24297-59-4

Usage

Uses

Used in Pharmaceutical Industry:
Indol-1-yl-acetic acid is used as a reactant for the preparation of conformationally restrained analogs of pravadoline. These analogs are of significant interest due to their potential applications in the development of new drugs targeting various medical conditions.
Used in Cannabinoid Receptor Research:
Indol-1-yl-acetic acid is utilized as a reactant in the synthesis of (aminoalkyl)?indole agonists of the cannabinoid receptor. These agonists exhibit nanomolar potency and enantioselectivity, making them valuable tools in the study of cannabinoid receptor function and the development of novel therapeutic agents.

InChI:InChI=1/C10H9NO2/c12-10(13)7-11-6-5-8-3-1-2-4-9(8)11/h1-6H,7H2,(H,12,13)

Upstream product

• 120-72-9 indole 
• 174667-12-0 1-ethoxycarbonylmethyl-indole-2-carboxylic acid 
• 79-08-3 bromoacetic acid 
• 96-32-2 bromoacetic acid methyl ester 
• 33140-80-6 methyl indol-1-ylacetate 
• 61155-69-9 ethyl 2-(1H-indol-1-yl)acetate 
• 16982-67-5 sodium salt of indole 
• 126718-55-6 1-(carboxymethyl)-1H-indole-2-carboxylic acid 
• 105-36-2 ethyl bromoacetate 
• 40899-71-6 1-benzenesulfonylindole 
• 910322-01-9 tert-butyl 1H-indol-1-ylacetate 
• 256931-80-3 ethyl 1-(2-ethoxy-2-oxoethyl)-1H-indole-2-carboxylate 

Downstream Products

• 33140-80-6 methyl indol-1-ylacetate 
• 438620-29-2 (1R,3R,4S)-menthyl 1-indoleacetate 
• 438620-35-0 (S)-N-(1-indolyl)acetyl-2-(methoxymethyl)pyrrolidine 
• 438620-32-7 (S)-N-(1-indolyl)acetyl-4-benzyl-2-oxazolidinone 
• 439098-07-4 (1R,3R,4S)-menthyl (1R*,2S*,6S*)-5-(2-acetoxyethyl)-3-[(E)-2-(methoxycarbonyl)vinyl]-1,2,5,6-tetrahydro-2,6-methano[1,4]diazocino[1,2-a]indole-1-carboxylate 
• 137794-99-1 (4-Methoxy-phenyl)-(2-morpholin-4-yl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-methanone 
• 733799-04-7 C₁₇H₁₆N₂O 

Relevant academic research and scientific papers

Novel hits for acetylcholinesterase inhibition derived by docking-based screening on ZINC database

The inhibition of the enzyme acetylcholinesterase (AChE) increases the levels of the neurotransmitter acetylcholine and symptomatically improves the affected cognitive function. In the present study, we searched for novel AChE inhibitors by docking-based virtual screening of the standard lead-like set of ZINC database containing more than 6 million small molecules using GOLD software. The top 10 best-scored hits were tested in vitro for AChE affinity, neurotoxicity, GIT and BBB permeability. The main pharmacokinetic parameters like volume of distribution, free fraction in plasma, total clearance, and half-life were predicted by previously derived models. Nine of the compounds bind to the enzyme with affinities from 0.517 to 0.735 μM, eight of them are non-toxic. All hits permeate GIT and BBB and bind extensively to plasma proteins. Most of them are low-clearance compounds. In total, seven of the 10 hits are promising for further lead optimisation. These are structures with ZINC IDs: 00220177, 44455618, 66142300, 71804814, 72065926, 96007907, and 97159977.

ACIDITIES OF 1-INDOLYLACETIC AND CARBAZOLACETIC ACIDS. INDUCTIVE CONSTANTS OF INDOLYL AND CARBAZOLYL GROUPS

The pKa values of 1-indolylacetic, 3-(9-ethyl)carbyzolylacetic, and a number of 3,6-disubstituted 9-carbazolylacetic acids in aqueous ethanol solutions were determined by potentiometry.The inductive constants of the corresponding heterocyclic fragments were calculated from the values obtained.It is shown that annelation of the benzene ring with the pyrrole ring of indole gives rise to a decrease in the negative inductive effect of the heteroring.A linear relationship between the acidic properties of carbazole and the corresponding 9-carbazolylacetic acids was established.

TOTAL SYNTHESIS AND STEREOCHEMICAL REASSIGNMENT OF THE INDOLE ALKALOID VINOXINE

The first total synthesis of the indole alkaloid vinoxine and the reassignment of the relative configuration at carbon-16 in this alkaloid is reported.

Crystal structure and DFT studies of (E)-1-(4-fluorophenyl)-3-(1H-indol-1-yl)-4-styrylazetidin-2-one

An unprecedented diasterospecific synthesis of (E)-1-(4-fluorophenyl)-3-(1H-indol-1-yl)-4-styrylazetidin-2-one (3) from Staudinger [2 + 2] cycloaddition reaction between (E)-4-fluoro-N-((E)-3-phenylallylidene)aniline (1) and indole ketene is herein described. The single crystal X-ray structure confirmed that compound 3 (C25H19FN2O) crystallizes in the monoclinic space group C2/c, with Z = 8, and unit cell parameters; a = 32.0225 (5) ?, b = 7.39970 (10) ?, c = 17.4100 (2) ?, β = 108.3010 (10)°, V = 3916.75 (10) ?3, Z = 8. Crystal structure 3 shows the absolute cis configuration of the molecule to be C9 (S) and C10 (R). In addition, the structural parameters (bond lengths, bond angles, and torsion angles) and electronic properties of 3 were computed using the B3LYP/6-31 + G (d,p) and M06-2X/6-31 + G (d,p) basis set in ground state. A good correlation (R2 = 0.9989) between the experimental and theoretical parameters was achieved.

Br?nsted Acid-Promoted Cyclodimerization of Indolyl Ketones: Construction of Indole Fused-Oxabicyclo[3.3.1]nonane and -Cyclooctatetraene Ring Systems

A Br?nsted acid-promoted cyclodimerization of C(3)-, C(2)-, or N(1)-substituted indole ketone derivatives is described. A wide range of structurally diverse bisindole fused-9-oxabicyclo[3.3.1]nonane and bisindole fused-cyclooctatetraene (COT) derivatives can be prepared in good to high yields with high efficiency.

Discovery of a novel and potent inhibitor with differential species-specific effects against NLRP3 and AIM2 inflammasome-dependent pyroptosis

The NLRP3 inflammasome, which regulated a proinflammatory programmed cell death form termed pyroptosis, is involved in the pathological process of various human diseases, such as multiple sclerosis, type 2 diabetes, and gout. Thus, compounds inhibiting activation of the NLRP3 inflammasome can be promising treatments for these diseases. In this study, we conducted a phenotypic screening against NLRP3-dependent pyroptosis and discovered the hit compound 1, which showed moderate antipyroptotic activity. Chemistry efforts to improve potency of 1 resulted in a novel compound 59 (J114), which exhibited a half-maximal inhibitory concentration (IC50) of 0.077 ± 0.008 μM against cell pyroptosis. Interestingly, unlike all pyroptosis inhibitors currently reported, the activity of J114 showed significant differences in human- and mouse-derived cells. The IC50 of J114-mediated inhibition of IL-1β secretion by human THP-1 macrophages was 0.098 μM, which was nearly 150-fold and 500-fold more potent than that of J774A.1 (14.62 μM) and bone marrow-derived macrophages (BMDMs) (48.98 μM), respectively. Further studies showed that J114 displayed remarkable inhibitory activity against NLRP3- and AIM2-but not NLRC4-dependent activation of caspase-1 and the release of IL-1β in human THP-1 macrophages. Mechanistically, J114 disturbed the interaction of NLRP3 or AIM2 with the adaptor protein ASC and inhibited ASC oligomerization. Overall, our study identified a unique molecule that inhibits NLRP3 and AIM2 inflammasome activation and has species differences, which is worthy of further research to understand the differential regulation of the NLRP3 and AIM2 inflammasomes in humans and mice.

Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls

The functionalization of aryl and heteroaryls using α-carbonyl sulfoxonium ylides without the help of a directing group has remained so far a neglected area, despite the advantageous safety profile of sulfoxonium ylides. Described herein are the cyclizations of α-carbonyl sulfoxonium ylides onto benzenes, benzofurans and N-p-toluenesulfonyl indoles in the presence of a base in HFIP, whereas pyrroles and N-methyl indoles undergo cyclization in the presence of an iridium catalyst. Significantly, these two sets of conditions are chemospecific for each groups of substrates.

SUBSTITUTED BENZOXAZINE AND RELATED COMPOUNDS

The present invention relates to compounds including but not limited to of any one of formulas Ia, Ib, IIa, IIb, IIIa, IIIb, and IV to VI, VIIa, VIIb, VIIIa, VIIIb and VIIIc as described herein and their tautomers and/or pharmaceutically acceptable salts, compositions, and methods of uses thereof.

SUBSTITUTED BENZOXAZINE AND RELATED COMPOUNDS

The present invention relates to compounds including but not limited to of any one of formulas Ia, Ib, IIa, IIb, IIIa, IIIb, and IV to VI, VIIa, VIIb, VIIIa, VIIIb and VIIIc as described herein and their tautomers and/or pharmaceutically acceptable salts, compositions, and methods of uses thereof.

The discovery of indole full agonists of the neurotensin receptor 1 (NTSR1)

Neurotensin (NT) is an endogenous tridecapeptide found in the central nervous system (CNS) and in peripheral tissues. Neurotensin exerts a wide range of physiological effects and it has been found to play a critical role in a number of human diseases, suc