117259-83-3

Basic information

• Product Name: Benzoic acid, 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]-, methyl ester
• CAS NO: 117259-83-3
• Molecular Formula: C23H26O3
• Molecular Weight: 350.458
• Mol File: 117259-83-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]-, methyl ester(117259-83-3)
• EPA Substance Registry System: Benzoic acid, 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]-, methyl ester(117259-83-3)

Safety Data

• Hazardous Substances Data: 117259-83-3(Hazardous Substances Data)

Upstream product

• 6683-46-1 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene 
• 7377-26-6 4-Methoxycarbonylbenzoyl chloride 

Downstream Products

• 156910-36-0 2-(4-carbomethoxyphenyl)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1,3-dithiolane 
• 156910-35-9 2-(4-carbomethoxyphenyl)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1,3-dithiane 
• 156910-42-8 methyl 4-<1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-methyl-1-propenyl>benzoate 
• 169126-56-1 4-[(Z)-1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propenyl]-benzoic acid methyl ester 
• 169126-57-2 4-[(E)-1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propenyl]-benzoic acid methyl ester 
• 146670-37-3 SR₁₁₂₃₄ 
• 156910-41-7 methyl 4-<1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)cyclopropyl>benzoate 
• 117168-39-5 SR₁₁₂₀₂ 
• 169126-55-0 methyl 4-<(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)methyl>benzoate 
• 156910-52-0 TTNEB 
• 188844-43-1 4-(1,7,7,10,10-Pentamethyl-2-oxo-2,3,7,8,9,10-hexahydro-1H-naphtho[2,3-e][1,4]diazepin-5-yl)-benzoic acid methyl ester 
• 188845-29-6 4-(7,7,10,10-Tetramethyl-2-oxo-2,3,7,8,9,10-hexahydro-1H-naphtho[2,3-e][1,4]diazepin-5-yl)-benzoic acid methyl ester 

Relevant articles and documents

Conformational effects on retinoid receptor selectivity. 2. Effects of retinoid bridging group on retinoid X receptor activity and selectivity

The natural retinoid 9-cis-retinoic acid is an activating ligand for both the retinoic acid receptors (BARs) and the retinoid X receptors (RXRs), which are members of the retinoid/thyroid hormone/steroid hormone family of nuclear receptor proteins that activate gene transcription through specific response elements. The pharmacophoric groups necessary to confer RXR selectivity were established by evaluating the ability of 21 conformationally restricted retinoids to activate the TREpal retinoic acid receptor response element for gene transcription in the presence of one of the three PAR subtypes or RXRα. In contrast to those retinoids selective for the RARs, these RXR-selective retinoids have one less atom in the bridge linking the hydrophobic and carboxylic acid termini of the retinoid skeleton. Therefore, a one-carbon bridge replaces the 19-methyl group and 9E-double bond of 9-cis-retinoic acid and is further functionalized by inclusion in an isopropylidene group, a dioxolane ring, or a cyclopropane ring for optimal RXRα activity and selectivity. In addition, the β-geranylidene and 20-methyl-(11E,13E)- dienoic acid groups of 9-cis-retinoic acid are replaced by a 5,6,7,8- tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl ring and a 4-carboxylphenyl ring, respectively, for optimal activation and selectivity. RXRα selectivity is reduced on replacement of the 4-carboxylphenyl group by a 2-carboxyl-5- thienyl group or the 9-cis-retinoic acid methylpentadienoic acid terminus.

Compounds activating pharmacological effects of retinoids

A compound represented by the formula (I) or (II) or a salt thereof wherein R1 represents hydrogen atom or a C1-6 alkyl group; R2 and R3 independently represent a hydrogen atom or a C1-6 alkyl group,

Bridged bicyclic aromatic compounds and their use in modulating gene expression of retinoid receptors

Bridged bicyclic aromatic compounds are provided having the structure STR1 wherein R1, R2, R3, R4, R5 and n are as defined herein. The novel compounds are useful for modulating gene expression of retinoic acid receptors, vitamin D receptors and thyroid receptors. Pharmaceutical compositions and methods for modulating gene expression are provided as well.