793713-91-4Relevant academic research and scientific papers
4-Cyanobenzenesulfonamides: Amine Synthesis and Protecting Strategy To Compliment the Nosyl Group
Schmidt, Michael A.,Stokes, Ryjul W.,Davies, Merrill L.,Roberts, Frederick
, p. 4550 - 4560 (2017)
4-Cyanobenzenesulfonamides of secondary amines were found to cleave to the parent amine cleanly under the action of thiol and base. This feature readily lends itself to the use of this motif as an amine protecting/activating group within a broader context of amine synthesis. The crystalline sulfonamides could be further elaborated by alkylation and arylation similarly to nitrobenzenesulfonamides. The sulfonamides could withstand conditions that functionalize nitroarenes, such as reductions and vicarious nucleophilic substitution reactions.
Benzsulfamide IDO1 inhibitor, and preparation method and application thereof
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Paragraph 0088; 0133-0136, (2017/08/29)
The invention belongs to the field of drugs, and particularly relates to a benzsulfamide compound having a structural characteristic as shown in formula (I) or pharmaceutically acceptable salt of the benzsulfamide compound, a preparation method of the benzsulfamide compound or the salt, and uses of the benzsulfamide compound or the salt as an indoleamine 2,3-dioxygenase 1 (IDO1) inhibitor. An experimental result indicates that the compound provided by the invention has an obvious inhibiting effect on the activity of the IDO1, can effectively promote T cell proliferation, inhibits native T cells from differentiating into regulatory T cells, reverses immunosuppression mediated by the IDO1, and can be used for treating relevant diseases having pathological characteristics of metabolic pathways of kynurenine mediated by the IDO1, including cancer, virus infection, neurodegenerative diseases, cataract, organ transplant rejection, depression, autoimmune diseases and the like. Formula (I) is shown in the description.
Active site mapping of trypsin, thrombin and matriptase-2 by sulfamoyl benzamidines
Dosa, Stefan,Stirnberg, Marit,Luelsdorff, Verena,Haeussler, Daniela,Maurer, Eva,Guetschow, Michael
supporting information, p. 6489 - 6505,17 (2012/12/11)
The benzamidine moiety, a well-known arginine mimetic, has been introduced in a variety of ligands, including peptidomimetic inhibitors of trypsin-like serine proteases. According to their primary substrate specificity, the benzamidine residue interacts with the negatively charged aspartate at the bottom of the S1 pocket of such enzymes. Six series of benzamidine derivatives (1-73) were synthesized and evaluated as inhibitors of two prototype serine proteases, that is, bovine trypsin and human thrombin. As a further target, human matriptase-2, a recently discovered type II transmembrane serine protease, was investigated. Matriptase-2 represents an important regulatory protease in iron homeostasis by down-regulation of the hepcidin expression. Compounds 1-73 were designed to contain a fixed sulfamoyl benzamidine moiety as arginine mimetic and a linker-connected additional substructure, such as a tert-butyl ester, carboxylate or second benzamidine functionality. A systematic mapping approach was performed with these inhibitors to scan the active site of the three target proteases. In particular, bisbenzamidines, able to interact with both the S1 and S3/S4 binding sites, showed notable affinity. In branched bisbenzamidines 66-73 containing a third hydrophobic residue, opposite effects of the stereochemistry on trypsin and thrombin inhibition were observed.
Biaryl sulfonamides from O-acetyl amidoximes: 1,2,4-Oxadiazole cyclization under acidic conditions
Dosa, Stefan,Daniels, Joerg,Guetschow, Michael
experimental part, p. 407 - 413 (2011/05/14)
A series of 4-cyanobenzenesulfonamides (1a-h) was converted to the corresponding O-acetylated amidoximes (2a-h). The reaction of 1a was exemplarily investigated with respect to the formation of a byproduct, which was identified as 1,2,4-oxadiazole derivative 3a. This observation led to the development of an improved procedure for the preparation of 2a-h. Compounds 2 could be transformed to 1,2,4-oxadiazoles 3a-h in high yields and purity upon heating in acetic acid.
