28755-03-5

Usage

Uses

Used in Organic Synthesis:
Ethanone, 2-chloro-1-(3-indolyl)is used as a reagent in organic synthesis for the preparation of various complex organic molecules. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable building block for the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Ethanone, 2-chloro-1-(3-indolyl)is used as a key intermediate in the synthesis of various drugs and drug candidates. Its ability to form a wide range of chemical bonds makes it a versatile component in the development of new therapeutic agents.
Used in the Preparation of 1,2-Dihydroazepino[4,5-b]indoles:
Ethanone, 2-chloro-1-(3-indolyl)is specifically used in the preparation of 1,2-dihydroazepino[4,5-b]indoles, which are a class of heterocyclic compounds with potential applications in medicinal chemistry. These compounds may exhibit various biological activities, such as anti-cancer, anti-inflammatory, or anti-microbial properties, making them valuable targets for drug discovery and development.

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

• 30256-72-5 8-oxo-N,N-dimethyltryptamine 
• 92292-25-6 2-diethylamino-1-indol-3-yl-ethanone 
• 2400-51-3 3-(hydroxyacetyl)indole 
• 87084-40-0 2-amino-1-(1H-indol-3-yl)ethan-1-one 
• 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 
• 30256-73-6 indol-3-yl piperidinomethyl ketone 
• 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 
• 1477-50-5 Indole-2-carboxylic acid 
• 113369-30-5 1-(3-indolyl)-2-<2-(3,4-dimethoxyphenyl)ethyl>aminoethanol 

Relevant academic research and scientific papers

4-(Indol-3-yl)thiazole-2-amines and 4-ιndol-3-yl)thiazole acylamines as novel antimicrobial agents: Synthesis, in silico and in vitro evaluation

This manuscript deals with the synthesis and computational and experimental evaluation of the antimicrobial activity of twenty-nine 4-(indol-3-yl)thiazole-2-amines and 4-ιndol-3-yl)thiazole acylamines. An evaluation of antibacterial activity against Gram (+) and Gram (?) bacteria revealed that the MIC of indole derivatives is in the range of 0.06–1.88 mg/mL, while among fourteen methylindole derivatives, only six were active, with an MIC in the range of of 0.47–1.88 mg/mL. S. aureus appeared to be the most resistant strain, while S. Typhimurium was the most sensitive. Compound 5x was the most promising, with an MIC in the range of 0.06–0.12 mg/mL, followed by 5d and 5m. An evaluation of these three compounds against resistant strains, namely MRSA P. aeruginosa and E. coli, revealed that they were more potent against MRSA than ampicillin. Furthermore, compounds 5m and 5x were superior inhibitors of biofilm formation, compared to ampicillin and streptomycin, in terms Compounds 5d, 5m, and 5x interact with streptomycin in additive manner. The antifungal activity of some compounds exceeded or was equipotent to those of the reference antifungal agents bifonazole and ketoconazole. The most potent antifungal agent was found to be compound 5g. Drug likeness scores of compounds was in a range of ?0.63 to 0.29, which is moderate to good. According to docking studies, E. coli MurB inhibition is probably responsible for the antibacterial activity of compounds, whereas CYP51 inhibition was implicated in antifungal activity. Compounds appeared to be non-toxic, according to the cytotoxicity assessment in MRC-5 cells.

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

Design, synthesis and evaluation of new indolylpyrimidylpiperazines for gastrointestinal cancer therapy

Human A3 adenosine receptor hA3AR has been implicated in gastrointestinal cancer, where its cellular expression has been found increased, thus suggesting its potential as a molecular target for novel anticancer compounds. Observation

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)

Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N-H) Indoles via Common N-Indolyl Triethylborate

A general and direct C3 functionalization of free (N-H) indoles with readily available electrophiles such as acid chlorides, chloroformates, thionyl chloride, and methylsulfonyl chloride via a common N-indolyl triethylborate intermediate is reported. The reaction proceeds smoothly under mild conditions in up to 93% yield. Indoles with substituents at the C2, C4, C5, C6, and C7 positions are well tolerated. The easy accessibility of a variety of important 3-acylindoles, indole-3-carboxylic esters, indole-3-sulfinic acids, and 3-(methylsulfonyl)indoles demonstrates the high degree of compatibility and practicability of this method.

A Scalable Method for Regioselective 3-Acylation of 2-Substituted Indoles under Basic Conditions

Privileged structures such as 2-arylindoles are recurrent molecular scaffolds in bioactive molecules. We here present an operationally simple, high yielding and scalable method for regioselective 3-acylation of 2-substituted indoles under basic conditions

Structure-Activity Relationship Refinement and Further Assessment of Indole-3-glyoxylamides as a Lead Series against Prion Disease

Structure-activity relationships within the indole-3-glyoxylamide series of antiprion agents have been explored further, resulting in discovery of several new compounds demonstrating excellent activity in a cell line model of prion disease (EC50 10 nM). After examining a range of substituents at the para-position of the N-phenylglyoxylamide moiety, five-membered heterocycles containing at least two heteroatoms were found to be optimal for the antiprion effect. A number of modifications were made to probe the importance of the glyoxylamide substructure, although none were well tolerated. The most potent compounds did, however, prove largely stable towards microsomal metabolism, and the most active library member cured scrapie-infected cells indefinitely on administration of a single treatment. The present results thereby confirm the indole-3-glyoxylamides as a promising lead series for continuing in vitro and in vivo evaluation against prion disease.Making mad cows a myth! The indole-3-glyoxylamide series of antiprion agents has been further optimised, and characteristics contributing to their activity have been identified by computational studies. Varying the glyoxylamide motif or introducing substitution at N-1 gave analogues with lower efficacy.

Synthesis and biological characterization of 3-substituted-1h-indoles as ligands of GluN2B-containing N-methyl-D-aspartate receptors

As an extension of our studies, novel indole derivatives were rationally designed and synthesized as ligands targeted to GluN2B/NMDA receptors. The 2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone (4i) and 1-(4-benzylpiperidin-1-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione (6i) showed high binding affinity in [3H]ifenprodil displacement assay. By computational studies, we suggested the hypothetical interactions playing a significant role during the binding process. However, in functional and in vivo studies the most potent compound 4i did not show any activity whereas it displayed relevant affinity toward the σ2 receptor.

Synthesis of bis(arylamino)thiazoloylindoles as novel analogs of dendrodoine

3-[2,4-Bis(arylamino)thiazol-5-oyl]indoles, as the analogs of the cytotoxic marine alkaloid dendrodoine, are synthesized from 1-(N,N'-diarylamidino)-3- arylthioureas which provided the four [S1-C2-N3-C4] ring atoms for the thiazole ring construction. The

Development of 3-substituted-1H-indole derivatives as NR2B/NMDA receptor antagonists

A combined ligand-based and structure-based approach has previously allowed us to identify NR2B/NMDA receptor antagonists containing indole scaffold. In order to further explore the main structure activity relationships of this class of derivatives we herein report the design, synthesis and biological evaluation of new analogues. Some derivatives demonstrated to produce significant anticonvulsant properties and NMDA antagonism. The most active of them (3d) showed NR2B binding affinity equipotent to that of ifenprodil. These results were also corroborated by computational studies.