445039-91-8

Basic information

• Product Name: (2-fluoro-5-methylphenyl)(6-(4-methylthiophenyl)(2H-benzo[d]1,3-dioxolan-5-yl))methan-1-ol
• Synonyms: (2-fluoro-5-methylphenyl)(6-(4-methylthiophenyl)(2H-benzo[d]1,3-dioxolan-5-yl))methan-1-ol
• CAS NO: 445039-91-8
• Molecular Weight: 382.455
• Mol File: 445039-91-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2-fluoro-5-methylphenyl)(6-(4-methylthiophenyl)(2H-benzo[d]1,3-dioxolan-5-yl))methan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2-fluoro-5-methylphenyl)(6-(4-methylthiophenyl)(2H-benzo[d]1,3-dioxolan-5-yl))methan-1-ol(445039-91-8)
• EPA Substance Registry System: (2-fluoro-5-methylphenyl)(6-(4-methylthiophenyl)(2H-benzo[d]1,3-dioxolan-5-yl))methan-1-ol(445039-91-8)

Safety Data

• Hazardous Substances Data: 445039-91-8(Hazardous Substances Data)

Upstream product

• 452-62-0 3-bromo-4-fluorotoluene 
• 445039-73-6 6-(4-methylthiophenyl)-2H-benzo[d]1,3-dioxolane-5-carbaldehyde 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 120-57-0 piperonal 

Downstream Products

• 445039-49-6 1-(6-((2-fluoro-5-methylphenyl)hydroxymethyl)(2H-benzo[3,4-d]1,3-dioxolan-5-yl))-4-(methylsulfonyl)benzene 

Relevant articles and documents

Synthesis and Structure-Activity Relationship of Novel, Highly Potent Metharyl and Methcycloalkyl Cyclooxygenase-2 (COX-2) Selective Inhibitors

A novel series of benzo-1,3-dioxolane metharyl derivatives was synthesized and evaluated for cyclooxygenase-2 (COX-2) and cyclooxygenase-1 (COX-1) inhibition in human whole blood (HWB). In the present study, structure-activity relationships (SAR) in the metharyl analogues were investigated. The spacer group and substitutions in the spacer group were found to be quite important for potent COX-2 inhibition. Compounds in which a methylene group (8a-c), carbonyl group (12a-c), or methylidene group (7a-c) connected cycloalkyl groups to the central benzo-1,3-dioxolane template were found to be potent and selective COX-2 inhibitors. Arylsubstituted compounds linked to the central ring by either a methylene or a carbonyl spacer resulted in potent, highly selective COX-2 inhibitors. In this series of substituted-(2H-benzo-[3,4-d]1,3-dioxolan-5-yl))-1-(methylsulfonyl)benzene compounds, SAR studies demonstrated that substitution at the 3-position of the aryl group optimized COX-2 selectivity and potency, whereas substitution at the 4-position attenuated COX-2 inhibition. Mono- or difluoro substitution at meta position(s), as in 22c and 22h, was advantageous for both in vitro COX-2 potency and selectivity (e.g., COX-2 IC50 for 22c = 1 μM and COX-1 IC50 for 22c = 20 μM in HWB assay). Several novel compounds in the (2H-benzo[3,4-d]1,3-dioxolan-5-yl))-1-(methylsulfonyl)benzene series, as shown in structures 7c, 8a, 12a, 21c, 22c, 22e, and 22h, selectively inhibited COX-2 activity by 40-50% at a test concentration of 1 μM in an in vitro HWB assay.