161796-11-8

Basic information

• Product Name: 3-Fluoro-4-(methoxycarbonyl)benzoic acid
• Synonyms: 3-Fluoro-4-(methoxycarbonyl)benzoic acid
• CAS NO: 161796-11-8
• Molecular Weight: 0
• Mol File: 161796-11-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 3-Fluoro-4-(methoxycarbonyl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluoro-4-(methoxycarbonyl)benzoic acid(161796-11-8)
• EPA Substance Registry System: 3-Fluoro-4-(methoxycarbonyl)benzoic acid(161796-11-8)

Safety Data

• Hazardous Substances Data: 161796-11-8(Hazardous Substances Data)

Upstream product

• 74733-29-2 2-methyl-3-hydroxybenzoic acid methyl ester 
• 7697-23-6 2-fluoro-4-methylbenzoic Acid 
• 85070-58-2 methyl 2-fluoro-4-formylbenzoate 
• 777074-54-1 4-benzyl 1-methyl 2-fluorobenzene-1,4-dioate 
• 5292-47-7 1,4-dimethyl 2-fluorobenzene-1,4-dicarboxylate 

Downstream Products

• 1190848-49-7 methyl 2-fluoro-4-(1-(1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalen-7-yl)vinyl)benzoate 
• 1190848-23-7 2-fluoro-4-(1-(1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalen-7-yl)vinyl)benzoic acid 
• 1190848-45-3 methyl 2-fluoro-4-((3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl)benzoate 

Relevant articles and documents

Synthesis of a new fluorine-18-labeled bexarotene analogue for PET imaging of retinoid X receptor

The reference standard 2-fluoro-4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)ben-zoic acid was synthesized from 2,5-dimethyl-2,5-hexanediol and 2-fluoro-4-methylbenzoic acid in 10 steps with 3% overall chemical yield. The precursor 2-nitro-4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetra-hydronaphthalen-2-yl)vinyl)benzoic acid was synthesized from 2,5-dimethyl-2,5-hexanediol and dimethyl-2-nitroterephthalate in seven steps with 2% overall chemical yield. The target tracer 2-[18F]flu-oro-4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic acid was synthesized from its nitro-precursor by the nucleophilic substitution with K[18F]F/Kryptofix 2.2.2 and isolated by HPLC combined with solid-phase extraction (SPE) purification in 20-30% radiochemical yield with 37-370 GBq/μmol specific activity at end of bombardment (EOB).

Modeling, synthesis and biological evaluation of potential Retinoid X Receptor (RXR) selective agonists: Novel analogues of 4-[1-(3,5,5,8,8- pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (bexarotene)

This report describes the synthesis of analogues of 4-[1-(3,5,5,8,8- pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (1), commonly known as bexarotene, and their analysis in acting as retinoid X receptor (RXR)-specific agonists. Compound 1 has FDA approval to treat cutaneous T-cell lymphoma (CTCL); however, its use can cause side effects such as hypothyroidism and increased triglyceride concentrations, presumably by disruption of RXR heterodimerization with other nuclear receptors. The novel analogues in the present study have been evaluated forRXR activation in an RXR mammalian-2-hybrid assay as well as an RXRE-mediated transcriptional assay and for their ability to induce apoptosis as well as for their mutagenicity and cytotoxicity. Analysis of 11 novel compounds revealed the discovery of three analogues that best induce RXR-mediated transcriptional activity, stimulate apoptosis, have comparable Ki and EC50 values to 1, and are selective RXR agonists. Our experimental approach suggests that rational drug design can develop new rexinoids with improved biological properties. 2009 American Chemical Society.

11-PHENYL-DIBENZODIAZEPINE DERIVATIVES AS RXR-ANTAGONISTS

The present invention relates to novel benzodiazepine compounds exhibiting RXR-antagonist efficacy, for delaying progression of, preventing or treating a condition or disease being associated with RXR-antagonism, in particular selected from diabetes, comp