Diastereomeric Separation of a Novel Chalcone Derivative by Chiral HPLC

In this study, a facile and versatile procedure for the synthesis of a chalcone derivate that a functionalized (E,Z)-2-(4-aminobenzylidene)acenaphthylen-1(2H)-one, 4 was synthesized and also characterized by using FT-IR, NMR and MS. A new HPLC method for the separation of its diastereomers was developed by using a chiral column that contains the amylose tris(3,5-dimethylphenylcarbamate) as a chiral selector since it is effective, reproducible and can be used for preparative purposes. High percentage recovery claims that the presented method was not affected by the impurities in the biological media. RSD% values for the repeatability studies suggest that the optimized method was highly precise and reproducible which is very important for these promising advances, chalcone-based science is expected to be applied in drug discovery.

Keywords:

Chalcone;, Diastereomeric separation;, Acenaphtenone;, Chiral column; HPLC,

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[1] Zhuang, C., Zhang, W., Sheng, C., Zhang, W., Xing, C., Miao, Z, Chalcone: a privileged structure in medicinal chemistry, Chemical Reviews, 117 (12), 7762-7810, 2017.
[2] De Mello, M.V.P., Abrahim-Vieira de A.B., Domingos, S.F.T., De Jesus, J.B., De Sousa, A.C.C., Rodrigues, C.R., De Souza, M.T.A., A comprehensive review of chalcone derivatives as antileishmanial agents, European Journal of Medicinal Chemistry, 150, 920-929, 2018.
[3] Yalçın, E., Kutlu, C.Y., Korkmaz, V., Şahin, E., Seferoğlu, Z., 2,6-Dicyanoaniline based donor-acceptor compounds: the facile synthesis of fluorescent 3, 5-diaryl/hetaryl-2, 6-dicyanoanilines, ARKIVOC, 202-218, 2015.
[4] Yalçın, E., Achelle, S., Bayrak, Y., Seferoğlu, N., Barsella, A., Seferoğlu, Z., Styryl-based NLO chromophores: synthesis, spectroscopic properties, and theoretical calculations, Tetrahedron Letters, 56 (20), 2586-2589, 2015.
[5] Rammohan, A., Reddy, J. S., Sravya, G., Rao, C. N., Zyryanov, V.G., Chalcone synthesis, properties and medicinal applications: a review, Environmental Chemistry Letters, 18 (2), 433-458, 2020.
[6] Gogolashvili, A., Tatunashvili, E., Chankvetadze, L., Sohajda, T., Gumustas, M., Ozkan, A.S., Salgado, A., Chankvetadze, B., Separation of brombuterol enantiomers in capillary electrophoresis with cyclodextrin‐type chiral selectors and investigation of structure of selector‐selectand complexes using nuclear magnetic resonance spectroscopy, Electrophoresis, 40 (15), 1904-1912, 2019.
[7] Gumustas, M., Kurbanoglu, S., Uslu, B., Ozkan, A.S., UPLC versus HPLC on drug analysis: advantageous, applications and their validation parameters, Chromatographia, 76 (21), 1365-1427, 2013.
[8] Ahirrao, V., Vipul, R., Patil, K., More, K., Jadhav, R., Yeole, R., Reverse‐phase chiral high‐performance liquid chromatography for separation of a diastereomer in alalevonadifloxacin: A novel antibacterial agent, Biomedical Chromatography, 35 (6), e5079, 2021.
[9] Zhang, Z., Yang, G., Liang, G., Liu, H., Chen, Y., Chiral separation of Tamsulosin isomers by HPLC using cellulose Tris (3, 5-dimethhylphenylcarbamate) as a chiral stationary phase, Journal of Pharmaceutical and Biomedical Analysis, 34 (3), 689-693, 2004.
[10] Pypowski, K., Uszyńska, I., Kluska, M., Chromatographic separation of isomers of tribenzylgermanium nitrile derivatives using chemically bonded aryl stationary phases, Journal of Liquid Chromatography & Related Technologies, 29 (20), 2989-2996, 2006.
[11] Gumustas, M., Ozkan, A.S., Chankvetadze, B., Analytical and preparative scale separation of enantiomers of chiral drugs by chromatography and related methods., Current Medicinal Chemistry, 25 (33), 4152-4188, 2018.
[12] Gumustas, M., Kurbanoglu, S., Uslu, B., Ozkan, A.S., UPLC versus HPLC on drug analysis: Advantageous, applications and their validation parameters, Chromatographia, 76 (21-22), 1365-1427, 2013
[13] Longstreet, A.R., Jo, M., Chandler, R.R., Hanson, K., Zhan, N., Hrudka, J.J., Hedi M., Shatruk, M., McQuade, D.T., Ylidenemalononitrile enamines as fluorescent “turn-on” indicators for primary amines, Journal of the American Chemical Society, 136 (44), 15493-15496, 2014.
[14] Charlesworth, E.H., Campbell, H., Conn, J.J., Elston, C.T., Stachiw, D.L., Some Acenaphtene Compounds, Canadian Journal of Chemistry, 35 (4), 351-357, 1957.
[15] ICH Harmonised Tripartite Guideline–Validation of Analytical Procedures: Text and Methodology, Available online:https://www.ema.europa.eu/en/ich-q2-r1-validation-analyticalprocedures-text-methodology(accessed on 4 May 2021), European Medicines Agency, Q2 (R1), 2014.
[16] Naresh, P., Pramodh, B., Naveen, S., Ganguly, S., Panda, J., Sunitha, K., Maniukiewicz, W., Lokanath, N.K., Cis and trans isomers of 1-(5-bromothiophen-2-yl)-3-(10-chloroanthracen-9-yl) prop-2-en-1-one: Synthesis and characterization, Journal of Molecular Structure, 1236, 130228, 2021.
[17] Wang, M., Lin, L., Lu, J-J., Chen, X., Pharmacological review of isobavachalcone, a naturally occurring chalcone, Pharmacological Research, 165, 105483, 2021.
[18] Kumar, A., Kumar, S., Coumarin-chalcone hybrids for biological potentials: a strategy of molecular hybridization for drug design, International Journal of Pharmaceutical Sciences Review and Research, 64 (2), 146-151, 2020.
[19] Yalçin, E., Matković, M., Jukić, M., Obrova, L.G., Piantanida, I., Seferoğlu, Z., Novel fluorene/fluorenone DNA and RNA binders as efficient non-toxic ds-RNA selective fluorescent probes, Tetrahedron, 74 (5), 535-543, 2018.
[20] Pasricha, S., Gahlot, P., Synthetic strategies and biological potential of coumarin-chalcone hybrids: a new dimension to drug design, Current Organic Chemistry, 24 (4), 402-438, 2020.