85926-99-4

Usage

Uses

Used in Pharmaceutical Industry:
Indoline-4-ol is used as an enzyme inhibitor for its potential anti-cancer properties. It modulates various biological pathways, making it a promising candidate for the development of new medications.
Used in Biomedical Research:
Indoline-4-ol is used as a research compound for studying its effects on the immune system and its potential applications in the development of novel therapeutic strategies.
Used in Chemical Research:
Indoline-4-ol is used as a versatile compound in chemical research, where its various modified forms can be explored for different applications, enhancing its utility in the synthesis of new compounds and materials.

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

Upstream product

• 496-15-1 1-indoline 
• 52537-01-6 4-aminoindoline 
• 118742-89-5 2-(2,6-diaminophenyl)ethanol 
• 2380-94-1 1H-indol-4-ol 
• 77759-08-1 2-(2,6-dinitrophenyl)ethanol 
• 606-20-2 2,6-dinitrotoluene 

Downstream Products

• 2380-94-1 1H-indol-4-ol 
• 737816-53-4 4-acetoxy-1-acetylindoline 
• 1452925-60-8 C₁₅H₁₅NO₃S 
• 1452925-63-1 C₂₀H₂₂BrNO₅S 
• 1452925-62-0 C₂₀H₂₃NO₅S 
• 1452925-61-9 C₂₂H₂₇NO₅S 
• 1452925-74-4 (2'S,3aR,6R,9R)-7-bromo-9-phenyl-1-tosyl-2,3-dihydro-1H,3'H-spiro[3a,6-ethanoindole-5,2'-furan]-4,5'(4'H,6H)-dione 
• 1452925-73-3 (2'S,3aR,6R,9S)-9-acetyl-7-bromo-1-tosyl-2,3-dihydro-1H,3'H-spiro[3a,6-ethanoindole-5,2'-furan]-4,5'(4'H,6H)-dione 
• 1452925-64-2 3-(7-bromo-4-hydroxy-1-tosylindolin-5-yl)propanoic acid 

Relevant academic research and scientific papers

550 nm excited rhodamine dye and preparation method thereof

The invention provides 550 nm excited rhodamine fluorescent dye and a preparation method thereof. The structural formula of the rhodamine fluorescent dye is as shown in (1), and through structural modification of a rigid five-membered ring, the absorption and emission wavelengths of the rhodamine fluorescent dye generate a certain red shift (about 50 nm) compared with rhodamine 110. Meanwhile, rawmaterials used in the invention are cheap and easily available, the operation is simple, requirements on experiments are low, and the obtained novel rhodamine fluorescent dye has high light stabilityand high quantum yield (up to 0.93 in ethanol), and can be widely applied to the field of biological fluorescence imaging.

Design, synthesis and characterization of potent microtubule inhibitors with dual anti-proliferative and anti-angiogenic activities

Microtubule has been an important target for anticancer drug development. Here we report the discovery and characterization of a series of fused 4-aryl-4H-chromene-based derivatives as highly potent microtubule inhibitors. Among a total of 37 derivatives synthesized, 23 exhibited strong in vitro anti-proliferative activities against A375 human melanoma cells. The relationship between the biological activities of these microtubule inhibitors and their chemical structure variations was analyzed. Studies of compounds 27a, 19a and 9a in parallel with colchicine as the positive control compound in a panel of biological assays revealed that these compounds blocked cell cycle progression, increased apoptosis, and inhibited HUVEC capillary tube formation at low nanomolar concentrations. The most potent compound 27a was also tested in eight additional cancer cell lines besides A375 cells and two non-cancer cells and showed potent and selective activity on these cancer cells. To understand the molecular and structure mechanism of action of these compounds, tubulin polymerization and molecular docking studies were carried out for 27a as the representative. The results were consistent with the mechanism by which 27a interacts with the colchicine binding site on tubulin and disrupts tubulin polymerization. With potent dual actions of microtubule destabilization and vascular disruption described above, this small molecule can serve as a valuable research probe of the function and role of microtubules in human diseases and promising lead for developing new therapeutic agents.

INDOLE, INDOLINE DERIVATIVES, COMPOSITIONS COMPRISING THEM AND USES THEREOF

The invention provides indole and indoline derivatives and slats thereof, compositions comprising them and uses thereof for the treatment of diseases and disorders.

Carbamate derivatives of indolines as cholinesterase inhibitors and antioxidants for the treatment of Alzheimer's disease

The cascade of events that occurs in Alzheimer's disease involving oxidative stress and the reduction in cholinergic transmission can be better addressed by multifunctional drugs than cholinesterase inhibitors alone. For this purpose, we prepared a large number of derivatives of indoline-3-propionic acids and esters. They showed scavenging activity against different radicals in solution and significant protection against cytotoxicity in cardiomyocytes and primary cultures of neuronal cells exposed to H2O2 species and serum deprivation at concentrations ranging from 1 nM to 10 μM depending on the compound. For most of the indoline-3-propionic acid derivatives, introduction of N-methyl-N-ethyl or N-methyl-N-(4-methoxyphenyl) carbamate moieties at positions 4, 6, or 7 conferred both acetyl (AChE) and butyryl (BuChE) cholinesterase inhibitory activities at similar concentrations to those that showed antioxidant activity. The most potent AChE inhibitors were 120 (3-(2-aminoethyl) indolin-4-yl ethyl(methyl)carbamate dihydrochloride) and 94 (3-(3-methoxy-3-oxopropyl)-4-(((4-methoxyphenyl)(methyl) carbamoyl)oxy)indolin- 1-ium hydrochloride) with IC50s of 0.4 and 1.2 μM, respectively.

S1P RECEPTORS MODULATORS

The invention relates to novel compounds that have S1P receptor modulating activity and, preferably, apoptotic activity and/or anti proliferative activity against cancer cells and other cell types. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, cancer. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as cancer.

PHOTOLABILE DINITROINDOLINYL BASED COMPOUNDS

The present invention relates to photolabile or photoreleasable compounds including a caging moiety linked to an effector moiety, wherein the compounds are capable of releasing the effector moiety on irradiation, typically by flash irradiation with UV light. These compounds are particularly suitable for focal 2-photon uncaging The photoreleasable compounds can be used to deliver effector moieties such as carboxylic acids, preferably, neuroactive amino acids to sites where their activity is required. In preferred embodiments of the invention, the caging moiety is based on 4-carboxymethoxy-5,7-dinitroinlinyl and derivatives thereof.

The effect of substitution on the utility of piperidines and octahydroindoles for reversible hydrogen storage

Substituted piperidines and octahydroindoles are compared in terms of their usability as reversible organic hydrogen storage liquids for hydrogen-powered fuel cells. Theoretical Gaussian calculations indicate which structural features are likely to lower the enthalpy of dehydrogenation. Experimental results show that attaching electron donating or conjugated substituents to the piperidine ring greatly increases the rate of catalytic dehydrogenation, with the greatest rates being observed with 4-aminopiperidine and piperidine-4-carboxamide. Undesired side reactions were observed with some compounds such as alkyl transfer reactions during the dehydrogenation of 4-dimethylaminopiperidine, C-O and C-N cleavage reactions during hydrogenation and/or subsequent dehydrogenation of 4-alkoxy and 4-amino indoles, and disproportionation during the hydrogenation of 4-aminopyridine. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

7-NITROINDOLINE DERIVATIVES AND THEIR USES

7-nitroindoline compounds are disclosed that comprise a triplet sensitising group such as substituted or unsubstituted benzophenone group and can be used to cage effector species. In particular, the inclusion of a triplet sensitising group linked to the 4 or 5 position of a 7-nitroindoline derivative provides compounds which can be photolysed to release the effector species with unexpectedly enhanced photolysis efficiency. The triplet sensitising group may be linked directly to the 7-nitroindoline or via a spacer group. In some examples, the triplet sensitising group and/or the spacer group can be selected to enhance other properties of the caged compound such as its solubility, spectroscopic properties or stability (e.g. stability of the linkage between the nitroindoline moiety and the triplet sensitiser). This can help to improve the performance of the caged compound, especially in aqueous environments containing dissolved oxygen.

HYDROXYLATION OF INDOLINES AND INDOLES BY HYDROGEN PEROXIDE IN SUPERACIDS

In SbF5-HF, indolines and indoles are hydroxylated on the aromatic ring, protonated hydrogen peroxide H3O2+ reacting on the protonated substrates.