Structure‐Based Organic Synthesis of Drug Prototypes: A Personal Odyssey

Hanessian, Stephen

doi:10.1002/cmdc.200600203

Cited by 35 publications

(25 citation statements)

References 408 publications

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“…As a consequence, huge investments have been made to study the chemistry of natural products. Nowadays, the use of natural molecular fingerprints as a source of inspiration for the acquisition of new bioactive chemical entities has proven to be a very promising and efficient method (Newman et al, 2000;Hanessian, 2006;Baker et al, 2007).…”

Section: Research Articlementioning

confidence: 99%

The anti-inflammatory activity of dillapiole and some semisynthetic analogues

Parise-Filho

Pastrello

Camerlingo

et al. 2011

Pharmaceutical Biology

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Section: Research Articlementioning

confidence: 99%

The anti-inflammatory activity of dillapiole and some semisynthetic analogues

Parise-Filho

Pastrello

Camerlingo

et al. 2011

Pharmaceutical Biology

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“…[ either reduction or oxidation gave the corresponding chiral pyrrolidine 11 a, acid 12 a, and diamine 12 aa. [1] The absolute stereochemistry of the highly substituted quaternary proline derivatives 8 was confirmed by the X-ray crystallographic analysis of 8 c (2S, 3R, 4R, 5S; Figure 2). [1] The absolute stereochemistry of the highly substituted quaternary proline derivatives 8 was confirmed by the X-ray crystallographic analysis of 8 c (2S, 3R, 4R, 5S; Figure 2).…”

Section: Yieldmentioning

confidence: 82%

Dynamic One‐Pot Three‐Component Catalytic Asymmetric Transformation by Combination of Hydrogen‐Bond‐Donating and Amine Catalysts

et al. 2011

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Ganz schön dynamisch: Die erste dynamische asymmetrische Umsetzung dreier Komponenten (Aldehyde, geschützte α‐Cyanglycinester und Enale) in einem Eintopfprozess unter Katalyse durch einen einfachen Wasserstoffbrückendonor und ein chirales Amin wird vorgestellt. Mehrfach substituierte Prolinderivate mit quartären Stereozentren in α‐Stellung wurden hoch endo‐, diastereo‐ und enantioselektiv synthetisiert (93–99 % ee).

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“…It is hoped that an effective therapeutic agent will emerge in the near future. In this regard, fruitful collaborations between academia and pharmaceutical or biotech companies could continue to play an important role [22]. …”

Section: Synopsismentioning

confidence: 99%

Structure-based synthesis: From natural products to drug prototypes

Hanessian

2009

Pure and Applied Chemistry

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X-ray crystallographic data available from complexes of natural and synthetic molecules with the enzyme thrombin has led to the design and synthesis of truncated and hybrid molecules exhibiting excellent inhibition in vitro. The design element has also been extended to the synthesis and in vitro inhibition of a series of achiral molecules deploying aromatic and heterocyclic core motifs with appropriately functionalized appendages that provide excellent binding interactions at the S 1 , S 2 , and S 3 sites of thrombin. Excellent selectivity for thrombin over trypsin has also been observed. Thus, studies in total synthesis of highly active natural aeruginosins have inspired further work toward truncated and hybrid analogs with excellent inhibitory activities. Structure-based organic synthesis has guided our research from natural products toward unnatural drug-like prototypes.

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Structure‐Based Organic Synthesis of Drug Prototypes: A Personal Odyssey

Cited by 35 publications

References 408 publications

The anti-inflammatory activity of dillapiole and some semisynthetic analogues

The anti-inflammatory activity of dillapiole and some semisynthetic analogues

Dynamic One‐Pot Three‐Component Catalytic Asymmetric Transformation by Combination of Hydrogen‐Bond‐Donating and Amine Catalysts

Structure-based synthesis: From natural products to drug prototypes

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