Next Article in Journal
Hypervalent Iodine Reagents in High Valent Transition Metal Chemistry
Previous Article in Journal
Alkamides from Anacyclus pyrethrum L. and Their in Vitro Antiprotozoal Activity
Article Menu
Issue 5 (May) cover image

Export Article

Open AccessArticle
Molecules 2017, 22(5), 785; doi:10.3390/molecules22050785

Design, Synthesis, Molecular Docking Analysis, and Carbonic Anhydrase IX Inhibitory Evaluations of Novel N-Substituted-β-d-Glucosamine Derivatives that Incorporate Benzenesulfonamides

Key Laboratory of Structure-Based Drugs Design and Discovery (Ministry of Education), School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Qi-Dong You
Received: 19 March 2017 / Revised: 4 May 2017 / Accepted: 8 May 2017 / Published: 12 May 2017
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [7381 KB, uploaded 12 May 2017]   |  

Abstract

A series of novel N-substituted-β-d-glucosamine derivatives that incorporate benzenesulfonamides were designed using a fragment-based drug design strategy. Each derivative was synthesized and evaluated in vitro for its inhibitory activity against human carbonic anhydrase (hCA) IX; several derivatives displayed desirable potency profiles against this enzyme. The molecular docking studies provided the design rationale and predicted potential binding modes for carbonic anhydrase (CA) IX and three target compounds, including the most potent inhibitor, compound 7f (IC50 = 10.01 nM). Moreover, the calculated Log P (cLog P) values showed that all the compounds tended to be hydrophilic. In addition, topological polar surface area (TPSA) value-based predictions highlighted the selectivity of these carbohydrate-based inhibitors for membrane-associated CA IX. View Full-Text
Keywords: N-substituted-β-d-glucosamine derivatives; benzenesulfonamides; human carbonic anhydrase IX; molecular docking N-substituted-β-d-glucosamine derivatives; benzenesulfonamides; human carbonic anhydrase IX; molecular docking
Figures

Figure 1

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).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Li, F.-R.; Fan, Z.-F.; Qi, S.-J.; Wang, Y.-S.; Wang, J.; Liu, Y.; Cheng, M.-S. Design, Synthesis, Molecular Docking Analysis, and Carbonic Anhydrase IX Inhibitory Evaluations of Novel N-Substituted-β-d-Glucosamine Derivatives that Incorporate Benzenesulfonamides. Molecules 2017, 22, 785.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top