16195-39-4Relevant academic research and scientific papers
Allylation and Alkylation of Biologically Relevant Nucleophiles by Diallyl Sulfides
Viswanatharaju Ruddraraju, Kasi,Parsons, Zachary D.,Lewis, Calvin D.,Gates, Kent S.
, p. 776 - 780 (2017/04/26)
Allyl sulfides are bioactive phytochemicals found in garlic, onion, and other members of the genus Allium. Here we showed that diallyl disulfide and diallyl trisulfide can transfer allyl side chains to low molecular weight thiols. Diallyl monosulfide is i
Synthesis of (bis)sulfonic acid, (bis)benzamides as follicle-stimulating hormone (FSH) antagonists.
Wrobel, Jay,Green, Daniel,Jetter, James,Kao, Wenling,Rogers, John,Perez, M Claudia,Hardenburg, Jill,Deecher, Darlene C,Lopez, Francisco J,Arey, Brian J,Shen, Emily S
, p. 639 - 656 (2007/10/03)
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.
