STEREOSELECTIVE REDUCTION OF THE ACTIVE SUBSTANCE OF THE MEDICINAL PREPARATION DIMEBON TO THE CORRESPONDING cis- AND trans-1,2,3,4,4a,9b-HEXAHYDRO DERIVATIVES

被引：3

作者：

Alekseyev, R. S. ^{[1
]}

Ivanov, A. S. ^{[1
]}

Kurkin, A. V. ^{[1
]}

Yurovskaya, M. A. ^{[1
]}

机构：

[1] Moscow MV Lomonosov State Univ, Moscow 199992, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2011年 / 46卷 / 10期

关键词：

Dimebon; 1,2,3,4-tetrahydro-gamma-carbolines; 1,2,3,4,4a,9b-hexahydro-gamma-carbolines; stereoselective reduction; STEREOSPECIFIC REDUCTION; INDOLES;

D O I：

10.1007/s10593-011-0658-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Convenient preparative methods have been developed for the reduction of the active substance of the medicinal preparation Dimebon (2,8-dimethyl-5-[2-(6-methylpyrid-3-yl)ethyl]-1,2,3,4-tetrahydro-gamma-carboline) to the corresponding racemic cis- and trans-1,2,3,4,4a,9b-hexahydro derivatives, distinguished by a high degree of stereoselectivity. The structures of the obtained diastereomeric hexahydro-gamma-carbolines were confirmed by various physicochemical methods, including X-ray structural analysis.

引用

页码：1239 / 1249

页数：11

共 50 条

[21] A NEW AND FACILE STEREOSELECTIVE SYNTHESIS OF CIS-4A-ARYL-1,2,3,4,4A,5,6,8A-OCTAHYDROISOQUINOLINE DERIVATIVES
KANO, S
YOKOMATSU, T
YUASA, Y
SHIBUYA, S
CHEMISTRY LETTERS, 1982, (12) : 1915 - 1918
[22] PREPARATION AND ASSIGNMENT OF CONFIGURATION OF CIS-2,3,4,4A,5,6-HEXAHYDRO-2-NAPHTHALENOL AND TRANS-2,3,4,4A,5,6-HEXAHYDRO-2-NAPHTHALENOL
UNDERINER, TL
GOERING, HL
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05): : 897 - 900
[23] THE RELATIVE STABILITIES OF SUBSTITUTED CIS AND TRANS-1,2,3,4,4A,9,10,10A-OCTAHYDROPHENANTHRENES, INCLUDING CONFIGURATIONAL CORRECTIONS IN THE ELAD-GINSBURG MORPHINE SYNTHESIS
DUTHALER, RO
GINSBURG, D
HELVETICA CHIMICA ACTA, 1986, 69 (07) : 1559 - 1566
[24] STUDIES ON ERGOT ALKALOIDS AND RELATED COMPOUNDS .15. REDUCTIONS OF CIS- AND TRANS-4-METHYL-2-METHYLEN-3-OXO-1,2,3,4,4A,5,6,10B-OCTAHYDROBENZO[F]QUINOLINES AND PREPARATION OF TRANS-SYN-2,4-DIMETHYL-1,2,3,4,4A,5,6,10B-OCTAHYDROBENZO-[F]QUINOLINE
HORII, ZI
KURIHARA, T
NINOMIYA, I
CHEMICAL & PHARMACEUTICAL BULLETIN, 1968, 16 (04) : 668 - +
[25] PHOTOCYCLISATION OF AN AROYLCYCLOHEXENE SYNTHESIS OF CIS-1,2,3,4,4A,9A-HEXAHYDRO-1-METHYL-6-METHOXY-9-OXOFLUORENE-1-CARBOXYLIC ACID
JACKMAN, LM
STEPHENS.EF
YICK, HC
TETRAHEDRON LETTERS, 1970, (38) : 3325 - &
[26] SYNTHESIS + EXHAUSTIVE METHYLATION OF CIS + TRANS ISOMERS OF 1,2,3,4,4A,5,6,10B-OCTAHYDROPHENANTHRIDINE + 1,2,3,4,4A,5,6,10B-OCTAHYDROBENZO)F)QUINOLINE
MASAMUNE, T
IWADARE, T
OHNO, M
OHUCHI, S
KOSHI, M
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (06): : 1419 - &
[27] CHEMISTRY OF PHOTODIMERS OF MALEIC AND FUMARIC ACID DERIVATIVES .2. PREPARATION OF CIS,TRANS,CIS- AND TRANS,TRANS,TRANS-1,2,3,4-TETRABENZOYLCYCLOBUTANE - ACID CHLORIDES OF 1,2,3,4-TETRACARBOXYCYCLOBUTANES
GRIFFIN, GW
VEBER, DF
HAGER, RB
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (06) : 1008 - &
[28] AMPHETAMINE DERIVATIVES - 10(E)-AMINO-1,2,3,4,4A,9,10,10A-(TRANS-4A,10A)-OCTAHYDROPHENANTHRENE AND 10(A)-AMINO-1,2,3,4,4A,9,10,10A-(TRANS-4A,10A)-OCTAHYDROPHENANTHRENE
NELSON, WL
SHERWOOD, BE
JOURNAL OF PHARMACEUTICAL SCIENCES, 1974, 63 (09) : 1467 - 1468
[29] CIS-4-N-PROPYL-1,2,3,4,4A,5,6,10B-OCTAHYDROBENZO(F)QUINOLINE AND TRANS-4-N-PROPYL-1,2,3,4,4A,5,6,10B-OCTAHYDROBENZO(F)QUINOLINE
CANNON, JG
KOBLESUAREZ, C
LONG, JP
ILHAN, M
BHATNAGAR, RK
JOURNAL OF PHARMACEUTICAL SCIENCES, 1985, 74 (06) : 672 - 675
[30] SYNTHESIS AND DOPAMINERGIC ACTIVITY OF TRANS-6-METHYL-7A,8,9,10,11,11A-HEXAHYDRO-7H-PYRROLO[3,2,1-GH]-4,7-PHENANTHROLINE AND TRANS-1,2,3,4,4A,5,6,10B-OCTAHYDRO-4,7-PHENANTHROLINE DERIVATIVES
CLAUDI, F
CRISTALLI, G
MARTELLI, S
PERLINI, V
MASSI, M
VENTURI, F
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (06) : 1061 - 1065

← 1 2 3 4 5 →