eur. J. Med. Chem. 146, 554–563 (2018).
  • 96. Li Y, Sun F, Zhang W. Bedaquiline and delamanid in the treatment of multidrug-resistant tuberculosis: promising but challenging. Drug Dev. Res. 80(1), 98–105 (2019).
  • 97. Somagond SM, Kamble RR, Kattimani PP et al. Design, docking, and synthesis of quinoline-2H-1,2,4-triazol-3(4H)-ones as potent anticancer and antitubercular agents. ChemistrySelect 3, 2004–2016 (2018).
  • 98. Papadopoulou MV, Bloomer WD, Rosenzweig HS, Kaiser M. The antitrypanosomal and antitubercular activity of some nitro(triazole/imidazole)-based aromatic amines. Eur. J. Med. Chem. 138, 1106–1113 (2017).
  • 99. Saundane AR, Kalpana R. Synthesis and biological evaluation of novel indolo[2,3-c]isoquinoline derivatives. Med. Chem. Res. 24, 1681–1695 (2015).
  • 100. Xu Z, Zhang S, Feng LS et al. Synthesis and in vitro antimycobacterial and antibacterial activity of 8-OMe ciprofloxacin-hydrozone/azole hybrids. Molecules 22, e1171 (2017).
  • 101. Peraman R, Varma RV, Reddy YP. Re-engineering nalidixic acid's chemical scaffold: a step towards the development of novel anti-tubercular and anti-bacterial leads for resistant pathogens. Bioorg. Med. Chem. Lett. 25, 4314–4319 (2015).
  • 102. Li Z, Bai X, Deng Q et al. Preliminary SAR and biological evaluation of antitubercular triazolothiadiazine derivatives against drug-susceptible and drug-resistant Mtb strains. Bioorg. Med. Chem. 25, 213–220 (2017).
  • 103. Kumar TNVG, Shenoy GG, Kar SS, Shenoy V, Bairy I. Design, synthesis and evaluation of antitubercular activity of novel 1,2,4-triazoles against MDR strain of Mycobacterium tuberculosis. Pharm. Chem. J. 51, 907–917 (2018).
  • 104. Mundhe D, Chandewar AV, Shiradkar MR. Design and synthesis of substituted clubbed triazolyl thiazole as XDR & MDR antituberculosis agents Part-II. Der Pharm. Chem. 3(6), 89–102 (2011).
  • 105. Patil PB, Awati SS, Kumbhoje SR, Ghotane RB, Patil SS. Synthesis and antitubercular activity of some novel N-methyl triazolone derivatives. Der Pharm. Chem. 6(1), 131–136 (2014).
  • 106. Asif M, Singh A, Khan SA, Husain A. Studies on new substituted pyridazinones: synthesis and biological evaluation. Braz. J. Pharm. Sci. 54(3), e00040 (2018).
  • 107. Prasad P, Kalola AG, Patel MP. Microwave assisted one-pot synthetic route to imidazo[1,2-a]pyrimidine derivatives of imidazo/triazole clubbed pyrazole and their pharmacological screening. New J. Chem. 42, 12666–12676 (2018).
  • 108. Sari KO, Tan OU, Sriram D, Balkan A. Some new hydrazone derivatives bearing the 1,2,4-triazole moiety as potential antimycobacterial agents. Turkish J. Pharm. Sci. 16, 432–436 (2019).
  • 109. Zampieri D, Cateni F, Moneghini M et al. Imidazole and 1,2,4-triazole-based derivatives gifted with antitubercular activity: cytotoxicity and computational assessment. Curr. Top. Med. Chem. 19, 620–632 (2019).
  • 110. Joshi SD, More Y, Vagdevi HM, Vaidya VP, Gadaginamath GS, Kulkarni VH. Synthesis of new 4-(2,5-dimethylpyrrol-1-yl)/4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: a novel class of potential antibacterial, antifungal and antitubercular agents. Med. Chem. Res. 22, 1073–1089 (2013).
  • 111. Krishna KM, Inturi B, Pujar GV, Purohit MN, Vijaykumar GS. Design, synthesis and 3D-QSAR studies of new diphenylamine containing 1,2,4-triazoles as potential antitubercular agents. Eur. J. Med. Chem. 84, 516–529 (2014).
  • 112. Tatar E, Kucukguzel SG, Karakus S et al. Synthesis and biological evaluation of some new 1,3,4-thiadiazole and 1,2,4-triazole derivatives from L-methionine as antituberculosis and antiviral agents. Marmara Pharm. J. 19, 88–102 (2015).
  • 113. Sonawane AD, Rode ND, Nawale L et al. Synthesis and biological evaluation of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione as antimycobacterial agents. Chem. Biol. Drug Des. 90(2), 200–209 (2017).
  • 114. Patel DM, Vala RM, Sharma MG, Rajani DP, Patel HM. A practical green visit to the functionalized [1,2,4]triazolo[5,1-b]quinazolin-8(4H)one scaffolds using the group-assisted purification (GAP) chemistry and their pharmacological testing. ChemistrySelect 4, 1031–1041 (2019).