56006-49-6Relevant academic research and scientific papers
SYNTHESIS OF SOME NEW CHOLESTERYL ESTERS OF CHIRAL ALKANOIC ACIDS.
Gibson
, p. 43 - 53 (1974)
Six new cholesteryl esters have been prepared from chiral alkanoic acids. Oxidation of 2(S)-methylbutanol and 2(S)-ethyl-3-methybutyraldehyde gave the corresponding butyric acids, while condensation of the tosylates of the corresponding alcohols with diethyl malonate led ultimately to the substituted hexanoic acids. 2(R)-Methylpentanoic and ( minus )-2-ethylhexanoic acids were commercially available.
Syntheses and evaluation of anticonvulsant activity of novel branched alkyl carbamates
Hen, Naama,Bialer, Meir,Yagen, Boris
experimental part, p. 2835 - 2845 (2012/06/15)
A novel class of 19 carbamates was synthesized, and their anticonvulsant activity was comparatively evaluated in the rat maximal electroshock (MES) and subcutaneous metrazol (scMet) seizure tests and pilocarpine-induced status epilepticus (SE) model. In spite of the alkyl-carbamates' close structural features, only compounds 34, 38, and 40 were active at the MES test. The analogues 2-ethyl-3-methyl-butyl-carbamate (34) and 2-ethyl-3-methyl-pentyl- carbamate (38) also exhibited potent activity in the pilocarpine-SE model 30 min postseizure onset. Extending the aliphatic side chains of homologous carbamates from 7 to 8 (34 to 35) and from 8 to 9 carbons in the homologues 38 and 43 decreased the activity in the pilocarpine-SE model from ED50 = 81 mg/kg (34) to 94 mg/kg (35) and from 96 mg/kg (38) to 114 mg/kg (43), respectively. The most potent carbamate, phenyl-ethyl-carbamate (47) (MES ED50 = 16 mg/kg) contains an aromatic moiety in its structure. Compounds 34, 38, 40, and 47 offer the optimal efficacy-safety profile and, consequently, are promising candidates for development as new antiepileptics.
Synthesis and evaluation of antiallodynic and anticonvulsant activity of novel amide and urea derivatives of valproic acid analogues
Kaufmann, Dan,Bialer, Meir,Shimshoni, Jakob Avi,Devor, Marshall,Yagen, Boris
experimental part, p. 7236 - 7248 (2010/07/04)
Valproic acid (VPA, 1) is a major broad spectrum antiepileptic and central nervous system drug widely used to treat epilepsy, bipolar disorder, and migraine. VPA's clinical use is limited by two severe and lifethreatening side effects, teratogenicity and hepatotoxicity. A number of VPA analogues and their amide, N-methylamide and urea derivatives, were synthesized and evaluated in animal models of neuropathic pain and epilepsy. Among these, two amide and two urea derivatives of 1 showed the highest potency as antineuropathic pain compounds, with ED50 values of 49 and 51 mg/kg for the amides (19 and 20) and 49 and 74 mg/kg for the urea derivatives (29 and 33), respectively. 19, 20, and 29 were equipotent to gabapentin, a leading drug for the treatment of neuropathic pain. These data indicate strong potential for the above-mentioned novel compounds as candidates for future drug development for the treatment of neuropathic pain. 2009 American Chemical Society.
SYNTHESIS OF (24R)-HOMOBRASSINOLIDE
Khripach, V.A.,Zhabinskii, V.N.,Ol'khovik, V.K.
, p. 352 - 356 (2007/10/02)
The synthesis from stigmasterol of C-29 brassinosteroids containing an (R)-ethyl group at C24 - (24R)-homocastasterone and (24R)-homobrassinolide - is described.The structure of the carbon skeleton of the side-chain was achieved by condensing a C-22 aldeh
Specificities of the α-Alkynone Cyclization
Karpf, Martin,Huguet, Joan,Dreiding, Andre S.
, p. 13 - 25 (2007/10/02)
Die Regio- und Stereospezifitaeten der α-Alkinon-Cyclisierung, einer thermischen Umwandlung von Alkinyl-alkyl-ketonen, welche in β'-Stellung mindestens ein H-Atom tragen, zu 2-Cyclopentenonen wurden untersucht.Cyclisierung zum hoeher substituierten C(β')-Atom ist dabei bevorzugt, vorausgesetzt, dass die zur Insertion zur Verfuegung stehende C(β'),H-Bindung zur Propioloylseitenkette eine moeglichst synplanare Anordnung einnehmen kann.In Cyclisierungen zu β'-Methylen-C-Atomen, welche diastereotope H-Atome tragen, wird daher eines der moeglichen epimeren Produkte bevorzugt oder ausschliesslich gebildet.Die mechanistischen Konsequenzen der gefundenen Specifitaeten werden diskutiert.
