42971-12-0

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl apovincaminate is used as a vasodilator for improving blood flow and reducing the risk of blood clot formation. Its vasodilating properties can be beneficial in treating conditions such as hypertension, peripheral vascular disease, and cerebral vascular insufficiency.
Used in Cardiovascular Applications:
In the field of cardiology, ethyl apovincaminate is used as a therapeutic agent for enhancing coronary blood flow and reducing the symptoms of angina pectoris. Its ability to dilate blood vessels can help alleviate chest pain and improve the overall cardiovascular health.
Used in Cerebral Insufficiency Treatment:
Ethyl apovincaminate is also used as a treatment for cerebral insufficiency, a condition characterized by reduced blood flow to the brain. By increasing blood flow, it can help improve cognitive function and reduce the risk of stroke and other neurological disorders.

InChI:InChI=1/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22+/m0/s1

Upstream product

• 74904-40-8 (10R,11R,11aS,11bR)-11a-Ethyl-11-hydroxy-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester 
• 105-39-5 chloroacetic acid ethyl ester 
• 51152-47-7 (1R*,5S*,12bS*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-carbaldehyde 
• 74904-40-8 (10S,11S,11aS,11bR)-11a-Ethyl-11-hydroxy-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester 
• 74904-40-8 (10S,11R,11aS,11bR)-11a-Ethyl-11-hydroxy-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester 
• 55390-29-9 1-ethyl-2,3,4,6,7,12-hexahydro-indolo(2,3-a)quinolizinium perchlorate 
• 74904-40-8 (10S,11S,11aS,11bS)-11a-Ethyl-11-hydroxy-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester 
• 74904-40-8 (10R,11R,11aS,11bS)-11a-Ethyl-11-hydroxy-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester 
• 43184-10-7 1α-ethyl-1-(2-hydroxy-2-ethoxycarbonylethyl)-1,2,3,4,6,7,12,12β-octahydroindolo-<2,3-a>quinolizine 
• 74904-38-4 (11aS,11bS)-11a-Ethyl-11-oxo-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester 
• 51049-28-6 14,15-dihydro-21-nor-1,14-secoeburnamenin-20-al 
• 74904-38-4 (11aS,11bR)-11a-Ethyl-11-oxo-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester 
• 66685-08-3 1-ethyl-2,3,4,6,7,12-hexahydroindolo<2,3-a>quinolizin-4(1H)-one 
• 66685-13-0 4-(4,9-dihydro-3H-β-carbolin-1-yl)-hexanoic acid methyl ester 

Downstream Products

• 23173-26-4 ((4¹S,13aS)-13a-ethyl-2,3,4¹,5,6,13a-hexahydro-1H-indolyl[3,2,1-de]pyridyl[3,2,1-ij][1,5]naphthyridine-12-yl)methanol 

Relevant academic research and scientific papers

A NEW APPROACH TO (+/-)-APOVINCAMINE

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

New synthetic analogs of Vinca minor alkaloids were described, together with a new total synthesis of ethyl apovincaminate.