3-Aminotetrahydrocarbazoles as a new series of central nervous system agents

Abstract

3-Dimethylamino-1,2,3,4-tetrahydrocarbazole, a structurally modified tryptamine, prevented amphetamine-induced stereotyped behavior in rats and prevented reserpine-induced ptosis in mice. Further study of this compound and a number of substituted derivatives indicated that either imipramine-like or chlorpromazine-like profiles were obtainable by changing substituents and their positions.

Synthesis of novel Mannich bases and hybrid Mannich bases related to isoindolin‐1,3‐dione

“…In addition, 1 was treated with formaldehyde and 6‐aminomethyl‐1,2,3,4‐tetrahydrocarbazole to give the bis‐(Mannich base): N , N ‐di((1,3‐dioxoisoindolin‐2‐yl)methyl)‐6‐aminomethyl‐1,2,3,4‐tetrahydrocarbazole ( 5 ). The formation of 5 is of interest, because tetrahydrocarbazoles form the core of a wide range of alkaloids, and several strategies exist for their construction, since many of their derivatives exhibit a broad range of potential pharmacological activities, such as central nervous system activity , antihistamine , and anti‐inflammatory properties , whereas the synthesis of the bis‐(Mannich base) 6 has been achieved by treating 1 with N , N ′‐bis( p ‐methoxybenzylidene)ethylenediamine.…”

2-{4-Methyl-N-[(2,3,4,9-tetrahydro-1H-carbazol-3-yl)methyl]benzenesulfonamido}ethyl 4-methylbenzenesulfonate

“…For the syntheses of tetrahydrocarbazolonebased antitumor-active compounds from tetrahydrocarbazoles, see: Chen et al (2009). For the syntheses of aminotetrahydrocarbazoles as central nervous system agents, see: Mooradian et al (1977). For bond-length data, see: Allen et al (1987).…”

“…Tetrahydrocarbazolone based antitumor active compounds were synthesized from tetrahydrocarbazoles (Chen et al, 2009). Aminotetrahydrocarbazoles were also synthesized as central nervous system agents (Mooradian et al, 1977). The present study was undertaken to ascertain the crystal structure of the title compound.…”

3-Methyl-3,4-dihydro-9H-carbazol-1(2H)-one

“…For the biological activity of substituted 2,3,4,9-tetrahydrocarbazoles, see: Mooradian et al (1977); Jean et al (2004); Biere et al (1973); Lacoume (1973). For carbazole alkaloids, such as clausenapin, murrayafoline-A, murrayafoline-B, murrayastine, murrayaquinone-A, with a methyl substituent at the C-3 position, see: Knolker & Reddy (2002).…”

“…Substituted 2,3,4,9-tetrahydrocarbazoles have been reported to possess many biological properties, such as central nervous system activity (Mooradian et al, 1977), antihistamine (Jean et al, 2004), antidiabetic (Biere et al, 1973) and anti-inflammatory properties (Lacoume, 1973). We have attached importance to the title compound since some of the carbazole alkaloids, such as clausenapin, murrayafoline-A, murrayafoline-B, murrayastine, murrayaquinone-A have the methyl group as substituent at the C-3 position (Knolker & Reddy, 2002).…”