227803-33-0

Usage

Uses

Used in Pharmaceutical Research:
5-CHLORO-2-(PHENYLMETHYL)-INDOLE is used as a research compound for the development of novel drugs targeting serotonin receptors. Its unique structure and pharmacological properties make it a valuable tool in the advancement of treatments for various conditions related to serotonin dysregulation.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5-CHLORO-2-(PHENYLMETHYL)-INDOLE is utilized as a starting material or a building block for the synthesis of new compounds with potential therapeutic applications. Its structural features allow for modifications and optimizations to enhance drug efficacy and safety.
Used in Drug Discovery:
5-CHLORO-2-(PHENYLMETHYL)-INDOLE serves as a candidate in drug discovery processes, where its interactions with biological targets are studied to identify potential lead compounds for the treatment of diseases. Its pharmacological profile is of interest for further development into effective therapeutic agents.
Used in Organic Synthesis:
5-CHLORO-2-(PHENYLMETHYL)-INDOLE is used as a reactant in the synthesis of various organic compounds and materials. Its functional groups and structural elements can be manipulated to create new molecules with specific properties for use in different industries.
Used in Material Science:
In material science, 5-CHLORO-2-(PHENYLMETHYL)-INDOLE may be employed in the development of new materials with unique properties. Its chemical structure could contribute to the creation of materials with applications in various fields, such as electronics, coatings, or pharmaceutical formulations.

InChI:InChI=1/C15H12ClN/c16-13-6-7-15-12(9-13)10-14(17-15)8-11-4-2-1-3-5-11/h1-7,9-10,17H,8H2

Upstream product

• 932-98-9 1-chloro-4-nitroso-benzene 
• 81784-69-2 N-Hydroxy-3-oxo-4,N-diphenyl-butyramide 
• 4436-24-2 1,2-epoxy-3-phenylpropane 
• 106-47-8 4-chloro-aniline 
• 17422-32-1 5-chloro-1H-indole 
• 100-39-0 benzyl bromide 
• 92433-38-0 1-benzyl-5-chloro-1H-indole 

Downstream Products

• 936244-01-8 N,N'-bis-Boc-N''-(2-benzyl-5-chloro-1H-indol-3-yl)guanidine 
• 936243-89-9 2-benzyl-5-chloro-1H-indol-3-ylamine 
• 936243-82-2 2-benzyl-5-chloro-3-nitro-1H-indole 

Relevant academic research and scientific papers

Efficient synthesis of 3-(4,5-dihydro-1H-imidazole-2-yl)-1H-indoles

A simple method for the synthesis of various 3-(4,5-dihydro-1H-imidazole-2-yl)-1H-indoles is described. Treatment of different substituted indoles with 1-acetyl-imidazolidin-2-one in the presence of phosphorus oxychloride afforded after hydrolysis in etha

Hypoglycemic imidazoline compounds

This invention relates to certain novel imidazoline compounds and analogues thereof, to their use for the treatment of diabetes, diabetic complications, metabolic disorders, or related diseases where impaired glucose disposal is present, to pharmaceutical compositions comprising them, and to processes for their preparation.

Ruthenium-catalyzed regioselective synthesis of 2-substituted indoles via ring-opening of epoxides by anilines

Anilines react with epoxides in dioxane at 180°C in the presence of a catalytic amount of a ruthenium catalyst along with tin(II) chloride to afford 2-substituted indoles in moderate to good yields.

Hypoglycemic imidazoline compounds

This invention relates to certain novel imidazoline compounds and analogues thereof, to their use for the treatment of diabetes, diabetic complications, metabolic disorders, or related diseases where impaired glucose disposal is present, to pharmaceutical compositions comprising them, and to processes for their preparation. The compounds have the following formula: whereinX is -O-, -S-, or -NR5-;R5 is hydrogen, C1-8 alkyl, or an amino protecting group;R1, R1', R2, and R3 are independently hydrogen or C1-8 alkyl;R1 and R2 optionally together form a bond and R1' and R3 are independently hydrogen or C1-8 alkyl;R1 and R2 optionally combine together with the carbon atoms to which they are attached form a C3-7 carbocyclic ring and R1' and R3 are independently hydrogen or C1-8 alkyl;R1 and R1' together with the carbon atom to which they are attached optionally combine to form a C3-7 spirocarbocyclic ring and R2 and R3 are independently hydrogen or C1-8 alkyl;R2 and R3 together with the carbon atom to which they are attached optionally combine to form a C3.7 spirocarbocyclic and R1 and R1' are independently hydrogen or C1-8 alkyl;n is 0, 1, or 2;m is 1 or2; 2;m' is 0, 1, or 2;q' is 0,1,2,3,4, or 5;R4 isY is -O-, -S-, or -NR8-;Y' is -O- or -S-;R6 and R7 are independently hydrogen, C1-8 alkyl, C3-7 cycloalkyl, C1-8 alkoxy, C1-8 alkylthio, halo C1-8 alkylthio, C1-8 alkylsulfinyl, C1-8 alkylsulfonyl. C3-7 cycloalkoxy, aryl-C1-8 alkoxy, halo, halo-C1-8 alkyl, halo-C1-8 alkoxy, nitro, -NR10R11, -CONR10R11, aryl C1-8 alkyl, optionally substituted heterocyclyl, optionally substituted phenyl, optionally substituted naphthyl, optionally halo substituted acylamino, cyano, hydroxy, COR12, halo C1-8 alkylsulfinyl, or halo C1-8 alkylsulfonyl, or alkoxyalkyl of the formulaCH3(CH2)p-O-(CH2)q-O-; wherep is 0, 1, 2, 3, or 4; andq is 1, 2, 3, 4, or 5;R12 is C1-8 alkyl or optionally substituted phenyl;R8 is hydrogen, C1-8 alkyl, halo-C1-8 alkyl, optionally substituted phenyl, optionally substituted heterocyclyl, COO C1-8 alkyl, optionally substituted COaryl, COC1-8 alkyl, SO2C1-8 alkyl, optionally substituted SO2 aryl, optionally substituted phenyl-C1-8 alkyl, CH3(CH2)p-O-(CH2)q-O-;R9 is hydrogen, halo, C1-8 alkyl, halo C1-8 alkyl, C1-8 alkylthio, halo C1-8 alkylthio, C3-7 cycloalkylthio, optionally substituted arylthio or heteroarylthio, C1-8 alkoxy, C3-8 cycloalkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, or optionally substituted aryl or heteroaryl, C3-7 cycloalkyl, halo C3-7 cycloalkyl, C3-7 cycloalkenyl, cyano, COOR10,CONR10R11 or NR10R11,C2-6 alkenyl, optionally substituted heterocyclyl, optionally substituted aryl C1-8 alkyl, optionally substituted heteroaryl C1-8 alkyl in which the alkyl group can be substituted by hydroxy, or C1-8 alkyl substituted by hydroxy,R10 and R11 are independently hydrogen, C1-8 alkyl, optionally substituted aryl C1-8 alkyl, optionally substituted phenyl, or R10 and R11 together with the nitrogen atom to which they are attached may combine to form a ring with up to six carbon atoms which optionally may be substituted with up to two C1-8 alkyl groups or one carbon atom may be replaced by oxygen or sulfur;R14 and R16 are independently hydrogen, halo, C1-8 alkyl, C3-7 cycloalkyl, C3-7 cycloalkoxy, C3-7 cycloalkylC1-8 alkoxy, halo-C1-8 alkyl, halo-C1-8 alkoxy, C1-8 alkoxy, carbo(C1-8)alkoxy, optionally substituted aryl, or optionally substituted heteroaryl;R15 and R17 are independently hydrogen, halo, C1-8 alkoxy, C3-7-cycloalkyl, C3-7 cycloalkylC1-8 alkoxy, C1-8 alkyl, C3-7 cycloalkoxy, hydroxy, halo C1-8 alkoxy, carbo(C1-8)alkoxy, optionally substituted phenyl, optionally substituted phenyl-C1-8 alkyl, optionally substituted phenyloxy, optionally substituted phenyl-C1-8 alkoxy, (tetrahydropyran-2-yl)methoxy, C1-8 alkyl-S(O)m-, optionally substituted aryl-C1-8 alkyl-S(O)m·-, CH3(CH2)p-Z1-(CH2)q-Z2-, or Z3-(CH2)q'-Z2-;Z1 and Z2 are independently abond, O, S, SO, SO2, sulphoximino, or NR10; andZ3 is hydroxy, protected hydroxy, NR10 R11, protected amino, SH or protected SH; ???provided that when R1, R1', R2 and R3 are all hydrogen; n is 0; R4 is naphthyl; and R14 R15 and R16, or R15, R16 and R17 are all hydrogen, then R17 or R14, respectively, is other than halo, methoxy, or C1-6 alkyl. ???or a pharmaceutically acceptable salt or ester thereof.

New route to 2-substituted indoles by pyrolysis of N-acylacetylphenylhydroxylamines

Convenient and regiospecific synthesis of 2-substituted indol (3) by thermolysis of N-acylacetylphenylhydroxylamine (1) and its mechanism including the formation of a radical intermediate are reported.