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Article

2D-QSAR and CoMFA Models for Antitubercular Activity of Scalarane-Type Sesterterpenes

1
Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Songkhla 90112, Thailand
2
Department of Natural Products Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zu Ching Zhu Road, Shanghai 201203, China
3
Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand
4
Department of Drug and Natural Product Synthesis, Althanstrasse 14, Universitat Wien, 1090 Wein, Austria
5
Institute of Pharmaceutical Technology and Biopharmacy, Althanstrasse 14, Universitat Wien, 1090 Wien, Austria
6
Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
*
Author to whom correspondence should be addressed.
Academic Editors: Roman B. Lesyk and William A. Donaldson
Sci. Pharm. 2022, 90(3), 47; https://doi.org/10.3390/scipharm90030047
Received: 9 June 2022 / Revised: 4 August 2022 / Accepted: 9 August 2022 / Published: 15 August 2022
(This article belongs to the Special Issue Heterocyclic Chemistry in Drug Design 2.0)
A series of scalarane sesterterpenes were prepared using heteronemin (1) as a primary precursor. Combined with the scalarane derivatives obtained from natural sources, a total of 22 antitubercular scalaranes were used to build QSAR models based in the 2D-QSAR and CoMFA approaches. Both models indicated the influences of substitutions in the vicinity of C-12 and C-16 of the scalaranes. A 2D-QSAR model suggested the necessity of hydrophilic functionalities on the peripherals with hydrophobic cores, and the lowering steric repulsion to improve the potential energy. This was complemented by the pictorial CoMFA model, which indicated the importance of the positive electrostatic with shortened steric extension crowning over C-12 and the lengthy negative functionalities extended from C-16. View Full-Text
Keywords: structure-activity relationship; sesterterpenes; tuberculosis; marine natural products structure-activity relationship; sesterterpenes; tuberculosis; marine natural products
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MDPI and ACS Style

Thengyai, S.; Guo, Y.; Suwanborirux, K.; Berner, H.; Spreitzer, H.; Wolschann, P.; Hannongbua, S.; Plubrukarn, A. 2D-QSAR and CoMFA Models for Antitubercular Activity of Scalarane-Type Sesterterpenes. Sci. Pharm. 2022, 90, 47. https://doi.org/10.3390/scipharm90030047

AMA Style

Thengyai S, Guo Y, Suwanborirux K, Berner H, Spreitzer H, Wolschann P, Hannongbua S, Plubrukarn A. 2D-QSAR and CoMFA Models for Antitubercular Activity of Scalarane-Type Sesterterpenes. Scientia Pharmaceutica. 2022; 90(3):47. https://doi.org/10.3390/scipharm90030047

Chicago/Turabian Style

Thengyai, Suriyan, Yuewei Guo, Khanit Suwanborirux, Heinz Berner, Helmut Spreitzer, Peter Wolschann, Supa Hannongbua, and Anuchit Plubrukarn. 2022. "2D-QSAR and CoMFA Models for Antitubercular Activity of Scalarane-Type Sesterterpenes" Scientia Pharmaceutica 90, no. 3: 47. https://doi.org/10.3390/scipharm90030047

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