27257-15-4

Basic information

• Product Name: 1-Methyl-1H-pyrrolo[2,3-b]pyridine
• Synonyms: 1-Methyl-1H-pyrrolo[2,3-b]pyridine;1-Methyl-7-azaindole;1H-Pyrrolo[2,3-b]pyridine, 1-Methyl-;1-Methylpyrrolo[2,3-b]pyridine
• CAS NO: 27257-15-4
• Molecular Formula: C₈H₈N₂
• Molecular Weight: 132.17
• Product Categories: Azaindoles
• Mol File: 27257-15-4.mol
• Article Data: 47

Chemical Properties

• Boiling Point: 254.2 °C at 760 mmHg
• Flash Point: 107.6 °C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 0.0279mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: 2-8°C
• PKA: 5.35±0.30(Predicted)
• CAS DataBase Reference: 1-Methyl-1H-pyrrolo[2,3-b]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-1H-pyrrolo[2,3-b]pyridine(27257-15-4)
• EPA Substance Registry System: 1-Methyl-1H-pyrrolo[2,3-b]pyridine(27257-15-4)

Safety Data

• Hazardous Substances Data: 27257-15-4(Hazardous Substances Data)

Usage

General Description

1-Methyl-1H-pyrrolo[2,3-b]pyridine is a chemical compound with the molecular formula C8H7N. It is a heterocyclic compound with a pyrrolopyridine core structure, and it belongs to the class of organic compounds known as pyrrolopyridines. 1-Methyl-1H-pyrrolo[2,3-b]pyridine is not naturally occurring, but it can be synthesized through various chemical reactions. It is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and organic materials. In addition, it has been studied for its potential therapeutic applications, including as an antiviral and anticancer agent. 1-Methyl-1H-pyrrolo[2,3-b]pyridine has also been investigated for its fluorescent properties, making it useful in various imaging and detection applications.

InChI:InChI=1/C8H8N2/c1-10-6-4-7-3-2-5-9-8(7)10/h2-6H,1H3

Upstream product

• 271-63-6 7-Azaindole 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 55052-24-9 1H-Pyrrolo[2,3-b]pyridine-7-oxide 
• 348640-02-8 1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine 
• 865-33-8 potassium methanolate 
• 373-68-2 tetramethylammonium fluoride 
• 62018-65-9 chloroform ethyl acetate 

Downstream Products

• 521984-94-1 1-methyl-2-phenyl-1H-pyrrolo-[2,3-b]pyridine 
• 281192-94-7 N-Methyl-7-azaisatin 
• 521985-24-0 1-methyl-1H-pyrrolo[2,3-b]pyridine-3-boric acid 
• 441715-88-4 C₃₀H₃₃FN₄O₅ 
• 441712-69-2 trans-4-[1-[[2-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridinyl)]-6-benzoxazolyl]acetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid 
• 1448610-92-1 C₁₈H₁₇IN₂ 
• 171919-36-1 1-methyl-1H-pyrrolo<2,3-b>pyridine-3-carbaldehyde 
• 521985-25-1 2-(4-fluorophenyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine 
• 1562571-62-3 4-methyl-N-(1-methyl-3-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-indol-2-yl)benzenesulfonamide 
• 1426654-57-0 (1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)(phenyl)methanone 

Relevant articles and documents

Fluorescent Species of 7-Azaindole and 7-Azatryptophan in Water

A study of the fluorescence lifetimes and quantum yields of 7-azaindole and its methylated derivatives N1-methyl-7-azaindole (1M7AI) and 7-methyl-7H-pyrrolopyridine (7M7AI) in water is performed in order to explain the observation that the fluorescence spectrum of 7-azaindole apparently consists of one band (λmax = 386 nm) whereas in alcohols the spectrum is bimodal (e.g., for methanol, λmax = 374, 505 nm).Careful measurements of the fluorescence decay as a function of emission wavelength indicate a small amplitude of an ca. 70-ps decaying component at the bluer wavelengths and a rising component of the same duration at the redder wavelengths.The small amplitude component, which comprises no more than 20percent of the fluorescence decay, is attributed to excited-state tautomerization that is mediated by the solvent.Particular attention is paid to the pH dependence of the fluorescence lifetimes and yields.We propose that upon tautomerization the basic 1-nitrogen (N1) of 7-azaindole is rapidly protonated giving rise to a species whose emission maximum is at ca. 440 nm.The fluorescence emission maximum and lifetime of 7-azaindole is dominated by the 80percent of the solute molecules that are blocked by unfavorable solvation from executing excited-state tautomerization.It is proposed that 10 ns is required for the surrounding water molecules to attain a configuration about 7-azaindole that is propitious for tautomerization.

A new oxadiazole-based topsentin derivative modulates cyclin-dependent kinase 1 expression and exerts cytotoxic effects on pancreatic cancer cells

Pancreatic ductal adenocarcinoma (PDAC) is a highly lethal form of cancer characterized by drug resistance, urging new therapeutic strategies. In recent years, protein kinases have emerged as promising pharmacological targets for the treatment of several solid and hematological tumors. Interestingly, cyclin-dependent kinase 1 (CDK1) is overexpressed in PDAC tissues and has been correlated to the aggressive nature of these tumors because of its key role in cell cycle progression and resistance to the induction of apoptosis. For these reasons, CDK1 is one of the main causes of chemoresistance, representing a promising pharmacological target. In this study, we report the synthesis of new 1,2,4-oxadiazole compounds and evaluate their ability to inhibit the cell growth of PATU-T, Hs766T, and HPAF-II cell lines and a primary PDAC cell culture (PDAC3). Compound 6b was the most active compound, with IC50 values ranging from 5.7 to 10.7 μM. Molecular docking of 6b into the active site of CDK1 showed the ability of the compound to interact effectively with the adenosine triphosphate binding pocket. Therefore, we assessed its ability to induce apoptosis (which increased 1.5-and 2-fold in PATU-T and PDAC3 cells, respectively) and to inhibit CDK1 expression, which was reduced to 45% in Hs766T. Lastly, compound 6b passed the ADME prediction, showing good pharmacokinetic parameters. These data demonstrate that 6b displays cytotoxic activity, induces apoptosis, and targets CDK1, supporting further studies for the development of similar compounds against PDAC.

Visible-Light-Induced Carbonylation of Indoles with Phenols under Metal-Free Conditions: Synthesis of Indole-3-carboxylates

A visible-light-induced carbonylation of indoles with phenols for the synthesis of indole-3-carboxylates has been developed. The reaction proceeded via a radical carbonylation process in which elementary I2 was used as an effective photosensitive initiator and, thus, avoided the use of transition metal catalysts. A series of different aryl indole-3-carboxylates were prepared in moderate to good yields. The broad applicability of this methodology was further highlighted by the late-stage functionalization of several phenol-containing natural products and pharmaceuticals.

TOPICAL FORMULATIONS

Provided herein are gelled topical formulations for the treatment of skin diseases comprising: a) a MEK inhibitor; b) one or more organic solvents in an amount of about 70% to about 99% by weight; and c) a gelling agent; wherein the one or more organic solvents are selected from the group consisting of C2-6 alcohol, a C2-6 alkylene glycol, a di-(C2-6 alkylene) glycol, a polyethylene glycol, C1-3 alkyl-(OCH2CH2)1-5-OH, DMSO, ethyl acetate, acetone, N-methyl pyrrolidone, benzyl alcohol, glycerin, and an oil; the gelling agent is hydroxypropyl cellulose having a molecular weight ranging from about 40,000 Dato about 2,500,000 Da; and wherein the gelled topical formulation has a viscosity of from 1 to 25,000 cps; and DMSO, when present, is combined with at least one other of said organic solvents such that DMSO is present in an amount of less than 50% by weight.