50614-86-3

Basic information

• Product Name: Ethanone, 1-(1H-indol-4-yl)- (9CI)
• Synonyms: Ethanone, 1-(1H-indol-4-yl)- (9CI);Ethanone,1-(1H-indol-4-yl)-;1-(1H-indol-4-yl)ethanone;4-acetylindole;1-(1H-Indol-4-yl)
• CAS NO: 50614-86-3
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18456
• Product Categories: ACETYLGROUP
• Mol File: 50614-86-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 161.5-162.4 °C
• Boiling Point: 333.9±15.0 °C(Predicted)
• Appearance: /
• Density: 1.193±0.06 g/cm3(Predicted)
• PKA: 15.68±0.30(Predicted)
• CAS DataBase Reference: Ethanone, 1-(1H-indol-4-yl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(1H-indol-4-yl)- (9CI)(50614-86-3)
• EPA Substance Registry System: Ethanone, 1-(1H-indol-4-yl)- (9CI)(50614-86-3)

Safety Data

• Hazardous Substances Data: 50614-86-3(Hazardous Substances Data)

Usage

General Description

Ethanone, 1-(1H-indol-4-yl)- (9CI) is a chemical compound with the molecular formula C10H9NO. It is also known as 1-acetylindole and belongs to the class of organic compounds known as indoles. Ethanone, 1-(1H-indol-4-yl)- (9CI) is commonly found in natural sources such as plants and animals. It is known for its potential pharmaceutical and industrial applications, including its use as a precursor in the synthesis of various pharmaceutical drugs and as a reagent in organic chemical reactions. Additionally, 1-(1H-indol-4-yl)-ethanone has been studied for its potential biological activities, including its antiviral and anti-inflammatory properties. Further research is ongoing to explore its potential uses in various fields.

Upstream product

• 1074-86-8 4-formyl indole 
• 75-16-1 methylmagnesium bromide 
• 73805-13-7 1-(1H-indol-4-yl)ethan-1-ol 
• 88059-19-2 trans-6-cyano-β-dimethylamino-2-nitrostyrene 
• 84341-19-5 ethyl 4-acetyl-1H-indole-2-carboxylate 
• 84341-20-8 acetyl-4 carboxy-2 indole 
• 16136-52-0 4-cyanoindole 
• 917-54-4 methyllithium 

Downstream Products

• 1425933-63-6 (+/-)-4-(1-bromoethyl)-1-tosyl-1H-indole 
• 112970-73-7 1-(1-tosyl-1H-indol-4-yl)ethanone 
• 120160-29-4 1-(1-methyl-1H-indol-4-yl)-ethanone 
• 88059-22-7 1-(t-butoxycarbonyl)-4-<1-hydroxy-2-(benzylmethylamino)ethyl>indole 
• 188260-50-6 {4-[1-(3-Amino-propyl)-1H-indol-4-yl]-pyrimidin-2-yl}-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-amine 

Relevant articles and documents

Design, synthesis and biological evaluation of quinoline-indole derivatives as anti-tubulin agents targeting the colchicine binding site

A series of novel isocombretastatin A-4 (isoCA-4) analogs were designed and synthesized by replacing 3,4,5-trimethoylphenyl and isovanillin of isoCA-4 with quinoline and indole moieties, respectively. The structure activity relationships (SARs) of these synthesized quinoline-indole derivatives have been intensively investigated. Two compounds 27c and 34b exhibited the most potent activities against five cancer cell lines with IC50 values ranging from 2 to 11 nM, which were comparable to those of Combretastatin A-4 (CA-4, 1). Further mechanism investigations revealed that 34b effectively inhibited the microtubule polymerization by binding to the colchicine site of tubulin. Further cellular mechanism studies elucidated that 34b disrupted cell microtubule networks, arrested the cell cycle at G2/M phase, induced apoptosis and depolarized mitochondria of K562 cells. Moreover, 34b displayed potent anti-vascular activity in both wound healing and tube formation assays. Importantly, 27c and 34b significantly inhibited tumor growth in H22 xenograft models without apparent toxicity, suggesting that 27c and 34b deserve further research as potent antitumor agents for cancer therapy.

ROCK KINASE INHIBITORS

The present invention relates to compounds that inhibit ROCK activity. In particular, the present invention relates to compounds, pharmaceutical compositions and methods of use, such as methods of inhibiting ROCK activity and methods for treating, for example cerebral cavernous malformation syndrome (CCM) and cardiovascular diseases using the compounds and pharmaceutical compositions of the present invention.

2-Aminoimidazole-based antagonists of the 5-HT6 receptor – A new concept in aminergic GPCR ligand design

A new strategy in the design of aminergic GPCR ligands is proposed – the use of aromatic, heterocyclic basic moieties in place of the evergreen piperazine or alicyclic and aliphatic amines. This hypothesis has been tested using a benchmark series of 5-HT6R antagonists obtained by coupling variously substituted 2-aminoimidazole moieties to the well established 1-benzenesulfonyl-1H-indoles, which served as the ligands cores. The crystallographic studies revealed that upon protonation, the 2-aminoimidazole fragment triggers a resonance driven conformational change leading to a form of higher affinity. This molecular switch may be responsible for the observed differences in 5-HT6R activity of the studied chemotypes with different amine-like fragments. Considering the multiple functionalization sites of the embedded guanidine fragment, diverse libraries were constructed, and the relationships between the structure and activity, metabolic stability, and solubility were established. Compounds from the N-(1H-imidazol-2-yl)acylamide chemotype (10a–z) exhibited high affinity for 5-HT6R and very high selectivity over 5-HT1A, 5-HT2A, 5-HT7 and D2 receptors (negligible binding), which was attributed to their very weak basicity. The lead compound in the series 4-methyl-5-[1-(naphthalene-1-sulfonyl)-1H-indol-3-yl]-1H-imidazol-2-amine (9i) was shown to reverse the cognitive impairment caused by the administration of scopolamine in rats indicating procognitive potential.