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Synthesis, Characterization, and Biological Evaluation of 2-(p-Nitrophenyl)quinazolin-4(3H)-one Derivatives

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Abstract

A series of novel 2-(4-nitrophenyl)-3-(R-benzothiazol-2-yl)quinazolin-4(3H)-ones 4a–4g (R = Alk, AlkO, Hal, NO2) were synthesized from the corresponding substituted 2-aminobenzothiazoles and 2-(4-nitrophenyl)-4H-3,1-benzoxazin-4-one via a nucleophilic addition reaction. The structures of the novel compounds were assigned on the basis of the elemental analyses and FTIR, 1H NMR, and mass spectra. The synthesized compounds were tested for anticonvulsant, antimicrobial, and antioxidant activities. All the compounds increased the seizure latency compared to control. Compound 4b (R = 6-NO2) exhibited significant anticonvulsant activity, comparable to that of the standard drug Phenytoin. Antimicrobial activity testing revealed moderate to good activity in all the test compounds, and 4a (R = H) and 4b compared in activity with the standard drug Chloramphenicol. The antioxidant activity of compounds 4a, 4d (R = 5-Br), and 4f (R = 4,6-Me2) (IC50 39.30, 15.55, and 42.95 µg/mL, respectively) was found to be higher compared to the standard drug ascorbic acid (IC50 48.30 µg/mL).

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REFERENCES

  1. Kusuma, P.K. and Vedula, G., Biosci. Biotech. Res. Asia, 2016, vol. 13, p. 1121. https://doi.org/10.13005/bbra/2141

    Article  Google Scholar 

  2. Mishra, A.D., Nepal J. Sci. Technol., 2011, vol. 12, p. 133. https://doi.org/10.3126/njst.v12i0.6491

    Article  Google Scholar 

  3. Abuelizz, H.A., El Dib, R., Marzouk, M., Anouar, El-H., Maklad, Y.A., Attia, H.N., and Al-Salahi, R., Molecules, 2017, vol. 22, p. 1. https://doi.org/10.3390/molecules22071094

    Article  CAS  Google Scholar 

  4. Hosseinzadeh, L., Aliabadi, A., Rahnama, M., Sadeghi, H.M.M., and Khajouei, M.R., Res. Pharm. Sci., 2017, vol. 12, p. 290. https://doi.org/10.4103/1735-5362.212046

    Article  PubMed  PubMed Central  Google Scholar 

  5. Saeedi, M., Mohammadi-Khanaposhtani, M., Pourrabia, P., Razzaghi, N., Ghadimi, R., Imanparast, S., Faramarzi, M.A., Bandarian, F., Esfahani, E.N., Safavi, M., Rastegar, H., Larijani, B., Mahdavi, M., and Akbarzadeh, T., Bioorg. Chem., 2019, vol. 83, p. 161. https://doi.org/10.1016/j.bioorg.2018.10.023

    Article  CAS  PubMed  Google Scholar 

  6. Osarumwense, P.O., Edema, M.O., and Usifoh, O., IOSR-JAC, 2018, vol. 11, p. 12. https://doi.org/10.9790/5736-1104011215

    Article  CAS  Google Scholar 

  7. Hosseinzadeh, L., Aliabadi, A., Kalantari, M., Mostafavi, A., and Khajouei, M.R., Res. Pharm. Sci., 2016, vol. 11, p. 210.

    PubMed  PubMed Central  Google Scholar 

  8. Karumanchi, A.D., Sarangapani, M., and Sriram, Int. J. Drug Dev. Res., 2014, vol. 6, p. 259.

    Google Scholar 

  9. Ibrahim, M.K., El-Adl, K., and Al-Karmalawy, A.A., Bull. Fac. Pharm. Cairo Univ., 2015, vol. 53, p. 101–116. https://doi.org/10.1016/j.bfopcu.2015.05.001

    Article  Google Scholar 

  10. Paneersalvam, P., Raj, T., Ishar, M.P.S., Singh, B., Sharma, V., and Rather, B.A., Indian. J. Pharm. Sci., 2010, vol. 72, p. 375. https://doi.org/10.4103/0250-474X.70488

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Zayed, M.F. and Hassan, M.H., Saudi Pharm. J., 2014, vol. 22, p. 157. https://doi.org/10.1016/j.jsps.2013.03.004

    Article  Google Scholar 

  12. Pawar, S., Pisal, P., Deodhar, M., Kale, A., and Nigade, G., Int. J. Pharm. Pharm. Sci., 2018, vol. 10, p. 57. https://doi.org/10.22159/ijpps.2018v10i10.28480

    Article  CAS  Google Scholar 

  13. Prabhu, P.P., Panneerselvam, T., Shastry, C.S., Sivakumar, A., and Pande, S.S., J. Saudi Chem. Soc., 2015, vol. 19, p. 181. https://doi.org/10.1016/j.jscs.2012.02.001

    Article  Google Scholar 

  14. Ajeet and Kumar, A., Am. J. Pharm. Sci., 2013, vol. 1, p. 116. https://doi.org/10.12691/ajps-1-6-2

    Article  CAS  Google Scholar 

  15. Gupta, A., Asian. J. Pharm. Clin. Res., 2018, vol. 11, p. 416. https://doi.org/10.22159/ajpcr.2018.v11i9.28095

    Article  CAS  Google Scholar 

  16. Shakya, A.K., Kumar, A., and Siddiqui, H.H., Indian J. Heterocycl. Chem., 2016, vol. 25, p. 243.

    Google Scholar 

  17. Dhamak, K.B., Gaware, V.M., and Somwanshi, S.B., Int. J. Pharm. Pharm. Res., 2015, vol. 3, p. 112.

    Google Scholar 

  18. Gollapalli, N., Karumudi, B.S., Kota, C., Gudipati, M., Suresh, P.V., and Ramarao, N., Indo Am. J. Pharm. Res., 2015, vol. 5, p. 1288.

    Google Scholar 

  19. Devmurari, V.P., Pandey, S., Goyani, M.B., Nandanwar, R.R., Jivani, N.P., and Perumal, P., Int. J. ChemTech. Res., 2010, vol. 2, p. 681.

    CAS  Google Scholar 

  20. Kabra, U., Chopde, C., and Wadodkar, S., J. Heterocycl. Chem., 2011, vol. 48, p. 1351. https://doi.org/10.1002/jhet.754

    Article  CAS  Google Scholar 

  21. Ugale, V.G., Wadodkar, S.G., and Chopde, C.T., Asian J. Res. Chem., 2011, vol. 4, p. 1717.

    Google Scholar 

  22. Ganguli, S., Panigrahi, M.K., Singh, P., and Shukla, P.K., Int. J. Pharm. Pharm. Sci., 2012, vol. 4, p. 434.

    CAS  Google Scholar 

  23. Laddha, S.S., Wadodkar, S.G., and Meghal, S.K., Arkivoc, 2006, vol. 11, p. 1. https://doi.org/10.3998/ark.5550190.0007.b01

    Article  Google Scholar 

  24. Vogel, H.G., Drug Discovery and Evaluation Pharmacological Assays, New York: Springer, 2002.

  25. Upadhaye, G.J. and Asnani, A.J., IJPSR, 2017, vol. 8, p. 1214. https://doi.org/10.13040/IJPSR.0975-8232.8(3).1314-18

    Article  Google Scholar 

  26. Kumar, C.T.K., Keshavayya, J., Ravi, B.N., and Patil, S.R., Int. J. Innov. Res. Dev., 2016, vol. 5, p. 13.

    Google Scholar 

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Smt. Kishoritai Bhoyar College of Pharmacy, 441002, Nagpur, India

    V. N. Giradkar, U. D. Kabra, R. S. Diwakar & R. T. Lohiya

  2. Department of Pharmaceutical Chemistry, Parul Institute of Pharmacy, Parul University, 391760, Vadodara, India

    U. D. Kabra

  3. Principal of Smt. Kishoritai Bhoyar College of Pharmacy, 441002, Nagpur, India

    M. J. Umekar

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  1. V. N. Giradkar
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  2. U. D. Kabra
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  3. R. S. Diwakar
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  4. R. T. Lohiya
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  5. M. J. Umekar
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Correspondence to R. T. Lohiya.

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Giradkar, V.N., Kabra, U.D., Diwakar, R.S. et al. Synthesis, Characterization, and Biological Evaluation of 2-(p-Nitrophenyl)quinazolin-4(3H)-one Derivatives. Russ J Org Chem 56, 1455–1461 (2020). https://doi.org/10.1134/S1070428020080175

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