112753-64-7Relevant academic research and scientific papers
Oxygen substituted derivatives of nucleophile-nitric oxide adducts as nitric oxide donor prodrugs
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, (2008/06/13)
There are disclosed cardiovascularly active compounds possessing antihypertensive properties, and pharmaceutical compositions containing these agents and a method of treating cardiovascular disorders with the compounds. The active components of the pharmaceutical compositions are compounds of formula I STR1 wherein R1 and R2 are independently chosen from straight chain and branched chain alkyl and olefinic groups, which may be unsubstituted or substituted; or R1 and R2 together with the nitrogen atom they are bonded to form a heterocyclic group; and R3 is a pharmaceutically acceptable organic group selected from alkyl and olefinic groups which may be unsubstituted or substituted, acyl, a sulfonyl, sulfinyl, sulfenyl, carbonate, or carbamate derivative; or R3 is a group of the formula--(CH2)n ONN(O)NR1 R2, wherein n is 2-8, and R1 and R2 are as described above. Novel compounds are disclosed wherein at least one of R1, R2 and R3 is an olefinic group or heteroatom-substituted straight or branched chain alkyl or olefinic group. Novel methods of synthesizing the compounds are also disclosed.
Secondary Amine/Nitric Oxide Complex Ions, R2N-. O-Functionalization Chemistry
Saavedra, Joseph E.,Dunams, Tambra M.,Flippen-Anderson, Judith L.,Keefer, Larry K.
, p. 6134 - 6138 (2007/10/02)
Alkylation of the R2N- anion has been studied with the aim of extending the reaction's scope, probing its stereochemistry, and exploring the reactivity of its variously functionalized products.Using the sodium salt of the R = Et ion (1) as the standard starting material, numerous novel products having the structure Et2NR'(2) were isolated from its reaction with alkyl halides, sulfate esters, and oxiranes.In addition to previously described examples in which R' is a simple straight-chain alkyl or benzyl group, new compound types in which R' is hydroxylated, halide-containing, α-methoxylated, and olefinic were prepared.The 2-bromoethyl derivative could be dehydrohalogenated to the O-vinyl compound or further reacted with other nucleophiles such as amines, water, or a second mole of 1 to produce additonal new compound types.Ethylation of 1 appeared to occur exclusively at the terminal oxygen to give Et2NN(O)=NOEt as the only isomer detected; this conclusion regarding the regiochemistry of the reaction conflicts with that found in the previous literature, but its generality was supported by X-ray crystallographic analysis of the Et2NN(O)=NOCH2CH2(NC5H5)+Br- analogue.Hydrolytic decomposition of 2 was slow, even for the O-vinyl and -methoxymethyl derivatives, as reflected in the sluggish loss of the intense chromophore these compounds characteristically show at 225-245 nm (ε (6.5-9) x 103 M-1 cm-1); half-lives at 37 deg C for the latter two compounds were 12 h in 0.1 M HCl and 9 h in 1 M HCl, respectively.N-Nitrosodiethylamine was a frequent byproduct of both the synthesis and hydrolysis of 2.The results should aid the effort to design prodrug derivatives of 1, a compound type which has recently been shown to exhibit useful pharmacological effects.
SYNTHESIS OF 1-ALKOXY-3,3-DIALKYLTRIAZENE 2-OXIDES FROM ALKOXYAMINES AND NITROSOAMINES
Artsybasheva, Yu. P.,Ioffe, B. V.
, p. 1056 - 1060 (2007/10/02)
The oxidation of O-alkylhydroxylamines by lead tetraacetate in the presence of dialkylnitrosoamines leads to the 1-alkoxy-3,3-dialkyltriazene 2-oxides in yields up to 50percent.The products were isolated by distillation.
