Journals / Adıyaman Üniversitesi Fen Bilimleri Dergisi / 2021 / Cilt: 11 - Sayı: 1

Diastereomeric Separation of a Novel Chalcone Derivative by Chiral HPLC

Kiral HPLC ile Yeni Bir Kalkon Bileşiğinin Diastereomerik Ayrılması

Pages
205–214
Publication Date
2022-10-12
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

RSD% values for the repeatability studiessuggest that the optimized method was highly precise and reproducible which is very importantfor these promising advances, chalcone-based science is expected to be applied in drug discovery.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:In this study, a facile and versatile procedure for the synthesis of a chalcone derivate thata functionalized (E,Z)-2-(4-aminobenzylidene)acenaphthylen-1(2H)-one, 4 was synthesized andalso characterized by using FT-IR, NMR and MS.
📊
Key Findings & Data:A new HPLC method for the separation of itsdiastereomers 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 usedfor preparative purposes.
💡
Conclusion & Impact:RSD% values for the repeatability studiessuggest that the optimized method was highly precise and reproducible which is very importantfor these promising advances, chalcone-based science is expected to be applied in drug discovery.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

In this study, a facile and versatile procedure for the synthesis of a chalcone derivate thata functionalized (E,Z)-2-(4-aminobenzylidene)acenaphthylen-1(2H)-one, 4 was synthesized andalso characterized by using FT-IR, NMR and MS. A new HPLC method for the separation of itsdiastereomers 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 usedfor preparative purposes. High percentage recovery claims that the presented method was notaffected by the impurities in the biological media. RSD% values for the repeatability studiessuggest that the optimized method was highly precise and reproducible which is very importantfor these promising advances, chalcone-based science is expected to be applied in drug discovery.

Özet

Bu çalışmada (E,Z)-2-(4-aminobenziliden)asenaftilen-1(2H)-on, 4 bileşiği kolay ve hızlı bir metodla sentezlenip FT-IR, NMR ve MS kullanılarak karakterize edilmiştir. Bileşiğin diastereomerlerinin ayrılması için etkili, tekrarlanabilir, preparatif amaçlar için uygun amiloz tris(3,5-dimetilfenilkarbamat) kiral seçici kolon kullanıldığı bir HPLC metodu geliştirilmiştir. Yüksek geri kazanım oranı bileşiğin biyolojik ortamdaki safsızlıklardan etkilenmediğini göstermektedir. Tekrarlanabilirlik ile ilgili çalışmalarda % BSS değerleri, optimize edilen metodun kalkon temelli bileşiklerin yer aldığı ilaç geliştirme çalışmalarında yüksek hassasiyet ve tekrarlanabilirlik değerleri ile kullanılabileceğini göstermiştir.

🔖

Cite This Article

YALÇIN, E. (2022). Diastereomeric Separation of a Novel Chalcone Derivative by Chiral HPLC. Adıyaman Üniversitesi Fen Bilimleri Dergisi, Cilt: 11 - Sayı: 1, 205–214. https://ajindex.com/articles/428411

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (11)

  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., Styrylbased 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