17133-48-1

Basic information

• Product Name: 2-CHLORO-1-(2,3-DIHYDRO-INDOL-1-YL)-ETHANONE
• Synonyms: TIMTEC-BB SBB000348;AKOS BBS-00005425;1-(CHLOROACETYL)INDOLINE;2-CHLORO-1-(2,3-DIHYDRO-INDOL-1-YL)-ETHANONE;ASISCHEM T66737;1-(Indoline-1-yl)-2-chloroethane-1-one;2-chloro-1-indolin-1-yl-ethanone;1-(2-CHLOROACETYL)INDOLINE
• CAS NO: 17133-48-1
• Molecular Formula: C₁₀H₁₀ClNO
• Molecular Weight: 195.65
• Mol File: 17133-48-1.mol
• Article Data: 19

Chemical Properties

• Melting Point: 130-132 °C
• Boiling Point: 388.3 °C at 760 mmHg
• Flash Point: 188.6 °C
• Appearance: /
• Density: 1.285 g/cm³
• Vapor Pressure: 3.1E-06mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 0.95±0.20(Predicted)
• CAS DataBase Reference: 2-CHLORO-1-(2,3-DIHYDRO-INDOL-1-YL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-1-(2,3-DIHYDRO-INDOL-1-YL)-ETHANONE(17133-48-1)
• EPA Substance Registry System: 2-CHLORO-1-(2,3-DIHYDRO-INDOL-1-YL)-ETHANONE(17133-48-1)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 17133-48-1(Hazardous Substances Data)

Usage

General Description

2-CHLORO-1-(2,3-DIHYDRO-INDOL-1-YL)-ETHANONE is a chemical compound with the molecular formula C10H10ClNO. It is an organic compound that contains a chlorine atom and a functional group known as an indole ring. 2-CHLORO-1-(2,3-DIHYDRO-INDOL-1-YL)-ETHANONE is commonly used in organic synthesis as a building block for the preparation of various pharmaceuticals, agrochemicals, and other fine chemicals. It is also used as an intermediate in the production of different types of polymers and other industrial products. The compound is known to have potential biological activity and is being studied for its potential use as a drug or therapeutic agent. However, it is important to handle and use this chemical with caution, as it may pose risks to human health and the environment.

InChI:InChI=1/C10H10ClNO/c11-7-10(13)12-6-5-8-3-1-2-4-9(8)12/h1-4H,5-7H2

Upstream product

• 496-15-1 1-indoline 
• 75-36-5 acetyl chloride 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 87866-11-3 2-chloro-1-(5-nitroindolin-1-yl)ethanone 
• 709010-77-5 N-{4-(diethylamino)phenyl}-2-(2-{indolin-1-yl}-2-oxoethoxy)benzamide 
• 1426446-32-3 (E)-3-(2-azidophenyl)-1-(indolin-1-yl)prop-2-en-1-one 
• 1426446-50-5 C₁₉H₁₆N₄O₃ 
• 103148-92-1 2,3-Dihydro-1-<(triphenylphosphoranyliden)acetyl>indol 
• 103148-85-2 <2-(2,3-Dihydro-1-indolyl)-2-oxoethyl>triphenylphosphoniumchlorid 
• 1414940-03-6 (S)-1-(indolin-1-yl)-2-(2-(phenoxymethyl)morpholino)ethanone 

Relevant articles and documents

Triazole-estradiol analogs: A potential cancer therapeutic targeting ovarian and colorectal cancer

1,2,3-triazoles have continuously shown effectiveness as biologically active systems towards various cancers, and when used in combination with steroid skeletons as a carrier, which can act as a drug delivery system, allows for a creation of a novel set of analogs that may be useful as a pharmacophore leading to a potential treatment option for cancer. A common molecular target for cancer inhibition is that of the Epidermal Growth Factor Receptor/Mitogen Activated Protein Kinase pathways, as inhibition of these proteins is associated with a decrease in cell viability. Estradiol-Triazole analogs were thus designed using a molecular modeling approach. Thirteen of the high scoring analogs were then synthesized and tested in-vitro on an ovarian cancer cell line (A2780) and colorectal cancer cell line (HT-29). The most active compound, Fz25, shows low micromolar activity in both the ovarian (15.29 ± 2.19 μM) and colorectal lines (15.98 ± 0.39 μM). Mechanism of action studies proved that Fz25 moderately arrests cells in the G1 phase of the cell cycle, specifically inhibiting STAT3 in both cell lines. Additionally, Fz57 shows activity in the colorectal line (24.19 ± 1.37 μM). Inhibition studies in both cell lines show inhibition against various proteins in the EGFR pathway, namely EGFR, STAT3, ERK, and mTOR. To further study their effects as therapeutics, Fz25 and Fz57 were studied against drug efflux proteins, which are associated with drug resistance, and were found to inhibit the ABC transporter P-glycoprotein. We can conclude that these estradiol-triazole analogs provide a key for future studies targeting protein inhibition and drug resistance in cancer.

Design, synthesis and in silico insights of new 7,8-disubstituted-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione derivatives with potent anticancer and multi-kinase inhibitory activities

Aiming to obtain an efficient anti-proliferative activity, structure- and ligand-based drug design approaches were expanded and utilized to design and refine a small compound library. Subsequently, thirty-two 7,8-disubstituted-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione derivatives were selected for synthesis based on the characteristic pharmacophoric features required for PI3K and B-Raf oncogenes inhibition. All the synthesized compounds were evaluated for their in vitro anticancer activity. Compounds 17 and 22c displayed an acceptable potent activity according to the DTP-NCI and were further evaluated in the NCI five doses assay. To validate our design, compounds with the highest mean growth inhibition percent were screened against the target PI3Kα and B-RafV600E to confirm their multi-kinase activity. The tested compounds showed promising multi-kinase activity. Compounds 17 and 22c anticancer effectiveness and multi-kinase activity against PI3Kα and B-RafV600E were consolidated by the inhibition of B-RafWT, EGFR and VEGFR-2 with IC50 in the sub-micromolar range. Further investigations on the most potent compounds 17 and 22c were carried out by studying their safety on normal cell line, in silico profiling and predicted ADME characteristics.

Latent Bronsted Base Solvent-Assisted Amide Formation from Amines and Acid Chlorides

Weakly basic amines, including even neutral amines such as nitroaniline and aminocarboxylic acids, react with acid chlorides very efficiently in N, N -dimethylacetamide (DMAC), without addition of a base, to give the corresponding amides in high yields. The role of DMAC and related solvents as latent Bronsted bases was studied in these amidation reactions. Less basic amines, such as aromatic amines, reacted with benzoyl chloride faster than more basic aliphatic amines.