Literature DB >> 21842835

Stereoselective synthesis of F-ring saturated estrone-derived inhibitors of Hedgehog signaling based on cyclopamine.

Zhihui Zhang1, Valérie Baubet, Christian Ventocilla, Chaomei Xiang, Nadia Dahmane, Jeffrey D Winkler.   

Abstract

Previous work in this laboratory established that the readily available F-ring aromatic analog of cyclopamine is a highly potent inhibitor of Hedgehog signaling. The synthesis and biological evaluation of two F-ring saturated analogs that are more potent than the F-ring aromatic structure are reported.
© 2011 American Chemical Society

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Year:  2011        PMID： 21842835      PMCID： PMC3170508          DOI： 10.1021/ol2017966

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  28 in total

1.  Semisynthetic cyclopamine analogues as potent and orally bioavailable hedgehog pathway antagonists.

Authors:  Martin R Tremblay; Marta Nevalainen; Somarajan J Nair; James R Porter; Alfredo C Castro; Mark L Behnke; Lin-Chen Yu; Margit Hagel; Kerry White; Kerrie Faia; Louis Grenier; Matthew J Campbell; Jill Cushing; Caroline N Woodward; Jennifer Hoyt; Michael A Foley; Margaret A Read; Jens R Sydor; Jeffrey K Tong; Vito J Palombella; Karen McGovern; Julian Adams
Journal:  J Med Chem       Date:  2008-10-09       Impact factor: 7.446

2.  Genentech obtains proof of concept for hedgehog inhibition.

Authors:  Cormac Sheridan
Journal:  Nat Biotechnol       Date:  2009-11       Impact factor: 54.908

3.  Steroids. LXXIX. Synthesis and reactions of oxiranes obtained from 3- and 17-keto steroids.

Authors:  C E Cook; R C Corley; M E Wall
Journal:  J Org Chem       Date:  1968-07       Impact factor: 4.354

Review 4.  Childhood medulloblastoma: novel approaches to the classification of a heterogeneous disease.

Authors:  David W Ellison
Journal:  Acta Neuropathol       Date:  2010-07-23       Impact factor: 17.088

5.  Frequent requirement of hedgehog signaling in non-small cell lung carcinoma.

Authors:  Z Yuan; J A Goetz; S Singh; S K Ogden; W J Petty; C C Black; V A Memoli; E Dmitrovsky; D J Robbins
Journal:  Oncogene       Date:  2006-08-14       Impact factor: 9.867

6.  Hedgehog signalling in prostate regeneration, neoplasia and metastasis.

Authors:  Sunil S Karhadkar; G Steven Bova; Nadia Abdallah; Surajit Dhara; Dale Gardner; Anirban Maitra; John T Isaacs; David M Berman; Philip A Beachy
Journal:  Nature       Date:  2004-09-12       Impact factor: 49.962

7.  Design and synthesis of inhibitors of Hedgehog signaling based on the alkaloid cyclopamine.

Authors:  Jeffrey D Winkler; André Isaacs; Laura Holderbaum; Valérie Tatard; Nadia Dahmane
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005

8.  Widespread requirement for Hedgehog ligand stimulation in growth of digestive tract tumours.

Authors:  David M Berman; Sunil S Karhadkar; Anirban Maitra; Rocio Montes De Oca; Meg R Gerstenblith; Kimberly Briggs; Antony R Parker; Yutaka Shimada; James R Eshleman; D Neil Watkins; Philip A Beachy
Journal:  Nature       Date:  2003-09-14       Impact factor: 49.962

9.  Sonic hedgehog regulates the growth and patterning of the cerebellum.

Authors:  N Dahmane; A Ruiz i Altaba
Journal:  Development       Date:  1999-06       Impact factor: 6.868

10.  The teratogenic Veratrum alkaloid cyclopamine inhibits sonic hedgehog signal transduction.

Authors:  J P Incardona; W Gaffield; R P Kapur; H Roelink
Journal:  Development       Date:  1998-09       Impact factor: 6.868
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  2 in total

1.  Ligand-Controlled Palladium-Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α-Methylene-β-Lactones.

Authors:  Yao Ge; Fei Ye; Jiawang Liu; Ji Yang; Anke Spannenberg; Haijun Jiao; Ralf Jackstell; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-17       Impact factor: 15.336

2.  C-H-Functionalization logic guides the synthesis of a carbacyclopamine analog.

Authors:  Sebastian Rabe; Johann Moschner; Marina Bantzi; Philipp Heretsch; Athanassios Giannis
Journal:  Beilstein J Org Chem       Date:  2014-07-09       Impact factor: 2.883
  2 in total

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