97903-37-2

Usage

Synonyms

1,23(OH)2D3-26,23-lactone

Type

Synthetic derivative of vitamin D3

Structure

Formed by the addition of a hydroxyl group at the 1 and 23 positions of the vitamin D3 molecule, and the removal of the side chain at the 24,25,26, and 27 positions

Therapeutic Applications

Extensively studied for potential use in treating various autoimmune and inflammatory diseases

Anti-inflammatory Effects

Exhibits potent anti-inflammatory properties

Immunomodulatory Effects

Demonstrates immunomodulatory effects

Anti-cancer Properties

Suggested to have anti-cancer properties and may play a role in regulating cell growth and differentiation

Further Research

More research is needed to fully understand the therapeutic potential and mechanisms of action of 1,23-dihydroxy-24,25,26,27-tetranorvitamin D3

InChI:InChI=1/C23H36O3/c1-15(10-12-24)20-8-9-21-17(5-4-11-23(20,21)3)6-7-18-13-19(25)14-22(26)16(18)2/h6-7,15,19-22,24-26H,2,4-5,8-14H2,1,3H3/b17-6+,18-7+/t15-,19-,20-,21+,22+,23-/m1/s1

Upstream product

• 32222-06-3 calcitriol 
• 145223-29-6 (R)-3-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)butanenitrile 
• 93489-71-5 (R)-3-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)butanal 
• 100928-04-9 (S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 4-methylbenzenesulfonate 
• 66774-80-9 (S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate 
• 71203-48-0 methyl 1α,3β-dihydroxy-9,10-seco-24-norchola-5,7-10(19)-trien-23-oate 
• 64190-52-9 (8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol 
• 138914-88-2 1α-hydroxy-24-oxavitamin D₃ 

Relevant academic research and scientific papers

Efficient and scalable total synthesis of calcitroic acid and its 13C-labeled derivative

Calcitroic acid, the deactivated form of the physiological active vitamin D3 metabolite calcitrol, and its 13C labeled derivative has been synthesized starting from the commercially available Inhoffen-Lythgoe diol in 11 steps with an

A new insight into the role of rat cytochrome P450 24A1 in metabolism of selective analogs of 1α,25-dihydroxyvitamin D3

We examined the metabolism of two synthetic analogs of 1α,25- dihydroxyvitamin D3 (1), namely 1α,25-dihydroxy-16-ene-23-yne- vitamin D3 (2) and 1α,25-dihydroxy-16-ene-23-yne-26,27- dimethyl-vitamin D3 (4) using rat cytochrome P450 24A1 (CYP24A1) in a reconstituted system. We noted that 2 is metabolized into a single metabolite identified as C26-hydroxy-2 while 4 is metabolized into two metabolites, identified as C26-hydroxy-4 and C26a-hydroxy-4. The structural modification of adding methyl groups to the side chain of 1 as in 4 is also featured in another analog, 1α,25-dihydroxy-22,24-diene-24,26,27-trihomo-vitamin D3 (6). In a previous study, 6 was shown to be metabolized exactly like 4, however, the enzyme responsible for its metabolism was found to be not CYP24A1. To gain a better insight into the structural determinants for substrate recognition of different analogs, we performed an in silico docking analysis using the crystal structure of rat CYP24A1 that had been solved for the substrate-free open form. Whereas analogs 2 and 4 docked similar to 1, 6 showed altered interactions for both the A-ring and side chain, despite prototypical recognition of the CD-ring. These findings hint that CYP24A1 metabolizes selectively different analogs of 1, based on their ability to generate discrete recognition cues required to close the enzyme and trigger the catalytic mechanism.

The Seleno-acetal Route to 1α-Hydroxy-vitamin D Analogues: Synthesis of 24-Oxa-1α-hydroxy-vitamin D3, A Useful Vitamin D Metabolism Probe

Alkylation of the lithio-demethylseleno-derivative of seleno-acetal 11 with chloromethyl isopropyl ether is the key reaction in the synthesis of the 24-oxa analogue (M