103586-51-2Relevant academic research and scientific papers
Triphenylphosphine catalyzed Michael addition of oximes onto activated olefins
Bhuniya, Debnath,Mohan, Sankar,Narayanan, Sanju
, p. 1018 - 1024 (2007/10/03)
A new reaction condition for Michael addition of oximes onto activated olefins has been discovered using a catalytic amount of triphenylphosphine. This is a first and milder alternative to classical base (hydroxide, alkoxide) catalyzed Michael addition of oximes. Various aldoximes 1a-h and ketoximes 2a-c (Figure 1) were reacted with different Michael acceptors such as ethyl acrylate, acrylonitrile, phenyl vinyl sulfone, methyl vinyl ketone, and 1-nitrocyclohex-1-ene to obtain the corresponding Michael adducts. About 35 different examples were attempted (Table 1 and Scheme 1); except in six cases where reactions did not produce desired products, yields varied from good to excellent. Reactions without triphenylphosphine did not proceed. A plausible mechanism of catalytic action in the present reactions is proposed (Figure 2).
Molecular design, synthesis, and antiinflammatory activity of a series of β-aminoxypropionic acids
Macchia,Balsamo,Lapucci,Macchia,Martinelli,Nencetti,Orlandini,Baldacci,Mengozzi,Soldani,Domiano
, p. 1423 - 1430 (2007/10/02)
Previous experimental and theoretical studies carried out on the mechanism of action of adrenergic drugs have shown that the (methyleneaminoxy)methyl moiety (C=NOCH2, MAOMM) can be considered as a 'bioisostere' of an aryl group (Ar). On this basis, a series of substituted β-aminoxypropionic acid (AOPAs) were synthesized as analogues of antiinflammatory arylacetic acids (ArAAs), in which the Ar portion is substituted by the MAOMM, with the aim of evaluating whether any antiinflammatory activity could be obtained from this class of drugs after the substitution of the Ar with the MAOMM. The antiinflammatory activity of the AOPAs synthesized was determined by carrageenan-induced rat paw edema, using diclofenac as the reference drug. The pharmacological data showed that most of the AOPAs examined exhibit a significant antiinflammatory activity, which in the case of the (E)-3-(benzylidineaminoxy)propionic acid (7q) is very close to that of the reference drug. Structural and theoretical studies were carried out in order to compare the conformation and the molecular reactivity of the AOPAs with those of the ArAAs. Pharmacological results showed that the ArAAs also generally exhibit an antiinflammatory activity after the substitution of the Ar with the MAOMM, thus supporting the hypothesis of a bioisosterelike relationship between these two moieties in this class of NSAIDs.
