Sulfamoyl azides. Hydrolysis rates and hypotensive activity

Matier, W. L.; Comer, W. T.; Deitchman, David

doi:10.1021/jm00275a025

Cited by 30 publications

(15 citation statements)

References 3 publications

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“…In chloroform the reaction is virtually insensitive to changing substituent and interestingly a similar was obtained in the hydrolysis in aqueous dioxane at 29 ЊC of the sulfamoyl azides (RNHSO 2 N 3 , R = Ph, p-ClC 6 H 4 and p-MeOC 6 H 4 ), which gave rates of 8.75, 6.68 and 8.68 (×10 2 min Ϫ1 ) respectively. 14 In acetonitrile in our system there is a notable increase in rate with a change from an electrondonating to an electron-withdrawing substituent (Table 8). Also, it is noticeable that the rates are considerably faster in acetonitrile: k CH 3 CN /k CHCl 3 for p-Me, H and p-Cl being respectively 19.5, 20.1 and 41.4.…”

Section: Substituent Effectsmentioning

confidence: 78%

Elimination mechanisms in the anilinolysis of sulfamoyl chlorides in chloroform and acetonitrile

Spillane¹,

Mchugh²,

Burke³

1998

J. Chem. Soc., Perkin Trans. 2

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Section: Substituent Effectsmentioning

confidence: 78%

Elimination mechanisms in the anilinolysis of sulfamoyl chlorides in chloroform and acetonitrile

Spillane¹,

Mchugh²,

Burke³

1998

J. Chem. Soc., Perkin Trans. 2

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“…Sulfamoyl azides are chemically stable even in strong basic or acidic conditions and are thermally stable up to at least 100 °C in the absence of solvent . They have recently been characterized as a new class of effective nitrene sources for metal-catalyzed C–H amination , as well as a new type of azide for applications in click chemistry .…”

Section: Resultsmentioning

confidence: 99%

Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study

Zou

et al. 2017

J. Org. Chem.

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The rearrangement of sulfamoyl azides under thermal conditions to form a C-C bond while breaking two C-N bonds is reported. Mechanistic study shows that this reaction goes through a Curtius-type rearrangement to form a 1,1-diazene, then which rearranges possibly through both a concerted rearrangement process and a stepwise radical process. This rearrangement could be used in the synthesis of complex biologically active molecules, such as sterols, and piperine derivatives.

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“…After cooling and concentration, the residue was purified by distillation to provide isopropylsulfamyl chloride (1. 46 This intermediate was elaborated to 40a following the procedure for 44a: 1 …”

Section: -[[[3-[4-(aminoiminomethyl)phenyl]-45-dihydro-5-isoxazolylmentioning

confidence: 99%

Orally Active Isoxazoline Glycoprotein IIb/IIIa Antagonists with Extended Duration of Action

Wityak

et al. 1999

J. Med. Chem.

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Modification of the alpha-carbamate substituent of isoxazoline GPIIb/IIIa (alphaIIb beta3) antagonist DMP 754 (7) led to a series of alpha-sulfonamide and alpha-sulfamide diaminopropionate isoxazolinylacetamides which were found to be potent inhibitors of in vitro platelet aggregation. Aryl- and heteroaryl-alpha-sulfonamide groups, in conjunction with (5R)-isoxazoline (2S)-diaminopropionate stereochemistry, were found to impart a pronounced duration of antiplatelet effect in dogs, potentially due to high affinity for unactivated platelets. Isoxazolylsulfonamide 34b (DMP 802), a highly selective GPIIb/IIIa antagonist, demonstrated a prolonged duration of action after iv and po dosing and high affinity for resting and activated platelets. The prolonged antiplatelet profile of DMP 802 in dogs and the high affinity of DMP 802 for human platelets may be predictive of clinical utility as a once-daily antiplatelet agent.

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Sulfamoyl azides. Hydrolysis rates and hypotensive activity

Cited by 30 publications

References 3 publications

Elimination mechanisms in the anilinolysis of sulfamoyl chlorides in chloroform and acetonitrile

Elimination mechanisms in the anilinolysis of sulfamoyl chlorides in chloroform and acetonitrile

Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study

Orally Active Isoxazoline Glycoprotein IIb/IIIa Antagonists with Extended Duration of Action

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