77549-94-1Relevant articles and documents
Synthesis and evaluation of 2′-hydroxyethyl trans-apovincaminate derivatives as antioxidant and cognitive enhancer agents
Nemes, András,Czibula, László,Szántay Jr., Csaba,Gere, Anikó,Kiss, Béla,Laszy, Judit,Gyertyán, István,Szombathelyi, Zsolt,Szántay, Csaba
, p. 479 - 486 (2008/09/18)
A series of trans-2′-hydroxyethyl and 2′-acyloxyethyl apovincaminates 4b-f and 7b-f has been synthesized and evaluated for their antioxidant and antiamnesic effects. The new esters were prepared from 4a and 7a ethyl esters or from the corresponding carbox
Synthesis of pentacyclic ring systems, indolo[2,3-a][1,2]-oxazino[5,6-i]quinolizine and indolo[2,3-a]pyrano[3,2-i]-quinolizine, and their application for the synthesis of eburnamine-vincamine alkaloids
Nemes, Andras,Kreidl, Janos,Czibula, Laszlo,Nogradi, Katalin,Farkas, Maria,Szantay Jr., Csaba,Tarkanyi, Gabor,Balogh, Gabor,Juhasz, Ida,Kalman, Alajos,Parkanyi, Laszlo
, p. 1697 - 1711 (2007/10/03)
15a-Ethyl-14-carboxylic esters of the title pentacycles (6) and (8) were prepared via Wenkert's enamine (4). Both compounds can be readily transformed into indoloquinolizinylpyruvate oxime esters (5), key intermediates for the synthesis of vincamine alkal
Syntheses and Cardiovascular Activity of Stereoisomers and Derivatives of Eburnane Alkaloids
Czibula, Laszlo,Nemes, Andras,Visky, Gyoergy,Farkas, Maria,Szombathelyi, Zsolt,et al.
, p. 221 - 230 (2007/10/02)
The synthesis of all the possible isomers of the eburnamenine-vincamine type alkaloids 1b, 2a*, 3a and derivatives 4, 8, 9, 10 is described.Structures were determined by 1H- and 13C-NMR spectroscopy including special techniques such as DR, DEPT, DNOE, and 2D-HSC.In contrast to the known cerebrovascular effects of cis-(3S,16S) compounds, trans-(3S,16R) derivatives show a significant peripheral vasodilator effect. Key Word: Eburnanes / Alkaloids / Cardiovascular effects / Indoloquinolizines
A NEW APPROACH TO (+/-)-APOVINCAMINE
Danieli, Bruno,Lesma, Giordano,Palmisano, Giovanni
, p. 257 - 268 (2007/10/02)
A new approach to (+/-)-apovincamine, 2, is reported which bypasses the formation of (+/-)-vincamine, 1, and includes the dehydration of the β-hydroxy ester 7, obtained by regio-controlled alkylation of the stereochemically suitable aldehyde 6 with methyl chloroacetate.Using ethyl chloroacetate, the clinically useful apovincamine analogue, (+/-)-Cavinton, 3, is obtained. (+/-)-Apovincamine is then converted to (+/-)-vincamine, 1, by base-catalyzed oxygenation of the mixture of (+/-)-dihydroapovincamines 8 and 9.
Synthesis of Some Isotype Analogs of Vincamine, Eburnamonine and Eburnamine, and an Alternative Approach to Ethyl Apovincaminate
Ono, Keiichi,Kawakami, Hajime,Katsube, Junki
, p. 411 - 414 (2007/10/02)
New synthetic analogs of Vinca minor alkaloids were described, together with a new total synthesis of ethyl apovincaminate.