BIOMAT Database Logo BIOMAT Database Logo

Synthesis of 11-phenyl-2,3,4,5-tetrahydro-1H-(1,4)diazepino(1,2-a)indoles and 1-(3-aminopropyl)-2-hydroxymethyl-3-phenylindoles as 5-hydroxytryptamine antagonists. 1990

S B Rajur, and A Y Merwade, and L D Basanagoudar
Department of Chemistry, Karnatak University, Dharwad, India.

A series of novel 11-phenyl-2,3,4,5-tetrahydro-1H-(1,4)diazepino(1,2-a) indoles (5a-f) and 1-(3-aminopropyl)-2-hydroxymethyl-3-phenylindoles (6a-f) are reported. The compounds (5a-f) were prepared by the lithium aluminum hydride (LAH) reduction of corresponding 11-phenyl-1H-1-oxo-2,3,4,5-tetrahydro(1,4)diazepino(1,2-a)indoles (4a-f). The precursors (4a-f) were, in turn, prepared by the catalytic reduction of 1-(2-cyanoethyl)-3-phenylindole-2-carboxylates (2a-f) and cyclization of the resulting 1-(3-aminopropyl)-3-phenylindole-2-carboxylates (3a-f) with sodium hydride in xylene. The LAH reduction of 2a-f gave exclusively 1-(3-aminopropyl)-2-hydroxymethyl-3-phenylindoles (6a-f) and not the diazepinoindoles (5a-f) which were expected. The title compounds and the intermediates have been screened for their anti-5-hydroxytryptamine (anti-5-HT) activity. The most potent anti-5-HT compounds of this series, 6a and 6e, were found to be weak compared with cyproheptadiene, a standard anti-5-HT drug.

UI MeSH Term Description Entries
D007082 Ileum The distal and narrowest portion of the SMALL INTESTINE, between the JEJUNUM and the ILEOCECAL VALVE of the LARGE INTESTINE.
D007211 Indoles Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D008297 Male Males
D009119 Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments. Inotropism,Muscular Contraction,Contraction, Muscle,Contraction, Muscular,Contractions, Muscle,Contractions, Muscular,Inotropisms,Muscle Contractions,Muscular Contractions
D009130 Muscle, Smooth Unstriated and unstriped muscle, one of the muscles of the internal organs, blood vessels, hair follicles, etc. Contractile elements are elongated, usually spindle-shaped cells with centrally located nuclei. Smooth muscle fibers are bound together into sheets or bundles by reticular fibers and frequently elastic nets are also abundant. (From Stedman, 25th ed) Muscle, Involuntary,Smooth Muscle,Involuntary Muscle,Involuntary Muscles,Muscles, Involuntary,Muscles, Smooth,Smooth Muscles
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D005260 Female Females
D006168 Guinea Pigs A common name used for the genus Cavia. The most common species is Cavia porcellus which is the domesticated guinea pig used for pets and biomedical research. Cavia,Cavia porcellus,Guinea Pig,Pig, Guinea,Pigs, Guinea
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D001381 Azepines Seven membered heterocyclic rings containing a NITROGEN atom. Hexamethyleneimines

Related Publications

S B Rajur, and A Y Merwade, and L D Basanagoudar
[Pyrazine-1,2-a-and 1,4-diazepino-1-2-1-indoles. I. Synthesis of 10-phenyl-1,2,3,4-yrytshyftopytsxino-1,2-a-indoles and of 11-phenyl-2,3,4,5-tetrahydro-1H-1,4-diazepino-1,2-a-indoles].
May 1974, Il Farmaco; edizione scientifica,
S B Rajur, and A Y Merwade, and L D Basanagoudar
[Pyrazino (1,2-a)- and 1,4-diazepino(1,2-a)indoles. II. Synthesis of 1-substituted 10-phenyl-3,4-dihydropyrazino(1,2-a)indoles and of 11-phenyl-4,5-dihydro-4H-diazepino(1,2-a)indoles].
January 1975, Il Farmaco; edizione scientifica,
S B Rajur, and A Y Merwade, and L D Basanagoudar
2,3,4,5-tetrahydro- and 2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indoles: new templates for 5-HT(2C) agonists.
July 2003, Bioorganic & medicinal chemistry letters,
S B Rajur, and A Y Merwade, and L D Basanagoudar
[Pyrazino(1,2-a)- and 1,4-diazepino(1,2-a)- indoles. III. Synthesis of pyrrolo(2',1':3,4)pyrazino(1,2-a)indoles and pyrrolo(2',1':3,4)-1,4-diazepino(1,2-a) indoles; isoindolo(2',1':3,4)pyrazino(1,2-a)-indoles and isoindolo(2',1':3,4)-1,4-diazepino(1,2-a)indoles; pyrazino(3,2,1-jk)- carbazoles and 1,4-diazepino(3,2,1-jk) carbazoles].
August 1975, Il Farmaco; edizione scientifica,
S B Rajur, and A Y Merwade, and L D Basanagoudar
Analgesic antagonists. I. 4-substituted 1-acyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepines.
January 1966, Journal of medicinal chemistry,
S B Rajur, and A Y Merwade, and L D Basanagoudar
Synthesis and pharmacological evaluation of new 1-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines as norepinephrine potentiators.
May 2009, Chemical & pharmaceutical bulletin,
S B Rajur, and A Y Merwade, and L D Basanagoudar
Synthesis and biological evaluation of novel 5,8-disubstituted-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b] indoles as 5-HT(6) and H(1) receptors antagonists.
December 2009, Archiv der Pharmazie,
S B Rajur, and A Y Merwade, and L D Basanagoudar
The synthesis of novel heteroaryl-fused 7,8,9,10-tetrahydro-6H-azepino[1,2-a]indoles, 4-oxo-2,3-dihydro-1H-[1,4]diazepino[1,7-a]indoles and 1,2,4,5-tetrahydro-[1,4]oxazepino[4,5-a]indoles. Effective inhibitors of HCV NS5B polymerase.
October 2011, Organic & biomolecular chemistry,
S B Rajur, and A Y Merwade, and L D Basanagoudar
Synthesis and structure-activity relationships of 4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indoles: novel PDE4 inhibitors.
January 2000, Bioorganic & medicinal chemistry letters,
S B Rajur, and A Y Merwade, and L D Basanagoudar
Synthesis and biological evaluation of tetrahydro[1,4]diazepino[1,2-a]indol-1-ones as cyclin-dependent kinase inhibitors.
August 2014, European journal of medicinal chemistry,
Copied contents to your clipboard!