Structure Modification of Quinine on C-9 Hydroxyl Group via Esterification Reaction
Teni Ernawati, Minarti Minarti, Puspa Dewi Narrij Lotulung
J. Pure App. Chem. Res. Vol 9, No 1 (2020), pp. 32-39
Submitted: November 07, 2019     Accepted: April 20, 2020     Published: April 20, 2020
DOI: http://dx.doi.org/10.21776/ub.jpacr.2020.009.01.505

Abstract


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Concept the role played by modified quinine in the asymmetric hydroxyl group inspired studies of modified quinine as chiral organic that lead to drug discovery development. A simple and efficient method for C-9 alkylation and arylation of quinine derivatives was reported. Series quinine derivatives were synthesized through the esterification of the hydroxyl group of quinine. The reaction with various alkyl and aryl carbonyl chloride resulted in the series of ester quinine derivatives. The structure of quinine derivatives was characterized by IR, melting point, UV, 1H NMR, 13C NMR, LCMS.


Keywords : modification, synthesis, quinine derivatives, ester
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References


[1] Phillipson, J.D., and O’Neill, M.J., Parasitol Today, 1986, 2(12), 355–359.

[2] Garfield, S.M., 2000, 224, Faber and Faber, London.

[3] Mitsui, N., Noro, T., Kuroyanagi, M., Miyase, T., Umehara, K., and Ueno, A. Chem Pharm Bull., 1989, 37(2), 363-366.

[4] Alonso, J. Tratado de Fitofármacos y Nutracéuticos., Barcelona: Corpus, 2004, 897-901.

[5] Marella, A., Tanwar, O.P., Saha, R., Ali, M.R, Srivastava, S., and Akhter., M. Saudi Pharm J, 2013, 21(1), 1-12.

[6] O’Neill, P. M., Harrison, A. C., Storr, R. C., Hawley, S. R., Ward, S. A., and Park,

B. K., J. Med.Chem, 1994, 37(9), 1362-1370.

[7] Krishnaveni, M., and Kathiresan, S., RJPBCS, 2015, 6(5), 295-301.

[8] Schlesinger, P.H., Krogstad, D.J., and Herwaldt, B.I, Antimicrob Agents Chemother, 1988, 32(6), 793–798.

[9] Nour, B.Y., Faragalla, I.A., Saeed, O.K., and Mohamadani, A.A., Saudi Med. J, 2006, 27(6), 808–812.

[10] Achan, J., Talisuna, A.O., Erhart, A., Yeka, A., Tibenderana, J.K., Baliraine, F.N., Rosenthal, P.J., and D’Alessandro, U., Malar. J, 2011, 10(1), 144.

[11] Mohapatra, P., Preet, R., Das, D., Satapathy, S.R., Choudhuri, T., Wyatt, M.D., and Kundu, C.N., Oncol. Res, 2012, 20(2-3), 81–91.

[12] Preet, R., Mohapatra, M., Das, D., Satapathy, S.R., Choudhuri, T., Wyatt, M.D. Kundu, C.N. Carcinogenesis, 2012, 34,277–286.

[13] Preet, R., Mohapatra, P., Mohanty, S., Sahu, S.K., Choudhuri, T., Wyatt, M.D., Kundu, C.N. Int. J. Cancer, 2012, 130, 1660–1670.

[14] Desai, N.C., Kotadiya, G.M., and Trivedi, A.R., Bioorg. Med. Chem. Lett., 2014, 24(14), 3126-3130.

[15] Sangani, C.B., Makawana, J.A., Zhang, X., Teraiya, S. B., Lin, L., and Zhu, H.L., Eur. J. Med. Chem., 2014, 76, 549-557.

[16] Taha, M., Ismail, N.H., Imran, S., Wadood, A., Rahim, F., Ali, M., and Rehman, A.U., Med. Chem. Commun., 2015, 6(10), 1826-1836.

[17] Kacprzak, K., and Gawronski., J. Synthesis, 2001, 961.

[18] Tian, S.K., Chen, Y., Hang, J., Tang, L., McDaid, P., and Deng, L., Acc. Chem.Res. 2004, 37(8), 621-631.

[19] Hoffmann, H. M. R., and Frackenpohl, Eur. J. Org. Chem, 2004, 4293.

[20] Palomo, C., Oiarbide, M., and Laso, A., Eur. J. Org. Chem, 2007, 2561

[21] Yoon, T. P., and Jacobsen, E.N., Science, 2003, 299(5613), 1691-1693.

[22] Brunner, H., Bugler, J., and Nuber, B. Tetrahedron Asymmetry, 1995, 6(7), 1699-1702.

[23] Vakulya, B., Varga, S., Csampai, A., and Soos, T., Org. Lett, 2005, 7(10), 1967-1969.

[24] Chen, W., Du, W., Duan, Y.Z., Wu, Y., Yang, S.Y., and Chen, Y.C., Angew. Chem., Int. Ed. 2007, 46, 7667.

[25] Kagan, H. B. Historical Perspective. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds Chapter 2, 1999, SpringerVerlag: Berlin.


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