27018-76-4 Usage
Description
1-Benzylindole-3-carboxylic acid is an organic compound with a molecular structure that features a benzyl group attached to an indole ring, with a carboxylic acid functional group at the 3rd position. It is a versatile chemical intermediate that can be utilized in the synthesis of various biologically active compounds and pharmaceuticals.
Uses
1-Benzylindole-3-carboxylic acid is used as a reactant for the preparation of several types of compounds, each with its specific application in different industries. Here are the applications categorized by the industry and the application type:
Used in Pharmaceutical Industry:
1-Benzylindole-3-carboxylic acid is used as a reactant for the preparation of Indoleacetic acid analogs, which serve as differentiation-inducing and antiproliferative agents for human myeloblastoma cells. These analogs are crucial in cancer research and treatment, as they can potentially halt the uncontrolled growth of cancer cells.
1-Benzylindole-3-carboxylic acid is also used as a reactant for the synthesis of Indole-carboxamide derivatives, which act as inhibitors of lipid peroxidation and superoxide anion formation. These derivatives are significant in the development of antioxidants that can protect cells from oxidative stress and damage, which are common in various diseases, including cancer and neurodegenerative disorders.
In addition, 1-Benzylindole-3-carboxylic acid is used to prepare Indole carboxamides, which function as hyaluronidase inhibitors. These inhibitors are essential in the pharmaceutical industry for the treatment of conditions where the breakdown of hyaluronic acid is a concern, such as in some cancer metastasis and inflammatory diseases.
Furthermore, it is used to produce Fuconojirimycin derivatives, which are inhibitors of α-fucosidases. These derivatives have potential applications in the treatment of lysosomal storage diseases, such as fucosidosis, where the lack of a specific enzyme leads to the accumulation of unwanted substances in cells.
1-Benzylindole-3-carboxylic acid is also utilized in the preparation of Indole-2 and 3-carboxamides, which are selective cyclooxygenase-2 (COX-2) inhibitors. These inhibitors are vital in the development of anti-inflammatory drugs and pain relievers, as they target the specific enzyme responsible for inflammation and pain without affecting the COX-1 enzyme, which is essential for maintaining the protective lining of the stomach.
Lastly, 1-Benzylindole-3-carboxylic acid is used to synthesize Indole amides, which have antihistaminic properties. These compounds are employed in the development of antihistamine drugs, which are used to treat allergic reactions and symptoms such as itching, swelling, and sneezing.
Check Digit Verification of cas no
The CAS Registry Mumber 27018-76-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,7,0,1 and 8 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 27018-76:
(7*2)+(6*7)+(5*0)+(4*1)+(3*8)+(2*7)+(1*6)=104
104 % 10 = 4
So 27018-76-4 is a valid CAS Registry Number.
InChI:InChI=1/C16H13NO2/c18-16(19)14-11-17(10-12-6-2-1-3-7-12)15-9-5-4-8-13(14)15/h1-9,11H,10H2,(H,18,19)/p-1
27018-76-4Relevant articles and documents
Pd(II)-Catalyzed asymmetric oxidative annulation of N-alkoxyheteroaryl amides and 1,3-dienes
Zhang, Tao,Shen, Hong-Cheng,Xu, Jia-Cheng,Fan, Tao,Han, Zhi-Yong,Gong, Liu-Zhu
supporting information, p. 2048 - 2051 (2019/03/29)
The first Pd(II)-catalyzed asymmetric oxidative annulation of N-alkoxyaryl amides and 1,3-dienes is reported, which features particular applicability for quick assembly of different types of chiral heterocycles with high yields and enantioselectivities. A novel chiral pyridine-oxazoline bearing a methoxyl group at the C-5 position and a gem-dimethyl group on the oxazoline moiety was found to be crucial for conversion.
Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles
Nemoto, Koji,Tanaka, Shinya,Konno, Megumi,Onozawa, Satoru,Chiba, Masafumi,Tanaka, Yuuki,Sasaki, Yosuke,Okubo, Ryo,Hattori, Tetsutaro
, p. 734 - 745 (2016/01/15)
Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by deprotonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively.
Hydroxamic acids block replication of hepatitis c virus
Ai, Teng,Xu, Yanli,Qiu, Li,Geraghty, Robert J.,Chen, Liqiang
, p. 785 - 800 (2015/01/30)
Intrigued by the role of protein acetylation in hepatitis C virus (HCV) replication, we tested known histone deacetylase (HDAC) inhibitors and a focused library of structurally simple hydroxamic acids for inhibition of a HCV subgenomic replicon. While known HDAC inhibitors with varied inhibitory profiles proved to be either relatively toxic or ineffective, structure-activity relationship (SAR) studies on cinnamic hydroxamic acid and benzo[b]thiophen-2-hydroxamic acid gave rise to compounds 22 and 53, which showed potent and selective anti-HCV activity and therefore are promising starting points for further structural optimization and mechanistic studies.
