ChemInform Abstract: STEREOSPECIFIC REDUCTION OF 1,2,3,4‐TETRAHYDRO‐Γ‐CARBOLINES BY BORON HYDRIDES

Zagorevskii, V. A.; Rozenberg, Sylvie; Sipilina, N. M.; Bykova, L. U.; Rodionov, A. P.

doi:10.1002/chin.198226193

Cited by 2 publications

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“…A modification of the method provides for the production of borane-tetrahydro-γ-carboline complexes by the action of BH 3 , generated in situ from sodium borohydride and the hydrochloride of the tetrahydro-γ-carboline derivative [136]. Tetrahydro-γ-carbolines containing a secondary N(2) atom do not undergo trans reduction under the influence of borane in hydrochloric acid.…”

Section: Synthesis Of Cis-derivativesmentioning

confidence: 99%

γ-Carbolines and their hydrogenated derivatives. 2.* Hydrogenated derivatives of γ-carbolines: methods of synthesis (review)

Alekseyev

Kurkin

Yurovskaya

2010

Chem Heterocycl Comp

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Section: Synthesis Of Cis-derivativesmentioning

confidence: 99%

γ-Carbolines and their hydrogenated derivatives. 2.* Hydrogenated derivatives of γ-carbolines: methods of synthesis (review)

Alekseyev

Kurkin

Yurovskaya

2010

Chem Heterocycl Comp

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“…Reduction with hydrogen over PtO 2 [13], with borane complexes with THF [14], with pyridine [15] or trimethylamine [16] in strongly acidic medium, NaBH 4 in carboxylic acids (as a rule in CF 3 CO 2 H) [17], and also with metallic Na in liquid ammonia [18] or triethylsilane in CF 3 CO 2 H [19] lead to the formation of isomers of hexahydro-γ-carbolines with a cis junction of the pyrroline and piperidine rings. In addition, reduction with Zn or Sn in acidic medium is mainly accompanied by the formation of the corresponding cis isomer [20].…”

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confidence: 99%

Stereoselective reduction of the active substance of the medicinal preparation dimeb n to the corresponding cis- and trans-1,2,3,4,4a,9b-hexahydro derivatives

Alekseyev

Иванов

Kurkin

et al. 2011

Chem Heterocycl Comp

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distinguished by a high degree of stereoselectivity. The structures of the obtained diastereomeric hexahydro-γ-carbolines were confirmed by various physicochemical methods, including X-ray structural analysis. Chemical modification of lead-compounds is one of the methods of creating and searching for new biologically active compounds, on the basis of which medicinal agents may be created which possess larger effect in comparison with the precursors [1]. Very frequently lead-compounds become known drugs released onto the market [2]. One of such lead-compounds without doubt is the original domestic preparation Dimebon (2,8-dimethyl-5-[2-(6-methylpyrid-3-yl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole, 1), which possesses a broad pharmacological profile [3]. At the present time it is used in medical practice as an antihistamine agent [4]. In addition Dimebon displays cardioprotective [5] and antiarrhythmic properties [6], it shows an effect on the transmission of nerve impulses and the metabolism of catecholamines in brain structures [7], protects neurons from the neurotoxic action of β-amyloid (EC 50 = 25μM), displays the action of a calcium channel blocker (IC 50 = 57 μM), it has inhibiting activity in relation to cholinesterases (IC 50 = 7.9 μM and 42 μM for butyryl-and acetylcholinesterase respectively) [8], and demonstrates improvement of memory and cognitive ability. It is also a blocker of the NMDA subtype of glutamate receptors (ED 50 = 42 mg/kg), activating the

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ChemInform Abstract: STEREOSPECIFIC REDUCTION OF 1,2,3,4‐TETRAHYDRO‐Γ‐CARBOLINES BY BORON HYDRIDES

Cited by 2 publications

References 0 publications

γ-Carbolines and their hydrogenated derivatives. 2.* Hydrogenated derivatives of γ-carbolines: methods of synthesis (review)

γ-Carbolines and their hydrogenated derivatives. 2.* Hydrogenated derivatives of γ-carbolines: methods of synthesis (review)

Stereoselective reduction of the active substance of the medicinal preparation dimeb n to the corresponding cis- and trans-1,2,3,4,4a,9b-hexahydro derivatives

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