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

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

Uses

Used in Organic Synthesis:
2-CHLORO-1-(2,3-DIHYDRO-INDOL-1-YL)-ETHANONE is used as a building block for the preparation of various pharmaceuticals, agrochemicals, and other fine chemicals. It serves as a key intermediate in the synthesis of complex organic molecules.
Used in Polymer Production:
2-CHLORO-1-(2,3-DIHYDRO-INDOL-1-YL)-ETHANONE is used as an intermediate in the production of different types of polymers and other industrial products, contributing to the development of new materials with specific properties.
Used in Drug Development:
2-CHLORO-1-(2,3-DIHYDRO-INDOL-1-YL)-ETHANONE is known to have potential biological activity and is being studied for its potential use as a drug or therapeutic agent. Its unique structure and functional groups make it a promising candidate for further research and development in the pharmaceutical industry.
Used in Research:
2-CHLORO-1-(2,3-DIHYDRO-INDOL-1-YL)-ETHANONE is utilized in research settings to explore its properties, reactivity, and potential applications in various fields, including material science, chemistry, and biology.
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 
• 79-04-9 chloroacetyl chloride 
• 75-36-5 acetyl chloride 

Downstream Products

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

COMBINATION THERAPY FOR TREATING MPS1

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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.

COMPOSITIONS AND METHODS FOR MODULATING PPP2R1A

Disclosed herein, inter alia, are compositions and methods useful for modulating PPP2R1 A and for the treatment of cancer.

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.

COMPOSITONS AND METHODS FOR MODULATING UBA5

Disclosed herein, inter alia, are compositions and methods useful for inhibiting ubiquitin-like modifier activating enzyme 5.

INDANE DERIVATIVES USEFUL AS MODULATORS OF MGLUR7

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein n, X, Y, Z, D, R1, R2, R3, R4, R12, R15nd R16 are as defined in the specification, a process for their preparation, pharmaceutical compositions containing them and their use as modulators of mGluR7.

Design, synthesis and apoptosis inducing effect of novel (Z)-3-(3′-methoxy-4′-(2-amino-2-oxoethoxy)-benzylidene)indolin-2-ones as potential antitumour agents

A series of new (Z)-3-(3′-methoxy-4′-(2-amino-2-oxoethoxy)benzylidene)indolin-2-one derivatives has been synthesized and evaluated for their cytotoxic activity against selected human cancer cell lines of prostate (PC-3 and DU-145), breast (BT-549 and MDA-MB-231) and non-tumorigenic prostate epithelial cells (RWPE-1). Among the tested, one of the compounds 4p exhibited potent cytotoxicity selectively on prostate cancer cell lines (PC-3 and DU-145; IC50: 1.89 ± 0.6 and 1.94 ± 0.2 μM, respectively). Further experiments were conducted with 4p on PC-3 cancer cells to study the mechanisms of growth inhibition and apoptosis inducing effect. Treatment of PC-3 cells with test compound 4p resulted in inhibition of cell migration through disorganization of F-actin protein. The flow-cytometry analysis results showed that the compound arrested PC-3 cancer cells in the G2/M phase of cell cycle in a dose dependent manner. Hoechst staining and annexin-V binding assay revealed that the compound 4p inhibited tumor cell proliferation through induction of apoptosis. Western blot studies demonstrated that the compound 4p treatment led to activation of caspase-3, increased expression of pro-apoptotic Bax and significantly decreased expression of anti-apoptotic Bcl-2 in human prostate cancer PC-3 cells. In addition, the mitochondrial membrane potential (ΔΦm) was also affected and the levels of intracellular Ca2+ were raised.

Identification of dual PPARα/γ agonists and their effects on lipid metabolism

The three peroxisome proliferator-activated receptor (PPAR) isoforms; PPARα, PPARγ and PPARδ, play central roles in lipid metabolism and glucose homeostasis. Dual PPARα/γ agonists, which stimulate both PPARα and PPARγ isoforms to similar extents, are gaining popularity as it is believed that they are able to ameliorate the unwanted side effects of selective PPARα and PPARγ agonists; and may also be used to treat dyslipidemia and type 2 diabetes mellitus simultaneously. In this study, virtual screening of natural product libraries, using both structure-based and ligand-based drug discovery approaches, identified ten potential dual PPARα/γ agonist lead compounds (9-13 and 16-20). In vitro assays confirmed these compounds to show no statistically significant toxicity to cells, with the exception of compound 12 which inhibited cell growth to 74.5% ± 3.5 and 54.1% ± 3.7 at 50 μM and 100 μM, respectively. In support of their potential as dual PPARα/γ agonists, all ten compounds upregulated the expression of cholesterol transporters ABCA1 and ABCG1 in THP-1 macrophages, with indoline derivative 16 producing the greatest elevation (2.3-fold; 3.3-fold, respectively). Furthermore, comparable to the activity of established PPARα and PPARγ agonists, compound 16 stimulated triacylglycerol accumulation during 3T3-L1 adipocyte differentiation as well as fatty acid β-oxidation in HuH7 hepatocytes.

Direct Catalytic Asymmetric Aldol Reaction of an α-Azido Amide

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