13314-85-7

Basic information

• Product Name: 5-Hydroxy-2-methylindole
• Synonyms: 5-HYDROXY-2-METHYLINDOLE;2-METHYL-1H-INDOL-5-OL;2-Methyl-5-Indanone;5-Hydroxy-2-Methyl-1H-indole;1H-Indol-5-ol,2-Methyl-;5-Hydroxy-2-methylindol
• CAS NO: 13314-85-7
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• EINECS: 236-345-0
• Product Categories: Indoles and derivatives;pharmacetical;Indoles
• Mol File: 13314-85-7.mol

Chemical Properties

• Melting Point: 130-132℃
• Boiling Point: 344.8 °C at 760 mmHg
• Flash Point: 162.4 °C
• Appearance: Brown/Solid
• Density: 1.262 g/cm³
• Vapor Pressure: 3.21E-05mmHg at 25°C
• Refractive Index: 1.703
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 10.05±0.40(Predicted)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 5-Hydroxy-2-methylindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxy-2-methylindole(13314-85-7)
• EPA Substance Registry System: 5-Hydroxy-2-methylindole(13314-85-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 13314-85-7(Hazardous Substances Data)

Usage

Application

5-Hydroxy-2-methylindole is a useful research chemical.

InChI:InChI=1/C9H9NO/c1-6-4-7-5-8(11)2-3-9(7)10-6/h2-5,10-11H,1H3

Upstream product

• 31720-90-8 acetoxy-5 methyl-2 indole 
• 7598-91-6 ethyl 5-hydroxy-2-methylindole-3-carboxylate 
• 30891-22-6 α-methyl-2,5-dihydroxyphenylethylamine 
• 1076-74-0 5-methoxy-2-methyl-1H-indole 
• 1266659-05-5 ethyl 2-(5-fluoro-2-nitrophenyl)-3-oxobutanoate 
• 1266659-06-6 1-(5-fluoro-2-nitrophenyl)propan-2-one 
• 446-35-5 2,4-Difluoronitrobenzene 
• 106-51-4 p-benzoquinone 
• 193466-60-3 [2-(2,5-Dihydroxy-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester 

Downstream Products

• 412021-98-8 5-hydroxy-2-methyl-indole-3-carbaldehyde 
• 124224-50-6 5-benzyloxy-2-methyl-indole 
• 440351-67-7 3-benzyl-2-methyl-1H-indole-5-ol 
• 756478-76-9 benzyl {[1-(4-butoxybenzoyl)-2-methyl-1H-indol-5-yl]oxy}acetate 
• 1363421-69-5 C₂₅H₂₀N₂O₄ 
• 1363421-55-9 C₁₈H₁₇NO₃ 
• 1392268-32-4 2-fluoro-N-(2-(6-methoxy-2-methyl-1H-indol-3-yl)ethyl)benzamide 

Relevant articles and documents

Indole Based Weapons to Fight Antibiotic Resistance: A Structure-Activity Relationship Study

Antibiotic resistance represents a worldwide concern, especially regarding the outbreak of methicillin-resistant Staphylococcus aureus, a common cause for serious skin and soft tissues infections. A major contributor to Staphylococcus aureus antibiotic resistance is the NorA efflux pump, which is able to extrude selected antibacterial drugs and biocides from the membrane, lowering their effective concentrations. Thus, the inhibition of NorA represents a promising and challenging strategy that would allow recycling of substrate antimicrobial agents. Among NorA inhibitors, the indole scaffold proved particularly effective and suitable for further optimization. In this study, some unexplored modifications on the indole scaffold are proposed. In particular, for the first time, substitutions at the C5 and N1 positions have been designed to give 48 compounds, which were synthesized and tested against norA-overexpressing S. aureus. Among them, 4 compounds have NorA IC50 values lower than 5.0 μM proving to be good efflux pump inhibitor (EPI) candidates. In addition, preliminary data on their ADME (absorption, distribution, metabolism, and excretion) profile is reported.

VEGFR TYROSINE KINASE INHIBITORS

Novel compounds, their prodrugs, and the pharmaceutically acceptable salts as pharmaceutical compositions containing such compounds useful in treating certain diseases modulated by the inhibition of vascular endothelial growth factors (VEGFs) receptor tyrosine kinases are provided. In particular, compounds and compositions and the methods for the prophylaxis, management and treatment of cancers through the inhibition of VEGF receptor tyrosine kinases are provided.

Structure-activity relationship of 5-chloro-2-methyl-3-(1,2,3,6- tetrahydropyridin-4-yl)-1H-indole analogues as 5-HT6 receptor agonists

To further investigate the structure-activity relationship (SAR) of the 5-hydroxytryptamine type 6 (5-HT6) receptor agonist 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (EMD386088, 6), a series of 2-methyl-3-(1,2,3,6-tetrahydr

Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death

Methuosis is a novel caspase-independent form of cell death in which massive accumulation of vacuoles derived from macropinosomes ultimately causes cells to detach from the substratum and rupture. We recently described a chalcone-like compound, 3-(2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1- one (i.e., MIPP), which can induce methuosis in glioblastoma and other types of cancer cells. Herein, we describe the synthesis and structure-activity relationships of a directed library of related compounds, providing insights into the contributions of the two aryl ring systems and highlighting a potent derivative, 3-(5-methoxy, 2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one (i.e., MOMIPP) that can induce methuosis at low micromolar concentrations. We have also generated biologically active azide derivatives that may be useful for future studies aimed at identifying the protein targets of MOMIPP by photoaffinity labeling techniques. The potential significance of these studies is underscored by the finding that MOMIPP effectively reduces the growth and viability of Temozolomide-resistant glioblastoma and doxorubicin-resistant breast cancer cells. Thus, it may serve as a prototype for drugs that could be used to trigger death by methuosis in cancers that are resistant to conventional forms of cell death (e.g., apoptosis).

Manufacturing synthesis of 5-hydroxy-2-methyl-1H-indole

The manufacturing synthesis of 5-hydroxy-2-methyl-1H-indole is described and two synthetic methods were used and the results discussed. Two small and three large runs with Nenitzescu's method were analyzed and results reported with different reaction conditions. Manufacturing issues encountered were discussed. Production scale of more than 60 kg of the 5-hydroxy-2-methyl-1H- indole-3-carboxylic acid ethyl ester and over 20 kg of the 5-hydroxy-2-methyl- 1H-indole were achieved. Based on these results, larger scale manufacturing of this product or similar products based on the optimized conditions is feasible.

Pyridyloxyindoles Inhibitors of VEGF-R2 and Use Thereof for Treatment of Disease

The invention relates to novel organic compounds of formula (I), and their use in the treatment of the animal or human body, to pharmaceutical compositions comprising a compound of formula I and to the use of a compound of formula I for the preparation of pharmaceutical compositions for use in the treatment of protein kinase dependent diseases, especially of proliferative diseases, such as in the treatment of tumour diseases and ocular neovascular diseases.

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.

Development of prostaglandin D2 receptor antagonist: discovery of highly potent antagonists.

The process of discovery for highly potent prostaglandin D(2) (PGD(2)) receptor antagonists is reported. A series of N-(p-alkoxy)benzoyl-2-methylindole-4-acetic acids were synthesized and identified as a new class of selective PGD(2) receptor antagonists.

Cinnoline compounds

The invention relatest to compounds of the formula (I) wherein either any one of G1, G2, G3, G4 and G5 is nitrogen and the other four are —CH—, or G1, G2, G3, G4 and G5 are all —CH—; Z is —O—, —NH—, —S—, —CH2— or a direct bond; Z is linked to any one of G1, G2, G3 and G4 which is a free carbon atom; n is an integer from 0 to 5; any of the substitutents R1 may be attached at any free carbon atom of the indole, azaindole or indazole group; m is an integer from 0 to 3; Ra represents hydrogen; Rb represents hydrogen or another value as defined herein; R1 represents hydrogen, oxo, hydroxy, halogeno, C1-4alkyl, C1-4alkoxy, C1-4alkoxy, C1-4-alkyl, aminoC1-4alkyl, C1-3alkylaminoC1-4alkyl, di(C1-3alkyl)aminoC1-4alkyl, —C1-5alkyl(ring B) wherein ring B is selected from azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, N-methylpiperazinly, N-ethylpiperazinyl, morpholino and thiomorpholino; R2 represents hydrogen, hydroxy, halogeno, cyano, nitro, trifluoromethyl, C1-3alkyl, C1-3alkoxy, C1-3aklylsulphanyl, —NR3R4 (wherein R3 and R4, which may be the same or different, each represents hydrogen or C1-3alkyl), or R5X1— (wherein R5 and X1 are as defined herein) and salts thereof, 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 the use of a compound of formula I in the manufacture of medicament for the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals. 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.

Cleavage of aromatic methyl ethers by chloroaluminate ionic liquid reagents

We have discovered serendipitously that chloroaluminate ionic liquids can cleave aromatic methyl ethers under surprisingly mild conditions. Three ionic liquids, viz. [TMAH]-[Al2Cl7], [BMIM][Al2Cl7], and [EMIM][Al2Cl6I], and aluminum chloride were compared in the selective demethylation of 4,5-dimethoxyindanone at the 4-methoxy-function. The ionic liquids exhibited a remarkably high selectivity (96:4) in comparison with aluminum chloride (70:30). In addition, the reaction time was drastically shortened when the ionic liquids were used. Interestingly, the three ionic liquids displayed the same reactivity in the demethylation of 4,5-dimethoxyindanone. Considering the lower cost and the bulk availability of the precursors of [TMAH][Al2Cl7], we conclude that this is the most attractive ionic liquid from an industrial point of view. To make the large-scale application of [TMAH][Al2Cl7] feasible, we have developed a safe upscalable method for its preparation. Furthermore, the scope of ether cleavage by the ionic liquid reagent [TMAH][Al2Cl7] was investigated and it was found that aromatic methyl-, al- lyl-, and benzyl-ether cleavage is applicable to a variety of heterocyclic compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.