Structure of Vincamine

Trojánek, J.; Štrouf, O.; Holubek, J.; Čekan, Z.

doi:10.1016/s0040-4039(01)91678-8

Cited by 28 publications

(3 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Vincamine, the ''mother compound'' of cerebrally active eburnamine derivatives was first isolated from the leaves of Vinca minor L. by Zabolatnaya 3 and independently by Schlittler and Furlenmejer. 4 Its structure was elucidated by Trojanek et al 5 Szász et al 6 was the first to work out a new method for the isolation of vincamine in a larger quantity. The first pharmacological studies were done by Raymond-Hamet 7 and Quevauviller et al 8 These studies demonstrated the beneficial effect of vincamine on circulation by decreasing arterial blood pressure, cardiac output, and heart rate.…”

Section: E B U R N a M I N E S T R U C T U R E S W I T H C E R E B mentioning

confidence: 99%

Eburnamine derivatives and the brain

Vas

Gulyás

2005

Medicinal Research Reviews

100

View full text Add to dashboard Cite

The Apocynaceae plant family contains a great number of so called eburnamine-vincamine alkaloids. Quite a few of these alkaloids exert varied pharmacological activities on the cell multiplication, cardiovascular system, and brain functions. Many derivatives were also synthesized to find pharmacologically active compounds better characterized and safer to be administered than the natural plant alkaloids themselves. We concentrate on the eburnamine structures with cerebral activities in this review. Vincamine, vinburnine, vindeburnol, apovincaminate, and vinpocetine (cis-ethyl-apovincaminate) all share modulatory effects on brain circulation and neuronal homeostasis, bear antihypoxic and neuroprotective potencies to various degrees. The most eminent compound of this class of alkaloids is vinpocetine. Since its introduction to the market as a neuroprotective agent many non clinical and clinical studies proved vinpocetine's effects on calmodulin dependent phosphodiesterase E1, on sodium, calcium channels, peripheral benzodiazepine receptor, and glutamate receptors as well as its clinical usefulness in the treatment of post-ischaemic stroke disease states and various disorders of cerebrovascular origin. Lately, positron emission tomography studies proved that vinpocetine has a rapid uptake in the primate and human brain with a heterogeneous distribution pattern (preference areas: thalamus, basal ganglia, and visual cortex) both after intravenous and oral administration. Vinpocetine exerts beneficial effects in cerebral glucose metabolism and regional cerebral blood flow in chronic post-stroke patients.

show abstract

Section: E B U R N a M I N E S T R U C T U R E S W I T H C E R E B mentioning

confidence: 99%

Eburnamine derivatives and the brain

Vas

Gulyás

2005

Medicinal Research Reviews

100

View full text Add to dashboard Cite

show abstract

“…In the present investigation, (nitrooxy)alkyl apovincaminates were synthesized and evaluated for their effects on vertebral and femoral blood flow. Also, the structures of 5 and 2 were determined by X-ray crystallography.vinpocetine (2) brovincamine (3)…”

mentioning

confidence: 99%

Synthesis and pharmacological evaluation of (nitrooxy)alkyl apovincaminate

Kawashima¹,

Ikemoto²,

Horiguchi³

et al. 1993

J. Med. Chem.

View full text Add to dashboard Cite

A series of (nitrooxy)alkyl apovincaminates has been synthesized and evaluated for their effects on vertebral and femoral blood flow. These derivatives were prepared from apovincaminic acid (4). In cerebral circulation, compound 5 (0.03-1.0 mg/kg iv) caused a dose-dependent increase in cerebral blood flow (CerBF) without affecting the blood pressure. It was more potent than vinpocetine (2). The structures of 2 and 5, determined by X-ray crystallography, showed differences in the electrostatic potential image and in the conformation of the ethyl group at the 16-position.

show abstract

“…Vincaminyl In the course of our investigations of the structures of vincamine and other alkaloids of Vinca minor, prior to the publication of the structure of vincamine by Trojanek, et al,2 we also studied the reduction of vincamine by lithium aluminum hydride. By means of lithium aluminum hydride vincamine was reduced to an amino alcohol which we have named vincaminyl alcohol.…”

mentioning

confidence: 99%

Experiments in the Synthesis of Pyridinium Amidines and Imino Esters

Poziomek¹

1963

J. Org. Chem.

View full text Add to dashboard Cite

The filtrate was freed of solvent by heating in vacuo.Vacuum distillation of the oily residue yielded 17.5 g. of unchanged indole (b.p. 90-110°/0.1-0.3 mm.) and 3.4 g. 3-indoleacetonitrile (0.021 mole; 14.5% yield at 6.5% conversion) (b.p. 160-180°/ 0.2 mm.). The nitrile was characterized as its 1,3,5-trinitrobenzene complex, m.p. 138-139.5°.Carrying out the above procedure with alumina (6 g., Alcoa F-20) and potassium acetate (5 g., 0.05 mole) in place of the dipotassium phosphate produced 3-indoleacetic acid in 55% yield and 3,3'-dimdolylmethane in 20% yield.3-Indoleacetonitrile from 1 -Acetyl-3-acetoxymethylindole.-1 -Acetyl-3-acetoxymethylindole (4.6 g., 0.02 mole) and potassium cyanide (2.6 g., 0.04 mole) were placed in ethanol (30 ml.) and water (30 ml.) and the mixture refluxed gently for 4 hr.Most of the solvent was then removed by heating in vacuo, and the residue obtained extracted with ether (three 50-ml. portions).These extracts were combined, dried over anhydrous sodium carbonate, and the ether removed by gentle heating. The residue (2.4 g.) was vacuum distilled and yielded 1.2 g. (0.0076 mole, 38%) 3-indoleacetonitrile (b.p. 155-163 °/0.10-0.15 mm.). The product was characterized as its 1,3,5-trinitrobenzene adduct, m.p. 138.5-139.5°.

show abstract

Structure of Vincamine

Cited by 28 publications

References 12 publications

Eburnamine derivatives and the brain

Eburnamine derivatives and the brain

Synthesis and pharmacological evaluation of (nitrooxy)alkyl apovincaminate

Experiments in the Synthesis of Pyridinium Amidines and Imino Esters

Contact Info

Product

Resources

About