1900-40-9Relevant academic research and scientific papers
Isopropyl N-arylmalonamates. Synthesis, structure, conformation and reactions with carbon disulfide
Rudorf, Wolf-Dieter,Loos, Dusan,Wybraniec, Joanna,Pronayova, Nad'a,Gawinecki, Ryszard,Sustekova, Zora
, p. 59 - 76 (2007/10/03)
Acylation of aromatic amines 1 with diisopropyl malonate (2) leads to a mixture of isopropyl N-arylmalonamates 3 and malonanilides 4. The reaction of 3 with carbon disulfide in the presence of sodium hydride gives disodium salts 5. Treatment of 5 with an alkylating agent yields the open-chain or cyclic ketene dithioacetals 6, 7 or 8. The molecular structure, hydrogen bonding and preferential conformation of the isopropyl N-arylmalonamates 3, 6 and 7 were investigated using correlation analyses of IR, 13C NMR and AMI semiempirical data.
Prostaglandin-H Synthase Inhibition by Malonamides. Ring-Opened Analogues of Phenylbutazone
Vennerstrom, Jonathan L.,Holmes, Thomas J.
, p. 434 - 437 (2007/10/02)
Recent reports of serious concern regarding the sfe clinical use of phenylbutazone and its hydroxylated metabolite (oxyphenbutazone) as antiinflammatory agents have prompted the further investigation of ring-opened (malonamide) derivatives as potentially preferable therapeutic derivatives.Earlier reports have claimed reduced toxicity among similar derivatives.These studies reveal the relative degree of prostaglandin-H (PGH) synthase inhibitory activity among a series of malonamide derivatives.Contrary to observations in the pyrazolidinedione series, incorporation of a nonpolar butyl side chain in these malonamides was not beneficial but, rather, detrimental to enzyme-inhibitory activity.Although nine of the reported nonbutylated malonamides was a potent an inhibitor of this enzyme as phenylbutazone, they all showed some inhibitory activity.PGH synthase inhibitory activity was especially pronounced in the bis(p-hydroxy anilide) derivatives, even extending to succinamide and adipamide derivatives.Of some interest is the observation that all of these p-hydroxy anilide derivatives were more potent inhibitors of this enzyme than acetaminophen.
REACTION OF DIAZOMETHANE WITH HYDROXYIMINOMALONANILIDES
Prosyanik, A. V.,Zorin, Ya. Z.,Solov'ev, E. L.
, p. 1353 - 1360 (2007/10/02)
The structures of the yellow and white crystalline modifications of para-substituted hydroxyiminomalonanilides and their reaction with diazomethane under various conditions, leading to the corresponding nitrones and oxime O-ethers, were investigated.Proba
