20289-27-4

Usage

Uses

Used in Pharmaceutical Industry:
7-Benzyloxyindole is used as a reactant for the preparation of pyrazolo-quinoline derivatives, which act as adenosine receptor antagonists. These antagonists have potential applications in the treatment of various disorders, including neurodegenerative diseases and cognitive impairments.
7-Benzyloxyindole is also used as a reactant for the asymmetric total synthesis of diazonamide A, a natural product with potential anticancer properties.
In addition, 7-Benzyloxyindole serves as a reactant for the preparation of HCV inhibitors, which are crucial in the development of treatments for Hepatitis C virus infections.
7-Benzyloxyindole is used as a reactant for the preparation of substituted 3-cyanoindoles and 3-(4-pyridinyl)indoles, which act as inhibitors of inosine monophosphate dehydrogenase. These compounds exhibit antiproliferative activity on peripheral blood mononuclear cells (PMBC), making them potential candidates for the development of antiviral and anticancer drugs.
7-Benzyloxyindole is also used as a reactant for the preparation of [(indolyl)methyl]hydantoin and -thiohydantoin derivatives, which have potential applications in the treatment of necroptosis, a form of programmed cell death.
Furthermore, 7-Benzyloxyindole is used as a reactant for the preparation of regioisomeric analogs of ED-110, indolocarbazole poisons of human topoisomerase I. These compounds have potential applications in the development of anticancer drugs.
Used in Chemical Industry:
7-Benzyloxyindole is used as an indole analogue inhibitor in various chemical reactions, providing a means to control and modulate the synthesis of target compounds.

InChI:InChI=1/C15H13NO/c1-2-5-12(6-3-1)11-17-14-8-4-7-13-9-10-16-15(13)14/h1-10,16H,11H2

Upstream product

• 4560-41-2 2-benzyloxynitrobenzene 
• 1826-67-1 vinyl magnesium bromide 
• 4920-77-8 3-methyl-2-nitrophenol 
• 876862-89-4 (E)-3-benzyloxy-2-nitro-β-pyrrolidinostyrene 
• 140640-07-9 7-(2-Cyano-1-methyl ethenyl) indole 
• 104019-20-7 1-(1H-indol-7-yl)ethan-1-one 
• 61535-21-5 1-(benzyloxy)-3-methyl-2-nitrobenzene 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 2380-84-9 7-Indolol 
• 100-39-0 benzyl bromide 
• 169615-68-3 5-(benzyloxy)bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-one 
• 88-75-5 2-hydroxynitrobenzene 

Downstream Products

• 220873-37-0 3-(7-benzyloxy-1H-indol-3-yl)-1-benzyloxymethyl-4-bromo-pyrrole-2,5-dione 
• 220873-43-8 3-(7-Benzyloxy-1H-indol-3-yl)-1-benzyloxymethyl-4-[7-benzyloxy-1-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1H-indol-3-yl]-pyrrole-2,5-dione 
• 92855-65-7 7-(benzyloxy)-1H-indole-3-carbaldehyde 
• 475577-34-5 7-benzyloxy-1-methyl-1H-indole 
• 941575-98-0 C₂₀H₁₉NO₄ 
• 941575-87-7 3-(benzofuran-3-yl)-4-(7-benzyloxy-1-methyl-1H-indol-3-yl)pyrrole-2,5-dione 
• 173447-79-5 7-Hydroxyindol-3-essigsaeure 
• 31677-75-5 2-(7-(benzyloxy)-1H-indol-3-yl)ethanamine 
• 99102-24-6 (7-benzyloxy-indol-3-yl)-acetonitrile 
• 858232-85-6 (7-benzyloxy-indol-3-yl)-acetic acid amide 
• 99102-25-7 (7-benzyloxy-indol-3-yl)-acetic acid 
• 94308-67-5 [2-(7-benzyloxy-indol-3-yl)-ethyl]-dimethyl-amine 
• 96072-98-9 phosphoric acid dibenzyl ester-[3-(2-dimethylamino-ethyl)-indol-7-yl ester] 

Relevant academic research and scientific papers

Total Synthesis of (+)-CC-1065 Utilizing Ring Expansion Reaction of Benzocyclobutenone Oxime Sulfonate

An indole synthesis via ring expansion of benzocyclobutenone oxime sulfonate was developed. Utility of the indole synthesis was demonstrated by the total synthesis of (+)-CC-1065. The middle and right segments were constructed by a sequential ring expansion of the symmetrical benzo-bis-cyclobutenone. The left segment was also constructed via ring expansion of the methyl-substituted benzocyclobutenone oxime sulfonates. After condensation of these three segments, the dienone cyclopropane structure was formed to complete the total synthesis.

An efficient and practical synthesis of N,N-diethyl-7-indolyloxyacetamide via 7-hydroxyindole

An efficient and practical synthesis of N, N-diethyl-7-indolyloxyacetamide (1) from 3-hydroxy-2-nitrotoluene (4) via 7-hydroxyindole (2) is described. Treatment of 3-benzyloxy-2-nitrotoluene (5) obtained from 4 with DMF dimethyl acetal and pyrrolidine afforded the (E)-2-nitro-β-pyrrolidinostyrene 6, which can be readily converted into the 2-nitrophenylacetaldehyde semicarbazone 7 without isolation of 6. Hydrogenation of 7 over Pd/C, followed by reaction of the resulting 2 with 2-chloro-N, N-diethylacetamide produced 1 in good yield.

One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols

Benzynes were selectively generated in situ from phenols and trapped regioselectively with potassium hexamethyldisilazide to form primary anilines following acidic workup. The direct conversion of a phenolic hydroxyl group into a free amino group is a useful method for the preparation of primary aryl amines that are hard to synthesize by using coupling reactions involving phenol derivatives with ammonia. Whereas reactions of ortho- and meta-substituted phenols produced meta-substituted anilines exclusively, those of para-substituted phenols provided ortho-silylanilines.

Highly chemoselective reduction using a Rh/C-Fe(OAc)2 system: Practical synthesis of functionalized indoles

Here, we report a highly effective and chemoselective method of preparing substituted indoles from (E)-2-nitropyrrolidinostyrenes via hydrogenation in the presence of a rhodium catalyst doped by additives such as Ni(NO 3)2·6H2O, Fe(OAc)2 or Co(acac)3. These hydrogenation conditions may also be applied to other substrates. Aromatic nitro compounds and olefins can be selectively reduced in the presence of aromatic benzyl ethers, aromatic halides and aromatic aldehydes.

Chemical compounds

Compounds of the general structural formula (I) and use of the compounds and salts and solvates thereof, as therapeutic agents.

Certain indole derivatives useful as leukotriene antagonists

A compound of the formula STR1 in which R1 is hydrogen, halo, C1-4 alkyl, C1-4 alkoxy, nitrile, optionally protected carboxy, optionally protected tetrazolyl, trihalomethyl, hydroxy-C1-4 alkyl, aldehydo, --CH2 Z, --CH=CH--Z or --CH2 CH2 Z where Z is optionally protected carboxy or optionally protected tetrazolyl; R2 is halo, nitrile, an optionally protected acid group or --CONR7 R8 where R7 and R8 are each hydrogen or C1-4 alkyl; R3 and R4 are each hydrogen, C1-4 alkyl, optionally substituted phenyl, or C1-4 alkyl substituted by --CONR7 R8 or an optionally protected acid group; R5 is STR2 where W is --CH=CH--, --CH=N--, --N=CH--, --O-- or --S--, R9 is hydrogen, halo, C1-4 alkyl, C1-4 alkoxy or trihalomethyl, and R10 is hydrogen, C1-4 alkyl, C2-6 alkenyl, C3-6 cycloalkyl or C1-4 alkyl-C3-6 cycloalkyl; R6 is hydrogen or C1-4 alkyl; X is --O--(CH2)n CR11 R12, --CR11 R12 --, --CR11 R12.(CH2)n.CR13 R14 -- or --CR11 =CR12 -- where R11, R12, R13 and R14 are each hydrogen or C1-4 alkyl, and n is 0, 1 or 2; and Y is --O--CR15 R16 --, --CR15 =CR16 -- or --CR15 R16.CR17 R18 -- where R15, R16, R17 and R18 are each hydrogen or C 1-4 alkyl; or a salt thereof. The compounds in unprotected form are active as leukotriene antagonists.

N-Benzyl-Indoles, processes for their preparation and pharmaceutical compositions containing them

A compound of the formula in which R1 is hydrogen, halo, C??? alkyl, C??? alkoxy, nitrile, optionally protected carboxy, optionally protected tetrazolyl, trihalomethyl, hydroxy-C??? alkyl, aldehydo,-CH?Z,-CH=CH-Z or-CH?CH?Z where Z is optionally protected carboxy or optionally protected tetrazolyl; R2 is halo, nitrile, an optionally protected acid group or-CONR?R? where R? and R? are each hydrogen or C??? alkyl, R3 and R? are each hydrogen, C??? alkyl, optionally substituted phenyl, or C??? alkyl substituted by-CONR?R? or an optionally protected acid group; R? is where W is-CH=CH-,-CH=N-,-N=CH-,-O-or-S-, R? is hydrogen, halo, C??? alkyl, C? ?? alkoxy or trihalomethyl, and R1? is hydrogen, C? ?? alkyl, C??? alkenyl, C??? cycloalkyl or C??? alkyl-C??? cycloalkyl; R? is hydrogen or C??? alkyl; X is-O-(CH?)nCR11CR12-,-CR11R12-,-CR11R12.(CH?) n.CR13R1?-or-CR11=CR12-where R11, R12, R13 and R1? are each hydrogen or C??? alkyl, and n is 0, 1 or 2; and Y is-O-CR1?R1?-,-CR1?=CR1?-or-CR1? R1?.CR1?R1?-where R1?, R1?, R1? and R1? are each hydrogen or C??? alkyl; or a salt thereof. The compounds in unprotected form are active as leukotriene antagonists.

The synthesis of 7-alkoxyindoles

A number of protected 7-hydroxyindoles was prepared by reaction of the protected 2-nitrophenols with vinylmagnesium bromide. Benzhydryl was shown to be the protecting group of choice, giving good yields of the indole and being readily removed for subsequent transformations of the 7-hydroxy function.

Substituted 1,3,4,9-tetrahydropyrano[3,4,-b]indole-1-acetic acids, pharmaceutical compositions containing them, and methods for treating inflammatory conditions and for analgesic purposes using them

Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid nucleus bearing a substituent in position 1,5, 6, 7 and 8. The derivatives are useful anti-inflammatory and analgesic agents and methods for their preparation