136167-29-8

Upstream product

• 371-41-5 4-Fluorophenol 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 1375958-86-3 C₁₁H₁₄FNO₅S 

Downstream Products

• 371-41-5 4-Fluorophenol 
• 1306748-18-4 4-fluorophenyl N-(cyclohex-2-en-1-yl)sulfamate 
• 5329-14-6 aminosulfonic acid 

Relevant academic research and scientific papers

Catalytic Sulfamoylation of Alcohols with Activated Aryl Sulfamates

We report a new catalytic method for alcohol sulfamoylation that deploys electron-deficient aryl sulfamates as activated group transfer reagents. The reaction utilizes the simple organic base N-methylimidazole, proceeds under mild conditions, and provides

N-(tert -butoxycarbonyl)- N -[(triethylenediammonium)sulfonyl]azanide: A convenient sulfamoylation reagent for alcohols

A convenient and efficient procedure is described for the sulfamoylation of alcohols using N-(tert-butoxycarbonyl)-N-[(triethylenediammonium)sulfonyl] azanide (1). The ambient temperature stable reagent 1 reacts with phenols as well as primary and secondary alcohols to give high to modest yields. The relative reaction rate of substrates was determined (primary > phenol > secondary ? tertiary). The reagent's utility as a selective sulfamoylation reagent with polyols is also demonstrated.

Intermolecular amination of allyl alcohols with sulfamates: Effective utilization of mercuric catalyst

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

Carbonic anhydrase inhibitors; Fluorinated phenyl sulfamates show strong inhibitory activity and selectivity for the inhibition of the tumor-associated isozymes IX and XII over the cytosolic ones I and II

A series of fluorinated-phenylsulfamates have been prepared by sulfamoylation of the corresponding phenols and the inhibition of four physiologically relevant carbonic anhydrase (CA, EC 4.2.1.1) isozymes, the cytosolic CA I and II (off-targets), and the t

Elimination mechanisms in the aminolysis of sulfamate esters of the type NH2SO2OC6H2X - Models of enzyme inhibitors

The kinetics of the reaction of 4-nitrophenyl sulfamate NH 2SO2OC6H4NO2-4 (1a) in acetonitrile (ACN) with a series of pyridines (pKa range ca. 8 units) and alicyclic amines (pKa range ca. 3.6 units) has been studied in the presence of excess amine at various temperatures. The compounds 1a-1f are important as model substrates for the medicinally important sulfamate esters 667-coumate and emate and analogues. Pseudo-first-order rate constants (k obsd.) have been obtained mainly by the release of 4-nitrophenol/4-nitrophenoxide. Slopes of plots of kobsd. vs. [amine] gave second-order rate constants (k2), and Broensted plots were biphasic for the aminolysis (with alicyclic amines) with an initial slope β1 = 0.53 and a subsequent slope β2 = 0.19. The change in slope occurs near the first pKa of 1a (17.9) in ACN. Leaving-group effects were probed by using the same series of phenyl sulfamates, i.e. 1a-f and the alicyclic amines N-formylpiperazine and pyrrolidine. The reactions were considered to be dissociative in nature involving E2- and E1cB- type mechanisms with the phenyl sulfamate anion 2 being involved in pyridine and in the weaker alicyclic amines (β1 segment) and a phenyl sulfamate dianion 3 being involved with the stronger alicyclic bases (β2 segment). The calculation of Leffler indices (α) for bond-forming (base...H+) and bond-breaking (S-OAr) steps allows fuller interpretation of the mechanisms occurring, which are seen as having the N-sulfonylamines, HN=SO2 and -N=SO2 on the reaction pathways leading to products. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

The mechanism of the irreversible inhibition of estrone sulfatase (ES) through the consideration of a range of methane- and amino-sulfonate-based compounds

We report the results of our study into a series of simple phenyl and alkyl sulfamates and alkyl methanesulfonates as potential inhibitors of the enzyme estrone sulfatase (ES). The results of the study show that the substituted phenyl sulfamates are good irreversible inhibitors; the alkyl sulfamate compounds were found to lack inhibitory activity; whilst the large alkyl chain containing methanesulfonate-based compounds were found to possess weak reversible inhibitory activity. Using the results of the inhibition study, we postulate the probable mechanism for ES and suggest that an attack by the gem-diol is a major requirement prior to the hydrolysis of the sulfamate group, following which, attack on the active site C=O occurs and which therefore leads to the production of an imine type functionality, resulting in irreversible inhibition.

Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES)

We report the initial results of the synthesis and biochemical evaluation of a series of aminosulfonate based compounds of phenol and the determination of the pKa of the parent phenol in an attempt to investigate the role of this physicochemical factor in the irreversible inhibition of the enzyme estrone sulfatase (ES). The results of the study show that there is a strong correlation between the observed pKa and inhibitory activity. We postulate that the stability of the phenoxide ion, as indicated by the acid dissociation constant, is an important factor in the irreversible inhibition of this enzyme.

Sulfamates as antiglaucoma agents

Sulfamate esters of the formula where A is aryloxyalkyl, p is the number of unreacted hydroxy groups present on the alkyl moiety and may be zero, z is the number of --OS(O)2 NR1 R2 groups attached to carbons of the alkyl moiety and is always at least one; R1 and R2 are selected from hydrogen, loweralkyl, carboxy, and the like are useful in treating glaucoma.

Compounds having one or more aminosulfaonyloxy radicals useful as pharmaceuticals

Methods of treating chronic arthritis and osteoporosis which utilize both known and novel compounds which would fall under the general formula:(HO)p--A--[--OS(O) 2 NR 1 R 2 ] zwherein A encompasses a wide range of values including but not limited to aryl, loweralkyl, cycloalkyl, and carbohydrates including sucrose and fructose; p is equal to the number of unreacted hydroxy groups contained on the molecule and may be zero; z is the number of --OS(O) 2 NR 1 R 2 groups and is always at least one; R 1 and R 2 are selected from hydrogen, loweralkyl, carboxy and the like; a novel process for preparing the compounds is provided wherein an appropriate sulfamic acid aryl ester is reacted with a hydroxy substituted A radical which may or may not contain thereon protected carboxyl, amino or hydroxy substituents, in an aprotic solvent containing a tertiary amine base. Pharmaceutical compositions for the treatment of chronic arthritis and osteoporosis are also provided.

Aryl and aryloxyalkyl sulfamate esters useful as anticonvulsants

Herein disclosed is a method of treating convulsions with a pharmaceutical composition containing a compound of the formula: where A is an aryl, arylalkyl, or aryloxyalkyl group and is substituted on 1 or more carbon atoms with a sulfamate group (--OSO2 NR1 R2) wherein R1 and R2, same or different, are hydrogen or loweralkyl wherein p is 0 or 1 and is the number of untreated hydroxyl groups and z is 1 or 2 and is the number of --OS(O2)NR1 R2 groups. Aryl is selected from phenyl, substituted phenyl, pyridinyl, naphthyl, quinolinyl, and the like. Phenyl substituents are selected from hydrogen, halo, hydroxy, phenyl, phenoxy, benzoyl, loweralkyl, loweralkoxy, carboxy, amino, loweralkylamino, diloweralkylamino, acetamido, cyano, nitro, loweralkoxycarboyl, aminosulfonyl, imidazolyl, triazolyl, and the like. Novel compounds not previously disclosed are also described.