5469-94-3Relevant articles and documents
Palladium-catalyzed asymmetric haloiminolactonization of D-allylmalonamides
Kuriyama, Masami,Yamamoto, Kosuke,Ishimaru, Keiko,Fujimura, Noriyuki,Minato, Daishiro,Onomura, Osamu
, p. 744 - 754 (2019/04/26)
A catalyst composed of 10 mol% of Pd(OAc)2 and (R,R)-PhBox was proven to be effective in the asymmetric haloiminolactonization of D-allylmalonamides with N-halosuccinimides, giving the dihalogenated cyclic products with good diastereomeric ratio (up to 89/11) and enantiomeric excess (up to 72% ee).
Copper malonamide complexes and their use in azide-alkyne cycloaddition reactions
Bent,Mahon,Webster
, p. 10253 - 10258 (2015/06/08)
We report a rare example of the malonamide functionality being used as a ligand in copper catalysis. We have ligated a homologous series of these O,O-chelating architectures to copper, investigated their structure and exploited them in azide-alkyne cycloa
Synthesis of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro- 1H-quinolin-2-ones, as novel quinoline derivatives with antibacterial activity
Ferretti, Matías D.,Neto, Alexandre T.,Morel, Ademir F.,Kaufman, Teodoro S.,Larghi, Enrique L.
, p. 253 - 266 (2014/06/09)
A novel series of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4- dihydro-1H-quinolin-2-ones was synthesized and tested as antimicrobials. The minimum inhibitory concentration (MIC) values of the most active heterocycles were slightly higher than those exhibited by levofloxacin, employed as comparator. Structural factors affecting the activity were explored along three diversification points, including the substituents of the aromatic rings of the 3-benzyl moieties, as well as the functionalization of both, the homocyclic ring of the heterocycle and the quinolonic nitrogen atom. 6-Chloro and 3,3-bis(4′-chlorobenzyl) derivatives showed the lower MIC values. Optimally substituted heterocycles were synthesized, which exhibited enhanced activity.
Ligand-based modelling followed by synthetic exploration unveil novel glycogen phosphorylase inhibitory leads
Habash, Maha,Taha, Mutasem O.
experimental part, p. 4746 - 4771 (2011/09/20)
Glycogen phosphorylase (GP) is a valid anti-diabetic target. Accordingly, we applied a drug discovery workflow to unveil novel inhibitory GP leads via combining pharmacophore modeling, QSAR analysis and in silico screening, followed by synthetic exploration of active hits. Virtual screening identified six low micromolar inhibitory leads from the National Cancer Institute (NCI) list of compounds. The most potent hits exhibited anti-GP IC50 values of 3.2 and 4.1 μM. Synthetic exploration of hit 59 (IC50 = 4.1 μM) yielded 25 lead inhibitors with the best illustrating IC50 of 3.0 μM. Interestingly, we prepared several novel mixed oxalyl amide anti-GP leads employing new chemical reaction involving succinic acid-based adducts.
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.
Quinone methide reactions: Synthesis of novel pyranodiquinolines
Balasubramanian, C.,Kumaraswami, K.,Dharmaraj, N.,Mohan, P. S.
, p. 460 - 462 (2007/10/02)
The reaction of alkaline 4-hydroxyquinolin-2(1H)-ones (1) with vinyl acetate has been studied.Interestingly, 1,1-diquonolinoethane formed via a quinoline-quinone methide intermediate undergoes dehydration in situ by two paths yielding the isomeric 7-methylpyranodiquinolines (3 and 4).
Quinoline Alkaloids. Synthesis of Khaplofoline, Ribalinine, and Flindersine
Subramanian, M.,Mohan, P. S.,Shanmugam, P.,Prasad, K. J. Rajendra
, p. 1016 - 1020 (2007/10/02)
Reaction of 4-hydroxy-3-prenylquinolin-2(1H)one (5a) with iodine and silver acetate gave a iodopyranoquinoline (6a), which was then converted into the alkaloids khaplofoline (1) and ribalinine (2).Reaction of 5a with iodine and mercuric oxide afforded a mixture of 6a and its angular isomer 7a; the conversion of latter into flindersine (10) is described.Keywords: Pyranoquinoline Alkaloids, Khaplofoline, Ribalinine, Flindersine
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 malondiamides with disulfur dichloride: a reinvestigation
Kutney, Gerald W.,Still, Ian W.J.
, p. 1233 - 1238 (2007/10/02)
The reaction of a series of N,N'-dialkyl and N,N'-diaryl malondiamides with disulfur dichloride have been reinvestigated.The claim, made almost 60 years ago, that the products of this reaction are dithioketones R2CS2, is shown to be unfounded.The structures of these products are shown to be the symmetrically substituted 1,2,4,5-tetrathianes, 8a-e.-
