299181-39-8

Basic information

• Product Name: 4-methoxy-3-(thiomorpholine-4-sulfonyl)-benzoic acid
• Synonyms: 4-methoxy-3-(thiomorpholine-4-sulfonyl)-benzoic acid
• CAS NO: 299181-39-8
• Molecular Weight: 317.387
• Mol File: 299181-39-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-methoxy-3-(thiomorpholine-4-sulfonyl)-benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxy-3-(thiomorpholine-4-sulfonyl)-benzoic acid(299181-39-8)
• EPA Substance Registry System: 4-methoxy-3-(thiomorpholine-4-sulfonyl)-benzoic acid(299181-39-8)

Safety Data

• Hazardous Substances Data: 299181-39-8(Hazardous Substances Data)

Upstream product

• 100-09-4 4-methoxybenzoic acid 
• 123-90-0 Thiomorpholin 
• 50803-29-7 3-chlorosulfonyl-4-methoxybenzoic acid 

Downstream Products

• 299181-04-7 2,2'-[(E)-1,2-ethenediyl]bis[5-[[4-methoxy-3-(4-thiomorpholinylsulfonyl)benzoyl]amino]benzenesulfonic acid] 
• 299181-91-2 C₄₄H₅₂N₄O₁₈S₆ 
• 299181-52-5 3-(1,1-dioxo-1-thiomorpholine-4-sulfonyl)-4-methoxy-benzoic acid 

Relevant articles and documents

Synthesis and Biological Evaluation of 4-Sulfamoylphenyl/Sulfocoumarin Carboxamides as Selective Inhibitors of Carbonic Anhydrase Isoforms hCA II, IX, and XII

With the aim to develop potent and selective human carbonic anhydrase inhibitors (hCAIs), we synthesized 4-sulfamoylphenyl/sulfocoumarin benzamides (series 5 a–r and series 7 a–q) and evaluated their inhibition profiles against five isoforms of the zinc-containing human carbonic anhydrase (hCA, EC 4.2.1.1): cytosolic hCA I and II, and the transmembrane isozymes hCA IV, IX, and XII. Compounds 5 a–r were found to selectively inhibit hCA II in the nanomolar range, while being less effective against the other hCA isoforms. As noted from the literature, sulfocoumarin (1,2-benzoxathiine 2,2-dioxide) acts as a “prodrug” inhibitor and is hydrolyzed by the esterase activity of hCA to form 2-hydroxyphenylvinylsulfonic acid, which thereafter binds to the enzyme in a manner similar to that of coumarins and sulfoxocoumarins. All these sulfocoumarins (compounds 7 a–q) were found to be very weak or ineffective as inhibitors of the housekeeping off-target hCA isoforms I and II, and effectively inhibited the transmembrane tumor-associated isoforms IX and XII in the high nanomolar to micromolar ranges. Further structural modifications of these molecules could be useful for the development of effective hCA inhibitors used for the treatment of glaucoma, epilepsy, and cancer.

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.