An unusual stereospecific reduction of some basic side-chain substituted indoles.

Berger, Joel G.; Teller, Sonia R.; Adams, Charlotte; Guggenberger, L. J.

doi:10.1016/s0040-4039(00)75262-2

Cited by 25 publications

(12 citation statements)

References 4 publications

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“…HCl [133]. This demonstrates how much the reaction conditions (in this case the order of addition of the reagents) can affect the stereochemistry of the reduction process.…”

Section: Synthesis Of Cis-derivativesmentioning

confidence: 87%

“…Another effective method for the stereospecific reduction of 1,2,3,4-tetrahydro-γ-carbolines to the cishexahydro-γ-carboline derivative uses metallic sodium in liquid ammonia [132][133][134]. Yet another promising method that makes it possible to realize the stereospecific reduction of tetrahydro-γ-carboline derivatives uses triethylsilane in trifluoroacetic acid [64,135].…”

Section: Synthesis Of Cis-derivativesmentioning

confidence: 99%

“…For example, it was shown that as a result of nonoxidative photocyclization N-arylenamines can be converted into the corresponding trans-hexa-hydro-γ-carbolines with the formation of the C(9a)-C(9b) bond and with observance of the orbital symmetry rules [133] by analogy with the process leading to trans-hexahydrocarbazoles [145]. Thus, the published data covered in the review demonstrate the variety of methods available for the synthesis of hydrogenated derivatives of γ-carbolines; this makes it possible to obtain an enormous range of varied prospective derivatives in the search for biologically active compounds having a broad spectrum of activity.…”

Section: Synthesis Of Cis-derivativesmentioning

confidence: 99%

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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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“…HCl [133]. This demonstrates how much the reaction conditions (in this case the order of addition of the reagents) can affect the stereochemistry of the reduction process.…”

Section: Synthesis Of Cis-derivativesmentioning

confidence: 87%

Section: Synthesis Of Cis-derivativesmentioning

confidence: 99%

Section: Synthesis Of Cis-derivativesmentioning

confidence: 99%

See 1 more Smart Citation

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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“…On the other hand, when hydrolysis of the boron complexes was effected with hydrochloric acid the pyridylmethylindoline XVIII was also isolated. Its formation is interpreted on the basis of the indole protonation and further reduction by intramolecular hydride transfer from the pyridine-borane adduct (30). In the nmr spectrum of indoline XVIII the absence of the indole fi proton and an upfield shift of its N-methyl group were observed.…”

Section: Vol 18mentioning

confidence: 96%

Benzomorphan related compounds. XIV. Synthesis of 2‐(2‐pyrrolylmethyl)‐ and 2‐(2‐indolylmethyl)tetrahydropyridines and cyclization to pyrrolo[3,2‐f]morphans

Bosch

Mauleón

Boncompte

et al. 1981

Journal of Heterocyclic Chem

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The synthesis of 2‐{2‐pyrrolylmethyl)‐ and 2‐(2‐indolylmethyl)tetrahydropyridines by condensation of 2‐cyanopyridines with appropriate pyrrole or indole derivatives followed by ketone reduction, quaternization and sodium borohydride reduction are described. The acid‐induced cyclization of 2‐(2‐pyrrolylmethyl)tetrahydropyridines affords 4,5,6,7,8,9‐hexahydro‐4,8‐methanopyrrolo[2,3‐d]azocine systems (pyrrolo[3,2‐f]‐morphans), although the method fails with N‐benzyl substituted pyrroles. The acid treatment of 2‐(2‐indolylmethyl)tetrahydropyridines and of 2‐indolyl tetrahydro‐2‐pyridyl ketones is not a suitable procedure for the preparation of indolo[3,2‐f]morphans, because of the protonation of indole nucleus or carbonyl group, respectively.

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“…Reduction of tetrahydro-γ-carbolines to the corresponding trans hexahydro derivatives is carried out, as a rule, using borane or its complexes with subsequent treatment with strong acid [21]. The key stage in this process is the formation of a borane-tetrahydro-γ-carboline complex at the N(2) atom.…”

mentioning

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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An unusual stereospecific reduction of some basic side-chain substituted indoles.

Cited by 25 publications

References 4 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)

Benzomorphan related compounds. XIV. Synthesis of 2‐(2‐pyrrolylmethyl)‐ and 2‐(2‐indolylmethyl)tetrahydropyridines and cyclization to pyrrolo[3,2‐f]morphans

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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