Literature DB >> 17218093

Difluoromethyl analogs of the natural hormone 1alpha,25-dihydroxyvitamin D3: Design, synthesis, and preliminary biological evaluation.

Gary H Posner1, Byung Chul Suh, Kimberly S Petersen, Patrick Dolan, Elin S Agoston, Thomas W Kensler, John T Koh, Sara Peleg.   

Abstract

Three new Vitamin D analogs 3-5 incorporating a -CHF(2) group as an -OH surrogate have been prepared. Two of these new analogs (3 and 5) are strongly antiproliferative toward murine keratinocytes and are approximately 50 times less calciuric in vivo than the natural hormone calcitriol. The transcriptional activity of the 25-CHF(2) analog 3 is higher than that of the 1-CHF(2) analog 4.

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Year:  2007        PMID： 17218093      PMCID： PMC2712873          DOI： 10.1016/j.jsbmb.2006.12.024

Source DB:  PubMed          Journal:  J Steroid Biochem Mol Biol        ISSN： 0960-0760            Impact factor:   4.292


  12 in total

1.  Potent, selective and low-calcemic inhibitors of CYP24 hydroxylase: 24-sulfoximine analogues of the hormone 1alpha,25-dihydroxyvitamin D(3).

Authors:  Mehmet Kahraman; Sandra Sinishtaj; Patrick M Dolan; Thomas W Kensler; Sara Peleg; Uttam Saha; Samuel S Chuang; Galina Bernstein; Bozena Korczak; Gary H Posner
Journal:  J Med Chem       Date:  2004-12-30       Impact factor: 7.446

2.  Anticancer effects of the novel 1alpha, 25-dihydroxyvitamin D3 hybrid analog QW1624F2-2 in human neuroblastoma.

Authors:  C Damodar Reddy; Ratnakar Patti; Asha Guttapalli; John M Maris; Niranjan Yanamandra; Aparna Rachamallu; Leslie N Sutton; Peter C Phillips; Gary H Posner
Journal:  J Cell Biochem       Date:  2006-01-01       Impact factor: 4.429

3.  2-(Quinazolin-4-ylamino)-[1,4]benzoquinones as covalent-binding, irreversible inhibitors of the kinase domain of vascular endothelial growth factor receptor-2.

Authors:  Allan Wissner; M Brawner Floyd; Bernard D Johnson; Heidi Fraser; Charles Ingalls; Thomas Nittoli; Russell G Dushin; Carolyn Discafani; Ramaswamy Nilakantan; Joseph Marini; Malini Ravi; Kinwang Cheung; Xingzhi Tan; Sylvia Musto; Tami Annable; Marshall M Siegel; Frank Loganzo
Journal:  J Med Chem       Date:  2005-12-01       Impact factor: 7.446

4.  Differential interaction of 1alpha,25-dihydroxyvitamin D3 analogues and their 20-epi homologues with the vitamin D receptor.

Authors:  Y Y Liu; E D Collins; A W Norman; S Peleg
Journal:  J Biol Chem       Date:  1997-02-07       Impact factor: 5.157

5.  Synthesis of vitamin D(3) and calcitriol dimers as potential chemical inducers of vitamin D receptor dimerization.

Authors:  J Pérez Sestelo; A Mouriño; L A Sarandeses
Journal:  J Org Chem       Date:  2000-12-01       Impact factor: 4.354

Review 6.  Structure-function relationships in the vitamin D endocrine system.

Authors:  R Bouillon; W H Okamura; A W Norman
Journal:  Endocr Rev       Date:  1995-04       Impact factor: 19.871

7.  Differential use of transcription activation function 2 domain of the vitamin D receptor by 1,25-dihydroxyvitamin D3 and its A ring-modified analogs.

Authors:  S Peleg; C Nguyen; B T Woodard; J K Lee; G H Posner
Journal:  Mol Endocrinol       Date:  1998-04

8.  Efficient synthesis of the A-ring phosphine oxide building block useful for 1 alpha,25-dihydroxy vitamin D(3) and analogues.

Authors:  Andrzej R Daniewski; Lisa M Garofalo; Stanley D Hutchings; Marek M Kabat; Wen Liu; Masami Okabe; Roumen Radinov; George P Yiannikouros
Journal:  J Org Chem       Date:  2002-03-08       Impact factor: 4.354

9.  Skin cancer prevention: a possible role of 1,25dihydroxyvitamin D3 and its analogs.

Authors:  K M Dixon; S S Deo; G Wong; M Slater; A W Norman; J E Bishop; G H Posner; S Ishizuka; G M Halliday; V E Reeve; R S Mason
Journal:  J Steroid Biochem Mol Biol       Date:  2005-07-20       Impact factor: 4.292

10.  Noncalcemic, antiproliferative, transcriptionally active, 24-fluorinated hybrid analogues of the hormone 1alpha, 25-dihydroxyvitamin D3. Synthesis and preliminary biological evaluation.

Authors:  G H Posner; J K Lee; Q Wang; S Peleg; M Burke; H Brem; P Dolan; T W Kensler
Journal:  J Med Chem       Date:  1998-07-30       Impact factor: 7.446
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