20289-27-4 Usage
Description
7-Benzyloxyindole is an indole analogue that serves as a versatile reactant and building block in the synthesis of various bioactive compounds and pharmaceutical agents. It is a pale-yellow solid with unique chemical properties that make it suitable for a range of applications in the pharmaceutical and chemical industries.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 20289-27-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,2,8 and 9 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 20289-27:
(7*2)+(6*0)+(5*2)+(4*8)+(3*9)+(2*2)+(1*7)=94
94 % 10 = 4
So 20289-27-4 is a valid CAS Registry Number.
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
20289-27-4Relevant articles and documents
Total Synthesis of (+)-CC-1065 Utilizing Ring Expansion Reaction of Benzocyclobutenone Oxime Sulfonate
Imaizumi, Taku,Yamashita, Yumi,Nakazawa, Yuki,Okano, Kentaro,Sakata, Juri,Tokuyama, Hidetoshi
, p. 6185 - 6189 (2019)
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.
One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols
Akai, Shuji,Ikawa, Takashi,Masuda, Shigeaki
, (2020/03/23)
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
Akao, Atsushi,Sato, Kimihiko,Nonoyama, Nobuaki,Mase, Toshiaki,Yasuda, Nobuyoshi
, p. 969 - 972 (2007/10/03)
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.
