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CuI Promoted Efficient Synthesis and Antimicrobial Activity of Substituted 8,8-Dimethyl-5-phenyl-2-(pyrazin-2-yl)-5,7,8,9-tetrahydro-6H-[1,3,4]thiadiazolo[2,3-b]quinazolin-6-one
Corresponding Author(s) : N. Krishna Rao
Asian Journal of Chemistry,
Vol. 36 No. 4 (2024): Vol 36 Issue 4, 2024
Abstract
In present study, an efficient synthesis of substituted 5,7,8,9-tetrahydro-6H-[1,3,4]thiadiazolo[2,3-b]quinazolin-6-one compounds promoted by CuI as catalyst was carried out. These derivatives were obtained from 1,3,4-thiadiazol-2-amine, dimedone and substituted aromatic aldehyde in presence of CuI in ethanol as solvent at 70 ºC. Initially, 1,3,4-thiadiazol-2-amine was synthesized from pyrazine-3- carboxylic acid reacted with thiosemicarbazide in the presence of 50% H2SO4 in acetonitrile at 70 ºC. All the newly obtained derivatives were evaluated by the spectroscopic techniques such as 1H NMR, 13C NMR and LCMS and structural determination of titled analogous were analyzed by elemental analysis. The antibacterial activities of the newly synthesized compounds were also screened.
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- V. Ivasiv, C. Albertini, A.E. Gonçalves, M. Rossi and M.L. Bolognesi, Curr. Top. Med. Chem., 19, 1694 (2019); https://doi.org/10.2174/1568026619666190619115735
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- Clinical and Laboratory Standards Institute, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. Approved Standard, Clinical and Laboratory Standards Institute; edn. 8, CLSI publication M07-A8, Wayne, PA, USA (2009).
References
V. Ivasiv, C. Albertini, A.E. Gonçalves, M. Rossi and M.L. Bolognesi, Curr. Top. Med. Chem., 19, 1694 (2019); https://doi.org/10.2174/1568026619666190619115735
F. Hassanzadeh, R.R. Nasab, G.A. Khodarahmi, M. Mirzaei, M. Rostami and A.J.-N. Abadi, Res. Pharm. Sci., 12, 444 (2017); https://doi.org/10.4103/1735-5362.217425
E. Jafari, F. Hassanzadeh, H. Sadeghi-Aliabadi, A. Sharifzadeh and N. Dana, Res. Pharm. Sci., 14, 408 (2019); https://doi.org/10.4103/1735-5362.268201
E. Jafari, F. Hassanzadeh, H. Sadeghi-aliabadi, S. Nikooei and G. Vaseghi, Res. Pharm. Sci., 14, 130 (2019); https://doi.org/10.4103/1735-5362.253360
M. Asif, Int. J. Med. Chem., 2014, 395637 (2014); https://doi.org/10.1155/2014/395637
S.A. Mir, P.P. Mohanta, R.K. Meher, I. Baitharu, M.K. Raval, A.K. Behera and B. Nayak, Saudi J. Biol. Sci., 29, 103478 (2022); https://doi.org/10.1016/j.sjbs.2022.103478
N.I. Krasovska, S.D. Koptieva, O.R. Posudiievska, S.V. Kyrylakha, O.Yu. Vosokoboynik, Sergiy I. Okovytyy and S.I. Kovalenko, J. Chem. Technol., 31, 385 (2023); https://doi.org/10.15421/jchemtech.v31i2.28019
S. Sharma, K. Sharma, S. Pathak, M. Kumar and P.K. Sharma, Open Med. Chem. J., 14, 108 (2020); https://doi.org/10.2174/1874104502014010108
M. Faisal and A. Saeed, Front. Chem., 8, 594717 (2021); https://doi.org/10.3389/fchem.2020.594717
A.J. Angulwar, G.S. Khansole and V.N. Bhosale, J. Synth. Chem., 1, 97 (2022); https://doi.org/10.22034/jsc.2022.155236
T.A. Farghaly, M.M. Edrees and M.A. Mosselhi, Molecules, 17, 8483 (2012); https://doi.org/10.3390/molecules17078483
H. Patel, A. Shirkhedkar, S. Bari, K. Patil, A. Arambhi, C.S. Pardeshi, A. Kulkarni, S. Surana, Bull. Facul. Pharm. Cairo Univ., 56, 83 (2018); https://doi.org/10.1016/j.bfopcu.2018.03.001
C.L. Jagani, N.A. Sojitra, S.F. Vanparia, T.S. Patel, R.B. Dixit and B.C. Dixit, J. Saudi Chem. Soc., 16, 363 (2012); https://doi.org/10.1016/j.jscs.2011.02.001
E.A.M. Saleh, A.M. Al-Dawsari, K. Husain, I.H. Kutty and K.M. Lokanatha Rai, Molecules, 26, 357 (2021); https://doi.org/10.3390/molecules26020357
H.J. Hess, T.H. Cronin and A. Scriabine, J. Med. Chem., 11, 130 (1968); https://doi.org/10.1021/jm00307a028
A.A. Farag, E.M. Khalifa, N.A. Sadik, S.Y. Abbas, A.G. Al-Sehemi and Y.A. Ammar, Med. Chem. Res., 22, 440 (2013); https://doi.org/10.1007/s00044-012-0046-6
A.A.-M. Abdel-Aziz, L.A. Abou-Zeid, K.E.H. ElTahir, R.R. Ayyad, M.A.-A. El-Sayed and A.S. El-Azab, Eur. J. Med. Chem., 121, 410 (2016); https://doi.org/10.1016/j.ejmech.2016.05.066
A.S. El-Azab and K.E.H. Eltahir, Bioorg. Med. Chem. Lett., 22, 1879 (2012); https://doi.org/10.1016/j.bmcl.2012.01.071
M. Ibrahim Abdou and S.S. Al-Neyadi, Heterocycl. Commun., 21, 115 (2015); https://doi.org/10.1515/hc-2014-0181
A.M.F. Al-Omary, G.S. Hassan, S.M. El-Messery and H.I. El-Subbagh, Eur. J. Med. Chem., 47, 65 (2012); https://doi.org/10.1016/j.ejmech.2011.10.023
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N.A. McIntyre, C. McInnes, G. Griffiths, A.L. Barnett, G. Kontopidis, A.M.Z. Slawin, W. Jackson, M. Thomas, D.I. Zheleva, S. Wang, D.G. Blake, N.J. Westwood and P.M. Fischer, J. Med. Chem., 53, 2136 (2010); https://doi.org/10.1021/jm901660c
A.S. El-Azab, A.A.-M. Abdel-Aziz, S. Bua, A. Nocentini, M.A. ElGendy, M.A. Mohamed, T.Z. Shawer, N.A. AlSaif and C.T. Supuran, Bioorg. Chem., 87, 78 (2019); https://doi.org/10.1016/j.bioorg.2019.03.007
A.D. Hudwekar, G.L. Reddy, P.K. Verma, S. Gupta, R.A. Vishwakarma and S.D. Sawant, ChemistrySelect, 2, 4963 (2017); https://doi.org/10.1002/slct.201700896
G. Qiu, Y. He and J. Wu, Chem. Commun., 48, 3836 (2012); https://doi.org/10.1039/c2cc30928a
A. Moradi, R. Heydari and M.T. Maghsoodlou, Res. Chem. Intermed., 41, 7377 (2015); https://doi.org/10.1007/s11164-014-1818-z
H. Behbehani and H.M. Ibrahim, Chem. Cent. J., 7, 82 (2013); https://doi.org/10.1186/1752-153X-7-82
Clinical and Laboratory Standards Institute, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. Approved Standard, Clinical and Laboratory Standards Institute; edn. 8, CLSI publication M07-A8, Wayne, PA, USA (2009).