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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Synthesis of 2-Hydroxynaphthyl Pyrazolines Containing Isoniazid Moiety: A Potential Antitubercular Agent

Author(s): Gajanan Kottapalle, Nagesh Deshmukh and Avinash Shinde*

Volume 19, Issue 3, 2022

Published on: 27 April, 2021

Page: [222 - 227] Pages: 6

DOI: 10.2174/1570178618666210427103249

Price: $65

Abstract

The new series of pyrazolines derivatives containing isoniazid moiety were synthesized from 2-hydroxynaphthyl functionalized chalcones and isoniazid using sodium hydroxide as a base in 2- ethoxy ethanol. We evaluated their antitubercular activity against Mycobacterium tuberculosis strain (H37Rv) by Microplate Alamar Blue Assay (MABA). Some of the tested compounds 3a, 3b, and 3c, were found to have higher antitubercular activity than the selected standard drugs, whereas compounds 3d, 3e, 3i and 3j were found to have higher antitubercular activity than Streptomycin and same as that of Pyrazinamide and Ciprofloxacin, while remaining compound showed moderate activity. Whereas it is found that the disubstituted halogen compound and electron-withdrawing group on the phenyl ring are important substitutions for an increase in antitubercular activity.

Keywords: Chalcones, pyrazolines, isoniazid, antitubercular activity, 2-hydroxynaphthyl pyrazolines, antitubercular agent.

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[1]
Ahmad, A.; Husain, A.; Khan, S.A.; Mujeeb, M. J. Saudi Chem. Soc., 2014, 8, 1-8.
[2]
Judge, V.; Narasimhan, B.; Ahuja, M. Med. Chem. Res., 2012, 21, 3940-3957.
[http://dx.doi.org/10.1007/s00044-011-9948-y]
[3]
Salve, P.S.; Alegaon, S.G. Med. Chem. Res., 2017, 27, 1-14.
[http://dx.doi.org/10.1007/s00044-017-1970-2]
[4]
Martinez, R.; Zamudio, G.J.N.; Pretelin-Castillo, G.; Torres-Ochoa, R.O.; Medina-Franco, J.L.; Pinzon, C.I.E.; Miranda, M.S.; Hernandez, E.; Alanis-Garza, B. Heterocycl. Commun., 2019, 25, 52-59.
[http://dx.doi.org/10.1515/hc-2019-0007]
[5]
Albalak, R.; O’Brien, R.J.; Kammerer, J.S.; O’Brien, S.M.; Marks, S.M.; Castro, K.G.; Moore, M. Arch. Intern. Med., 2007, 167, 263-266.
[http://dx.doi.org/10.1001/archinte.167.22.2443]
[6]
Corbett, E.L.; Watt, C.J.; Walker, N.; Maher, D.; Williams, B.G.; Raviglione, M.C.; Dye, C. Arch. Intern. Med., 2003, 163(9), 1009-1021.
[http://dx.doi.org/10.1001/archinte.163.9.1009] [PMID: 12742798]
[7]
Alvarez, M.A.; Debattista, N.B.; Pappano, N.B. Folia Microbiol. (Praha), 2008, 53(1), 23-28.
[http://dx.doi.org/10.1007/s12223-008-0003-4] [PMID: 18481214]
[8]
Ali, M.A.; Yar, M.S.; Kumar, M.; Pandian, G.S. Nat. Prod. Res., 2007, 21(7), 575-579.
[http://dx.doi.org/10.1080/14786410701369367] [PMID: 17613813]
[9]
Gupta, R.A.; Kaskhedikar, S.G. Med. Chem. Res., 2013, 22, 3863-3880.
[http://dx.doi.org/10.1007/s00044-012-0385-3]
[10]
Hans, R.H.; Guantai, E.M.; Lategan, C.; Smith, P.J.; Wan, B.; Franzblau, S.G.; Gut, J.; Rosenthal, P.J.; Chibale, K. Bioorg. Med. Chem. Lett., 2010, 20, 942-944.
[http://dx.doi.org/10.1016/j.bmcl.2009.12.062] [PMID: 20045640]
[11]
Sellamuthu, S.; Bhat, M.F.; Kumar, A.; Nath, G.; Singh, S.K. Curr. Bioact. Compd., 2018, 14, 14-23.
[12]
Jadhav, S.B.; Fatema, S.; Sanap, G.; Farooqui, M.J. Het. Chem., 2018, 55, 1634-1644.
[http://dx.doi.org/10.1002/jhet.3198]
[13]
Palaska, E.; Erol, D.; Demirdamar, R. Eur. J. Med. Chem., 1996, 31, 43-47.
[http://dx.doi.org/10.1016/S0223-5234(96)80005-5]
[14]
Kumar, S.; Meenakshi, K.S.; Kumar, P. Med. Chem. Res., 2013, 22, 433-439.
[http://dx.doi.org/10.1007/s00044-012-0045-7]
[15]
Abid, M.; Bhat, A.R.; Athar, F.; Azam, A. Eur. J. Med. Chem., 2009, 44(1), 417-425.
[http://dx.doi.org/10.1016/j.ejmech.2007.10.032] [PMID: 18068873]
[16]
Bhandari, S.; Tripathi, A.C.; Saraf, S.K. Med. Chem. Res., 2013, 22, 5290-5296.
[http://dx.doi.org/10.1007/s00044-013-0530-7]
[17]
Ozdemir, Z.; Kandilci, H.B.; Gümüşel, B.; Caliş, U.; Bilgin, A.A. Eur. J. Med. Chem., 2007, 42(3), 373-379.
[http://dx.doi.org/10.1016/j.ejmech.2006.09.006] [PMID: 17069933]
[18]
Amin, K.M.; Eissa, A.A.; Abou-Seri, S.M.; Awadallah, F.M.; Hassan, G.S. Eur. J. Med. Chem., 2013, 60, 187-198.
[http://dx.doi.org/10.1016/j.ejmech.2012.12.004] [PMID: 23291120]
[19]
Sharma, S.; Sharma, P.K.; Kumar, N.; Dudhe, R. Biomed. Pharmacother., 2011, 65(4), 244-251.
[http://dx.doi.org/10.1016/j.biopha.2011.04.005] [PMID: 21715130]
[20]
Krasavin, M.; Lukin, A.; Vedekhina, T.; Manicheva, O.; Dogonadze, M.; Vinogradova, T.; Zabolotnykh, N.; Rogacheva, E. Eur. J. Med. Chem., 2018, 157, 1115-1126.
[http://dx.doi.org/10.1016/j.ejmech.2018.08.068] [PMID: 30179748]
[21]
Chiarelli, L.R.; Mori, M.; Barlocco, D.; Beretta, G.; Gelain, A.; Pini, E.; Porcino, M.; Mori, G.; Stelitano, G.; Costantino, L.; Lapillo, M.; Bonanni, D.; Poli, G.; Tuccinardi, T.; Villa, S.; Meneghetti, F. Eur. J. Med. Chem., 2018, 155, 754-763.
[http://dx.doi.org/10.1016/j.ejmech.2018.06.033] [PMID: 29940465]
[22]
Yempalla, K.R.; Munagala, G.; Singh, S.; Magotra, A.; Kumar, S.; Rajput, V.S.; Bharate, S.S.; Tikoo, M.; Singh, G.D.; Khan, I.A.; Vishwakarma, R.A.; Singh, P.P. ACS Med. Chem. Lett., 2015, 6(10), 1041-1046.
[http://dx.doi.org/10.1021/acsmedchemlett.5b00141] [PMID: 26487909]
[23]
Rizvi, S.U.F.; Siddiqui, H.L.; Johns, M.; Detorio, M.; Schinazi, R.F. Med. Chem. Res., 2012, 21, 3741-3749.
[http://dx.doi.org/10.1007/s00044-011-9912-x]
[24]
Bashir, R.; Ovais, S.; Yaseen, S. Bioorg. Med. Chem. Lett., 2011, 21, 4301-4305.
[http://dx.doi.org/10.1016/j.bmcl.2011.05.061] [PMID: 21664130]
[25]
Amir, M.; Kumar, H.; Khan, S.A. Med. Chem. Lett., 2008, 18, 918-922.
[http://dx.doi.org/10.1016/j.bmcl.2007.12.043]
[26]
Lachtova, V.S.; Brulikova, L. Disc, 2018, 3, 4653-4662.
[27]
Manna, K.; Agrawal, Y.K. Eur. J. Med. Chem., 2010, 45(9), 3831-3839.
[http://dx.doi.org/10.1016/j.ejmech.2010.05.035] [PMID: 20576327]
[28]
Yar, M.S.; Siddiqui, A.A.; Ali, M.A. Bioorg. Med. Chem. Lett., 2006, 16, 4571-4574.
[http://dx.doi.org/10.1016/j.bmcl.2006.06.021] [PMID: 16784842]
[29]
Abunada, N.M.; Hassaneen, H.M.; Kandile, N.G.; Miqdad, O.A. Molecules, 2008, 13(4), 1011-1024.
[http://dx.doi.org/10.3390/molecules13041011] [PMID: 18463603]
[30]
Shaaban, M.R.; Mayhoub, A.S.; Farag, A.M. Expert Opin. Ther. Pat., 2012, 22(3), 253-291.
[http://dx.doi.org/10.1517/13543776.2012.667403] [PMID: 22397588]
[31]
Ahmad, A.; Husain, A.; Khan, S.A.; Mujeeb, M.; Bhandari, A. J. Saudi Chem. Soc., 2016, 20, 577-584.
[http://dx.doi.org/10.1016/j.jscs.2014.12.004]
[32]
Gurdere, M.B.; Aydin, A.; Yencilek, B.; Erturk, E.; Ozbek, O.; Erkan, S.; Budak, Y.; Ceylan, M. Chem. Biodivers., 2020, 17e20001
[33]
Ozbek, O.; Gurdere, M.B. Med. Chem. Res., 2020, 29, 1553-1578.
[http://dx.doi.org/10.1007/s00044-020-02595-4]
[34]
Avila, H.P. Smânia, Ede.F.; Monache, F.D.; Smânia, A. Jr Bioorg. Med. Chem., 2008, 16(22), 9790-9794.
[http://dx.doi.org/10.1016/j.bmc.2008.09.064] [PMID: 18951808]
[35]
Ali, M.A.; Shaharyar, M.; Siddiqui, A.A. Eur. J. Med. Chem., 2007, 42(2), 268-275.
[http://dx.doi.org/10.1016/j.ejmech.2006.08.004] [PMID: 17007966]
[36]
Kottapalle, G.D.; Deshmukh, N.J.; Shinde, A.T. Curr. Bioact. Compd., 2020, 16, 892-899.
[http://dx.doi.org/10.2174/1573407215666190401202553]
[37]
Lourenco, M.C.; de Souza, M.V.; Pinheiro, A.C.; Ferreira, Md. ARKIVOC, 2007, 5, 181-191.
[38]
Anandam, R.; Jadav, S.S.; Ala, V.B.; Ahsan, M.J.; Bollikolla, H.B. Med. Chem. Res. 2018, 27, 1690-1704.
[http://dx.doi.org/10.1007/s00044-018-2183-z]
[39]
Sivakumar, D.; Geetha, G. J. Pharm. Teach., 2019, 11, 31536-31548.

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