Synthesis, Anticancer and Antioxidant Evaluation of Some New 2-Aryl and 2-Pyrazole-2,3-dihydroquinazolin-4(1H)-ones

Ramesh Navudu; Gangadhara Rao Mannem; Tirumala Margani; Uma Maheswara Rao Vanga; Hari Babu Bollikolla

doi:10.14233/ajchem.2016.19676

Issue

Vol. 28 No. 6 (2016): Vol 28 Issue 6

Issue Published : February 29, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Anticancer and Antioxidant Evaluation of Some New 2-Aryl and 2-Pyrazole-2,3-dihydroquinazolin-4(1H)-ones

https://doi.org/10.14233/ajchem.2016.19676

Ramesh Navudu

Department of Chemistry, Acharya Nagarjuna University, Nagarjuna Nagar-522 510, India

Gangadhara Rao Mannem

Department of Chemistry, Acharya Nagarjuna University, Nagarjuna Nagar-522 510, India

Tirumala Margani

Department of Chemistry, Acharya Nagarjuna University, Nagarjuna Nagar-522 510, India

Uma Maheswara Rao Vanga

Department of Botany & Microbiology, Acharya Nagarjuna University, Nagarjuna Nagar-522 510, India

Hari Babu Bollikolla

Department of Chemistry, Acharya Nagarjuna University, Nagarjuna Nagar-522 510, India

Corresponding Author(s) : Hari Babu Bollikolla

dr.b.haribabu@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 6 (2016): Vol 28 Issue 6
Article Published : February 29, 2016

Abstract

A new and direct synthetic method was developed for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones by condensing 2-aminobenzamide and aldehydes in ethanol using thionyl chloride as a catalyst at room temperature. The simple reaction conditions, small timing, easy work up and very good yields are the greatest advantages of this methodology. By utilizing the approach six novel derivatives of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones (3a-3f) were synthesized. All the compounds were tested for their anticancer activity on A549 cell line and antioxidant activity by using DPPH method. Compounds 3c (74.22 %) and 3e (73.45 %) showed better anticancer activity towards the A549 cell line.

Keywords

SOCl2 Anthranilamide Novel pyrazole derivatives Anticancer Antioxidant activity

Navudu, R., Mannem, G. R., Margani, T., Rao Vanga, U. M., & Bollikolla, H. B. (2016). Synthesis, Anticancer and Antioxidant Evaluation of Some New 2-Aryl and 2-Pyrazole-2,3-dihydroquinazolin-4(1H)-ones. Asian Journal of Chemistry, 28(6), 1321–1324. https://doi.org/10.14233/ajchem.2016.19676

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J.B. Jiang, D.P. Hesson, B.A. Dusak, D.L. Dexter, G.J. Kang and E. Hamel, J. Med. Chem., 33, 1721 (1990); doi:10.1021/jm00168a029.

G.L. Neil, H. Li L, H. H. Buskirk and T. E. Moxley, Gan To Kagaku Ryoho, 56, 163 (1972).

G. Bonola, P. Da Re, M.J. Magistretti, E. Massarani and I. Setnikar, J. Med. Chem., 11, 1136 (1968); doi:10.1021/jm00312a007.

H.L. Yale and M. Kalkstein, J. Med. Chem., 10, 334 (1967); doi:10.1021/jm00315a010.

R.J. Alaimo and H.E. Russell, J. Med. Chem., 15, 335 (1972); doi:10.1021/jm00273a034.

E. Cohen, B. Klarberg and J.R. Vaughan Jr., J. Am. Chem. Soc., 81, 5508 (1959); doi:10.1021/ja01529a062.

I. Levin, P.S. Chan, T. Bailey, A.S. Katocs Jr. and A.M. Venkatesan, Bioorg. Med. Chem. Lett., 4, 1141 (1994); doi:10.1016/S0960-894X(01)80244-4.

K. Okumura, T. Oine, Y. Yamada, G. Hayashi and M. Nakama, J. Med. Chem., 11, 348 (1968); doi:10.1021/jm00308a036.

G.M. Chinigo, M. Paige, S. Grindrod, E. Hamel, S. Dakshanamurthy, M. Chruszcz, W. Minor and M.L. Brown, J. Med. Chem., 51, 4620 (2008); doi:10.1021/jm800271c.

M. Sharma, S. Pandey, K. Chauhan, D. Sharma, B. Kumar and P.M.S. Chauhan, J. Org. Chem., 77, 929 (2012); doi:10.1021/jo2020856.

M. Wang, J.J. Gao, Z.G. Song and L. Wang, Chem. Heterocycl. Compd., 47, 851 (2011); doi:10.1007/s10593-011-0846-5.

Q.S. Ding, J.L. Zhang, J.X. Chen, M.C. Liu, J.C. Ding and H.Y. Wu, J. Heterocycl. Chem., 49, 375 (2012); doi:10.1002/jhet.759.

K.J. Zahed and Z. Leila, S. Afr. J. Chem., 65, 36 (2012).

J. Chen, D. Wu, F. He, M. Liu, H. Wu, J. Ding and W. Su, Tetrahedron Lett., 49, 3814 (2008); doi:10.1016/j.tetlet.2008.03.127.

A. Rostami and A. Tavakoli, Chin. Chem. Lett., 22, 1317 (2011); doi:10.1016/j.cclet.2011.06.008.

A. Davoodnia, S. Allameh, A.R. Fakhari and N. Tavakoli-Hoseini, Chin. Chem. Lett., 21, 550 (2010); doi:10.1016/j.cclet.2010.01.032.

J.-H. Tang, D.-X. Shi, L.-J. Zhang, Q. Zhang and J.-R. Li, Synth. Commun., 40, 632 (2010); doi:10.1080/00397910902908822.

A. Kamal, E.V. Bharathi, J.S. Reddy, M.J. Ramaiah, D. Dastagiri, M.K. Reddy, A. Viswanath, T.L. Reddy, T.B. Shaik, S.N.C.V.L. Pushpavalli and M.P. Bhadra, Eur. J. Med. Chem., 46, 691 (2011); doi:10.1016/j.ejmech.2010.12.004.

A.J.A. Watson, A.C. Maxwell and J.M.J. Williams, Org. Biomol. Chem., 10, 240 (2012); doi:10.1039/C1OB06516E.

R.Z. Qiao, B.L. Xu and Y.H. Wang, Chin. Chem. Lett., 18, 656 (2007); doi:10.1016/j.cclet.2007.04.036.

D. Shi, C. Shi, J. Wang, L. Rong, Q. Zhuang and X. Wang, J. Hetrocycl. Chem., 42, 173 (2005); doi:10.1002/jhet.5570420201.

M. Abdollahi-Alibeik and E. Shabani, Chin. Chem. Lett., 22, 1163 (2011); doi:10.1016/j.cclet.2011.05.011.

J. Zhang, Y. Yang, L. Lei and M.L. Tian, Med. Sci. Monit., 21, 2535 (2015); doi:10.12659/MSM.895084.

A.L. Chew, J.J.A. Jessica and S. Sasidharan, Asian Pacific J. Trop. Biomed., 2, 176 (2012); doi:10.1016/S2221-1691(12)60037-9.

Issue

Vol. 28 No. 6 (2016): Vol 28 Issue 6

Synthesis, Anticancer and Antioxidant Evaluation of Some New 2-Aryl and 2-Pyrazole-2,3-dihydroquinazolin-4(1H)-ones

Corresponding Author(s) : Hari Babu Bollikolla

Abstract

Keywords

Full Article

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