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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Review Article

Synthetic Utility of Aminomercapto[1,2,4]triazoles in the Preparation of Fused Triazoles

Author(s): Sayed M. Riyadh, Tariq Z. Abolibda, Abdelwahed R. Sayed and Sobhi M. Gomha*

Volume 26, Issue 7, 2022

Published on: 27 May, 2022

Page: [693 - 714] Pages: 22

DOI: 10.2174/1385272826666220417131159

Price: $65

Abstract

Triazoles and their fused derivatives are regarded as one of the most pharmacologically significant pillars due to their potent, broad, and numerous activities. This current review presents recent progress in the synthetic utility of 3-substituted-4-amino-5-mercapto[1,2,4]- triazoles as building blocks for a diverse range of fused [1,2,4]triazoles with pharmacological interest eg. pyrazolo-triazoles, triazolo-thiadiazoles, triazolo-triazoles, triazolo-thiadiazines, triazolo-triazines, triazolo-tetrazines, triazolo-thiadiazepines, and others. The biological activity of some triazoles and their fused derivatives are also presented. This suggests that triazoles can be particularly promising synthons in synthesis of functionalized heterocyclic compounds used in the design of novel, highly effective pharmaceuticals with a broad spectrum of bioresponses. All of these topics are drawn in this review from the period from 2000 to 2020.

Keywords: 1, 2, 4-Triazoles, fused triazoles, azolo[1, 4]triazoles, 1, 4-triazoloazines, cyclizations, biological activity

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[1]
Rao, D.N.; Prasad, A.R.G.; Spoorthy, Y.N.; Rao, D.R.; Ravindranath, L.K. Synthesis, characterization and pharmacological studies of sulphur containing 1,2,4-triazole derivatives. J. Taibah Univ. Med. Sci., 2014, 9(4), 293-300.
[http://dx.doi.org/10.1016/j.jtumed.2014.06.002]
[2]
Peyton, L.R.; Gallagher, S.; Hashemzadeh, M. Triazole antifungals: A review. Drugs Today (Barc), 2015, 51(12), 705-718.
[PMID: 26798851]
[3]
Maddila, S.; Pagadala, R.; Jonnalagadda, S.B. 1,2,4-Triazoles: A Review of Synthetic Approaches and the Biological Activity. Lett. Org. Chem., 2013, 10(10), 693-714.
[http://dx.doi.org/10.2174/157017861010131126115448]
[4]
Laverdiere, M.; Bow, E.J.; Rotstein, C.; Autmizguine, J.; Broady, R.; Garber, G.; Haider, S.; Hussaini, T.; Husain, S.; Ovetchkine, P.; Seki, J.T.; Théorêt, Y. Therapeutic drug monitoring for triazoles: A needs assessment review and recommendations from a Canadian perspective. Can. J. Infect. Dis. Med. Microbiol., 2014, 25(6), 327-343.
[http://dx.doi.org/10.1155/2014/340586] [PMID: 25587296]
[5]
Balaydın, H.T.; Özil, M.; Şentürk, M. Synthesis and glutathione reductase inhibitory properties of 5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one’s aryl Schiff base derivatives. Arch Pharm Chem Life Sci, 2018, 351.
[6]
El-Saghier, A.M.; Mohamed, M.A.; Abd-Allah, O.A.; Kadry, A.M.; Ibrahim, T.M.; Bekhit, A.A. Green synthesis, antileishmanial activity evaluation, and in silico studies of new amino acid-coupled 1,2,4-triazoles. Med. Chem. Res., 2019, 28(2), 169-181.
[http://dx.doi.org/10.1007/s00044-018-2274-x]
[7]
Rao, G.; Rajasekaran, S.; Attimarad, M. Synthesis and antimicrobial activity of some 5-phenyl-4- substituted amino-3-mercapto (4H)-1,2,4-triazoles. Indian J. Pharm. Sci., 2000, 62(6), 475-477.
[8]
Patel, K.D.; Mistry, B.D.; Desai, K.R. Synthesis and antimicrobial activity of 1,2,4-triazoles. J. Indian Chem. Soc., 2002, 79, 964-965.
[9]
Jilloju, P.C.; Srikanth, M.; Kumar, S.V.; Vedula, R.R. One-pot, multi-component synthesis of substituted 2-(6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-2,3-dihydrophthalazine-1,4-diones. Polycycl. Aromat. Compd., 2020, 1-12.
[10]
Kumar, V.; Kumar, M.; Kumar, S. (Diacetoxyiodo) benzene mediated fused 1,2,4-triazole derivatives: Synthetic and medicinal perspective. Mini Rev. Org. Chem., 2018, 16(1), 12-25.
[http://dx.doi.org/10.2174/1570193X15666180406142116]
[11]
Singh, R.; Kashaw, S.K.; Mishra, V.K.; Mishra, M.; Rajoriya, V.; Kashaw, V. Design and synthesis of new bioactive 1,2,4-triazoles, potential antitubercular and antimi-crobial agents. Indian J. Pharm. Sci., 2018, 80(01), 36-45.
[http://dx.doi.org/10.4172/pharmaceutical-sciences.1000328]
[12]
€Unver, Y.; Deniz, S.; C¸elik, F.; Akar, Z.; K€uc¸€uk, M.; Sancak, K. Synthesis of new 1,2,4-triazole compounds containing schiff and mannich bases (morpholine) with antioxidant and antimicrobial activities. Journal of Enzyme Inhibition and Medicinal Chemistry, 2016, 31(sup3), 89-95.
[13]
Aly, A.A.; Hassan, A.A.; Makhlouf, M.M. Molecules, 2020, 25(13), 3036-3090.
[http://dx.doi.org/10.3390/molecules25133036]
[14]
Akhter, M.W.; Hassan, M.Z.; Amir, M. Synthesis and pharmacological evaluation of 3-diphenylmethyl-6-substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles: A con-densed bridgehead nitrogen heterocyclic system. Arab. J. Chem., 2014, 7(6), 955-963.
[http://dx.doi.org/10.1016/j.arabjc.2014.05.036]
[15]
Baviskar, B.A.; Khadabadia, S.S.; Deore, S.L.; Shiradkar, M.R. Synthesis of clubbed triazolyl indeno [1, 2-c] isoquinolines as an novel anticancer agent. Pharm. Sin., 2012, 3(1), 24-30.
[16]
Turan-Zitouni, G.; Kaplancikli, Z. A.; Erol, K.; Kilic, F. S. Synthesis and analgesic activity of some triazoles and triazolothiadiazines. Farmaco (Societa Chimica Italiana : 1989),, 1999, 54(4), 218-23.
[http://dx.doi.org/10.1016/S0014-827X(99)00016-6]
[17]
Przegali_nski, E.; Lewandowska, A. The effect of etoperidone, a new potential antidepressant drug, on the central serotonin system. J. Neural Transm. (Vienna), 1979, 46(4), 303-312.
[http://dx.doi.org/10.1007/BF01259336]
[18]
Hameed, A.A.; Hassan, F. Synthesis, Characterization and Antioxidant Activity of Some 4-Amino-5-Phenyl-4h-1,2,4-Triazole-3-Thiol Derivatives. Int. J. Appl. Sci. Technol., 2014, 4(2), 202-211.
[19]
Jess, S.; Kildea, S.; Moody, A.; Rennick, G.; Murchie, A.K.; Cooke, L.R. European Union policy on pesticides: Implications for agriculture in Ireland. Pest Manag. Sci., 2014, 70(11), 1646-1654.
[http://dx.doi.org/10.1002/ps.3801] [PMID: 24753219]
[20]
Zhang, S.; Xu, Z.; Gao, C.; Ren, Q.C.; Chang, L.; Lv, Z.S.; Feng, L.S. Triazole derivatives and their anti-tubercular activity. Eur. J. Med. Chem., 2017, 138, 501-513.
[http://dx.doi.org/10.1016/j.ejmech.2017.06.051] [PMID: 28692915]
[21]
Rani, S.; Agaiah, B.; Sarangapani, M. Antioxidant and DNA binding study 3,3;-(5,5;-methylene bis(3-mercapto-4H-1,2,4-triazole-5,4-diyl)bis(azan-1-yl-1-ylidene)diindolin-2-ones. Int. J. Pharm. Tech., 2010, 2, 366-374.
[22]
Gomha, S.M.; Badrey, M.G.; Abdalla, M.M. Isoxazolopyrimidinthione and isoxazolopyridopyrimidinthione derivatives: Key intermediates for synthesis of novel fused triazoles as potent 5α-reductase inhibitors and anti-prostate cancer. J. Heterocycl. Chem., 2016, 53(2), 558-565.
[http://dx.doi.org/10.1002/jhet.2417]
[23]
Navidpour, L.; Shafaroodi, H.; Abdi, K.; Amini, M.; Ghahremani, M.H.; Dehpour, A.R.; Shafiee, A. Design, synthesis, and biological evaluation of substituted 3-alkylthio-4,5-diaryl-4H-1,2,4-triazoles as selective COX-2 inhibitors. Bioorg. Med. Chem., 2006, 14(8), 2507-2517.
[http://dx.doi.org/10.1016/j.bmc.2005.11.029] [PMID: 16337127]
[24]
Sumangala, V.; Poojary, B.; Chidananda, N.; Arulmoli, T.; Shenoy, S. Synthesis and biological evaluation of some Schiff bases of 4-amino-5-(4-methylsulfonyl)benzyl-2,4-dihydro-3H-[1,2,4]-triazole-3-thione. Med. Chem. Res., 2013, 22(6), 2921-2928.
[http://dx.doi.org/10.1007/s00044-012-0294-5]
[25]
Gomha, S.M.; Abdel-aziz, H.M.; Badrey, M.G.; Abdulla, M.M. Efficient synthesis of some new 1,3,4-thiadiazoles and 1,2,4-triazoles linked to Pyrazolylcoumarin ring system as potent 5α-reductase inhibitors. J. Heterocycl. Chem., 2019, 56(4), 1275-1282.
[http://dx.doi.org/10.1002/jhet.3487]
[26]
Deng, X.Q.; Dong, Z.Q.; Song, M.X.; Shu, B.; Wang, S.B.; Quan, Z.S. Synthesis and anticonvulsant activities of some triazolothiadiazole derivatives. Arch. Pharm. (Weinheim), 2012, 345(7), 565-573.
[http://dx.doi.org/10.1002/ardp.201100326] [PMID: 22532235]
[27]
Prasad, D.J.; Ashok, M.; Karegoudar, P.; Poojary, B.; Holla, B.S.; Kumari, N.S. Synthesis and antimicrobial activities of some new triazolothiadiazoles bearing 4-methylthiobenzyl moiety. Eur. J. Med. Chem., 2009, 44(2), 551-557.
[http://dx.doi.org/10.1016/j.ejmech.2008.03.025] [PMID: 18508161]
[28]
Purohit, D.H.; Dodiya, B.L.; Ghetiya, R.M.; Vekariya, P.B.; Joshi, H.S. Synthesis and antimicrobial activity of some new 1,3,4-thiadiazoles and 1,3,4-thiadiazines con-taining 1,2,4-Triazolo nucleus. Acta Chim. Slov., 2011, 58(1), 53-59.
[PMID: 24061943]
[29]
Karabasanagouda, T.; Adhikari, A.V.; Shetty, N.S. Synthesis and antimicrobial activities of some novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines carrying thioalkyl and sulphonyl phenoxy moieties. Eur. J. Med. Chem., 2007, 42(4), 521-529.
[http://dx.doi.org/10.1016/j.ejmech.2006.10.010] [PMID: 17156898]
[30]
Kamal, A.; Khan, M.N.A.; Srikanth, Y.V.V.; Reddy, K.S.; Juvekar, A.; Sen, S.; Kurian, N.; Zingde, S. Synthesis, DNA-binding ability and evaluation of antitumour activ-ity of triazolo[1,2,4]benzothiadiazine linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates. Bioorg. Med. Chem., 2008, 16(16), 7804-7810.
[http://dx.doi.org/10.1016/j.bmc.2008.06.056] [PMID: 18657979]
[31]
Skoumbourdis, A.P.; Leclair, C.A.; Stefan, E.; Turjanski, A.G.; Maguire, W.; Titus, S.A.; Huang, R.; Auld, D.S.; Inglese, J.; Austin, C.P.; Michnick, S.W.; Xia, M.; Thomas, C.J. Exploration and optimization of substituted triazolothiadiazines and triazolopyridazines as PDE4 inhibitors. Bioorg. Med. Chem. Lett., 2009, 19(13), 3686-3692.
[http://dx.doi.org/10.1016/j.bmcl.2009.01.057] [PMID: 19464886]
[32]
Omar, A.M.; Abd El Razik, H.A.; Hazzaa, A.A.; El-Attar, M.A.Z.; El Demellawy, M.A.; Abdel Wahab, A.E.; El Hawash, S.A.M. New pyrimidines and triazolopyrim-idines as antiproliferative and antioxidants with cyclooxygenase-1/2 inhibitory potential. Future Med. Chem., 2019, 11(13), 1583-1603.
[http://dx.doi.org/10.4155/fmc-2018-0285] [PMID: 31469327]
[33]
Badr, S.M.I.; Barwa, R.M. Synthesis of some new [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles starting from 5-nitro-2-furoic acid and evaluation of their antimicrobial activity. Bioorg. Med. Chem., 2011, 19(15), 4506-4512.
[http://dx.doi.org/10.1016/j.bmc.2011.06.024] [PMID: 21723735]
[34]
Hassan, F.A.; Younus, K.W. Biological evaluation of some azole derivatives in cooling fluids (Lubricant Oils). Res. J. Biol. Sci., 2012, 7(1), 48-51.
[http://dx.doi.org/10.3923/rjbsci.2012.48.51]
[35]
Hassan, A.Y. Synthesis and reactions of new fused heterocycles derived from 5-substituted-4-amino-3-mercapto-(4H)-1,2,4-triazole with biological interest. Phos., Sulfur. Silicon, 2009, 184(11), 2759-2776.
[http://dx.doi.org/10.1080/10426500802470769]
[36]
Abdallah, M.A.; Riyadh, S.M.; Abbas, I.M.; Gomha, S.M. Synthesis and biological activities of 7-arylazo-7H-pyrazolo[5,1-c][1,2,4]triazol-6(5H)-ones and 7-Arylhydrazono-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines. J. Chin. Chem. Soc. (Taipei), 2005, 52(5), 987-994.
[http://dx.doi.org/10.1002/jccs.200500137]
[37]
Khan, I.; Ibrar, A.; Abbas, N. Triazolothiadiazoles and triazolothiadiazines--biologically attractive scaffolds. Eur. J. Med. Chem., 2013, 63, 854-868.
[http://dx.doi.org/10.1016/j.ejmech.2013.01.060] [PMID: 23603045]
[38]
Demirbas, N.; Demirbas, A.; Karaoglu, S.A.; Celik, E. Synthesis and antimicrobial activities of some new [1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles and [1,2,4]triazolo[3,4-b][1,3,4] thiadiazines. ARKIVOC, 2005, 2005(i), 75-91.
[http://dx.doi.org/10.3998/ark.5550190.0006.108]
[39]
Mathew, V.; Giles, D.; Keshavayya, J.; Vaidya, V.P. Studies on synthesis and pharmacological activities of 1,2,4-triazolo[3,4-b]1,3,4-thiadiazoles and their dihydro analogues. Arch. Pharm. (Weinheim), 2009, 342(4), 210-222.
[http://dx.doi.org/10.1002/ardp.200800073] [PMID: 19340834]
[40]
Puthiyapurayil, P.; Poojary, B.; Kumar, S.; Hunnur, R. Synthesis and biological activities of a novel series of 3,6-disubstituted-1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles Containing Gem-dimethylbenzyl Moiety. J. Heterocycl. Chem., 2011, 48(5), 998-1005.
[http://dx.doi.org/10.1002/jhet.674]
[41]
Udupi, R.H.; Manjunath, C.J. Synthesis and biological evaluation of certain n-bridged 1,2,4-triazole analogues. J. Pharm. Sci. Res, 2019, 11, 44-49.
[42]
Raviprabha, K.; Poojary, B.; Manjunatha, K.; Vasantha, K.; Fernandes, N.J.; Kumari, N.S. Synthesis and biological activities of some triazolothiadiazoles containing ibuprofen moiety. Pharma Chem., 2016, 8, 1-9.
[43]
Amir, M.; Kumar, H.; Javed, S.A. Synthesis and pharmacological evaluation of condensed heterocyclic 6-substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives of naproxen. Bioorg. Med. Chem. Lett., 2007, 17(16), 4504-4508.
[http://dx.doi.org/10.1016/j.bmcl.2007.06.003] [PMID: 17576062]
[44]
Ilango, K.; Valentina, P. Facile synthesis and cytotoxic activity of 3,6-disubstituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles. Eur. J. Chem., 2010, 1(1), 50-53.
[http://dx.doi.org/10.5155/eurjchem.1.1.50-53.4]
[45]
Ilango, K.; Valentina, P. Synthesis and biological activities of novel 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles. Pharma Chem., 2010, 2, 16-22.
[46]
Khan, I.; Zaib, S.; Ibrar, A.; Rama, N.H.; Simpson, J.; Iqbal, J. Synthesis, crystal structure and biological evaluation of some novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines. Eur. J. Med. Chem., 2014, 78, 167-177.
[http://dx.doi.org/10.1016/j.ejmech.2014.03.046] [PMID: 24681981]
[47]
Kamel, M.M.; Megally Abdo, N.Y. Synthesis of novel 1,2,4-triazoles, triazolothiadiazines and triazolothiadiazoles as potential anticancer agents. Eur. J. Med. Chem., 2014, 86, 75-80.
[http://dx.doi.org/10.1016/j.ejmech.2014.08.047] [PMID: 25147148]
[48]
Li, Y.J.; Liu, L.J.; Jin, K.; Xu, Y.T.; Sun, S.Q. Synthesis and bioactivity of a novel series of 3,6-disubstituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles. Chin. Chem. Lett., 2010, 21(3), 293-296.
[http://dx.doi.org/10.1016/j.cclet.2009.11.008]
[49]
Aggarwal, N.; Kumar, R.; Dureja, P.; Khurana, J.M. Synthesis, antimicrobial evaluation and QSAR analysis of novel nalidixic acid based 1,2,4-triazole derivatives. Eur. J. Med. Chem., 2011, 46(9), 4089-4099.
[http://dx.doi.org/10.1016/j.ejmech.2011.06.009] [PMID: 21752498]
[50]
Wagle, S.; Adhikari, A.V.; Kumari, N.S. Antimicrobial and antiinflammatory studies on some 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines and 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazoles Containing Quinoxaline. Asian J. Chem., 2008, 20, 629-641.
[51]
Nagaraju, K.; Kotaiah, Y.; Sampath, C.; Harikrishna, N.; Rao, C.V. A facile synthesis of some novel fused [1,2,4]triazolo[3,4-b][1,3,4]thiadiazol derivatives. J. Sulfur Chem., 2013, 34(3), 264-275.
[http://dx.doi.org/10.1080/17415993.2012.734306]
[52]
Patil, R.D.; Biradar, J.S. Synthesis and biological activities of fused biheterocycles containing indole nucleus: Reactions of 3-(5;-substituted-3;-phenylindol-2;-yl)-4-amino-4,5-dihydro-s-triazol-5-thiones. Indian J. Chem., 2000, 39B, 929-935.
[53]
Suresh Kumar, G.V.; Rajendra Prasad, Y.; Mallikarjuna, B.P.; Chandrashekar, S.M. Synthesis and pharmacological evaluation of clubbed isopropylthiazole derived triazolothiadiazoles, triazolothiadiazines and mannich bases as potential antimicrobial and antitubercular agents. Eur. J. Med. Chem., 2010, 45(11), 5120-5129.
[http://dx.doi.org/10.1016/j.ejmech.2010.08.023] [PMID: 20797808]
[54]
Aouad, M.R.; Al-Saedi, A.M.H.; Ali, A.A.; Rezki, N.; Messali, M. Preparation of novel 3-fluorophenyl triazolothiadiazoles and of triazolothiadiazines. Org. Prep. Proced. Int., 2016, 48(4), 355-370.
[http://dx.doi.org/10.1080/00304948.2016.1194134]
[55]
Mathew, V.; Keshavayya, J.; Vaidya, V.P. Synthesis, characterization and pharmacological activities of 3,6-disubstituted-1,2,4-triazolo [3,4-b]-1,3,4-thiadiazoles and their dihydro analogues. E-J. Chem., 2007, 4(3), 320-342.
[http://dx.doi.org/10.1155/2007/605058]
[56]
Shiradkar, M.; Shivaprasad, H.N. Microwave-assisted synthesis and bioactivity of s-triazolo[3,4-b][1,3,4]thiadiazoles, s-triazolo[3,4-b][1,3,4]thiadiazines and s-triazolo[3;4;2,3] thiadiazino[5,6-b]quinoxaline. Asian J. Chem., 2006, 18, 319-324.
[57]
Dong, H-S.; Wei, K.; Wang, Q-L.; Quan, B.; Zhang, Z-Y. Synthesis of 3-[5-methyl-1-(4-methylphenyl)-1, 2,3-triazol-4-yl]-6-substituted-s-triazolo[3,4-b]-1,3,4-thiadiazoles. J. Chin. Chem. Soc. (Taipei), 2000, 47(2), 343-346.
[http://dx.doi.org/10.1002/jccs.200000044]
[58]
Holla, B.S.; Shridhara, K.; Shuvanada, M.K. Synthesis and antibacterial activity of N-bridged heterocycles derived from aryloxymethyltriazoles. Indian J. Chem., 2002, 41B, 1257-1262.
[59]
Abd El Salam, H.A.; Yakout, E.M.A.; Nawwar, G.A.M.; El-Hashash, M.A.; Mossa, A.H. Synthesis of some new 1,2,4-triazoles containing olyl moiety and evaluation of their antimicrobial and antioxidant activities. Monatsh. Chem., 2017, 148(2), 291-304.
[http://dx.doi.org/10.1007/s00706-016-1751-5]
[60]
Kattimani, P.P.; Kamble, R.R.; Dorababu, T.; Hunnur, R.K.; Kamble, A.A.; Devarajegowda, H.C. C5-Alkyl-1,3,4-oxadiazol-2-ones undergo dealkylation upon nitrogen insertion to form 2H-1,2,4-Triazol-3-ones: Synthesis of 1,2,4-Triazol-3-one hybrids with triazolothiadiazoles and triazolothiadiazines. J. Heterocycl. Chem., 2017, 54(4), 2258-2265.
[http://dx.doi.org/10.1002/jhet.2813]
[61]
Tang, Z.; Peng, Y.; Liu, F. Design and synthesis of novel quinoline derivatives bearing oxadiazole, isoxazoline, triazolothiadiazole, triazolothiadiazine, and piperazine moieties. J. Heterocycl. Chem., 2020, 57(6), 2330-2338.
[http://dx.doi.org/10.1002/jhet.3907]
[62]
Sagredou, S.; Dalezis, P.; Nikoleousakos, N.; Nikolaou, M.; Voura, M.; Almpanakis, K.; Panayiotidis, M.I.; Sarli, V.; Trafalis, D.T. 3,6-Disubstituted 1,2,4-triazolo[3,4-b]thiadiazoles with anticancer activity targeting topoisomerase II alpha. OncoTargets Ther., 2020, 13, 7369-7386.
[http://dx.doi.org/10.2147/OTT.S254856] [PMID: 32801761]
[63]
El Ashry, E.S.H.; Kassem, A.A.; Abdel-Hamid, H.; Louis, F.F.; Khattab, S.A.N.; Aouad, M.R. Synthesis of 4-amino-5-(3-chlorobenzo[b]thien-2-yl)-3-mercapto-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and triazolo[3,4,b][1,3,4]thiadiazines under classical and microwave conditions. ARKIVOC, 2006, XIV, 119-132.
[64]
Ghorab, M.M.; El-Sharief, A.M.S.; Ammar, Y.A.; Mohamed, S.I. Synthesis and antifungal activity of some new miscellaneous s-triazoles. Phosphorus Sulfur Silicon Relat. Elem., 2001, 173(1), 223-233.
[http://dx.doi.org/10.1080/10426500108045271]
[65]
Al-Sehemi, A.G.M. Structural study and biological evaluation of some novel 1,2,4-triazole, thiazole, and bisthiazole derivatives bearing a sulfonamide moiety. Phosphorus Sulfur Silicon Relat. Elem., 2009, 148(8), 1991-2003.
[http://dx.doi.org/10.1080/10426500802417323]
[66]
Amir, M.; Kumar, H.; Javed, S.A. Condensed bridgehead nitrogen heterocyclic system: Synthesis and pharmacological activities of 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole derivatives of ibuprofen and biphenyl-4-yloxy acetic acid. Eur. J. Med. Chem., 2008, 43(10), 2056-2066.
[http://dx.doi.org/10.1016/j.ejmech.2007.09.025] [PMID: 18023930]
[67]
Abdel-Rahman, R.M.; Footy, K.O.; Aqlan, F.M. Synthesis and antiinflammatory evaluation of some more new 1,2,4-triazolo[3,4-b]thiadiazoles as an antimicrobial agent: Part-I. Int. J. Chemtech Res., 2011, 3, 423-434.
[68]
El-Sayed, R. Synthesis, antibacterial, and surface activity of 1,2,4-triazole derivatives. Indian J. Chem., 2006, 45B, 738-746.
[69]
Dhiman, A.M.; Wadodkar, K.N.; Patil, S.D. Synthesis and antimicrobial activiy of some bridgehead nitrogen heterocycles. Indian J. Chem., 2001, 40B, 640-643.
[70]
Brand, G.; Gomes, C.M.B.; Costa, W.F.; Foglio, M.A.; Ruiz, A.L.T.G.; Sarragiotto, M.H. Synthesis and antitumor activity of novel 1-substituted 3-(4,5-Substituted 1,2,4-Triazol-3-yl)-β-carboline derivatives. Synthesis, 2019, 51(2), 573-577.
[http://dx.doi.org/10.1055/s-0037-1610291]
[71]
Ramadan, S.K.; Abou-Elmaged, W.S.I. Synthesis and anti H5N1 activities of some novel fused heterocycles bearing pyrazolyl moiety. Synth. Commun., 2018, 48(18), 2409-24019.
[http://dx.doi.org/10.1080/00397911.2018.1491995]
[72]
Ammar, Y.A.; Salem, M.A.; Fayed, E.A.; Helal, M.H.; El-Gaby, M.S.A.; Thabet, K. Naproxen derivatives: Synthesis, reactions, and biological applications. Synth. Commun., 2017, 47(15), 1341-1367.
[http://dx.doi.org/10.1080/00397911.2017.1328066]
[73]
Ahlawat, A.R. Condensed bridgehead nitrogen heterocyclic systems: Synthesis and bioactivity of imidazo[2, 1-b] -1, 3, 4-thiadiazolo [2,3-c]-s-triazoles, s-triazolo[3,4-b]-1,3,4-thladiazolo [3,2-b]imidazo[4,5-b]quinoxaline and bis-(s-triazolo[3,4-b]-1,3,4-thiadiazolo[3,2-b][imidazo [4,5-b]cyclohexane]-5a,6a-diene). Heterocycl. Lett, 2017, 7, 1147-1151.
[74]
El-Sayed, H.A.; Assy, M.G.; Mohamed, A.S. An efficient synthesis and antimicrobial activity of N-bridged triazolo[3,4-b]thiadiazine and triazolo[3,4-b]thiadiazole derivatives under microwave irradiation. Synth. Commun., 2020, 50, 997-1007.
[http://dx.doi.org/10.1080/00397911.2020.1726397]
[75]
Deohate, P.P. The conventional and MW assisted syntheses of some bridgehead nitrogen containing triazolo-thiadiazoles by cyclocondensation using N-aryl isocy-anodichlorides and antimicrobial evaluation. Indian J. Heterocycl. Chem., 2017, 27, 377-382.
[76]
Kaushik, N.; Kumar, N.; Kumar, A. Synthesis of triazolothiadiazine derivatives as antioxidant agents. Int. J. Pharm. Pharm. Sci., 2015, 7, 120-123.
[77]
Altıntop, M.D.; Kaplancıklı, Z.A.; Turan-Zitouni, G.; Özdemir, A.; İşcan, G.; Akalın, G.; Yıldırım, Ş. Synthesis and anticandidal activity of new triazolothiadiazine derivatives. Eur. J. Med. Chem., 2011, 46(11), 5562-5566.
[http://dx.doi.org/10.1016/j.ejmech.2011.09.020] [PMID: 21959231]
[78]
Aytaç, P.S.; Durmaz, I.; Houston, D.R.; Çetin-Atalay, R.; Tozkoparan, B. Novel triazolothiadiazines act as potent anticancer agents in liver cancer cells through Akt and ASK-1 proteins. Bioorg. Med. Chem., 2016, 24(4), 858-872.
[http://dx.doi.org/10.1016/j.bmc.2016.01.013] [PMID: 26810835]
[79]
Sim, K-M.; Chan, P-Q.; Boo, X-L.; Heng, K-S.; Lye, K-W.; Teo, K-C. Synthesis, characterization and antibacterial activity of some new 1,2,4-triazole schiff bases and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines. Lett. Org. Chem., 2018, 15(7), 575-582.
[http://dx.doi.org/10.2174/1570178614666171129160503]
[80]
Sever, B. Altıntop, M.D.; Kuş, G.; Özkurt, M.; Özdemir, A.; Kaplancıklı, Z.A. Indomethacin based new triazolothiadiazine derivatives: Synthesis, evaluation of their anticancer effects on T98 human glioma cell line related to COX-2 inhibition and docking studies. Eur. J. Med. Chem., 2016, 113, 179-186.
[http://dx.doi.org/10.1016/j.ejmech.2016.02.036] [PMID: 26927686]
[81]
Jin, J-Y.; Zhang, L-X.; Zhang, A-J.; Lei, X.X.; Zhu, J-H. Synthesis and biological activity of some novel derivatives of 4-amino-3-(D-galactopentitol-1-yl)-5-mercapto-1,2,4-triazole. Molecules, 2007, 12(8), 1596-1605.
[http://dx.doi.org/10.3390/12081596] [PMID: 17960075]
[82]
Ye, X.; Chen, Z.; Zhang, A.; Zhang, L. The synthesis and biological activities of 6-aryl-3-(D-glucoheptonic-hexitol-1-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines. J. Chem. Res., 2007, 2007(4), 244-246.
[http://dx.doi.org/10.3184/030823407X210901]
[83]
Singh, R.J. Antibactericidal effect of some substituted-1, 2, 4-triazole derivatives. J. Chem. Soc. Pak., 2010, 33, 485-489.
[84]
Lechani, N.; Hamdi, M.; Kheddis-Boutemeur, B.; Talhi, O.; Laichi, Y.; Bachari, K.; Silva, A.M.S. Synthetic approach toward heterocyclic hybrids of [1,2,4]triazo-lo[3,4-b][1,3,4] thiadiazines. Synlett, 2018, 29(11), 1502-1504.
[http://dx.doi.org/10.1055/s-0036-1591991]
[85]
Li, Z.; Bai, X.; Deng, Q.; Zhang, G.; Zhou, L.; Liu, Y.; Wang, J.; Wang, Y. Preliminary SAR and biological evaluation of antitubercular triazolothiadiazine derivatives against drug-susceptible and drug-resistant Mtb strains. Bioorg. Med. Chem., 2017, 25(1), 213-220.
[http://dx.doi.org/10.1016/j.bmc.2016.10.027] [PMID: 27810439]
[86]
Sumangala, V.; Poojary, B.; Chidananda, N.; Arulmoli, T.; Shenoy, S. Facile synthesis, cytotoxic and antimicrobial activity studies of a new group of 6-aryl-3-[4-(methylsulfonyl)benzyl]-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines. Eur. J. Med. Chem., 2012, 54, 59-64.
[http://dx.doi.org/10.1016/j.ejmech.2012.04.024] [PMID: 22633832]
[87]
Demirbas, A.; Ahin, D.; Demirbas, N.; Karaoglu, S.A.; Bektas, H. Synthesis and antimicrobial activities of 2-(5-mercapto)-1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives. Turk. J. Chem., 2010, 34, 347-358.
[88]
Raslan, M.A.; Khalil, M.A. Heterocyclic synthesis containing bridgehead nitrogen atom: Synthesis of 3-[(2H)-2-Oxobenzo[b]pyran-3-yl]-s-triazolo[3,4-b]-1,3,4-thiadiazine and thiazole derivatives. Heteroatom Chem., 2003, 14(2), 114-120.
[http://dx.doi.org/10.1002/hc.10109]
[89]
Hegazi, B.; Abdel-Gawad, H.; Mohamed, H.A.; Badria, F.A.; Farag, A.M. Synthesis of new indeno[1,2-c]pyrazole-based heterocycles and evaluation of their protective effect against dna damage induced by bleomycin-iron. ChemInform, 2013, 50, 355-360.
[90]
El-Husseiny, W.M.; El-Sayed, M.A.A.; Abdel-Aziz, N.I.; El-Azab, A.S.; Asiri, Y.A.; Abdel-Aziz, A.A.M. Structural alterations based on naproxen scaffold: Synthesis, evaluation of antitumor activity and COX-2 inhibition, and molecular docking. Eur. J. Med. Chem., 2018, 158, 134-143.
[http://dx.doi.org/10.1016/j.ejmech.2018.09.007] [PMID: 30216848]
[91]
Dubey, P.K.; Babu, B. Synthesis of some 2-heteryl-substituted indoles. Indian J. Heterocycl. Chem., 2007, 16, 357-360.
[92]
Farghaly, A.A.H. Synthesis, reactions and antimicrobial activity of some new indolyl-1,3,4-oxadiazole, triazole and pyrazole derivatives. J. Chin. Chem. Soc. (Taipei), 2004, 51(1), 147-156.
[http://dx.doi.org/10.1002/jccs.200400023]
[93]
Motamedi, R.; Monfared, A.; Nezamabadi, Z.G.; Bamoharram, F.F. Facile one-pot synthesis of [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and 3,7-dimethyl-4h-[1,2,4]triazino[3,4-b][1,3,4] thiadiazin-6-one using heteropolyacid catalysts. J. Heterocycl. Chem., 2011, 48(3), 604-607.
[http://dx.doi.org/10.1002/jhet.407]
[94]
Shivarama Holla, B.; Sooryanarayana Rao, B.; Sarojini, B.K.; Akberali, P.M.; Suchetha Kumari, N. Synthesis and studies on some new fluorine containing triazolothiadi-azines as possible antibacterial, antifungal and anticancer agents. Eur. J. Med. Chem., 2006, 41(5), 657-663.
[http://dx.doi.org/10.1016/j.ejmech.2006.02.001] [PMID: 16616396]
[95]
Alafeefy, A.M.; Abdel-Aziz, H.A.; Vullo, D.; Al-Tamimi, A-M.S.; Awaad, A.S.; Mohamed, M.A.; Capasso, C.; Supuran, C.T. Inhibition of human carbonic anhydrase isozymes I, II, IX and XII with a new series of sulfonamides incorporating aroylhydrazone-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazinyl- or 2-(cyanophenylmethylene)-1,3,4-thiadiazol-3(2H)-yl moieties. J. Enzyme Inhib. Med. Chem., 2015, 30, 52-56.
[http://dx.doi.org/10.3109/14756366.2013.877897] [PMID: 24666294]
[96]
Farghaly, T.A.; Abdallah, M.A.; Mahmoud, H.K. Synthesis of novel 1,2,4-triazoles and triazolo-thiadiazines as anticancer agents. Turk. J. Chem., 2015, 39, 955-969.
[http://dx.doi.org/10.3906/kim-1504-13]
[97]
Abdelrazek, F.M.; Gomha, S.M.; Shaaban, M.E.B.; Lotfi, A.I.; El-Shemy, H.N. Facile synthesis of some novel triazolo[3,4-b]thiadiazines and triazolo[4,3-b]tetrazines. Synth. Commun., 2018, 48(1), 32-37.
[http://dx.doi.org/10.1080/00397911.2017.1385084]
[98]
Gomha, S.M.; Riyadh, S.M. Synthesis of triazolo[4,3-b][1,2,4,5]tetrazines and triazolo[3,4-b] [1,3,4]thiadiazines using chitosan as ecofriendly catalyst under microwave irradiation. ARKIVOC, 2009, 2009(XI), 58-68.
[http://dx.doi.org/10.3998/ark.5550190.0010.b06]
[99]
El-Sherief, H.A.H.; Hozien, Z.A.; El-Mahdy, A.F.M.; Sarhan, A.A.O. Novel method for the synthesis of s-triazolo[3,4-b][1,3,4]thiadiazines. Synthesis, 2010, 15(15), 2636-2642.
[http://dx.doi.org/10.1055/s-0030-1258153]
[100]
Heravi, M.M.; Bakherad, M.; Rahimzadeh, M.; Bakavoli, M. Solid acid induced cyclocondensation: A facile, one-pot synthesis of 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines. Phosphorus Sulfur Silicon Relat. Elem., 2002, 177(10), 2403-2407.
[http://dx.doi.org/10.1080/10426500214303]
[101]
Deohate, P.P. Synthesis, structural study and biological activity of bridgehead nitrogen containing triazolo-thiadiazinone heterocycles. Pharma Chem., 2012, 4, 2042-2046.
[102]
Pandey, V.K.; Tusi, Z.; Tusi, S.; Joshi, M. Synthesis and biological evaluation of some novel 5-[(3-aralkyl amido/imidoalkyl) phenyl]-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines as antiviral Agents. ISRN Org. Chem., 2012, 2012, 760517.
[http://dx.doi.org/10.5402/2012/760517] [PMID: 24052850]
[103]
Kaur, N. Role of microwaves in the synthesis of fused five-membered heterocycles with three N-heteroatoms. Synth. Commun., 2015, 45(4), 403-431.
[http://dx.doi.org/10.1080/00397911.2013.824981]
[104]
Cetin, A. Accelerated synthesis of novel 1,2,4-triazolo[3,4-b][1,3,4]thiadiazepines under microwave irradiation. Heterocycles, 2006, 68(9), 1901-1907.
[http://dx.doi.org/10.3987/COM-06-10802]
[105]
Gomha, S.M.; Abdel-aziz, H.M.; Abolibda, T.Z.; Hassan, S.A.; Abdalla, M.M. Green synthesis, molecular docking and pharmacological evaluation of new triazolo-thiadiazepinylcoumarine derivatives as sedative-hypnotic scaffold. J. Heterocycl. Chem., 2020, 57(3), 1034-1043.
[http://dx.doi.org/10.1002/jhet.3827]
[106]
Khalafy, J.; Mohammadlou, M.; Mahmoody, M.; Salami, F.; Marjani, A.P. Facile synthesis of new 10-substituted-5H-naphtho[1,2-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-5-ones. Tetrahedron Lett., 2015, 56(12), 1528-1530.
[http://dx.doi.org/10.1016/j.tetlet.2015.02.002]
[107]
El-Reedy, A.A.M.; Soliman, N.K. Synthesis, biological activity and molecular modeling study of novel 1,2,4-triazolo[4,3-b][1,2,4,5]tetrazines and 1,2,4-triazolo[4,3-b][1,2,4]triazines. Sci. Rep., 2020, 10(1), 6137.
[http://dx.doi.org/10.1038/s41598-020-62977-x] [PMID: 32273529]

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