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Molecules 2017, 22(5), 827; doi:10.3390/molecules22050827

Highly Stereoselective Synthesis of a Compound Collection Based on the Bicyclic Scaffolds of Natural Products

1
Max-Planck-Institut für molekulare Physiologie, Otto-Hahn-Straße 11, 44227 Dortmund, Germany
2
Medicinal Chemistry, Taros Chemicals GmbH & Co. KG, Emil Figge-Str. 76a, 44227 Dortmund, Germany
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 12 April 2017 / Revised: 11 May 2017 / Accepted: 12 May 2017 / Published: 18 May 2017
(This article belongs to the Special Issue Natural Product Inspired Scaffolds Designs)
View Full-Text   |   Download PDF [2627 KB, uploaded 18 May 2017]   |  

Abstract

Despite the great contribution of natural products in the history of successful drug discovery, there are significant limitations that persuade the pharmaceutical industry to evade natural products in drug discovery research. The extreme scarcity as well as structural complexity of natural products renders their practical synthetic access and further modifications extremely challenging. Although other alternative technologies, particularly combinatorial chemistry, were embraced by the pharmaceutical industry to get quick access to a large number of small molecules with simple frameworks that often lack three-dimensional complexity, hardly any success was achieved in the discovery of lead molecules. To acquire chemotypes beholding structural features of natural products, for instance high sp3 character, the synthesis of compound collections based on core-scaffolds of natural products presents a promising strategy. Here, we report a natural product inspired synthesis of six different chemotypes and their derivatives for drug discovery research. These bicyclic hetero- and carbocyclic scaffolds are highly novel, rich in sp3 features and with ideal physicochemical properties to display drug likeness. The functional groups on the scaffolds were exploited further to generate corresponding compound collections. Synthesis of two of these collections exemplified with ca. 350 compounds are each also presented. The whole compound library is being exposed to various biological screenings within the European Lead Factory consortium. View Full-Text
Keywords: natural products; drug discovery; scaffolds; Aza-heterocycles; European Lead Factory natural products; drug discovery; scaffolds; Aza-heterocycles; European Lead Factory
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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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Annamalai, M.; Hristeva, S.; Bielska, M.; Ortega, R.; Kumar, K. Highly Stereoselective Synthesis of a Compound Collection Based on the Bicyclic Scaffolds of Natural Products. Molecules 2017, 22, 827.

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