133433-34-8

Upstream product

• 612-42-0 phenylglycine-o-carboxylic acid 
• 79-11-8 chloroacetic acid 
• 635-21-2 5-chloroanthranilic acid 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 56-40-6 glycine 
• 50-79-3 2,5-dichlorobenzoic acid 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 1223386-17-1 C₁₁H₁₂ClNO₄ 
• 21739-93-5 2-bromo-5-chlorobenzoic acid 

Downstream Products

• 700838-62-6 [2-(1-(2'-bromobenzenesulfonyl)-5-chloro-1H-indol-3-yloxy)ethyl]dimethylamine 
• 1310369-78-8 C₁₉H₂₀BrClN₂O₃S 
• 1310369-79-9 C₁₉H₂₀BrClN₂O₃S 
• 62486-02-6 1-acetyl-5-chloro-1,2-dihydro-3H-indol-3-one 
• 108761-32-6 1-acetyl-5-chloro-1H-indol-3-yl acetate 
• 21716-60-9 5-Chlor-2-methoxycarbonylmethylamino-benzoesaeuremethylester 

Relevant academic research and scientific papers

Total Synthesis of the Chlorinated Indigo-N-Glycosides Akashin A, B and C

A total synthesis of the indigo-derived natural products akashin A-C was developed. The key step was the N-glycosylation of soluble N-benzylated-indigos with a suitably protected viosaminyl trichloroacetimidate. This donor was obtained from D-galactose. U

Indirubin Derivatives as Dual Inhibitors Targeting Cyclin-Dependent Kinase and Histone Deacetylase for Treating Cancer

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.

Design, synthesis and pharmacological evaluation of conformationally restricted N-arylsulfonyl-3-aminoalkoxy indoles as a potential 5-HT6 receptor ligands

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.

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.

5,5′-substituted indirubin-3′-oxime derivatives as potent cyclin-dependent kinase inhibitors with anticancer activity

To enhance the ability of indirubin derivatives to inhibit CDK2/cyclin E, a target of anticancer agents, we designed and synthesized a new series of indirubin-3′-oxime derivatives with combined substitutions at the 5 and 5′ positions. A molecular docking

AZAINDOLE-INDOLE COUPLED DERIVATIVES, PREPARATION METHODS AND USES THEREOF

A novel class of azaindole-indole coupled derivatives, their preparation methods, pharmaceutical compositions containing the same and the uses thereof. The common structural feature of these derivatives is that they are coupled by azaindole and indole bi-molecule at different positions, forming extended pi-conjugated systems. Such derivatives inhibited cell growth and proliferation by various mechanisms. The present compounds have improved solubility, increased bioavailability, and thus have enhanced drug actions, and reduced medical dosages and undesired responses.

AZAINDOLE-INDOLE COUPLED DERIVATIVES, PREPARATION METHODS AND USES THEREOF

A novel class of azaindole-indole coupled derivatives, their preparation methods, pharmaceutical compositions containing the same and the uses thereof. The common structural feature of these derivatives is that they are coupled by azaindole and indole bi-molecule at different positions, forming extended pi-conjugated systems. Such derivatives inhibited cell growth and proliferation by various mechanisms. The present compounds have improved solubility, increased bioavailability, and thus have enhanced drug actions, and reduced medical dosages and undesired responses.

Ultrasound-promoted reaction of 2-chlorobenzoic acids and aliphatic amines

An improvement to the use of DMF as a solvent for the condensation of 2-chlorobenzoic acids with aliphatic primary or secondary amines was described. A number of alkylaminobenzoic acids and dialkylaminobenzoic acids were synthesized in acceptable-to-good yield. The advantages of this procedure include readily available substrates, the use of an inexpensive copper powder without taking any precautions to exclude moisture under mild conditions and experimental ease. Furthermore, this condensation could also be achieved under nonclassical conditions by using ultrasonic irradiation at room temperature. We demonstrated that ultrasound-promoted condensation of 2-chlorobenzoic acid with aliphatic amines with the use of DMF as the solvent, especially in the case of secondary amines, affords products in high yields and reduces the reaction time to minutes. The results proved to be highly reproducible because the relevant sonochemical parameters were rigorously controlled. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.