4307-97-5

Basic information

• Product Name: [1-Benzyl-indol-3-yl]-acetic acid
• Synonyms: [1-Benzyl-indol-3-yl]-acetic acid
• CAS NO: 4307-97-5
• Molecular Formula: C₁₇H₁₅NO₂
• Molecular Weight: 265
• Mol File: 4307-97-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 148 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 500.1±38.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• PKA: 4.53±0.30(Predicted)
• CAS DataBase Reference: [1-Benzyl-indol-3-yl]-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [1-Benzyl-indol-3-yl]-acetic acid(4307-97-5)
• EPA Substance Registry System: [1-Benzyl-indol-3-yl]-acetic acid(4307-97-5)

Safety Data

• Hazardous Substances Data: 4307-97-5(Hazardous Substances Data)

Usage

General Description

[1-Benzyl-indol-3-yl]-acetic acid is a chemical compound that belongs to the class of indole derivatives. It is formed by the combination of benzyl, indole, and acetic acid moieties. [1-Benzyl-indol-3-yl]-acetic acid has been studied for its potential pharmacological activities, including anti-inflammatory and analgesic properties. It is also being investigated for its role in the regulation of neurotransmitters and neuroprotection. Additionally, [1-Benzyl-indol-3-yl]-acetic acid has shown potential anticancer activity in preclinical studies. Overall, this chemical compound exhibits promising biological activities and may have potential applications in the field of medicine and drug development.

Upstream product

• 778-82-5 ethyl 3-indoleacetate 
• 87-51-4 indole-3-acetic acid 
• 4276-25-9 ethyl 2-(1-benzyl-1H-indol-3-yl)acetate 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 51499-29-7 1-(1-benzyl-1H-indol-3-yl)propan-2-one 
• 125923-35-5 methyl (N¹-benzyl-3-indolyl)acetate 
• 125313-88-4 3-(1-Benzyl-3-indolyl)-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione 
• 104819-27-4 2-[2-(1-Benzyl-1H-indol-3-yl)-acetyl]-malonic acid diethyl ester 
• 104819-25-2 ethyl 4-(1-benzylindol-3-yl)-3-oxobutanoate 

Relevant articles and documents

Enantioselective Syntheses of Strychnos and Chelidonium Alkaloids through Regio- and Stereocontrolled Cooperative Catalysis

We describe enantioselective syntheses of strychnos and chelidonium alkaloids. In the first case, indole acetic acid esters were established as excellent partner nucleophiles for enantioselective cooperative isothiourea/Pd catalyzed α-alkylation. This provides products containing indole-bearing stereocenters in high yield and with excellent levels of enantioinduction in a manner that is notably independent of the N-substituent. This led to concise syntheses of (?)-akuammicine and (?)-strychnine. In the second case, the poor performance of ortho-substituted cinnamyl electrophiles in the enantioselective cooperative isothiourea/Ir catalyzed α-alkylation was overcome by appropriate substituent choice, leading to enantioselective syntheses of (+)-chelidonine, (+)-norchelidonine, and (+)-chelamine.

Design, synthesis and biological evaluation of thiazole- and indole-based derivatives for the treatment of type II diabetes

Present studies have shown that the lipid carrier has a significant role in several aspects of metabolic syndrome in A-FABP/ap2-deficient mice, including type 2 diabetes and atherosclerosis. 38 Thiazole- and indole-based derivatives were synthesized and investigated for their inhibitory effects on the production of LPS-stimulated TNF-α. Among them, 12b exhibited an excellent inhibitory efficiency compared to BMS309403 (95% vs. 85%) at the concentration of 10 μM and a binding affinity for ap2 with the apparent Ki values 33 nM. Oral administration of 12b at a dosage of 50 mg/kg effectively reduced the levels of plasma blood glucose, triglycerides, insulin, total cholesterol and alanine aminotransferase in high-fat/diet-induced obesity model. The results highlighted that 12b was a potent anti-diabetic agent.

Synthesis and pharmacological evaluation of (indol-3-yl)alkylamides as potent analgesic agents

A series of (indol-3-yl)alkylamides was synthesized and evaluated for analgesic activity. Two N-(pyridin-4-yl)acetamides, compounds 24 and 25, bearing benzyl or 4-fluorobenzyl moieties in 1-position of indole ring exhibited promising analgesic properties (ED50 = 8.1 and 11 mg/kg p.o., respectively), being as potent as the reference drugs flupirtine (CAS 56995-20-1), ibuprofen (CAS 15687-27-1) and diclofenac (CAS 15307-86-5). The two test compounds were tested for their anti-inflammatory activity by carrageenin-induced edema in rat paw test. 4-Fluorobenzyl derivative 25 whose ID50 was 0.085 ± 0.021 mmol/kg was selected as a lead compound for further pharmacomodulation.