4013-73-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Methylbenzofuran-7-ylamine is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with specific therapeutic properties.
Used in Chemical Synthesis:
In the field of organic chemistry, 2-Methylbenzofuran-7-ylamine serves as a valuable building block for the synthesis of more complex molecules. Its reactivity and functional groups make it suitable for further chemical modifications and the creation of novel compounds with diverse applications.
Used in Research and Development:
Due to its unique chemical structure, 2-Methylbenzofuran-7-ylamine is utilized in research and development for the exploration of new chemical reactions and the study of its properties. This can lead to the discovery of new applications and the development of innovative products in various industries.
Used in the Synthesis of 4-Isocyanatopyridine:
2-Methylbenzofuran-7-ylamine is used as an intermediate in the synthesis of 4-Isocyanatopyridine (I809020). 4-Isocyanatopyridine is a crucial compound in the preparation of thiadiazolopiperazinyl ureas, which are inhibitors of fatty acid amide hydrolase. These inhibitors have potential applications in the treatment of various conditions related to the endocannabinoid system.
Additionally, 4-Isocyanatopyridine is used in the preparation of pyridyl-substituted pyrazolotriazolopyrimidine, a water-soluble human A3 adenosine receptor antagonist. 2-Methylbenzofuran-7-ylamine has potential therapeutic applications in the treatment of various diseases, including inflammation, cancer, and neurodegenerative disorders.

Upstream product

• 54-85-3 isoniazid 
• 55-22-1 pyridine-4-carboxylic acid 
• 14254-57-0 4-(chlorocarbonyl)pyridine 
• 144223-31-4 1-(4-Pyridylcarbonyl)benzotriazole 

Downstream Products

• 98874-04-5 N-isonicotinoyl-DL-phenylalanine 
• 26377-17-3 ethyl 3-oxo-3-(4-pyridyl)propanoate 
• 2015-20-5 ((4-pyridylcarbonyl)amino)acetic acid 
• 124420-89-9 1-(2-Dimethylamino-phenyl)-3-pyridin-4-yl-urea 
• 103791-66-8 N-isonicotinoyl-O-(4-pyridylcarbamoyl)-2-(4-nitrophenyl)-2-hydroxyethylamine 
• 103791-71-5 N,O-di(4-pyridylcarbamoyl)-2-(4-nitrophenyl)-2-hydroxyethylamine 
• 14548-56-2 N-(4-methylphenyl)-4-pyridinecarboxamide 
• 13256-77-4 N-(4-methylphenyl)-N′-(4-pyridinyl)urea 
• 3034-31-9 N-phenylisonicotinamide 
• 1932-35-0 N-phenyl-N'-(pyridin-4-yl)urea 
• 70301-26-7 N-o-Tolyl-isonicotinamide 
• 13289-27-5 N-(2-methylphenyl)-N′-(4-pyridinyl)urea 
• 67036-49-1 Isonicotinylamide GABA 
• 70067-45-7 4-pyridyl isocyanate 

Relevant academic research and scientific papers

Synthesis, biological properties, and molecular modeling investigation of the first potent, selective, and water-soluble human A3 adenosine receptor antagonist

A new, highly potent, selective, and water-soluble antagonist of the hA3 adenosine receptor was synthesized and tested in binding and functional assays. Compound 4 (5-[[(4-pyridyl)amino]carbonyl]amino-8-methyl-2-(2-furyl)-pyrazolo-[4,3-e] 1,2,4-triazolo[1,5-c]pyrimidine hydrochloride) displayed high water solubility (15 mM) and the highest affinity (Ki = 0.01 nM) and selectivity for the hA3 versus A1, A2A, and A2B receptors (> 10000-fold) ever reported. A Schild analysis of the antagonism by 4 of agonist-induced inhibition of cAMP production in CHO cells expressing the hA3 receptor indicated a KB value of 0.20 nM.

Sulfate binding with a tripodal tris(4-pyridylurea) receptor

The tris(2-aminoethyl)amine (tren)-based tris(4-pyridylurea) receptor L has been synthesized and its anion binding properties were studied. The ligand forms a 2:1 (host/guest) complex with MgSO4, [SO4 2-aSL2], in which a sulfate ion is encapsulated by six urea groups from the two ligands through multiple hydrogen bonds. The metal ions do not coordinate to the pyridyl groups but exist as the hydrate [Mg(H2O)6]2+ and interact with the [SO4aSL2] capsules in the outer coordination sphere to form a three dimensional extended structure. The anion binding behavior of ligand L in solution was studied. The tripodal tris(4-pyridylurea) receptor (L) was synthesized and its anion binding properties studied. The ligand forms a 2:1 (H/G) complex with MgSO4, [SO4 2-aSL2], in which a sulfate ion is encapsulated by six urea groups as in the analogous complex of the 3-pyridyl-substituted ligand. The anion binding behavior of ligand L in solution was studied. Copyright

S1PR2 inhibitors potently reverse 5-FU resistance by downregulating DPD expression in colorectal cancer

In this study, S1PR2 was reckoned as a brand-new GPCR target for designing inhibitors to reverse 5-FU resistance. Herein a series of pyrrolidine pyrazoles as the S1PR2 inhibitors were designed, synthesized and evaluated for their activities of anti-FU-resistance. Among them, the most promising compound JTE-013, exhibited excellent inhibition on DPD expression and potent anti-FU-resistance activity in various human cancer cell lines, along with the in vivo HCT116DPD cells xenograft model, in which the inhibition rate of 5-FU was greatly increased from 13.01percent–75.87percent. The underlying mechanism was uncovered that JTE-013 demonstrated an anti-FU-resistance activity by blocking S1PR2 internalization to the endoplasmic reticulum (ER), which inhibited the degradation of 5-FU into α-fluoro-β-alanine (FBAL) by downregulating tumoral DPD expression. Overall, JTE-013 could serve as the lead compound for the discovery of new anti-FU-resistance drugs. Significance: This study provides novel insights that S1PR2 inhibitors could sensitize 5-FU therapy in colorectal cancer.

Spectroscopic Characterization of Nicotinoyl and Isonicotinoyl Nitrenes and the Photointerconversion of 4-Pyridylnitrene with Diazacycloheptatetraene

Recently, nicotinoyl nitrene (2) has been generated from the photodecomposition of nicotinoyl azide (1) and used as the key intermediate in probing nucleobase solvent accessibility inside cells. Following the 266 nm laser photolysis of nicotinoyl azide (1) and isonicotinoyl azide (5) in solid N2 matrices at 15 K, nicotinoyl nitrene (2) and isonicotinoyl nitrene (6) have now been identified by matrix-isolation infrared (IR) spectroscopy. Both aroyl nitrenes 2 and 6 adopt closed-shell singlet ground states stabilized by significant Nnitrene···O interactions, which is consistent with the spectroscopic analysis and calculations at the CBS-QB3 level of theory. Upon subsequent visible light irradiations, 2 (400 ± 20 nm) and 6 (532 nm) undergo rearrangement to pyridyl isocyanates 3 and 7. Further dissociation of 3 and 7 under 193 nm laser irradiation results in CO elimination and formation of ketenimines 12 and 13 via the ring opening of elusive pyridyl nitrenes 4 and 8, respectively. In addition to the IR spectroscopic identification of 8 in the triplet ground state, its reversible photointerconversion with ring expansion to diazacycloheptatetraene 9 has been observed directly. The spectroscopic identification of the nitrene intermediates was aided by calculations at the B3LYP/6-311++G(3df,3pd) level, and the mechanism for their generation in stepwise decompositions of the azides is discussed in the light of CBS-QB3 calculations.

Direct and facile synthesis of acyl azides from carboxylic acids using the trichloroisocyanuric acid-triphenylphosphine system

A mild, efficient, and practical method for the one-step synthesis of acyl azides from carboxylic acids using a safe and inexpensive mixed reagent, trichloroisocyanuric acid-triphenylphosphine, is described.

Photolysis and thermolysis of pyridyl carbonyl azide monolayers on single-crystal platinum

The photochemical and thermal reactivity of a number of acyl azide-substituted pyridine compounds, namely nicotinyl azide, isonicotinyl azide, picolinyl azide and dinicotinyl azide with investigated as saturated monolayers on a single-crystal Pt(111) surface in an ultrahigh vacuum chamber. Multilayers of the substrates exhibited a maximum rate of desorption at 270 K, above which, stable saturated monolayers formed as characterized by reflection-absorption infrared spectroscopy by observation of C=O and N 3 bands at 1700 cm-1, and 2100 and 1300 cm-1 respectively. The monolayers were stable up to 400 K. Photolysis of the monolayer (or heating above 400 K) results in the formation of the respective isocyanate intermediate after loss of nitrogen as evidenced by the appearance of a new infrared band at 2260 cm-1 with concomitant loss of the azide bands. The resulting isocyanate saturated monolayer is stable in absence of nucleophiles, but can be quenched with appropriate nucleophiles. Saturated monolayers of a number of acyl azide-substituted pyridine compounds, namely nicotinyl azide, isonicotinyl azide, picolinyl azide and dinicotinyl azide, were formed on single-crystal Pt(111) surfaces in a UHV chamber. These monolayers were characterized by RAIR and thermal programmed desorption. Photolysis or thermolysis of these saturated monolayers leads to the corresponding isocyanate via a Curtius rearrangement.

1H-INDOL-1-YL-UREA COMPOUNDS

Compounds of formula (I): wherein: R1 and R2, which may be the same or different, represent a hydrogen atom or a linear or branched (C1-C6)alkyl group, R3 represents a hydrogen or halogen atom, a linear or branched (C1-C6)alkyl group, or a linear or branched (C1-C6)alkoxy group, Het represents a pyridyl, pyrimidinyl or piperidyl group, which are optionally substituted by one or more groups selected from halogen, linear or branched (C1-C6)alkyl and linear or branched (C1-C6)alkoxy, —represents a single bond or a double bond, their enantiomers and diastereoisomers, and also addition salts thereof with a pharmaceutically acceptable acid or base. Medicinal products containing the same which are useful in the treatment of depression, anxiety, disorders of memory in the course of aging and/or neurodegenerative diseases, and in the palliative treatment of Parkinson's disease, and for adaptation to stress.

Preparation of polyfunctional acyl azides

(Chemical Equation Presented) A general synthesis of acyl azides from the corresponding N-acyl benzotriazoles is described. The procedure affords acyl azides in good yields and avoids the use of acid activators and NO+ equivalents typically emp

Synthesis and biological studies of a new series of 5- heteroarylcarbamoylaminopyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidines as human A3 adenosine receptor antagonists. Influence of the heteroaryl substituent on binding affinity and molecular modeling investigations

Some pyrazolotriazolopyrimidines bearing different heteroarylcarbamoylamino moieties at the N5-position are described. We previously reported the synthesis of a water soluble compound with high potency and selectivity versus the human A3 adenosine receptor as antagonist, and herein we present an enlarged series of compounds related to the previously mentioned one. These compounds showed A3 adenosine receptor affinity in the nanomolar range and different levels of selectivity evaluated in radioligand binding assays at human A1, A2A, A2B, and A3 adenosine receptors. In particular, the effect of the heteroaryl substituents at the N5 position has been analyzed. This study allows us to recognize that the presence of a pyridinium moiety in this position not only increases water solubility but also improves or retains potency and selectivity at the human A3 adenosine receptors. In contrast, replacement of pyridine with different heterocycles produces loss of affinity and selectivity at the human A3 adenosine receptors. A molecular modeling study has been carried out with the aim to explain these various binding profiles.

(+)-(2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6- (trifluoromethyl)pyridin-3-yl]piperazine-1-carboxamide (YM580) as an orally potent and peripherally selective nonsteroidal androgen receptor antagonist

A novel series of trans-N-aryl-2,5-dimethylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic effects were evaluated. Pharmacological assays indicated that compound 33 was a potent AR antagonist, and subsequent optical resolution provided (+)-(2R,5S)4-[4-cyano-3-(trifluoromethyl)phenyl]-2, 5-dimethyl-N-[6(triflouromethyl)pyridin-3-yl]piperazine-1-carboxamide (33a, YM580) which exhibited the most potent antiandrogenic activity. Unlike bicalutamide, compound 33a decreased the weight of rat ventral prostate in a dose-dependent manner (ED50 = 2.2 mg/kg/day), and induced the maximum antiandrogenic effect, comparable to that of surgical castration, without significantly affecting serum testosterone levels. Compound 33a is a promising clinical candidate for prostate cancer monotherapy.