16195-44-1

Basic information

• Product Name: 4-allylsulfonylbenzoic acid
• Synonyms: 4-allylsulfonylbenzoic acid
• CAS NO: 16195-44-1
• Molecular Weight: 226.253
• Mol File: 16195-44-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-allylsulfonylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-allylsulfonylbenzoic acid(16195-44-1)
• EPA Substance Registry System: 4-allylsulfonylbenzoic acid(16195-44-1)

Safety Data

• Hazardous Substances Data: 16195-44-1(Hazardous Substances Data)

Upstream product

• 16195-39-4 4-(allylthio)benzoic acid 
• 1074-36-8 4-mercaptobenzoic acid 

Downstream Products

• 16195-45-2 p-Allylsulfonylbenzoylchlorid 

Relevant articles and documents

Synthesis of (bis)sulfonic acid, (bis)benzamides as follicle-stimulating hormone (FSH) antagonists.

Screening efforts identified (bis)sulfonic acid, (bis)benzamides (1-3) as compounds that interact with the follicle stimulating-hormone receptor (FSHR) and inhibit FSH-stimulated cAMP accumulation with IC(50) values in the low micromolar range. Structure-activity relationship studies using novel analogues of 1-3 revealed that two phenylsulfonic acid moieties were necessary for activity and that the carbon-carbon double bond of the stilbene sub-series was the optimum spacer connecting these groups. Selected analogues (2, 14, and 50) were also able to block FSHR-dependent estradiol production in rat primary ovarian granulosa cells and progesterone secretion in a clonal mouse adrenal Y1 cell line. IC(50) values for these compounds in these assays were in the low micromolar range. Optimization of the benzoic acid side chains of 1-3 led to gains in selectivity versus activity at the thyroid stimulating hormone (TSH) receptor (TSHR). For instance, while stilbene (bis)sulfonic acid congener 2 was only 10-fold selective for FSHR over TSHR, analogue 50 with an IC(50) value of 0.9 microM in the FSHR-cAMP assay was essentially inactive at 30 microM in the TSHR-cAMP assay.