7257-25-2

Basic information

• Product Name: 7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one
• Synonyms: 7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one;7,8,9,10-Tetrahydro-5H-cyclohepta[b]indol-6-one
• CAS NO: 7257-25-2
• Molecular Formula: C₁₃H₁₃NO
• Molecular Weight: 199.24842
• Mol File: 7257-25-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one(7257-25-2)
• EPA Substance Registry System: 7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one(7257-25-2)

Safety Data

• Hazardous Substances Data: 7257-25-2(Hazardous Substances Data)

Upstream product

• 64-19-7 acetic acid 
• 14192-58-6 2-[(2-phenylhydrazino)methylidene]cycloheptanone 
• 56382-69-5 cycloheptanone p-tolylsulfonylhydrazone 
• 287944-13-2 2-(cyclohept-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 835882-35-4 (Z)-cyclohept-1-en-1-ylboronic acid 
• 100-63-0 phenylhydrazine 
• 3008-39-7 cycloheptane-1,2-dione 
• 62-53-3 aniline 
• 105553-58-0 2-(phenylamino)cyclohept-2-enone 
• 934-20-3 2-(hydroxymethylene)cycloheptanone 
• 502-42-1 cycloheptanone 
• 64-18-6 formic acid 
• 52851-01-1 methyl 1H-indole-2-pentanoic acid 
• 64799-08-2 2-formylcycloheptanone 

Downstream Products

• 1262726-91-9 4-chloro-6-phenyl-7,8,9,14-tetrahydroquinolino[2',3':7,6]cyclohept[b]indole 
• 1356957-89-5 1-phenyl-4,5,6,11-tetrahydropyrazolo[4',3':6,7]cyclohepta[b]indole 
• 1357598-38-9 6-phenyl-7,8,9,14-tetrahydroquinolino[2',3':7,6]cyclohept[1,2-b]indole 

Relevant articles and documents

Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles

We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.

Synthesis and Oxidative Cleavage of Oxazinocarbazoles: Atropselective Access to Medium-Sized Rings

Polycyclic systems can be converted into medium-sized-ring-containing compounds through the controlled oxidative cleavage of internal double bonds. This approach is particularly accessible in systems that contain a suitably substituted indole ring. Here, a robust approach to the synthesis of the understudied oxazinocarbazole system is reported. After regioselective incorporation of a carbonyl functional group, m-chloroperoxybenzoic acid (MCPBA) is used to cleave the indole 2,3-double bond that this system contains. This results in a competition between two processes, oxidative cleavage of the double bond and a pinacol-type rearrangement, both of which occur with very high diastereoselectivity. The balance between the two processes is studied as a function of the substrate structure. Extensive use of X-ray crystallographic analysis of the products enables detailed mechanistic conclusions to be drawn.

Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C-C bond formation

A variety of tetrahydro-1H-carbazol-1-ones and analogs were conveniently synthesized from the reaction of the corresponding 2-(phenylamino)cyclohex-2- enone with hypervalent iodine reagent PhI(OCOCF3)2 (PIFA), through a direct intramolecular oxidative C(sp2)-C(sp2) bond formation. This approach realized the construction of the biologically important tetrahydro-1H-carbazol-1-one and tetrahydrocyclohepta[b]indol-6(5H)- one skeletons. The mechanism of the process was proposed and briefly discussed.

A novel necroptosis inhibitor - Necrostatin-21 and its SAR study

An initial structure-activity relationship study of the novel necroptosis inhibitor Nec-21 was described. Any changes of the tetracyclic scaffold were detrimental for the activity. Introduction of a substituent to 7 or 8 position (e.g., cyano or methoxy group, respectively), would increase the activity. The 7 and 8-position disubstituted compound 17b was 35-fold as potent as the lead, while EC50 reached 14 nM.

A back-to-front fragment-based drug design search strategy targeting the DFG-out pocket of protein tyrosine kinases

We present a straightforward process for the discovery of novel back pocket-binding fragment molecules against protein tyrosine kinases. The approach begins by screening against the nonphosphorylated target kinase with subsequent counterscreening of hits against the phosphorylated enzyme. Back pocket-binding fragments are inactive against the phosphorylated kinase. Fragment molecules are of insufficient size to span both regions of the ATP binding pocket; thus, the outcome is binary (back pocket-binding or hinge-binding). Next, fragments with the appropriate binding profile are assayed in combination with a known hinge-binding fragment and subsequently with a known back pocket-binding fragment. Confirmation of back pocket-binding by Yonetani-Theorell plot analysis progresses candidate fragments to crystallization trials. The method is exemplified by a fragment screening campaign against vascular endothelial growth factor receptor 2, and a novel back pocket-binding fragment is presented.

Structural investigations on 4-chloro-6-phenyl-7,8,9,14-tetrahydroquinolino [2′,3′:7,6]cyclohept[b]indoles

Several 4-chloro-6-phenyl-7,8,9,14-tetrahydroquinolino[2′,3′:7, 6]cyclohept[b]indole derivatives were obtained in one pot synthesis reactions via acid catalyzed condensation and cyclization of 1-oxo-1,2,3,4,5,10- hexahydrocyclohept[b]indoles with 2-amino-5-chlorobenzophenone in glacial acetic acid. Parent 4-chloro-6-phenyl-7,8,9,14-tetrahydroquinolino[2′,3′: 7,6]cyclohept[b]indole and the 10, 11, 12 and 13-methyl derivatives all crystallize in the triclinic space group P overline{1}. The 11-methyl derivative crystallizes with Z?= 2, the 10 and 12-methyl isomers cocrystallize as a solid solution of the two molecules, and the 13-methyl derivative and the parent compound each with Z?= 1. The unit cell parameters for the four structures are a = 10.1826(8), b = 12.3918(7), c = 16.3825(8)A, α = 91.626(1), β = 95.718(1), γ = 94.966(1)° and V = 2,047.7(2) A3 for the 11 methyl derivative; a = 10.168(2), b = 10.304(2), c = 10.610(2)A, α = 89.169(3), β = 87.774(3), γ = 63.726(2)° and V = 996.0(3) A3 for the solid solution of the 10 and 12-methyl derivative, a = 9.0412(5), b = 10.4926(6), c = 10.9093(6)A, α = 94.482(1), β = 102.181(1), γ = 95.812(1)° and V = 1,001.13(10) A3 for the 13-methyl compound, and a = 9.6463(6), b = 10.2395(6), c = 10.6062(6)A, α = 91.7263(8), β = 94.7200(8), γ = 114.0812(7)° and 950.85(10) A3 for the unsubstituted parent compound. The molecular shape of the molecules is not affected by the substitution pattern and all molecules exhibit the same conformation with very similar geometries. Intermolecular interactions are limited to weak C-H???Cl hydrogen bonds, a small number of π???π stacking interactions and several C-H???π interactions, which, in combination with shape recognition, dominate the packing of the quinolinocyclohept[b]indoles.

1, 2, 3, 9-tetrahydro-4H-carbazol-4-one and 8, 9-dihydropyrido- [1, 2-a]indol-6(7H)-one from 1H-indole-2-butanoic acid

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A pentacyclic aurora kinase inhibitor (AKI-001) with high in vivo potency and oral bioavailability

Aurora kinase inhibitors have attracted a great deal of interest as a new class of antimitotic agents. We report a novel class of Aurora inhibitors based on a pentacyclic scaffold. A prototype pentacyclic inhibitor 32 (AKI-001) derived from two early lead

INDOLE DERIVATIVE AND USE FOR TREATMENT OF CANCER

The present invention relates to a compound represented by the formula (I’) wherein A is a benzene ring optionally having substituents, R1, R2a and R3 are each a hydrogen atom, a hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents, R1 and R2a may form a ring via X, when R1 and R2a form a ring via X, R1 and R2a are each a bond or a divalent C1-5 acyclic hydrocarbon group optionally having substituents, and X is a bond, an oxygen atom, an optionally oxidized sulfur atom or an imino group optionally having a substituent, provided that R1, R2a and X are not bonds at the same time, or a salt thereof, and an agent for inhibiting kinase (phosphorylation enzyme), which contains this compound or a prodrug thereof. The compound of the present invention has an inhibitory activity against kinase such as a vascular endothelial growth factor receptor (VEGFR) and the like, and is useful as an agent for the prophylaxis or threatment of cancer and the like.

Polyaza-Cavity Shaped Molecules. 14. Annelated 2-(2'-Pyridyl)indoles, 2,2'-Biindoles, and Related Systems

The Fisher indole synthesis has been employed with a series of α-keto-2,3-cycloalkenopyridines to provide 3,3'-polymethylene bridged derivatives of 2-(2'-pyridyl)indole.The same reaction with α,α'-diketodicycloalkenopyridines provides bis-annelat