23173-26-4

Basic information

• Product Name: Apovincaminol
• Synonyms: Apovincaminol;(3α,16α)-Eburnamenine-14-methanol
• CAS NO: 23173-26-4
• Molecular Formula: C₂₀H₂₄N₂O
• Molecular Weight: 308.41736
• Mol File: 23173-26-4.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Apovincaminol(CAS DataBase Reference)
• NIST Chemistry Reference: Apovincaminol(23173-26-4)
• EPA Substance Registry System: Apovincaminol(23173-26-4)

Safety Data

• Hazardous Substances Data: 23173-26-4(Hazardous Substances Data)

Upstream product

• 53412-07-0 (4¹S,13aS)-13a-ethyl-2,3,4¹,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carbaldehyde 
• 1617-90-9 vincamin 
• 42971-09-5 Vinpocetine 
• 42971-09-5 ethyl eburnamenine-14-carboxylate 
• 186887-54-7 (1S,11aS,11bR)-11a-Ethyl-1-methoxy-10-methyl-1,2,4,5,11a,11b-hexahydro-3a,9b-diaza-benzo[cd]fluoranthen-3-one 
• 186887-52-5 (1S,11aS,11bS)-11a-Ethyl-1-methoxy-10-methyl-1,2,4,5,11a,11b-hexahydro-3a,9b-diaza-benzo[cd]fluoranthen-3-one 
• 186887-50-3 (11aS,11bS)-11a-Ethyl-10-methyl-4,5,11a,11b-tetrahydro-3a,9b-diaza-benzo[cd]fluoranthen-3-one 
• 186887-60-5 (11R,11aR,11bS)-11-Bromo-10-[1-bromo-meth-(E)-ylidene]-11a-ethyl-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene 
• 186887-58-1 (11aS,11bS)-11a-Ethyl-10-methyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene 
• 4880-92-6 apovincamine 

Relevant articles and documents

Studies in the eburnane series: A new dimerization process

The behaviour of the synthetic (-)-16-(aminomethyl)eburnamenine (prepared from apovincamine) with formaldehyde was studied. Carrying out the reaction in acetic acid led to an original dimer, while in trifluoroacetic acid a 12-functionalized eburnamonine was isolated.

Design, synthesis and biological evaluation of vincamine derivatives as potential pancreatic β-cells protective agents for the treatment of type 2 diabetes mellitus

A series of vincamine derivatives were designed, synthesized and evaluated as pancreatic β-cells protective agents for type 2 diabetes mellitus. Most of the compounds displayed potent pancreatic β-cells protective activities and five derivatives were found to exhibit 20–50-fold higher activities than vincamine. Especially for compounds Vin-C01 and Vin-F03, exhibited a remarkable EC50 value of 0.22 μM and 0.27 μM, respectively. Their pancreatic β-cells protective activities increased approximately 2 times than vincamine. In cell viability assay, compounds Vin-C01 and Vin-F03 could effectively promote β-cell survival and protect β-cells from STZ-induced apoptosis. Further cellular mechanism of action studies demonstrated that their potent β-cells protective activities were achieved by regulating IRS2/PI3K/Akt signaling pathway. The present study evidently showed that compounds Vin-C01 and Vin-F03 were two more potent pancreatic β-cells protective agents compared to vincamine and might serve as promising lead candidates for the treatment of type 2 diabetes mellitus.

General and Phosphine-Free Cobalt-Catalyzed Hydrogenation of Esters to Alcohols

Catalytic hydrogenation of esters is essential for the sustainable production of alcohols in organic synthesis and chemical industry. Herein, we describe the first non-noble metal catalytic system that enables an efficient hydrogenation of non-activated esters to alcohols in the absence of phosphine ligands (with a maximum turnover number of 2391). The general applicability of this protocol was demonstrated by the high-yielding hydrogenation of 39 ester substrates including aromatic/aliphatic esters, lactones, polyesters and various pharmaceutical molecules.