6915-67-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenyl-1H-Indole-2-carboxylic Acid is used as a reagent for the preparation of cholesterol acyltransferase inhibitors. These inhibitors are essential in the development of medications aimed at regulating lipid metabolism and reducing the risk of cardiovascular diseases. Cholesterol acyltransferase enzymes are responsible for the synthesis of cholesteryl esters, which contribute to the formation of atherosclerotic plaques. By inhibiting these enzymes, the development of atherosclerosis and related complications can be mitigated.

InChI:InChI=1/C15H11NO2/c17-15(18)14-13(10-6-2-1-3-7-10)11-8-4-5-9-12(11)16-14/h1-9,16H,(H,17,18)

Upstream product

• 37129-23-0 ethyl 3-phenyl-1H-indole-2-carboxylate 
• 4757-69-1 2-methyl-3-phenyl-1H-indole 
• 138043-75-1 methyl 3-phenyl-1H-indole-2-carboxylate 
• 620-79-1 Ethyl 2-benzylacetoacetate 
• 153827-71-5 ethyl 1-(benzenesulfonyl)-1H-3-iodoindole-2-carboxylate 
• 98-80-6 phenylboronic acid 
• 91348-45-7 3-bromo-1H-indole-2-carboxylic acid ethyl ester 
• 36963-38-9 3-phenyl-2-phenylhydrazono-propionic acid 
• 117786-09-1 N-(1-methyl-2-phenyl-ethylidene)-N'-phenyl-hydrazine 

Downstream Products

• 1504-16-1 3-phenyl-1H-indole 
• 52839-31-3 3-phenyl-indole-2-carbonyl chloride 
• 138043-75-1 methyl 3-phenyl-1H-indole-2-carboxylate 
• 199434-17-8 1-(tert-butyloxycarbonyl)-3-phenylindole-2-(N,N-bis-tert-butyloxycarbonyl)carboxamide 
• 121649-71-6 3-phenyl-indole-2-carboxylic acid benzylidenehydrazide 
• 105492-12-4 3-phenyl-indole-2-carboxylic acid hydrazide 
• 120608-14-2 2-[(3-Phenyl-1H-indole-2-carbonyl)-amino]-benzoic acid ethyl ester 
• 120608-24-4 13-Phenyl-11H-benzo[5,6][1,4]diazepino[1,2-a]indole-6,12-dione 
• 199434-16-7 3-phenylindole-2-carboxamide 

Relevant academic research and scientific papers

BACTERIAL EFFLUX PUMP INHIBITORS

Disclosed herein are compounds of formula I: (formula I) and salts thereof. Also disclosed are compositions comprising compounds of formula I and methods using compounds of formula I.

Design and synthesis of calindol derivatives as potent and selective calcium sensing receptor agonists

We report the first comprehensive structure-activity study of calindol (4, (R)-N-[(1H-indol-2-yl)methyl]-1-(1-naphthyl)ethanamine), a positive allosteric modulator, or calcimimetic, of the calcium sensing receptor (CaSR). While replacement of the naphthyl moiety of calindol by other aromatic groups (phenyl, biphenyl) was largely detrimental to calcimimetic activity, incorporation of substituents on the 4, 5 or 7 position of the indole portion of calindol was found to provide either equipotent derivatives compared to calindol (e.g., 4-phenyl, 4-hydroxy, 5-hydroxycalindol 44, 52, 53) or, in the case of 7-nitrocalindol (51), a 6-fold more active calcimimetic displaying an EC50 of 20 nM. Unlike calindol, the more active CaSR calcimimetics were shown not to act as antagonists of the closely related GPRC6A receptor, suggesting a more selective profile for these new analogues.

Versatile base-catalyzed route to polycyclic heteroaromatic compounds by intramolecular Aza-Michael addition

A catalytic new synthetic approach to 3,4-dihydropyrazino[1,2-α] indol-1(2H)-ones by intramolecular 1,4-addition of readily available α,β-unsaturated esters, is described. Here, the use of a range of organic as well as inorganic bases (5-10 mol-%) allowed

Synthesis and structural analysis of (e)-2-(2'-nitrovinyl)indoles from the corresponding 2-formylindole derivatives

Preparation of 2-formylindoles was carried out from the appropriate methylindole by oxidation with selenium dioxide and by Vilsmeier formylation. The 2-(2'-nitrovinyl)indoles have been obtained by condensation of 2-formylindoles with nitroalkanes in the presence of ammonium chloride in good yields. In this reaction, only the (E)-isomer of the 2-(2'-nitrovinyl)indoles was observed by 1H nmr and NOE experiments. Evidence for an extended conjugation through the double bond and the nitro group can be evaluate by the deshielding effect on the olefinic protons. Moreover, the non-Beer's law behaviour in the uv-visible spectra suggest the existence of some sort of complex for these compounds.

Regiospecific functionalization of indole-2-carboxylates and diastereoselective preparation of the corresponding indolines

The N-acyl derivatives of 3-substituted indole-2-carboxylates prepared through several routes were submitted to catalytic hydrogenation affording either cis- or trans-indoline diastereomers after quantitative C-2 epimerization.

Synthesis of 3-phenylindoline-2-carboxamides as semi-rigid phenylalanine mimetics

Regioselective catalytic hydrogenation of N-acyl 3-phenylindole-2-carboxylates is the key step for tile preparation of cis and trans ndoline-2-carboxamides which can be considered as phenylalanine semi-rigid derivatives.