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Molecules 2015, 20(11), 20926-20938; doi:10.3390/molecules201119740

Synthesis, Crystal Structure, Absolute Configuration and Antitumor Activity of the Enantiomers of 5-Bromo-2-chloro-N-(1-phenylethyl)pyridine-3-sulfonamide

1
Key Laboratory of Structure-Based Drug Design and Discovery, Shenyang Pharmaceutical University, Ministry of Education, Shenyang 110016, China
2
Pharmacy Department, Shenyang Pharmaceutical University, Shenyang 110016, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Maria Emília de Sousa
Received: 24 September 2015 / Revised: 30 October 2015 / Accepted: 18 November 2015 / Published: 24 November 2015
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Pyridinesulfonamide is an important fragment which has a wide range of applications in novel drugs. R- and S-isomers of 5-bromo-2-chloro-N-(1-phenylethyl)pyridine-3-sulfonamide have been synthesized, and the stereostructures have been researched. Single crystals of both compounds were obtained for X-ray analysis, and the absolute configurations (ACs) have been further confirmed by electronic circular dichroism (ECD), optical rotation (OR) and quantum chemical calculations. The crystal structures and calculated geometries were extremely similar, which permitted a comparison of the relative reliabilities of ACs obtained by ECD analyses and theoretical simulation. In addition, the effect of stereochemistry on the PI3Kα kinase and anticancer activity were investigated. Compounds 10a and 10b inhibit the activity of PI3Kα kinase with IC50 values of 1.08 and 2.69 μM, respectively. Furthermore, molecular docking was performed to analyze the binding modes of R- and S-isomers. View Full-Text
Keywords: pyridinesulfonamide; enantiomer; X-ray diffraction; absolute configuration; DFT; ECD; PI3K; antitumor activity pyridinesulfonamide; enantiomer; X-ray diffraction; absolute configuration; DFT; ECD; PI3K; antitumor activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Zhou, Z.; Li, L.; Yan, N.; Du, L.; Sun, C.; Sun, T. Synthesis, Crystal Structure, Absolute Configuration and Antitumor Activity of the Enantiomers of 5-Bromo-2-chloro-N-(1-phenylethyl)pyridine-3-sulfonamide. Molecules 2015, 20, 20926-20938.

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