108761-32-6

Basic information

• Product Name: Acetic acid 1-acetyl-5-chloro-1H-indol-3-yl ester
• Synonyms: Acetic acid 1-acetyl-5-chloro-1H-indol-3-yl ester;1-ACETYL-5-CHLORO-1H-INDOL-3-YL ACETATE;RARECHEM AK MA K327
• CAS NO: 108761-32-6
• Molecular Formula: C12H10ClNO3
• Molecular Weight: 0
• Mol File: 108761-32-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Acetic acid 1-acetyl-5-chloro-1H-indol-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid 1-acetyl-5-chloro-1H-indol-3-yl ester(108761-32-6)
• EPA Substance Registry System: Acetic acid 1-acetyl-5-chloro-1H-indol-3-yl ester(108761-32-6)

Safety Data

• Hazardous Substances Data: 108761-32-6(Hazardous Substances Data)

Upstream product

• 133433-34-8 5-chloro-2-<(carboxymethyl)amino>-benzoic acid 
• 108-24-7 acetic anhydride 
• 79-11-8 chloroacetic acid 
• 635-21-2 5-chloroanthranilic acid 
• 21739-93-5 2-bromo-5-chlorobenzoic acid 
• 127-09-3 sodium acetate 

Downstream Products

• 344287-26-9 1-acetyl-5-chloro-3-hydroxyindole 
• 114306-00-2 3-acetoxy-5-chloroindole 
• 62486-02-6 1-acetyl-5-chloro-1,2-dihydro-3H-indol-3-one 
• 700838-62-6 [2-(1-(2'-bromobenzenesulfonyl)-5-chloro-1H-indol-3-yloxy)ethyl]dimethylamine 
• 1310369-78-8 C₁₉H₂₀BrClN₂O₃S 
• 1310369-79-9 C₁₉H₂₀BrClN₂O₃S 

Relevant articles and documents

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To utilize the unique scaffold of a natural product indirubin, we herein adopted the strategy of combined pharmacophores to design and synthesize a series of novel indirubin derivatives as dual inhibitors against cyclin-dependent kinase (CDK) and histone deacetylase (HDAC). Among them, the lead compound 8b with remarkable CDK2/4/6 and HDAC6 inhibitory activity of IC50 = 60.9 ± 2.9, 276 ± 22.3, 27.2 ± 4.2, and 128.6 ± 0.4 nM, respectively, can efficiently induce apoptosis and S-phase arrest in several cancer cell lines. In particular, compound 8b can prevent the proliferation of a non-small-cell lung cancer cell line (A549) through the Mcl-1/XIAP/PARP axis, in agreement with the unique modes of action of the combined agents of HDAC inhibitors and CDK inhibitors. In an A549 xerograph model, compound 8b showed significant antitumor efficacy correlated with its dual inhibition. Our data demonstrated that compound 8b as a single agent could be a promising drug candidate for cancer therapy in combination with CDK and HDAC inhibitors.

Indoxyl-based umpolung strategy for the synthesis of unsymmetrical 3,3′-biindoles

3,3′-Bisindoles are known to be important structural motifs found in bioactive natural products, pharmaceuticals, and functional materials. Herein, a novel indoxyl-based approach was established for the synthesis of unsymmetrical 3,3′-biindoles from indoles and indoxyls. This approach generated moderate to excellent yields of the desired products (24 examples, up to 98% yield). The present method features broad substrate scope, operational simplicity, high atom economy, and utilization of non-toxic and inexpensive molecular iodine as catalyst. The applicability of this method has been demonstrated by the facile gram-scale synthesis.

INDIRUBIN-3'-OXIME DERIVATIVES AS POTENT CYCLIN DEPENDENT KINASE INHIBITORS

The present invention relates to an indirubin-3′-oxime derivative as potent cyclin dependent kinase inhibitor with anti-cancer activity. More particularly, this invention relates to an indirubin-3′-oxime derivative as potent cyclin dependent kinase inhibitor having excellent anti-cancer activity against human lung cancer cell, human fibro sarcoma cell, human colon cancer cell, human leukemia cell, human stomach cancer cell, human nasopharyngeal cancer cell and/or human breast cancer cell.

INDIRUBIN-3'-OXIME DERIVATIVES AS POTENT CYCLIN DEPENDENT KINASE INHIBITORS

The present invention relates to an indirubin-3'-oxime derivative as potent cyclin dependent kinase inhibitor with anti-cancer activity. More particularly, this invention relates to an indirubin-3'-oxime derivative as potent cyclin dependent kinase inhibitor having excellent anti-cancer activity against human lung cancer cell, human fibro sarcoma cell, human colon cancer cell, human leukemia cell, human stomach cancer cell, human nasopharyngeal cancer cell and/or human breast cancer cell.

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A series of novel conformationally restricted N1-arylsulfonyl-3-aminoalkoxy indoles were designed and synthesized as 5-HT6 receptor (5-HT6R) ligands. Many of the synthesized compounds have moderate in vitro-binding affinities at 5-HT6R. The lead compound 8b (% inhibition=97.2 at 1 μM) from this series has good pharmacokinetic profile in male Wister rats and is active in animal model of cognition like Morris water maze. The details of chemistry, SAR, pharmacokinetics and pharmacological data constitute the subject matter of this report.

Indole-3-piperazinyl derivatives: Novel chemical class of 5-HT6 receptor antagonists

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AZAINDOLE-INDOLE COUPLED DERIVATIVES, PREPARATION METHODS AND USES THEREOF

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