28755-03-5

Basic information

• Product Name: Ethanone, 2-chloro-1-(3-indolyl)-
• Synonyms: Ethanone, 2-chloro-1-(3-indolyl)-;3-chloroacetylindole;2-chloro-1-(1H-indol-3-yl)ethanone(SALTDATA: FREE);2-Chloro-1-(1H-indol-3-yl)ethan-1-one, 3-(2-Chloroethanoyl)-1H-indole;3CAI;Chloromethyl indol-3-yl ketone;Ethanone, 2-chloro-1-(1H-indol-3-yl)-;Ethanone, 2-chloro-1H-indol-1-yl-
• CAS NO: 28755-03-5
• Molecular Formula: C₁₀H₈ClNO
• Molecular Weight: 193.63
• Mol File: 28755-03-5.mol
• Article Data: 25

Chemical Properties

• Melting Point: 212-214 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 379.1°C at 760 mmHg
• Flash Point: 183°C
• Appearance: yellow to brown/
• Density: 1.337g/cm³
• Vapor Pressure: 6.02E-06mmHg at 25°C
• Refractive Index: 1.659
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble5mg/mL, clear
• PKA: 15.08±0.30(Predicted)
• CAS DataBase Reference: Ethanone, 2-chloro-1-(3-indolyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 2-chloro-1-(3-indolyl)-(28755-03-5)
• EPA Substance Registry System: Ethanone, 2-chloro-1-(3-indolyl)-(28755-03-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 28755-03-5(Hazardous Substances Data)

Usage

Uses

3-(Chloroacetyl)indole is a reagent used in organic synthesis. Used in the preparation of 1,?2-?dihydroazepino[4,?5-?b]?indoles.

Biological Activity

3cai is a potent allosteric and specific inhibitor of akt, which directly binds with akt1 or akt2 in an atp noncompetitive manner and shows 60% inhibition of akt1 kinase activity at 1 μm [1]. the serine/threonine kinase akt includes three members, akt1, akt2, and akt3. akt plays a critical role in promoting transformation and chemoresistance through inducing proliferation and inhibiting apoptosis. therefore, akt is regarded as a potential target for cancer therapy.

in vitro

3cai (1 and 4 μm) significantly inhibited akt1 kinase activity and decreased expression of akt direct downstream targets including mtor and gsk3β, respectively. 3cai (4 μm) efficiently induced growth inhibition and apoptosis in hct116 or hct29 colon cancer cells [1].

in vivo

3cai (30 mg/kg, oral administration) significantly suppressed colon cancer growth in an in vivo xenograft mouse model and inhibited the expression of akt-target protein such as mtor and gsk3βin hct116 colon tumor tissues [1].

target

akt

IC 50

1 μm

references

1. kim dj, reddy k, kim mo, li y, nadas j, cho yy, et al. (3-chloroacetyl)-indole, a novel allosteric akt inhibitor, suppresses colon cancer growth in vitro and in vivo. cancer prev res (phila). 2011;4(11):1842-51.

InChI:InChI=1/C10H8ClNO/c11-5-10(13)8-6-12-9-4-2-1-3-7(8)9/h1-4,6,12H,5H2

Upstream product

• 120-72-9 indole 
• 2315-36-8 2-Chloro-N,N-diethylacetamide 
• 2675-89-0 2-chloro-N,N-dimethylacetamide 
• 100124-77-4 2-chloro-1-(1-chloroacetyl-indol-3-yl)-ethanone 
• 124-40-3 dimethyl amine 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 15849-26-0 indol-3-yl-(3-phenyl-oxiranyl)-methanone 
• 33022-99-0 [3-(4-bromo-phenyl)-oxiranyl]-indol-3-yl-methanone 
• 22258-56-6 2-amino-4-(indol-3'-yl)thiazole 
• 34651-63-3 indol-3-yl-[3-(4-isopropyl-phenyl)-oxiranyl]-methanone 
• 139963-67-0 3-(N-1-ethoxycarbonyl-2-benzylthioethylglycycl)indole 
• 113369-28-1 1-(3-indolyl)-2-<2-(3,4-dimethoxyphenyl)ethyl>aminoethanol 
• 139963-64-7 di-<2-(indol-3-yl)-2-oxoethyl> sulfide 
• 916818-18-3 3-(2-chloroacetyl)indole-1-carboxylic acid tert-butyl ester 
• 113369-30-5 1-(3-indolyl)-2-<2-(3,4-dimethoxyphenyl)ethyl>aminoethanol 
• 113369-32-7 acid oxalate of N-<2-(3-indolyl)ethyl>-2-(3,4-dimethoxyphenyl)ethylamine 
• 53552-11-7 <2-(1H-indol-3-yl)-2-oxoethyl> ammonium chloride 
• 91543-08-7 1-(indol-3-yl)-3-(p-nitrophenyl)-2-propen-1-one 
• 91543-07-6 triphenylphosphonium-(indol-3-ylcarbonyl)methylide 
• 65040-49-5 3-(2-methyl-thiazol-4-yl)-1-(3,4,5-trimethoxy-benzoyl)-indole 

Relevant articles and documents

Synthesis of 1-, 2-, and 3-(aminoacetyl)indoles and 1-(aminoacetyl)indolines

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TARGETING PLECKSTRIN-2 FOR TREATING CANCER

Disclosed herein are compounds, compositions, and methods for treating cell proliferative diseases and disorders based on present inventors discovery that Pleckstrin-2 (Plek2) can be targeted to treat cell proliferative diseases and disorders. The composi

A indole compound and its preparation method and application (by machine translation)

The invention discloses a indole compound and its preparation method and application. The indole compounds of the structural formula such as formula (I) is shown. The indoles, rice galenical demonstrate the excellent inhibitory activity, the effect of most of the compound is obviously better than the positive control drug validamycin; especially compound I - 43, I - 44, I - 54, I - 73, II - 7 and II - 17, its galenical very good living body protection and treating effect, effect is better than the positive control; more specifically, compound I - 43 of the rice sheath blight bacteriostatic activity than validamycin activity is improved by nearly 300 times. The indole compounds in the prevention and/or treatment of rice sheath blight has great application prospects. In addition the compound of the invention is simple in construction, the preparation method is simple, and is suitable for large-scale industrial production. (I). (by machine translation)