Copyright (c) 2016 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Characterization of Novel Pyridine Associated 1,2,4-Triazolo-1,3,4-thiadiazines
Corresponding Author(s) : B. Satyanarayana
Asian Journal of Chemistry,
Vol. 28 No. 8 (2016): Vol 28 Issue 8
Abstract
A series of novel 3-(1-methyl-1H-pyrazol-4-yl)-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadaizine and its derivatives (8a-f) were synthesized by using 1-methyl-1H-pyrazole-4-carboxylic acid (3) as starting material and by involving 1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (4), 1-methyl-1H-pyrazole-4-carboxylic acid hydrazide (5), 5-(1-methyl-1H-pyrazol-4-yl)-[1,3,4]oxadiazole-2-thiol (6) and 4-amino-5-(1-methyl-1H-pyrazol-4-yl)-4H-[1,2,4]triazole-3-thiol (7) as intermediate.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- V. Padmavathi, G. Sudhakar Reddy, A. Padmaja, P.Kondaiah and Ali-Shazia, Eur. J. Med. Chem., 44, 2106 (2009); doi:10.1016/j.ejmech.2008.10.012.
- R.S. Lamani, N.S. Shetty, R.R. Kamble and I.A.M. Khazi, Eur. J. Med. Chem., 44, 2828 (2009); doi:10.1016/j.ejmech.2008.12.019.
- A. Foroumadi, S. Emami, A. Hassanzadeh, M. Rajaee, K. Sokhanvar, M. Moshafi and A. Shafiee, Bioorg. Med. Chem. Lett., 15, 4488 (2005); doi:10.1016/j.bmcl.2005.07.016.
- T. Önkol, D.S. Dogruer, L. Uzun, S. Adak, S. Özkan and M. Fethi Şahin, J. Enzyme Inhib. Med. Chem., 23, 277 (2008); doi:10.1080/14756360701408697.
- N. Siddiqui and M.S. Alam, Biosci. Biotechnol. Res. Asia, 6, 261 (2009).
- P. Karegoudar, D.J. Prasad, M. Ashok, M. Mahalinga, B. Poojary and B.S. Holla, Eur. J. Med. Chem., 43, 808 (2008); doi:10.1016/j.ejmech.2007.06.026.
- T. Karabasanagouda, A.V. Adhikari and N.S. Shetty, Eur. J. Med. Chem., 42, 521 (2007); doi:10.1016/j.ejmech.2006.10.010.
- V. Mathew, J. Keshavayya, V.P. Vaidya and D .Giles, Eur. J. Med. Chem., 42, 823 (2007); doi:10.1016/j.ejmech.2006.12.010.
- U. Salgin-Göksen, N. Gökhan-Kelekçi, Ö. Göktas, Y. Köysal, E. Kilic, S. Isik, G. Aktay and M. Özalp, Bioorg. Med. Chem., 15, 5738 (2007); doi:10.1016/j.bmc.2007.06.006.
- S. Schenone, C. Brullo, O. Bruno, F. Bondavalli, A. Ranise, W. Filippelli, B. Rinaldi, A. Capuano and G. Falcone, Bioorg. Med. Chem., 14, 1698 (2006); doi:10.1016/j.bmc.2005.10.064.
- V. Mathew, J. Keshavayya, V.P. Vaidya and D. Giles, Eur. J. Med. Chem., 42, 823 (2007); doi:10.1016/j.ejmech.2006.12.010.
- A.A. Kadi, E.S. Al-Abdullah, I.A. Shehata, E.E. Habib, T.M. Ibrahim and A.A. El-Emam, Eur. J. Med. Chem., 45, 5006 (2010); doi:10.1016/j.ejmech.2010.08.007.
- M. Amir, H. Kumar and S.A. Javed, Eur. J. Med. Chem., 43, 2056 (2008); doi:10.1016/j.ejmech.2007.09.025.
- H.N. Hafez, M.I. Hegab, I.S. Ahmed-Farag and A.B.A. El-Gazzar, Bioorg. Med. Chem. Lett., 18, 4538 (2008); doi:10.1016/j.bmcl.2008.07.042.
- M.-X. Wei, L. Feng, X.-Q. Li, X.-Z. Zhou and Z.-H. Shao, Eur. J. Med. Chem., 44, 3340 (2009); doi:10.1016/j.ejmech.2009.03.023.
- D.A. Ibrahim, Eur. J. Med. Chem., 44, 2776 (2009); doi:10.1016/j.ejmech.2009.01.003.
- J. Matysiak and A. Opolski, Bioorg. Med. Chem., 14, 4483 (2006); doi:10.1016/j.bmc.2006.02.027.
- J. Matysiak, A. Nasulewicz, M. Pelczynska, M. Switalska, I. Jaroszewicz and A. Opolski, Eur. J. Med. Chem., 41, 475 (2006); doi:10.1016/j.ejmech.2005.12.007.
- A.T. Mavrova, D. Wesselinova, Y.A. Tsenov and P. Denkova, Eur. J. Med. Chem., 44, 63 (2009); doi:10.1016/j.ejmech.2008.03.006.
- N. Siddiqui, Indian J. Heterocycl. Chem., 14, 159 (2004).
- A. Gupta, P. Mishra, S.N. Pandeya, S.K.Kashaw, V.Kashaw and J.P.Stables, Eur. J. Med. Chem., 44, 1100 (2009); doi:10.1016/j.ejmech.2008.06.015.
- A. Gupta, P. Mishra, S.K. Kashaw, V. Kashaw and J.P. Stables, Eur. J. Med. Chem., 43, 749 (2008); doi:10.1016/j.ejmech.2007.05.008.
- N. Siddiqui, M.F. Arshad, S.A. Khan and W. Hasan, J. Pharm. Res., 7, 122 (2008).
- V. Jatav, P. Mishra, S. Kashaw and J.P. Stables, Eur. J. Med. Chem., 43, 1945 (2008); doi:10.1016/j.ejmech.2007.12.003.
- M. Yusuf, R.A. Khan and B. Ahmed, Bioorg. Med. Chem., 16, 8029 (2008); doi:10.1016/j.bmc.2008.07.056.
- P. Pattanayak, R. Sharma and P.K. Sahoo, Med. Chem. Res., 18, 351 (2009); doi:10.1007/s00044-008-9132-1.
- C. Kus, G. Ayhan-Kilcigil, S. Özbey, F.B. Kaynak, M. Kaya, T. Çoban and B. Can-Eke, Bioorg. Med. Chem., 16, 4294 (2008); doi:10.1016/j.bmc.2008.02.077.
- C. Prouillac, P. Vicendo, J.-C. Garrigues, R. Poteau and G. Rima, Free Radic. Biol. Med., 46, 1139 (2009); doi:10.1016/j.freeradbiomed.2009.01.016.
- D. Cressier, C. Prouillac, P. Hernandez, C. Amourette, M. Diserbo, C. Lion and G. Rima, Bioorg. Med. Chem., 17, 5275 (2009); doi:10.1016/j.bmc.2009.05.039.
- A. Foroumadi, S. Emami, S. Pournourmohammadi, A. Kharazmi and A. Shafiee, Eur. J. Med. Chem., 40, 1346 (2005); doi:10.1016/j.ejmech.2005.07.002.
- M. Behrouzi-Fardmoghadam, F. Poorrajab, S.K. Ardestani, S. Emami, A. Shafiee and A. Foroumadi, Bioorg. Med. Chem., 16, 4509 (2008); doi:10.1016/j.bmc.2008.02.052.
- F.Z. Smaine, F. Pacchiano, M. Rami, V. Barragan-Montero, D. Vullo, A. Scozzafava, J.-Y. Winum and C.T. Supuran, Bioorg. Med. Chem. Lett., 18, 6332 (2008); doi:10.1016/j.bmcl.2008.10.093.
- G.L. Almajan, A. Innocenti, L. Puccetti, G. Manole, S. Barbuceanu, I. Saramet, A. Scozzafava and C.T. Supuran, Bioorg. Med. Chem. Lett., 15, 2347 (2005); doi:10.1016/j.bmcl.2005.02.088.
- A. Varvarason, A. Tantili-Kakoulidou, T. Siatra-Papastasikoudi and E. Tiligada, Arzneimittelforschung, 50, 48 (2000); doi:10.1055/s-0031-1300163.
- M. Gökce, B. Cakir, K. Erol and M.F. Sahin, Arch. Pharm., 334, 279 (2001);
- doi:10.1002/1521-4184(200109)334:8/9<279::AID-ARDP279>3.0.CO;2-W.
- O. Pintilie, L. Profire, V. Sunel, M. Popa and A. Pui, Molecules, 12, 103 (2007); doi:10.3390/12010103.
- A. Faroumadi, M. Mirzaei and A. Shafiee, Pharmazie, 56, 610 (2001).
- M.G. Mamolo, V. Falagiani, D. Zampieri, L. Vio and E. Banfi, Farmaco, 56, 587 (2001); doi:10.1016/S0014-827X(01)01097-7.
- K. Zamani, K. Faghifi, I. Tefighi and R. Sharlatzadeh, Turk. J. Chem., 28, 95 (2004).
- X.-J. Zou, L.-H. Lai, G.-Y. Jin and Z.-X. Zhang, J. Agric. Food Chem., 50, 3757 (2002); doi:10.1021/jf0201677.
- H. Chen, Z. Li and Y. Han, J. Agric. Food Chem., 48, 5312 (2000); doi:10.1021/jf991065s.
- F. Clerici, D. Pocar, M. Guido, A. Loche, V. Perlini and M. Brufani, J. Med. Chem., 44, 931 (2001); doi:10.1021/jm001027w.
- T. Onkol, B. Cakir and M.F. Sahin, Turk. J. Chem., 28, 461 (2004).
- S. Schenone, O. Bruno, A. Ranise, F. Bondavalli, W. Filippelli, G. Falcone, L. Giordano and M.R. Vitelli, Bioorg. Med. Chem., 9, 2149 (2001); doi:10.1016/S0968-0896(01)00121-3.
- L. Labanauskas, V. Kalcas, E. Uderenaite, P. Gaidelis, A. Brukstus and V. Dauksas, Pharmazie, 56, 617 (2001).
- E. Palaska, G. Şahin, P. Kelicen, N.T. Durlu and G. Altinok, Farmaco, 57, 101 (2002); doi:10.1016/S0014-827X(01)01176-4.
- S.L. Vasoya, D.J. Paghdar, P.T. Chovatia and H.S. Joshi, J. Sci. Islamic Rep. Iran, 16, 33 (2005).
- M. Barboiu, M. Cimpoesu, C. Guran and C. Supuran, Met. Based Drugs, 3, 227 (1996); doi:10.1155/MBD.1996.227.
- A. Ali, V. Nasim, T. Sayyed Abbas, K. Abbas and S. Abbas, Acta Chim. Slov., 54, 317 (2007).
- J.K. Gupta, R.K. Yadav, D. Rupesh and P.R. Sharma, J. Pharm. Tech. Res., 2, 1493 (2010).
References
V. Padmavathi, G. Sudhakar Reddy, A. Padmaja, P.Kondaiah and Ali-Shazia, Eur. J. Med. Chem., 44, 2106 (2009); doi:10.1016/j.ejmech.2008.10.012.
R.S. Lamani, N.S. Shetty, R.R. Kamble and I.A.M. Khazi, Eur. J. Med. Chem., 44, 2828 (2009); doi:10.1016/j.ejmech.2008.12.019.
A. Foroumadi, S. Emami, A. Hassanzadeh, M. Rajaee, K. Sokhanvar, M. Moshafi and A. Shafiee, Bioorg. Med. Chem. Lett., 15, 4488 (2005); doi:10.1016/j.bmcl.2005.07.016.
T. Önkol, D.S. Dogruer, L. Uzun, S. Adak, S. Özkan and M. Fethi Şahin, J. Enzyme Inhib. Med. Chem., 23, 277 (2008); doi:10.1080/14756360701408697.
N. Siddiqui and M.S. Alam, Biosci. Biotechnol. Res. Asia, 6, 261 (2009).
P. Karegoudar, D.J. Prasad, M. Ashok, M. Mahalinga, B. Poojary and B.S. Holla, Eur. J. Med. Chem., 43, 808 (2008); doi:10.1016/j.ejmech.2007.06.026.
T. Karabasanagouda, A.V. Adhikari and N.S. Shetty, Eur. J. Med. Chem., 42, 521 (2007); doi:10.1016/j.ejmech.2006.10.010.
V. Mathew, J. Keshavayya, V.P. Vaidya and D .Giles, Eur. J. Med. Chem., 42, 823 (2007); doi:10.1016/j.ejmech.2006.12.010.
U. Salgin-Göksen, N. Gökhan-Kelekçi, Ö. Göktas, Y. Köysal, E. Kilic, S. Isik, G. Aktay and M. Özalp, Bioorg. Med. Chem., 15, 5738 (2007); doi:10.1016/j.bmc.2007.06.006.
S. Schenone, C. Brullo, O. Bruno, F. Bondavalli, A. Ranise, W. Filippelli, B. Rinaldi, A. Capuano and G. Falcone, Bioorg. Med. Chem., 14, 1698 (2006); doi:10.1016/j.bmc.2005.10.064.
V. Mathew, J. Keshavayya, V.P. Vaidya and D. Giles, Eur. J. Med. Chem., 42, 823 (2007); doi:10.1016/j.ejmech.2006.12.010.
A.A. Kadi, E.S. Al-Abdullah, I.A. Shehata, E.E. Habib, T.M. Ibrahim and A.A. El-Emam, Eur. J. Med. Chem., 45, 5006 (2010); doi:10.1016/j.ejmech.2010.08.007.
M. Amir, H. Kumar and S.A. Javed, Eur. J. Med. Chem., 43, 2056 (2008); doi:10.1016/j.ejmech.2007.09.025.
H.N. Hafez, M.I. Hegab, I.S. Ahmed-Farag and A.B.A. El-Gazzar, Bioorg. Med. Chem. Lett., 18, 4538 (2008); doi:10.1016/j.bmcl.2008.07.042.
M.-X. Wei, L. Feng, X.-Q. Li, X.-Z. Zhou and Z.-H. Shao, Eur. J. Med. Chem., 44, 3340 (2009); doi:10.1016/j.ejmech.2009.03.023.
D.A. Ibrahim, Eur. J. Med. Chem., 44, 2776 (2009); doi:10.1016/j.ejmech.2009.01.003.
J. Matysiak and A. Opolski, Bioorg. Med. Chem., 14, 4483 (2006); doi:10.1016/j.bmc.2006.02.027.
J. Matysiak, A. Nasulewicz, M. Pelczynska, M. Switalska, I. Jaroszewicz and A. Opolski, Eur. J. Med. Chem., 41, 475 (2006); doi:10.1016/j.ejmech.2005.12.007.
A.T. Mavrova, D. Wesselinova, Y.A. Tsenov and P. Denkova, Eur. J. Med. Chem., 44, 63 (2009); doi:10.1016/j.ejmech.2008.03.006.
N. Siddiqui, Indian J. Heterocycl. Chem., 14, 159 (2004).
A. Gupta, P. Mishra, S.N. Pandeya, S.K.Kashaw, V.Kashaw and J.P.Stables, Eur. J. Med. Chem., 44, 1100 (2009); doi:10.1016/j.ejmech.2008.06.015.
A. Gupta, P. Mishra, S.K. Kashaw, V. Kashaw and J.P. Stables, Eur. J. Med. Chem., 43, 749 (2008); doi:10.1016/j.ejmech.2007.05.008.
N. Siddiqui, M.F. Arshad, S.A. Khan and W. Hasan, J. Pharm. Res., 7, 122 (2008).
V. Jatav, P. Mishra, S. Kashaw and J.P. Stables, Eur. J. Med. Chem., 43, 1945 (2008); doi:10.1016/j.ejmech.2007.12.003.
M. Yusuf, R.A. Khan and B. Ahmed, Bioorg. Med. Chem., 16, 8029 (2008); doi:10.1016/j.bmc.2008.07.056.
P. Pattanayak, R. Sharma and P.K. Sahoo, Med. Chem. Res., 18, 351 (2009); doi:10.1007/s00044-008-9132-1.
C. Kus, G. Ayhan-Kilcigil, S. Özbey, F.B. Kaynak, M. Kaya, T. Çoban and B. Can-Eke, Bioorg. Med. Chem., 16, 4294 (2008); doi:10.1016/j.bmc.2008.02.077.
C. Prouillac, P. Vicendo, J.-C. Garrigues, R. Poteau and G. Rima, Free Radic. Biol. Med., 46, 1139 (2009); doi:10.1016/j.freeradbiomed.2009.01.016.
D. Cressier, C. Prouillac, P. Hernandez, C. Amourette, M. Diserbo, C. Lion and G. Rima, Bioorg. Med. Chem., 17, 5275 (2009); doi:10.1016/j.bmc.2009.05.039.
A. Foroumadi, S. Emami, S. Pournourmohammadi, A. Kharazmi and A. Shafiee, Eur. J. Med. Chem., 40, 1346 (2005); doi:10.1016/j.ejmech.2005.07.002.
M. Behrouzi-Fardmoghadam, F. Poorrajab, S.K. Ardestani, S. Emami, A. Shafiee and A. Foroumadi, Bioorg. Med. Chem., 16, 4509 (2008); doi:10.1016/j.bmc.2008.02.052.
F.Z. Smaine, F. Pacchiano, M. Rami, V. Barragan-Montero, D. Vullo, A. Scozzafava, J.-Y. Winum and C.T. Supuran, Bioorg. Med. Chem. Lett., 18, 6332 (2008); doi:10.1016/j.bmcl.2008.10.093.
G.L. Almajan, A. Innocenti, L. Puccetti, G. Manole, S. Barbuceanu, I. Saramet, A. Scozzafava and C.T. Supuran, Bioorg. Med. Chem. Lett., 15, 2347 (2005); doi:10.1016/j.bmcl.2005.02.088.
A. Varvarason, A. Tantili-Kakoulidou, T. Siatra-Papastasikoudi and E. Tiligada, Arzneimittelforschung, 50, 48 (2000); doi:10.1055/s-0031-1300163.
M. Gökce, B. Cakir, K. Erol and M.F. Sahin, Arch. Pharm., 334, 279 (2001);
doi:10.1002/1521-4184(200109)334:8/9<279::AID-ARDP279>3.0.CO;2-W.
O. Pintilie, L. Profire, V. Sunel, M. Popa and A. Pui, Molecules, 12, 103 (2007); doi:10.3390/12010103.
A. Faroumadi, M. Mirzaei and A. Shafiee, Pharmazie, 56, 610 (2001).
M.G. Mamolo, V. Falagiani, D. Zampieri, L. Vio and E. Banfi, Farmaco, 56, 587 (2001); doi:10.1016/S0014-827X(01)01097-7.
K. Zamani, K. Faghifi, I. Tefighi and R. Sharlatzadeh, Turk. J. Chem., 28, 95 (2004).
X.-J. Zou, L.-H. Lai, G.-Y. Jin and Z.-X. Zhang, J. Agric. Food Chem., 50, 3757 (2002); doi:10.1021/jf0201677.
H. Chen, Z. Li and Y. Han, J. Agric. Food Chem., 48, 5312 (2000); doi:10.1021/jf991065s.
F. Clerici, D. Pocar, M. Guido, A. Loche, V. Perlini and M. Brufani, J. Med. Chem., 44, 931 (2001); doi:10.1021/jm001027w.
T. Onkol, B. Cakir and M.F. Sahin, Turk. J. Chem., 28, 461 (2004).
S. Schenone, O. Bruno, A. Ranise, F. Bondavalli, W. Filippelli, G. Falcone, L. Giordano and M.R. Vitelli, Bioorg. Med. Chem., 9, 2149 (2001); doi:10.1016/S0968-0896(01)00121-3.
L. Labanauskas, V. Kalcas, E. Uderenaite, P. Gaidelis, A. Brukstus and V. Dauksas, Pharmazie, 56, 617 (2001).
E. Palaska, G. Şahin, P. Kelicen, N.T. Durlu and G. Altinok, Farmaco, 57, 101 (2002); doi:10.1016/S0014-827X(01)01176-4.
S.L. Vasoya, D.J. Paghdar, P.T. Chovatia and H.S. Joshi, J. Sci. Islamic Rep. Iran, 16, 33 (2005).
M. Barboiu, M. Cimpoesu, C. Guran and C. Supuran, Met. Based Drugs, 3, 227 (1996); doi:10.1155/MBD.1996.227.
A. Ali, V. Nasim, T. Sayyed Abbas, K. Abbas and S. Abbas, Acta Chim. Slov., 54, 317 (2007).
J.K. Gupta, R.K. Yadav, D. Rupesh and P.R. Sharma, J. Pharm. Tech. Res., 2, 1493 (2010).