195052-28-9Relevant academic research and scientific papers
Solid Phase Synthesis of N-Alkyl Sulfonamides
Dankwardt, Sharon M.,Smith, David B.,Porco Jr., John A.,Nguyen, Cindy H.
, p. 854 - 856 (1997)
Polymer-supported sulfonamides were alkylated using alkyl halides in the presence of DBU or with alcohols via the Mitsunobu reaction.
DITHIAZOLE COMPOUNDS, MATRIX METALLOPROTEASE INHIBITORS AND EXTERNAL PREPARATIONS FOR THE SKIN
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Page 16, (2008/06/13)
A dithiazole compound or a salt thereof expressed by formula (I): wherein R1, is hydrogen atom, alkyl, etc.; R2 is hydrogen atom, hydroxy, alkyl, aryl, arylalkoxy, arylalkyl, etc.; R3 is one group of formulae (II), (III) and (IV): This compound has an excellent inhibiting action on matrix metalloprotease (MMPs) activity, and is useful for pharmaceutical, cosmetic and skin external compositions.
Protease inhibitors - Part 5. Alkyl/arylsulfonyl- and arylsulfonylureido-/arylureido- glycine hydroxamate inhibitors of Clostridium histolyticum collagenase
Scozzafava, Andrea,Supuran, Claudiu T.
, p. 299 - 307 (2007/10/03)
Reaction of alkyl/arylsulfonyl halides with glycine afforded a series of derivatives which were first N-benzylated by treatment with benzyl chloride, and then converted to the corresponding hydroxamic acids with hydroxylamine in the presence of carbodiimide derivatives. Other derivatives were obtained by reaction of N-benzyl-glycine with aryl isocyanates, arylsulfonyl isocyanates or benzoyl isothiocyanate, followed by conversion of their COOH group into the CONHOH moiety, as mentioned above. The 90 new compounds reported here were assayed as inhibitors of the Clostridium histolyticum collagenase (EC 3.4.24.3), a zinc enzyme which degrades triple helical regions of native collagen. The prepared hydroxamate derivatives were generally 100-500 times more active than the corresponding carboxylates. In the series of synthesized hydroxamates, substitution patterns leading to the best inhibitors were those involving perfluoroalkylsulfonyl- and substituted- arylsulfonyl moieties, such as pentafluorophenylsulfonyl, 3- and 4- carboxyphenylsulfonyl-, 3-trifluoromethyl-phenylsulfonyl or 1- and 2-naphthyl among others. Thus, it seems that similarly to the matrix metalloproteinase (MMP) hydroxamate inhibitors, Clostridium histolyticum collagenase inhibitors should incorporate hydrophobic moieties at the P1, and P2, sites, whereas the α-carbon substituent may be a small and compact moiety (such as H. for the Gly derivatives reported here). Such compounds might lead to the design of collagenase inhibitor-based drugs useful as anti-cancer, anti-arthritis or anti-bacterial agents for the treatment of corneal keratitis. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
