4307-97-5

Usage

Uses

Used in Pharmaceutical Industry:
[1-Benzyl-indol-3-yl]-acetic acid is used as a potential therapeutic agent for its anti-inflammatory and analgesic properties, aiming to provide relief from inflammation and pain.
Used in Neurological Applications:
[1-Benzyl-indol-3-yl]-acetic acid is used as a regulator of neurotransmitters and for neuroprotection, potentially benefiting patients with neurological disorders.
Used in Anticancer Applications:
[1-Benzyl-indol-3-yl]-acetic acid is used as an anticancer agent, showing potential activity against various types of cancer in preclinical studies. It may be further developed to target and inhibit cancer cell growth and progression.
Used in Drug Development:
[1-Benzyl-indol-3-yl]-acetic acid is used as a compound in the development of new drugs, leveraging its diverse pharmacological activities to create novel therapeutic options for various medical conditions.

Upstream product

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

Downstream Products

• 126774-82-1 9-benzyl-1-methylpyrano<3,4-b>indol-3-one 
• 104819-24-1 1-benzylindole-3-acetic chloride 
• 85620-05-9 N-benzyl-2,3,3a,8aβ-tetrahydro-3aβ-hydroxyfuro(2,3-b)indol-2-one 
• 125923-35-5 methyl (N¹-benzyl-3-indolyl)acetate 
• 51499-29-7 1-(1-benzyl-1H-indol-3-yl)propan-2-one 

Relevant academic research and scientific papers

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.

Integrated strategies for identifying leads that target the ns3 helicase of the hepatitis C virus

Future treatments for individuals infected by the hepatitis C virus (HCV) will likely involve combinations of compounds that inhibit multiple viral targets. The helicase of HCV is an attractive target with no known drug candidates in clinical trials. Here

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.

Effect of indole-3-acetic acid analogs on the differentiation of HL-60 cells

In continuing search for novel cell differentiation agents, a series of derivatives of indole-3-acetic acid and indole-3-carboxylic acid were prepared and tested against HL-60 cells for their differentiation and antiproliferation activities. Among them, N-ethyl-1-benzylindole-3-carboxamide (14) was the most potent, whereas N-methyl 1-benzylindole-3-acetamide (5) and N-methyl 1-benzylindole-3-carboxamide (13) synergistically potentiated with all-trans-retinoic acid to induce cell differentiation as well as antiproliferation. Our results indicate that these compounds are effective cell differentiation and antiproliferation agents in combination with retinoic acid.

Synthesis of indomethacin analogues for evaluation as modulators of MRP activity

Synthesis of a range of indomethacin analogues, required for investigation in combination toxicity assays, bearing both N-benzyl and N-benzoyl groups, is described. Copyright

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.

Heterocyclic compounds, their preparation and their therapeutic use

A compound of formula (I): STR1 wherein Y1, Y2, Y3 and Y4 are each hydrogen, halogen, nitro, cyano, hydroxyl, thiol, amino, alkyl, haloalkyl, alkylthio, a protected or unprotected carboxyl, a protected or unprotected sulfonamide, or tetrazol; one of R1 and R2 is hydrogen, alkyl, aryl, aralkyl, oxazolyl, or a protected or unprotected carboxyl and the other of R1 and R2 is hydrogen, alkyl, aryl or aralkyl; and R3 is hydrogen or an amino protecting group, and pharmaceutically acceptable salts or esters thereof. The compounds are effective for treating dementia, Alzheimer's disease and delirium and are effective as sedatives.

Indole derivatives useful to treat estrogen-related neoplasms and disorders

The present invention relates to novel indole derivatives useful in down-regulating estrogen receptor expression. Also included are methods for the treatment of neoplasms or of controlling the growth of a neoplasm in a patient afflicted with a neoplastic disease, especially estrogen-dependent neoplasms such as those associated with breast, ovarian and cervical tissue. Another embodiment of the present invention is a method of prophylactically treating a patient at risk of developing a neoplastic disease state. Also provided is a method for treating autoimmune diseases. Also included are pharmaceutical compositions of the novel indole derivatives.

REACTIONS OF β-KETO ESTERS WITH 2-CYANO-1,2,5,6-TETRAHYDROPYRIDINES

Reaction of the sodium salts of β-keto esters 13a and 13b with the 2-cyano-tetrahydropyridines 11 and 12 afforded the 4-substituted piperidine derivatives 21-23.The structures were assigned on the basic of their (1)H-and (13)C-NMR spectra and by comparison with the model compounds 24-26.The stereochemistry and the mechanism of the reactions are discussed.

CONVERSION OF INDOLES INTO QUINOLINES THROUGH THE N-1-C-2 FISSION BY SINGLET-OXYGEN AS A MODEL EXPERIMENT OF BIOMIMETIC SYNTHESIS OF QUININE ALKALOIDS

Photo-oxygenation of indole-3-acetaldehydes (28-30) followed by treatments with dimethyl sulphide and then dilute acetic acid gave 4-acylquinolines (13, 31 and 32), respectively.