Advanced search
Publication Cover
Future Medicinal Chemistry Volume 13, 2021 - Issue 7
Submit an article Journal homepage
146
Views
0
CrossRef citations to date
0
Altmetric
Review

Triazole-Containing Hybrids With Anti-Mycobacterium Tuberculosis Potential – Part I: 1,2,3-Triazole

Zhenyou Tan1 Guangdong Xianqiang Pharmaceutical Co., LtdGuangzhouPR ChinaCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0003-3085-6267
ORCID Icon,
Jun Deng2 Guangdong Zhongsheng Pharmaceutical Co., LtdDongguanGuangdongPR China
,
Qiongxian Ye2 Guangdong Zhongsheng Pharmaceutical Co., LtdDongguanGuangdongPR China
&
Zhenfeng Zhang2 Guangdong Zhongsheng Pharmaceutical Co., LtdDongguanGuangdongPR China
Pages 643-662 | Received 26 Sep 2020, Accepted 20 Jan 2021, Published online: 23 Feb 2021

References

  • Tornheim JA , DooleyKE. The global landscape of tuberculosis therapeutics. Ann. Rev. Med.70, 105–120 (2019).
  • Saleem A , AzherM. The next pandemic – tuberculosis: the oldest disease of mankind rising one more time. Br. J. Med. Pract.6(1), a615 (2013).
  • Turner RD . Cough in pulmonary tuberculosis: existing knowledge and general insights. Pulm. Pharmacol. Ther.55, 89–94 (2019).
  • Abdisamadov A , TursunovO. Ocular tuberculosis epidemiology, clinic features and diagnosis: a brief review. Tuberculosis124, e101963 (2020).
  • World Health Organization . Global tuberculosis report 2019. https://apps.who.int/iris/bitstream/handle/10665/329368/9789241565714-eng.pdf?ua=1
  • Natarajan A , BeenaPM , DevnikarAV , MaliS. A systemic review on tuberculosis. Indian J. Tuberculosis67(3), 295–311 (2020).
  • Huszar S , ChibaleK , SinghV. The quest for the holy grail: new antitubercular chemical entities, targets and strategies. Drug Discov. Today25(4), 772–780 (2020).
  • Mishra R , KrishanS , SiddiquiANet al. Potential role of adjuvant drugs on efficacy of first line oral antitubercular therapy: drug repurposing. Tuberculosis120, e101902 (2020).
  • Knight GM , McQuaidCF , DoddPJ , HoubenRMGJ. Global burden of latent multidrug-resistant tuberculosis: trends and estimates based on mathematical modelling. Lancet Infect. Dis.19(8), 903–912 (2019).
  • Garcia-Basteiro AL , JenkinsHE , RangakaM. The burden of latent multidrug-resistant tuberculosis. Lancet Infect. Dis.19(8), 802–803 (2019).
  • Gatadi S , NanduriS. New potential drug leads against MDR-MTB: a short review. Bioorg. Chem.95, e103534 (2020).
  • Gawad J , BondeC. Current affairs, future perspectives of tuberculosis and antitubercular agents. Indian J. Tuberculosis65(1), 15–22 (2018).
  • Neto JSS , ZeniG. A decade of advances in the reaction of nitrogen sources and alkynes for the synthesis of triazoles. Coordin. Chem. Rev.409, e213217 (2020).
  • Bozorov K , ZhaoJ , AisaHA. 1,2,3-triazole-containing hybrids as leads in medicinal chemistry: a recent overview. Bioorg. Med. Chem.27(16), 3511–3531 (2019).
  • Xia LW , BaMY , LiuWet al. Triazol: a privileged scaffold for proteolysis targeting chimeras. Future Med. Chem.11(22), 2919–2973 (2019).
  • Kacprzak K , SkieraI , PiaseckaM , ParyzekZ. Alkaloids and isoprenoids modification by copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition (click chemistry): toward new functions and molecular architectures. Chem Rev.116, 5689–5743 (2016).
  • Johansson JR , Beke-SomfaiT , SaidSA , KannN. Ruthenium-catalyzed azide alkyne cycloaddition reaction: scope, mechanism, and applications. Chem. Rev.116, 14726–14768 (2016).
  • Totobenazara J , BurkeAJ. New click-chemistry methods for 1,2,3-triazoles synthesis: recent advances and applications. Tetrahedron Lett.56, 2853–2859 (2015).
  • Xu M , PengY , WangSLet al. Triazole derivatives as inhibitors of Alzheimer's disease: current developments and structure-activity relationships. Eur. J. Med. Chem.180, 656–672 (2019).
  • Kaur A , MannS , KaurAet al. Multi-target-directed triazole derivatives as promising agents for the treatment of Alzheimer's disease. Bioorg. Chem.87, 572–584 (2019).
  • Xu Z . 1,2,3-triazole-containing hybrids with potential antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Eur. J. Med. Chem.206, e112686 (2020).
  • Zhang B . Comprehensive review on the anti-bacterial activity of 1,2,3-triazole hybrids. Eur. J. Med. Chem.168, 357–372 (2019).
  • Xu Z , ZhaoSJ , LiuY. 1,2,3-triazole-containing hybrids as potential anticancer agents: current developments, action mechanisms and structure-activity relationships. Eur. J. Med. Chem.183, e111700 (2019).
  • Farrer NJ , GriffithDM. Exploiting azide-alkyne click chemistry in the synthesis, tracking and targeting of platinum anticancer complexes. Curr. Opin. Chem. Biol.55, 59–68 (2020).
  • Chu XM , WangC , WangWLet al. Triazole derivatives and their antiplasmodial and antimalarial activities. Eur. J. Med. Chem.166, 206–223 (2019).
  • Kharb R , SharmaPC , YarMS. Pharmacological significance of triazole scaffold. J. Enzym. Inhib. Med. Chem.26(1), 1–21 (2011).
  • Zhang S , XuZ , GaoCet al. Triazole derivatives and their anti-tubercular activity. Eur. J. Med. Chem.138, 501–513 (2017).
  • Bozorov K , ZhaoJ , AisaH. 1,2,3-triazole-containing hybrids as leads in medicinal chemistry: a recent overview. Bioorg. Med. Chem.27(16), 3511–3531 (2019).
  • Feng LS , ZhengMJ , ZhaoF , LiuD. 1,2,3-triazole hybrids with anti-HIV-1 activity. Arch. Pharm.354(1), e2000163 (2021).
  • Kumar R , YarMS , ChaturvediS , SrivastavaA. Triazole as pharmaceuticals potentials. Int. J. Pharm. Tech. Res.5(4), 1844–1869 (2013).
  • Feng LS , XuZ , ChangLet al. Hybrid molecules with potential in vitro antiplasmodial and in vivo antimalarial activity against drug-resistant Plasmodium falciparum. Med. Res. Rev.40(3), 931–971 (2020).
  • Gao F , HuangG , XiaoJ. Chalcone hybrids as potential anticancer agents: current development, mechanism of action, and structure-activity relationship. Med. Res. Rev.40(5), 2049–2084 (2020).
  • Dheer D , SinghV , ShankarR. Medicinal attributes of 1,2,3-triazoles: current developments. Bioorg. Chem.71, 30–54 (2017).
  • Thirmurugan P , MatosiukD , JozwiakK. Click chemistry for drug development and diverse chemical–biology applications. Chem. Rev.113(7), 4905–4979 (2013).
  • Rani A , SinghG , SinghAet al. CuAAC-ensembled 1,2,3-triazole-linked isosteres as pharmacophores in drug discovery: review. RSC Adv.10, 5610–5635 (2020).
  • Bancet A , RaingevalC , LombergetTet al. Fragment linking strategies for structure-based drug design. J. Med. Chem.63(20), 11420–11435 (2020).
  • Nalla V , ShaikhA , BapatSet al. Identification of potent chromone embedded [1,2,3]-triazoles as novel anti-tubercular agents. R. Soc. Open Sci.5, e171750 (2018).
  • Stanley SA , KawateT , IwaseNet al. Diarylcoumarins inhibit mycolic acid biosynthesis and kill Mycobacterium tuberculosis by targeting FadD32. PNAS110(28), 11565–11570 (2013).
  • Keri RS , NagarajaBM , SantosMA. Recent progress in the drug development of coumarin derivatives as potent antituberculosis agents. Eur. J. Med. Chem.100, 257–269 (2015).
  • Hu YQ , XuZ , ZhangSet al. Recent developments of coumarin-containing derivatives and their anti-tubercular activity. Eur. J. Med. Chem.136, 122–130 (2017).
  • Khare SP , DeshmukhTR , SangshettiJNet al. Design, synthesis and molecular docking studies of novel triazole-chromene conjugates as antitubercular, antioxidant and antifungal agents. ChemistrySelect3, 13113–13122 (2018).
  • Ashok D , ChiranjeeviP , KumarAVet al. 1,2,3-Triazole-fused spirochromenes as potential anti-tubercular agents: synthesis and biological evaluation. RSC Adv.8, 16997–17007 (2018).
  • Goud GL , RameshS , AshokDet al. Design, synthesis, molecular docking and antimycobacterial evaluation of some novel 1,2,3-triazolyl xanthenones. MedChemComm8, 559–570 (2017).
  • Shaikh MH , SubhedarDD , ShingateBBet al. Synthesis, biological evaluation and molecular docking of novel coumarin incorporated triazoles as antitubercular, antioxidant and antimicrobial agents. Med. Chem. Res.25, 790–804 (2016).
  • Ambekar SP , MohanCD , ShirahattiAet al. Synthesis of coumarin-benzotriazole hybrids and evaluation of their anti-tubercular activity. Lett. Org. Chem.15, 23–31 (2018).
  • Ashok D , GunduS , AmateVKet al. Dimers of coumarin-1,2,3-triazole hybrids bearing alkyl spacer: design, microwave-assisted synthesis, molecular docking and evaluation as antimycobacterial and antimicrobial agents. J. Mol. Struct.1157, 312–321 (2018).
  • Danne AB , ChoudhariAS , SarkarDet al. Synthesis and biological evaluation of novel triazole-biscoumarin conjugates as potential antitubercular and anti-oxidant agents. Res. Chem. Intermed.44, 6283–6310 (2018).
  • Viana JO , MonteiroAFM , FilhoJMBet al. The azoles in pharmacochemistry: perspectives on the synthesis of new compounds and chemoinformatic contributions. Curr. Pharm. Des.25(44), 4702–4716 (2019).
  • Das R , AsthanaGS , SuriKAet al. Recent developments in azole compounds as antitubercular agent. Mini-Rev. Org. Chem.16(3), 290–306 (2019).
  • Keri RS , ChandK , RamakrishnappaT , NagarajaBM. Recent progress on pyrazole scaffold-based antimycobacterial agents. Arch. Pharm.348(5), 299–314 (2015).
  • Keri RS , PatilSA , BudagumpiS , NagarajaBM. Triazole: a promising antitubercular agent. Chem. Biol. Drug Des.86(4), 410–423 (2015).
  • Shinde V , MahulikarP , MhaskePCet al. Synthesis and biological evaluation of new 2-aryl-4-((4-aryl-1H−1,2,3-triazol-1-yl)methyl)thiazole derivatives. Res. Chem. Intermed.44, 1247–1261 (2018).
  • Shinde V , MhaskePC , SinghAet al. Synthesis and biological evaluation of new 4-(4-(1-benzyl-1H−1,2,3-triazol-4-yl)phenyl)-2-phenylthiazole derivatives. J. Heterocycl. Chem.56, 3093–3111 (2019).
  • Shinde V , MahulikarP , MhaskePCet al. Synthesis and antimycobacterial evaluation of new 5-(1-benzyl-1H− 1,2,3-triazol-4-yl)-4-methyl-2-arylthiazole derivatives. Med. Chem. Res.28, 805–819 (2019).
  • Karan S , KashyapVK , ShafiS , SaxenaAK. Structural and inhibition analysis of novel sulfur-rich 2-mercaptobenzothiazole and 1,2,3-triazole ligands against Mycobacterium tuberculosis DprE1 enzyme. J. Mol. Model.23, e241 (2017).
  • Nayak N , RamprasadJ , DalimbaUet al. Synthesis of new pyrazole-triazole hybrids by click reaction using a green solvent and evaluation of their antitubercular and antibacterial activity. Res. Chem. Intermed.42, 3721–3741 (2016).
  • Naidu KM , SrinivasaraoS , AgnieszkaNet al. Seeking potent anti-tubercular agents: design, synthesis, antitubercular activity and docking study of various ((triazoles/indole)-piperazin-1-yl/1,4-diazepan-1-yl)benzo[d]isoxazole derivatives. Bioorg. Med. Chem. Lett.26, 2245–2250 (2016).
  • Ashok D , GunduS , AamateVK , DevulapallyMG. Conventional andmicrowave-assisted synthesis of new indole-tethered benzimidazole-based 1,2,3-triazoles and evaluation of their antimycobacterial, antioxidant and antimicrobial activities. Mol. Divers.22, 769–778 (2018).
  • Reddyrajula R , DalimbaUK. Structural modification of zolpidem led to potent antimicrobial activity in imidazo[1,2-a]pyridine/pyrimidine-1,2,3-triazoles. New J. Chem.43, 16281–16299 (2019).
  • Adeniji SE , UbaS , UzairuA. Geometrical and topological descriptors for activities modeling of some potent inhibitors against Mycobacterium tuberculosis: a genetic functional approach. Egypt. J. Chem.62(7), 1235–1247 (2019).
  • Deniji SE , UbaS , UzairuA. In silico study for evaluating the binding mode and interaction of 1,2,4-triazole and its derivatives as potent inhibitors against Lipoate protein B (LipB). J. King Saud Univers.-Sci.32, 475–485 (2020).
  • Deshmukh TR , KhareSP , KrishnaVSet al. Synthesis, bioevaluation and molecular docking study of new piperazine and amide linked dimeric 1,2,3-triazoles. Synth. Commun.50(2), 271–288 (2020).
  • Deshmukh TR , KhareSP , KrishnaVSet al. Design and synthesis of new aryloxy-linked dimeric 1,2,3-triazoles via click chemistry approach: biological evaluation and molecular docking study. J. Heterocycl. Chem.56, 2144–2162 (2019).
  • Nainwal LM , TasneemS , AkhtarWet al. Green recipes to quinoline: a review. Eur. J. Med. Chem.164, 121–170 (2019).
  • Villamizar-Mogotocoro AF , Vargas-MéndezLY , KouznetsovVV. Pyridine and quinoline molecules as crucial protagonists in the never-stopping discovery of new agents against tuberculosis. Eur. J. Pharm. Sci.151, e105374 (2020).
  • Makafe GG , HussainM , SurineniGet al. Quinoline derivatives kill Mycobacterium tuberculosis by activating glutamate kinase. Cell Chem. Biol.26(8), 1187–1194 (2019).
  • Pham TDM , ZioraZM , BlaskovichMAT. Quinolone antibiotics. MedChemComm10(10), 1719–1739 (2019).
  • Chahine EB , KaraouiLR , MansourH. Bedaquiline: a novel diarylquinoline for multidrug-resistant tuberculosis. Ann. Pharmacother.48(1), 107–115 (2014).
  • Fan YL , WuJB , ChengXWet al. Fluoroquinolone derivatives and their anti-tubercular activities. Eur. J. Med. Chem.146, 554–563 (2018).
  • Liu B , LiF , ZhouTet al. Quinoline derivatives with potential activity against multidrug-resistant tuberculosis. J. Heterocyclic Chem.55(8), 1863–1873 (2018).
  • Reddyrajula R , DalimbaU. Quinoline-1,2,3-triazole hybrids: design and synthesis through click reaction, evaluation of anti-tubercular activity, molecular docking and in silico ADME studies. ChemistrySelect4, 2685–2693 (2019).
  • Ramprasad J , SthalamVK , ThampunuriRLMet al. Synthesis and evaluation of a novel quinoline-triazole analogs for antitubercular properties via molecular hybridization approach. Bioorg. Med. Chem. Lett.29, e126671 (2019).
  • Banu S , BolluR , NagarapuLet al. Design, synthesis, and in vitro antitubercular activity of 1,2,3-triazolyl-dihydroquinoline derivatives. Chem. Biol. Drug Des.92, 1315–1323 (2018).
  • Cilliers P , SeldonR , SmitFJet al. Design, synthesis, and antimycobacterial activity of novel ciprofloxacin derivatives. Chem. Biol. Drug Des.94, 1518–1536 (2019).
  • Hu YQ , ZhangS , ZhaoFet al. Isoniazid derivatives and their anti-tubercular activity. Eur. J. Med. Chem.133, 255–267 (2017).
  • Chaudhari KS , PatelHM , SuranaSJ. Pyridines: multidrug-resistant tuberculosis (MDR-TB) inhibitors. Indian J. Tuberculosis64(2), 119–128 (2017).
  • Badar AD , SulakheSM , MulukMBet al. Synthesis of isoniazid-1,2,3-triazole conjugates: antitubercular, antimicrobial evaluation and molecular docking study. J. Heterocycl. Chem.57(10), 3544–3557 (2020).
  • Patil PS , KasareSL , HavalNBet al. Novel isoniazid embedded triazole derivatives: synthesis, antitubercular and antimicrobial activity evaluation. Bioorg. Med. Chem. Lett.30, e127434 (2020).
  • Shaikh MH , SubhedarDD , NawaleLet al. Novel benzylidenehydrazide-1,2,3-triazole conjugates as antitubercular agents: Synthesis and molecular docking. Mini-Rev. Med. Chem.19, 1178–1194 (2019).
  • Yan M , XuL , WangYet al. Opportunities and challenges of using five-membered ring compounds as promising antitubercular agents. Drug Dev. Res.81(4), 402–418 (2020).
  • Gholap SS . Pyrrole: an emerging scaffold for construction of valuable therapeutic agents. Eur. J. Med. Chem.110, 13–31 (2016).
  • Surineni G , YogeeswariP , SriramD , KantevariS. Click-based synthesis and antitubercular evaluation of dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides. Bioorg. Med. CHem. Lett.26, 3684–3689 (2016).
  • Chirke SS , KrishnaJS , RathodBBet al. Synthesis of triazole derivatives of 9-ethyl-9H-carbazole and dibenzo[b,d]furan and evaluation of their antimycobacterial and immunomodulatory activity. ChemistrySelect2, 7309–7318 (2017).
  • Vartak A , GoinsC , MouraVCNet al. Biochemical and microbiological evaluation of N-aryl urea derivatives against mycobacteria and mycobacterial hydrolases. MedChemComm10, 1197–1204 (2019).
  • Devi ML , ReddyPL , YogeeswariPet al. Design and synthesis of novel triazole linked pyrrole derivatives as potent Mycobacterium tuberculosis inhibitors. Med. Chem. Res.26, 2985–2999 (2017).
  • Pulipati L , YogeeswariP , SriramD , KantevariS. Click-based synthesis and antitubercular evaluation of novel dibenzo[b,d]thiophene-1,2,3-triazoles with piperidine, piperazine, morpholine and thiomorpholine appendages. Bioorg. Med. Chem. Lett.26, 2649–2654 (2016).
  • Marvadi SK , KrishnaVS , SriramD , KantevariS. Synthesis and evaluation of novel substituted 1,2,3-triazolyldihydroquinolines as promising antitubercular agents. Bioorg. Med. Chem. Lett.29, 529–533 (2019).
  • Marvadi SK , KrishnaVS , SinegubovaEOet al. 5-Chloro-2-thiophenyl-1,2,3-triazolylmethyldihydroquinolines as dual inhibitors of Mycobacterium tuberculosis and influenza virus: synthesis and evaluation. Bioorg. Med. Chem. Lett.29, 2664–2669 (2019).
  • Reddyrajula R , DalimbaU. The bioisosteric modification of pyrazinamide derivatives led to potent antitubercular agents: synthesis via click approach and molecular docking of pyrazine-1,2,3-triazoles. Bioorg. Med. Chem. Lett.30, e126846 (2020).
  • Shaikh MH , SubhedarDD , ArkileMet al. Synthesis and bioactivity of novel triazole incorporated benzothiazinone derivatives as antitubercular and antioxidant agent. Bioorg. Med. Chem. Lett.26, 561–569 (2016).
  • Reddyrajula R , DalimbaU , KumarSM. Molecular hybridization approach for phenothiazine incorporated 1,2,3-triazole hybrids as promising antimicrobial agents: design, synthesis, molecular docking and in silico ADME studies. Eur. J. Med. Chem.168, 263–282 (2019).
  • Srinivasarao S , NandikollaA , SureshAet al. Discovery of 1,2,3-triazole based quinoxaline-1,4-di-N-oxide derivatives as potential anti-tubercular agents. Bioorg. Chem.100, e103955 (2020).
  • Maddali NK , ViswanathIVK , MurthyYLNet al. Design, synthesis and molecular docking studies of quinazolin-4-ones linked to 1,2,3-triazol hybrids as Mycobacterium tuberculosis H37Rv inhibitors besides antimicrobial activity. Med. Chem. Res.28, 559–570 (2019).
  • Kumar R , BimalD , KumarMet al. Synthesis and antitubercular activity of 4,5-disubstituted N1-(5′-deoxythymidin-5′-yl)-1,2,3-triazoles. ChemistrySelect5, 8839–8845 (2020).
  • Venugopala KN , RaoGBD , BhandarySet al. Design, synthesis, and characterization of (1-(4-aryl)-1H−1,2,3-triazol-4-yl)methyl, substituted phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates against Mycobacterium tuberculosis. Drug Des. Dev. Ther.10, 2681–2690 (2016).
  • Hajlaoui K , GuesmiA , HamadiNB , MsaddekM. One-pot synthesis of new triazole-sucrose derivatives via click chemistry and evaluation of their antitubercular activity. Heterocycl. Commun.22(4), 239–242 (2016).
  • Abdu-Allah HHM , YoussifBGM , AbdelrarahmanNHet al. Synthesis and anti-mycobacterial activity of 4-(4-phenyl-1H−1,2,3-triazol-1-yl)salicylhydrazones: revitalizing an old drug. Arch. Pharm. Res.40, 168–179 (2017).
  • Bua S , OsmanSM , PreteSDet al. Click-tailed benzenesulfonamides as potent bacterial carbonic anhydrase inhibitors for targeting Mycobacterium tuberculosis and Vibrio cholera. Bioorg. Chem.86, 183–186 (2019).
  • Sajja Y , VanguruS , VulupalaHRet al. Design, synthesis and in vitro anti-tuberculosis activity of benzo[6,7]cyclohepta[1,2-b]pyridine-1,2,3-triazole derivatives. Bioorg. Med. Chem. Lett.27, 5119–5121 (2017).
  • Suresh A , SrinivasaraoS , AgnieszkaNet al. Design and synthesis of 9H-fluorenone based 1,2,3-triazole analogues as Mycobacterium tuberculosis InhA inhibitors. Chem. Biol. Drug Des.91, 1078–1086 (2018).
  • Danne AB , ChoudhariAS , ChakrabortySet al. Triazole-di-indolylmethane conjugates as new antitubercular agents: synthesis, bioevaluation and molecular docking. MedChemComm9, 1114–1130 (2018).
  • Zhao SJ , LvZS , DengJLet al. Design, synthesis, and in vitro anti-mycobacterial activities of 1,2,3-triazole-tetraethylene glycol tethered isatin dimers. J. Heterocycl. Chem.55, 3006–3010 (2018).
  • Iannazzo L , SorokaD , TribouletSet al. Routes of synthesis of carbapenems for optimizing both the inactivation of L,D-transpeptidase LdtMt1 of Mycobacterium tuberculosis and the stability toward hydrolysis by β-lactamase BlaC. J. Med. Chem.59, 3427–3438 (2016).
  • Phatak PS , BakaleRD , DhumalSTet al. Synthesis, antitubercular evaluation and molecular docking studies of phthalimide bearing 1,2,3-triazoles. Synth. Commun.49(6), 2017–2028 (2019).
  • Ruysscher DD , PangL , MattelaerCAet al. Phenyltriazole-functionalized sulfamate inhibitors targeting tyrosyl- or isoleucyl-tRNA synthetase. Bioorg. Med. Chem.28, e115580 (2020).
  • Negi B , RawatDS. Synthesis, characterization, and antimycobacterial activity of novel thymol-triazole hybrids. Indian J. Heterocycl. Chem.28, 113–123 (2018).
  • Sajja Y , VanguruS , JillaLet al. A convenient synthesis and screening of benzosuberone bearing 1,2,3-triazoles against Mycobacterium tuberculosis. Bioorg. Med. Chem. Lett.26, 4292–4295 (2016).
  • Liu B , HuG , TangXet al. 1H−1,2,3-triazole-tethered isatin-coumarin hybrids: design, synthesis and in vitro anti-mycobacterial evaluation. J. Heterocycl. Chem.55, 775–780 (2018).
  • Huang GC , XuY , XuZet al. Propylene-1H−1,2,3-triazole-4-methylene-tethered isatin-coumarin hybrids: design, synthesis, and in vitro anti-tubercular evaluation. J. Heterocycl. Chem.55, 830–835 (2018).
  • Xu Y , DangR , GuanJet al. Isatin-(thio)semicarbazide/oxime-1H−1,2,3-triazole-coumarin hybrids: design, synthesis, and in vitro anti-mycobacterial evaluation. J. Heterocycl. Chem.55, 1069–1073 (2018).
  • Jin X , YangX , ChenXet al. Design, synthesis and in vitro anti-microbial evaluation of ethylene/propylene-1H−1,2,3-triazole-4-methylene-tethered isatin-coumarin hybrids. Curr. Top. Med. Chem.17, 3213–3218 (2017).
  • Srivastava S , BimalD , BohraKet al. Synthesis and antimycobacterial activity of 1-(β-D-Ribofuranosyl)-4-coumarinyloxymethyl-/-coumarinyl-1,2,3-triazole. Eur. J. Med. Chem.150, 268–281 (2018).
  • Somagond SM , KambleRR , BayannavarPKet 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(10), e1900013 (2019).
  • Khanapurmath N , KulkarniMV , JoshiSD , KumarGNA. A click chemistry approach for the synthesis of cyclic ureido tethered coumarinyl and 1-aza coumarinyl 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis H37Rv and their in silico studies. Bioorg. Med. Chem.27, e115054 (2019).
  • Xu Z , LvZS , SongXF , QiangM. Ciprofloxacin-isatin-1H−1,2,3-triazole hybrids: design, synthesis, and in vitro anti-tubercular activity against M. tuberculosis. J. Heterocycl. Chem.55, 97–101 (2018).
  • Hu YQ , MengLD , QiangM , SongXF. Design, synthesis, and in vitro anti-mycobacterial evaluation 1H−1,2,3-triazole-tethered ciprofloxacin and isatin conjugates. J. Heterocycl. Chem.54, 3725–3729 (2017).
  • Chen RX , ZhangH , MaTet al. Ciprofloxacin-1,2,3-triazole-isatin hybrids tethered via amide: design, synthesis, and in vitro anti-mycobacterial activity evaluation. Bioorg. Med. Chem. Lett.29, 2635–2637 (2019).
  • Xu Z , SongX , HuYet al. Design, synthesis and in vitro anti-mycobacterial activities of 8-OMe ciprofloxacin-1H−1,2,3-triazole-isatin-(thio) semicarbazide/oxime hybrids. J. Heterocycl. Chem.55, 192–198 (2018).
  • Xu Z , SongXF , QiangM , LvZS. 1H−1,2,3-triazole-tethered 8-OMe ciprofloxacin and isatin hybrids: design, synthesis and in vitro anti-mycobacterial activities. J. Heterocycl. Chem.54, 3735–3761 (2017).
  • Xu Z , SongXF , HuYQet al. Azide-alkyne cycloaddition towards 1H−1,2,3-triazole-tethered gatifloxacin and isatin conjugates: design, synthesis and in vitro anti-mycobacterial evaluation. Eur. J. Med. Chem.138, 66–71 (2017).
  • Xu Z , ZhangS , SongXet al. Design, synthesis and in vitro anti-mycobacterial evaluation of gatifloxacin-1H−1,2,3-triazole-isatin hybrids. Bioorg. Med. Chem. Lett.27, 3643–3646 (2017).
  • Ding Z , HouP , LiuB. Gatifloxacin-1,2,3-triazole-isatin hybrids and their antimycobacterial activities. Arch. Pharm.352, e1900135 (2019).
  • Xu Z , SongXF , FanJ , LvZS. Design, synthesis, and in vitro anti-mycobacterial evaluation of propylene-1H−1,2,3-triazole-4-methylene-tethered (thio)semicarbazone-isatin-moxifloxacin hybrids. J. Heterocycl. Chem.55, 77–82 (2018).
  • Hu YQ , XuZ , QiangM , LvZS. Design, synthesis and in vitro antimycobacterial activities of isatin-1,2,3-triazole-moxifloxacin hybrids. J. Heterocycl. Chem.55, 187–191 (2018).
  • Hu YQ , FanJ , SongX. Design, synthesis and in vitro anti-mycobacterial activity of propylene-1H−1,2,3-triazole-4-methylene-tethered isatin-moxifloxacin hybrids. J. Heterocycl. Chem.55, 246–250 (2018).
  • Yan X , LvZ , WenJet al. Synthesis and in vitro evaluation of novel substituted isatinpropylene-1H−1,2,3-triazole-4-methylene-moxifloxacin hybrids for their anti-mycobacterial activities. Eur. J. Med. Chem.143, 899–904 (2019).
  • Jiang Y , QianA , LiY. 1H−1,2,3-Triazole tethered isatin-moxifloxacin: Design, synthesis and in vitro anti-mycobacterial evaluation. Arch. Pharm.352, e1900040 (2019).
  • Gao F , ChenZ , MaLet al. Synthesis and biological evaluation of moxifloxacin-acetyl-1,2,3-1H-triazole-methylene-isatin hybrids as potential anti-tubercular agents against both drug-susceptible and drug-resistant Mycobacterium tuberculosis strains. Eur. J. Med. Chem.180, 648–655 (2019).
  • Bangalore PK , VagoluSK , BollikandaRKet al. Usnic acid enaminone-coupled 1,2,3-triazoles as antibacterial and antitubercular agents. J. Nat. Prod.83, 26–35 (2020).
  • Singh A , ViljoenA , KremerL , KumarV. Azide-alkyne cycloaddition en route to 4-aminoquinoline-ferrocenylchalcone conjugates: Synthesis and anti-TB evaluation. Future Med. Chem.9, 1701–1708 (2017).
  • Singh A , BiotC , ViljoenAet al. 1H−1,2,3-triazole-tethered uracil-ferrocene and uracil-ferrocenylchalcone conjugates: synthesis and antitubercular evaluation. Chem. Biol. Drug Des.89, 856–861 (2017).
  • Raju KS , AnkiReddyS , SabithaGet al. Synthesis and biological evaluation of 1H-pyrrolo[2,3-d]pyrimidine-1,2,3-triazole derivatives as novel anti-tubercular agents. Bioorg. Med. Chem. Lett.29, 284–290 (2019).

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:

Order Reprints Request Corporate Permissions

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:

Request Academic Permissions

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.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.