Literature DB >> 7966133

Synthesis and biological activity of 2-hydroxy and 2-alkoxy analogs of 1 alpha,25-dihydroxy-19-norvitamin D3.

R R Sicinski1, K L Perlman, H F DeLuca.   

Abstract

1 alpha, 2 alpha,25-Trihydroxy-19-norvitamin D3, 1 alpha, 2 beta,25-trihydroxy-19-norvitamin D3, and their alkoxy analogs were efficiently prepared in a convergent synthesis, starting with (-)-quinic acid and a Windaus--Grundmann type ketone. Configurations of the A-ring fragment substituents were determined by 1H,1H COSY 2D spectra and 1H NOE difference spectroscopy. The new analogs exhibited selective activity in stimulating intestinal calcium transport while having little or no activity in mobilizing bone calcium. They also showed HL-60-differentiating activity equal to or 10 times lower than that of 1 alpha,25-dihydroxyvitamin D3.

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Year:  1994        PMID: 7966133     DOI: 10.1021/jm00048a009

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  3 in total

1.  Removal of the 20-methyl group from 2-methylene-19-nor-(20S)-1alpha,25-dihydroxyvitamin D(3) (2MD) selectively eliminates bone calcium mobilization activity.

Authors:  Rafal Barycki; Rafal R Sicinski; Lori A Plum; Pawel Grzywacz; Margaret Clagett-Dame; Hector F Deluca
Journal:  Bioorg Med Chem       Date:  2009-09-29       Impact factor: 3.641

Review 2.  Vitamin D and Its Synthetic Analogs.

Authors:  Miguel A Maestro; Ferdinand Molnár; Carsten Carlberg
Journal:  J Med Chem       Date:  2019-04-02       Impact factor: 7.446

3.  Synthesis of C2-Alkoxy-Substituted 19-Nor Vitamin D3 Derivatives: Stereoselectivity and Biological Activity.

Authors:  Yuka Mizumoto; Ryota Sakamoto; Akiko Nagata; Suzuka Sakane; Atsushi Kittaka; Minami Odagi; Masayuki Tera; Kazuo Nagasawa
Journal:  Biomolecules       Date:  2022-01-04
  3 in total

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