19792-91-7Relevant articles and documents
Inhibition of carbonic anhydrase-II by sulfamate and sulfamide groups: An investigation involving direct thermodynamic binding measurements
Klinger, Alexandra L.,McComsey, David F.,Smith-Swintosky, Virginia,Shank, Richard P.,Maryanoff, Bruce E.
, p. 3496 - 3500 (2006)
This paper examines the relative effectiveness of bioisosteric sulfamate and sulfamide derivatives for inhibition of human carbonic anhydrase-II (CA-II) by using a direct binding assay based on the ThermoFluor method (Matulis et al. Biochemistry 2005, 44, 5258). Compounds 1-10, which represent five cognate sulfamate/ sulfamide pairs, were studied by ThermoFluor to obtain binding affinities (Ka values). The corresponding dissociation constants, Kd, provide an independent measure of CA-II activity relative to commonly used Ki values from enzyme kinetics studies. There was a sizable difference in potency between the sulfamates and sulfamides, with the sulfamides being much less potent, by factors ranging from 25 (7/8) to 1200 (3/4), These results are consistent with our recent report that sulfamides tend to be much weaker inhibitors of CA-II than their corresponding sulfamates (Maryanoff et al. J. Med. Chem. 2005, 48, 1941). Additionally, for arylsulfamides 10-12 the Kd values determined by ThermoFluor and the Ki values determined from enzyme kinetics are consistent. It appears that the sulfamide group is less suitable than the sulfamate group for obtaining potent inhibition of CA-II.
Efficient synthesis of N-oxysulfonyl formamidines through thionyl chloride-promoted reaction of sulfamates with formamides
Wusiman, Abudureheman,Hudabaierdi, Ruzeahong
supporting information, p. 2015 - 2021 (2017/10/13)
N-Oxysulfonyl formamidine derivatives have been efficiently synthesized under mild conditions through direct condensation of various sulfamates and formamides in the presence of thionyl chloride. The scope of this reaction was investigated, and a plausible mechanism was proposed. The resulting N-oxysulfonyl formamidines can be converted to sulfamates through appropriate deprotection.
Selective intermolecular amination of C-H bonds at tertiary carbon centers
Roizen, Jennifer L.,Zalatan, David N.,Du Bois
supporting information, p. 11343 - 11346 (2013/11/06)
C-H insertion: A method for intermolecular amination of tertiary C-H bonds is described that uses limiting amounts of substrate and a convenient phenol-derived nitrogen source. Structure-selectivity and mechanistic studies suggest that steric interaction between the substrate and active oxidant is the principal determinant of product selectivity. Copyright
Intermolecular amination of allyl alcohols with sulfamates: Effective utilization of mercuric catalyst
Yamamoto, Hirofumi,Ho, Elisabeth,Sasaki, Ikuo,Mitsutake, Mizuho,Takagi, Yuichi,Imagawa, Hiroshi,Nishizawa, Mugio
supporting information; experimental part, p. 2417 - 2420 (2011/06/10)
Herein, we describe the intermolecular amination of allyl alcohols with sulfamates, which have been underutilized as nitrogen nucleophiles for allylic amination. Methyl sulfamate is a good nucleophile in the presence of mercuric triflate and efficiently generates monoallylation products in excellent yield at room temperature. Furthermore, the solid-supported mercuric catalyst silaphenyl mercuric triflate also showed remarkable catalytic activity for the allylic amination. Intermolecular amination of allyl alcohol with sulfamate as a modifiable nitrogen nucleophile is presented. Mercuric reagents act as highly efficient catalyst for the allylic amination, and the procedure was applied to the preparation of various amine derivatives. In many cases, the reaction can be carried out at room temperature and is applicable to a large range of allylic alcohols to give the monoallylated products in excellent yield. Copyright