172078-33-0

Basic information

• Product Name: 2,3-DIHYDROINDOL-5-OL
• Synonyms: 2,3-DIHYDROINDOL-5-OL;1H-INDOL-5-OL, 2,3-DIHYDRO-;Indolin-5-ol;5-Hydroxy-2,3-dihydro-1H-indole;2,3-Dihydroindol-5-ol HCl
• CAS NO: 172078-33-0
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16
• Product Categories: pharmacetical
• Mol File: 172078-33-0.mol

Chemical Properties

• Boiling Point: 322.212 °C at 760 mmHg
• Flash Point: 194.755 °C
• Appearance: /
• Density: 1.196 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 11.47±0.20(Predicted)
• CAS DataBase Reference: 2,3-DIHYDROINDOL-5-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIHYDROINDOL-5-OL(172078-33-0)
• EPA Substance Registry System: 2,3-DIHYDROINDOL-5-OL(172078-33-0)

Safety Data

• Hazardous Substances Data: 172078-33-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Dihydroindol-5-ol is used as a building block for the synthesis of pharmaceuticals due to its versatile chemical structure and pharmacological properties.
Used in Organic Chemistry:
2,3-Dihydroindol-5-ol is used as a key intermediate in organic chemistry for the development of new compounds and materials.
Used in Antioxidant Applications:
2,3-Dihydroindol-5-ol is used as an antioxidant agent for its ability to neutralize free radicals and protect cells from oxidative damage.
Used in Anti-inflammatory Applications:
2,3-Dihydroindol-5-ol is used as an anti-inflammatory agent for its potential to reduce inflammation and alleviate symptoms associated with inflammatory conditions.
Used in Antitumor Applications:
2,3-Dihydroindol-5-ol is used as an antitumor agent for its potential to inhibit tumor growth and progression, making it a promising candidate for cancer research and treatment.

InChI:InChI=1/C8H9NO/c10-7-1-2-8-6(5-7)3-4-9-8/h1-2,5,9-10H,3-4H2

Upstream product

• 21857-45-4 5-methoxyindoline 
• 1953-54-4 indol-5-ol 

Downstream Products

• 1953-54-4 indol-5-ol 
• 87-62-7 2,6-dimethylaniline 
• 62-53-3 aniline 
• 1266120-63-1 5-(4-trifluoromethyl-cyclohexyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 
• 1266116-48-6 (2-{2-[5-(trans-4-tert-butyl-cyclohexyloxy)-2,3-dihydro-indol-1-yl]-2-oxo-ethylamino}-ethyl)-phosphonic acid 
• 1266116-47-5 (2-{2-[5-(trans-4-tert-butyl-cyclohexyloxy)-2,3-dihydro-indol-1-yl]-2-oxo-ethylamino}-ethyl)-phosphonic acid diethyl ester 
• 1266116-46-4 1-[5-(trans-4-tert-butyl-cyclohexyloxy)-2,3-dihydro-indol-1-yl]-2-chloro-ethanone 
• 1266116-41-9 3-amino-4-[5-(trans-4-tert-butyl-cyclohexyloxy)-2,3-dihydro-indol-1-yl]-4-oxo-butyric acid trifluoroacetate 
• 1266116-37-3 3-tert-butoxycarbonylamino-4-[5-(trans-4-tert-butyl-cyclohexyloxy)-2,3-dihydro-indol-1-yl]-4-oxo-butyric acid tert-butyl ester 

Relevant articles and documents

Increased antibacterial properties of indoline-derived phenolic Mannich bases

The search for antibacterial agents for the combat of nosocomial infections is a timely problem, as antibiotic-resistant bacteria continue to thrive. The effect of indoline substituents on the antibacterial properties of aminoalkylphenols was studied, leading to the development of a library of compounds with minimum inhibitory concentrations (MICs) as low as 1.18 μM. Two novel aminoalkylphenols were identified as particularly promising, after MIC and minimum bactericidal concentrations (MBC) determination against a panel of reference strain Gram-positive bacteria, and further confirmed against 40 clinical isolates (Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Enterococcus faecium, and Listeria monocytogenes). The same two aminoalkylphenols displayed low toxicity against two in vivo models (Artemia salina brine shrimp and Saccharomyces cerevisiae). The in vitro cytotoxicity evaluation (on human keratinocytes and human embryonic lung fibroblast cell lines) of the same compounds was also carried out. They demonstrated a particularly toxic effect on the fibroblast cell lines, with IC50 in the 1.7–5.1 μM range, thus narrowing their clinical use. The desired increase in the antibacterial properties of the aminoalkylphenols, particularly indoline-derived phenolic Mannich bases, was reached by introducing an additional nitro group in the indolinyl substituent or by the replacement of a methyl by a bioisosteric trifluoromethyl substituent in the benzyl group introduced through use of boronic acids in the Petasis borono-Mannich reaction. Notably, the introduction of an additional nitro moiety did not confer added toxicity to the aminoalkylphenols.

Pd/C-Catalyzed transfer hydrogenation ofN-H indoles with trifluoroethanol and tetrahydroxydiboron as the hydrogen source

Under the guidance of the known mechanism of the hydrogenation of indoles and transfer hydrogenation with tetrahydroxydiboron (B2(OH)4), Pd/C catalyzed transfer hydrogenation ofN-H indoles with trifluoroethanol and tetrahydroxydiborane as the hydrogen source has been developed. This provides an efficient strategy and catalytic system for the reduction of un-activatedN-H indoles, andN-H indolines are obtained with good to excellent yields. In addition, a series of the isotopic labelling experiments were carried out to probe the mechanism.

Dual-Active-Sites Design of Co@C Catalysts for Ultrahigh Selective Hydrogenation of N-Heteroarenes

The dual-active-sites Co@C catalyst provides a general powerful strategy to break the limitation of scaling relation on traditional metal surfaces and thus affords unprecedentedly selective hydrogenation of various N-heteroarenes as well as high activity and stability. A porous carbon shell not only allows H2 diffusion to Co sites for activation but also blocks accessibility of N-heteroarenes, and the hydrogenation of N-heteroarenes is achieved on carbon by the spilled hydrogen from Co sites. In addition, the presence of surface/subsurface carbon at the Co sites shows high anti-sulfur poisoning and anti-oxidant capability. Ideal heterogeneous metal hydrogenation catalysts are featured by simultaneously high activity, selectivity, and stability. Herein, we report a general yet powerful strategy to design and fabricate dual-active-sites Co@C core-shell nanoparticle for boosting selective hydrogenation of various N-heteroarenes. It can break the limitation of scaling relation on traditional metal surfaces, and thus afford unprecedentedly high selectivity, activity, and stability. Combining kinetics analysis and DFT calculations with multiple techniques directly unveil that the critical porous carbon shell with a pore size of 0.53 nm not only allows H2 diffusion to Co sites for activation and blocks accessibility of N-heteroarenes but also catalyzes hydrogenation of N-heteroarenes via hydrogen spillover from Co sites. In addition, the presence of surface/subsurface carbon at the Co sites shows high anti-sulfur poisoning and anti-oxidant capability. This work is valuable for guiding the design and manipulation of cost-effective and robust hydrogenation catalysts. Our research can provide an environmentally friendly approach to afford unprecedentedly selective N-heteroarenes hydrogenation, which will greatly reduce the resource and energy consumption and decrease the amount of waste discharge and water pollution. Therefore, these results could help in achieving the “Clean water and sanitation” goal in the 10 UN Sustainable Development Goals. Meanwhile, the products of N-heteroarenes hydrogenation are the core structural motifs in both fine and bulk chemicals, which will make our life more beautiful. Thus, our research also benefits the “Good health and well-being” goal.

TYROSINE KINASE INHIBITOR AND PHARMACEUTICAL COMPOSITION COMPRISING SAME

The present invention relates to a tyrosine kinase inhibitor and a pharmaceutical composition comprising same. The tyrosine kinase inhibitor of the present invention has the structures as shown in the following formula (I) or (II):

NOVEL COMPOUNDS

The present invention relates to new CGRP-antagonists of general formula I wherein U, V, X, Y, R1, R2, R3 and R4 are defined as in the description, the tautomers, the isomers, the diastereomers, the enantiomers, the hydrates, the mixtures thereof and the salts thereof and the hydrates of the salts, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, medicaments containing these compounds, their use and processes for preparing them.

NPY ANTAGONISTS, PREPARATION AND USES

The present invention concerns novel compounds, their preparation and their uses, therapeutic uses in particular. More specifically it concerns derivative compounds having at least two aromatic cycles, their preparation and their uses, in particular in the area of human or animal health. These compounds have an affinity for the biological receptors of neuropeptide Y, NPY, present in the central and peripheral nervous systems. The compounds of the invention are preferably NPY antagonists, and more particularly antagonists of sub-type NPY Y1, and can therefore be used for the therapeutic or prophylactic treatment of any disorder involving NPY. The present invention also concerns pharmaceutical compositions containing said compounds, their preparation and their uses, as well as treatment methods using said compounds.

QUINAZOLINE DERIVATIVES AS ANGIOGENESIS INHIBITORS

The invention relates to the use of compounds of the formula I: wherein ring C is an 8, 9, 10, 12 or 13-membered bicyclic or tricyclic moiety which optionally may contain 1-3 heteroatoms selected independently from O, N and S; Z is -O-, -NH-, -S-, -CH2- or a direct bond; n is 0-5; m is 0-3; R represents hydrogen, hydroxy, halogeno, cyano, nitro, trifluoromethyl, C1-3alkyl, C1-3alkoxy, C1-3alkylsulphanyl, -NRR (wherein R and R, which may be the same or different, each represents hydrogen or C1-3alkyl), or RX- (wherein X and R are as defined herein; R represents hydrogen, oxo, halogeno, hydroxy, C1-4alkoxy, C1-4alkyl, C1-4alkoxymethyl, C1-4alkanoyl, C1-4haloalkyl, cyano, amino, C2-5alkenyl, C2-5alkynyl, C1-3alkanoyloxy, nitro, C1-4alkanoylamino, C1-4alkoxycarbonyl, C1-4alkylsulphanyl, C1-4alkylsulphinyl, C1-4alkylsulphonyl, carbamoyl, N-C1-4alkylcarbamoyl, N,N-di(C1-4alkyl)carbamoyl, aminosulphonyl, N-C1-4alkylaminosulphonyl, N,N-di(C1-4alkyl)aminosulphonyl, N-(C1-4alkylsulphonyl)amino, N-(C1-4alkylsulphonyl)-N-(C1-4alkyl)amino, N,N-di(C1-4alkylsulphonyl)amino, a C3-7alkylene chain joined to two ring C carbon atoms, C1-4alkanoylaminoC1-4alkyl, carboxy or a group RX (wherein X and R are as defined herein); and salts thereof, in the manufacture of a medicament for use in the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals, processes for the preparation of such compounds, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient and compounds of formula I. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.