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Literature DB >> 31541729

Introduction of fluorine atoms to vitamin D₃ side-chain and synthesis of 24,24-difluoro-25-hydroxyvitamin D₃.

Fumihiro Kawagoe¹, Sayuri Mototani², Kaori Yasuda³, Kazuo Nagasawa⁴, Motonari Uesugi⁵, Toshiyuki Sakaki³, Atsushi Kittaka⁶.

Abstract

During our ongoing studies of vitamin D, we focused on the vitamin D3 side-chain 24-position, which is the major metabolic site of human CYP24A1. In order to inhibit the metabolism of vitamin D3, 24,24-difluorovitamin D3analogues are important candidates. In this paper, we report the practical introduction of the difluoro-unit to the 24-position to synthesize 24,24-difluoro-CD ring (1) and 24,24-difluoro-25-hydroxyvitamin D3 (2).

Entities: Chemical Gene Species

Keywords: 24,24-Difluoro-CD rings; 24,24-Difluorovitamin D(3) analogues; CYP24A1; Synthesis; Vitamin D(3) metabolite

Year: 2019 PMID： 31541729 DOI： 10.1016/j.jsbmb.2019.105477

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

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Cited

3 in total

1. Stereoselective Synthesis of 24-Fluoro-25-Hydroxyvitamin D₃ Analogues and Their Stability to hCYP24A1-Dependent Catabolism.

Authors: Fumihiro Kawagoe; Sayuri Mototani; Kaori Yasuda; Hiroki Mano; Toshiyuki Sakaki; Atsushi Kittaka
Journal: Int J Mol Sci Date: 2021-11-01 Impact factor: 5.923

Review 2. Development of In Vitro and In Vivo Evaluation Systems for Vitamin D Derivatives and Their Application to Drug Discovery.

Authors: Kaori Yasuda; Miyu Nishikawa; Hiroki Mano; Masashi Takano; Atsushi Kittaka; Shinichi Ikushiro; Toshiyuki Sakaki
Journal: Int J Mol Sci Date: 2021-10-31 Impact factor: 5.923

3. The First Convergent Synthesis of 23,23-Difluoro-25-hydroxyvitamin D₃ and Its 24-Hydroxy Derivatives: Preliminary Assessment of Biological Activities.

Authors: Sayuri Mototani; Fumihiro Kawagoe; Kaori Yasuda; Hiroki Mano; Toshiyuki Sakaki; Atsushi Kittaka
Journal: Molecules Date: 2022-08-22 Impact factor: 4.927

3 in total

Introduction of fluorine atoms to vitamin D3 side-chain and synthesis of 24,24-difluoro-25-hydroxyvitamin D3.

1. Stereoselective Synthesis of 24-Fluoro-25-Hydroxyvitamin D3 Analogues and Their Stability to hCYP24A1-Dependent Catabolism.

Review 2. Development of In Vitro and In Vivo Evaluation Systems for Vitamin D Derivatives and Their Application to Drug Discovery.

3. The First Convergent Synthesis of 23,23-Difluoro-25-hydroxyvitamin D3 and Its 24-Hydroxy Derivatives: Preliminary Assessment of Biological Activities.

Introduction of fluorine atoms to vitamin D₃ side-chain and synthesis of 24,24-difluoro-25-hydroxyvitamin D₃.

1. Stereoselective Synthesis of 24-Fluoro-25-Hydroxyvitamin D₃ Analogues and Their Stability to hCYP24A1-Dependent Catabolism.

3. The First Convergent Synthesis of 23,23-Difluoro-25-hydroxyvitamin D₃ and Its 24-Hydroxy Derivatives: Preliminary Assessment of Biological Activities.