13754-86-4

Usage

Uses

1. Used in Pharmaceutical Synthesis:
1,5,6,7-Tetrahydro-4H-indol-4-one is used as a reactant in the synthesis of Psammopemmin A, an antitumor agent. Its unique structure makes it a valuable component in the development of new cancer treatments.
2. Used in Organic Chemistry:
1,5,6,7-Tetrahydro-4H-indol-4-one is used as a reactant in the synthesis of 1,3,4,5-tetrahydrobenzindole β-ketoesters and tricyclic tetrahydrobenzindoles via C-H insertion reactions. These compounds have potential applications in various chemical and pharmaceutical processes.
3. Used in Enzyme Inhibition:
1,5,6,7-Tetrahydro-4H-indol-4-one is used as a reactant in the preparation of tricyclic indole and dihydroindole derivatives, which act as inhibitors of guanylate cyclase. These inhibitors can be used in the development of drugs targeting specific enzyme pathways.
4. Used in Condensed Pyrroloindole Synthesis:
1,5,6,7-Tetrahydro-4H-indol-4-one is used as a reactant in the preparation of condensed pyrroloindoles via Pd-catalyzed intramolecular C-H bond functionalization of (halobenzyl)pyrroles. These condensed pyrroloindoles have potential applications in the development of novel pharmaceutical compounds.
5. Used in Asymmetric Synthesis:
1,5,6,7-Tetrahydro-4H-indol-4-one is used as a reactant in the enantioselective preparation of arylalkenyl indoles via asymmetric C-H insertion of rhodium carbenoids. This process allows for the creation of chiral molecules with specific configurations, which can be crucial in the development of effective drugs with minimal side effects.

InChI:InChI=1/C8H9NO/c10-8-3-1-2-7-6(8)4-5-9-7/h4-5,9H,1-3H2

Upstream product

• 56671-28-4 4,5,6,7-tetrahydro-4-oxobenzofuran-3-carboxylic acid 
• 504-02-9 1,3-cylohexanedione 
• 109-92-2 ethyl vinyl ether 
• 16806-93-2 4-oxo-4,5,6,7-tetrahydrobenzofuran 
• 76327-74-7 2-ethoxy-2,3,6,7-tetrahydrobenzofuran-4(5H)-one 
• 110545-27-2 (S)-3-((1S,2R,3R,4R)-1,2,3,4,5-Pentahydroxy-pentyl)-1,2,3,5,6,7-hexahydro-indol-4-one 
• 110545-27-2 (S)-3-((1S,2R,3S,4R)-1,2,3,4,5-Pentahydroxy-pentyl)-1,2,3,5,6,7-hexahydro-indol-4-one 
• 16179-66-1 3-((2-hydroxyethyl)amino)cyclohex-2-enone 
• 879214-86-5 3-[(2,2-diethoxyethyl)amino]cyclohex-2-en-1-one 
• 35768-38-8 3-hydroxy-3,5,6,7-tetrahydro-2H-benzofuran-4-one 
• 110545-25-0 Acetic acid (1S,2R,3R,4R)-2,3,4,5-tetraacetoxy-1-((S)-4-oxo-2,3,4,5,6,7-hexahydro-1H-indol-3-yl)-pentyl ester 
• 110545-25-0 (3S)-3-(1,2,3,4,5-penta-O-acetyl-D-galacto-pentitol-1-yl)-1,2,3,5,6,7-hexahydroindol-4-one 
• 141-43-5 ethanolamine 
• 76327-75-8 2-(2',2'-diethoxyethyl)-1,3-cyclohexanedione 

Downstream Products

• 87549-07-3 1-(2-phenylsulfonylethyl)-4-oxo-4,5,6,7-tetrahydroindole 
• 13618-91-2 4,5,6,7-tetrahydroindole 
• 2380-94-1 1H-indol-4-ol 
• 95991-85-8 5-Chloro-1,5,6,7-tetrahydro-indol-4-one 
• 27866-27-9 1,5,6,7-tetrahydro-indol-4-one oxime 
• 392232-66-5 benzyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-1-carboxylate 
• 877170-76-8 4-oxo-4,5,6,7-tetrahydro-indole-1-carboxylic acid tert-butyl ester 
• 442563-32-8 1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine 
• 186808-28-6 (4-Nitro-phenyl)-(5,6,7,8-tetrahydro-1H-pyrrolo[3,2-b]azepin-4-yl)-methanone 
• 186808-30-0 (1-Methyl-5,6,7,8-tetrahydro-1H-pyrrolo[3,2-b]azepin-4-yl)-(4-nitro-phenyl)-methanone 
• 120-72-9 indole 
• 2380-84-9 7-Indolol 
• 13307-67-0 ethyl 1H-indole-1-carboxylate 
• 73-22-3 L-Tryptophan 

Relevant academic research and scientific papers

ISOQUINOLINESULFONYL DERIVATIVE AS RHO KINASE INHIBITOR

The present invention discloses a class of isoquinolinesulfonyl derivatives as RHO kinase inhibitors, and pharmaceutical compositions thereof, and relates to pharmaceutically acceptable uses thereof. Specifically, the present invention relates to a compound as represented by formula (I), or a pharmaceutically acceptable salt thereof.

Formation of N-substituted 4- and 7-oxo-4,5,6,7-tetrahydroindoles revisited: A mechanistic interpretation and conversion into 4- and 7-oxoindoles

An efficient method for the preparation of 4-oxo-4,5,6,7-tetrahydroindoles was successfully applied to the synthesis of N-substituted 7-oxo-4,5,6,7- tetrahydroindoles for the first time. Both isomers where converted into their corresponding 4- and 7-oxoindoles in good yields utilizing a novel aromatization protocol. Based on the impurity profile obtained, however, different mechanisms for the formation of the 4- and 7-oxo-4,5,6,7-tetrahydroindole derivatives are discussed. In addition, the reaction sequences appear to be stereospecific allowing for the direct introduction of a chiral center α to the nitrogen and preparation of enantiomerically enriched products.

New and general nitrogen heterocycle synthesis: Use of heteropoly acids as a heterogeneous recyclable catalyst

An efficient synthetic method of six-and five-member nitrogen heterocyclic compounds was developed. Nitrogen heterocyclic compounds were prepared by condensation of the-dicarbonyl compounds with the corresponding-or-amino alcohols, subsequent cyclization, and spontaneous aromatization in the presence of a catalytic amount of Keggin-type heteropoly acids under very mild conditions. Copyright

Tricyclic indole and dihydroindole derivatives as new inhibitors of soluble guanylate cyclase

The synthesis of new tricyclic fused indole and dihydroindole derivatives and preliminary results from their in vitro inhibitory activity against soluble guanylate cyclase (sGC) are presented.

Synthesis of 3-Acylpyrroles, 3-(Alkoxycarbonyl)pyrroles, 1,5,6,7-Tetrahydro-4H-indol-4-ones and 3-Benzoylpyridines Based on Staudinger-Aza-Wittig Reactions of 1,3-Dicarbonyl Compounds with 2- and 3-Azido-1,1-dialkoxy- alkanes

The Staudinger-aza-Wittig reaction of 1,3-dicarbonyl compounds with 2-azido-1,1-diethoxyethane and subsequent cy- clization allowed an efficient synthesis of a variety of pyrroles, 1,5,6,7-tetrahydro-4H-indol-4-ones, and of a pyridine. Georg Thieme Verlag

Efficient synthesis of pyrroles and 4,5,6,7-tetrahydroindoles via palladium-catalyzed oxidation of hydroxy-enamines

Facile and one-pot synthetic route of poly-substituted pyrroles and 4-oxo-4,5,6,7-tetrahydroindoles is established, which consists of three steps: (1) palladium-catalyzed oxidation of hydroxy-enamines by using tetrakis(triphenylphosphine)palladium and mesityl bromide oxidation system, (2) intramolecular cyclization, and (3) dehydration.

Discovery and synthesis of tetrahydroindolone derived semicarbazones as selective Kv1.5 blockers

A novel class of tetrahydroindolone-derived semicarbazones has been discovered as potent Kv1.5 blockers. In in vitro studies, several compounds exhibited very good potency for blockade of Kv1.5. Compound 8i showed good selectivity for blockade of Kv1.5 vs hERG and L-type calcium channels. In an anesthetized pig model, compounds 8i and 10c increased atrial ERP about 28%, 18%, respectively, in the right atrium without affecting ventricular ERP.

Synthesis of functionalized pyrroles and 6,7-dihydro-1H-indol-4(5H)-ones by reaction of 1,3-dicarbonyl compounds with 2-azido-1,1-diethoxyethane

The condensation of 1,3-dicarbonyl compounds with 2-azido-1,1- diethoxyethane and subsequent cyclization allowed an efficient synthesis of a variety of pyrroles and 6,7-dihydro-1H-indol-4(5H)-ones.

Selective cleavage of Cbz-protected amines

(MatrixPresented) Under conditions of catalytic Ni(0) and in most cases just over 1 equiv of Me2NH·Br3/K2CO3 or Cs2CO3, a Cbz-protected nitrogen, which is part of a heteroaromatic ring, can