5264-35-7

Usage

Uses

Used in Pharmaceutical Industry:
5-METHOXY-3,4-DIHYDRO-2H-PYRROLE is used as a reagent for the design and preparation of dihydroindolones and dihydroindolizinones. These compounds serve as orally available MEK inhibitors, which have demonstrated potent in vivo antitumor efficacy. MEK inhibitors are a class of drugs that target the MAPK/ERK signaling pathway, which is often dysregulated in various types of cancer, making them a promising therapeutic approach.
Used in Antiviral Applications:
5-METHOXY-3,4-DIHYDRO-2H-PYRROLE is also utilized in the synthesis of methylenedioxy mappicine ketone analogs, which exhibit anti-HSV (herpes simplex virus) activity. These analogs can potentially be developed into antiviral drugs to combat herpes infections, which are common and can lead to severe health complications if left untreated.

InChI:InChI=1/C5H9NO/c1-7-5-3-2-4-6-5/h2-4H2,1H3

Upstream product

• 616-45-5 2-pyrrolidinon 
• 77-78-1 dimethyl sulfate 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 584-08-7 potassium carbonate 
• 96-42-4 pyrrolidin-3-one 
• 123-75-1 pyrrolidine 
• 71-43-2 benzene 

Downstream Products

• 98336-89-1 N-pyrrolidin-2-yliden-alanine 
• 108800-61-9 3-Carbamoyl-4.5-trimethylen-1.2.4-triazol 
• 530-53-0 deoxyvasicinone 
• 116056-05-4 4,5-Trimethylen-1,2,4-triazol 
• 116056-07-6 2,5,6,7-tetrahydro-pyrrolo[2,1-c][1,2,4]triazol-3-one 
• 123-75-1 pyrrolidine 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 103861-77-4 2-(3-methoxyphenyl)pyrrolidine 
• 62686-84-4 3-(pyrrolidin-2-ylidene)pentane-2,4-dione 
• 43003-15-2 N-(2-phenyl-2-oxoethyl)-2-pyrrolidinone 
• 953813-96-2 C₁₇H₂₂N₂O₃ 
• 716364-40-8 N-(pyrrolidin-2-ylidene)sulfamide 
• 64944-81-6 1-phenyl-2-(pyrrolidin-2-ylidene)butane-1,3-dione 

Relevant academic research and scientific papers

Synthesis of 3-(Piperidin-4-yl)-6,7-dihydro-5H-pyrrolo-[2,1-c][1,2,4]triazole and Theoretical Study of the Hydrazone-Hydrazine Tautomerism of the Intermediate Hydrazonation Product

3-(Piperidin-4-yl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole was synthesized through a four-step process including etherification, hydrazonation, cyclization, and reduction with an overall yield of 39%. The final product was characterized by 1/su

γ-Lactam-Based Antifungal Compounds against the Wheat Pathogen Zymoseptoria tritici

As new environmentally friendly and effective antifungal agents are deeply needed, efficient ecofriendly strategies were designed to access two series of compounds inspired from natural γ-lactams. Designed compounds were fully characterized and evaluated as antifungal candidates against Zymoseptoria tritici, the main pathogen on wheat crops. The targeted derivatives were prepared from natural resources using green solvents, simple procedures, and limited purification steps. These bio-inspired compounds revealed as good candidates for further development of efficient crop protection products. Indeed, the HIT compounds exhibited IC50 around 1 μg/mL and were more active than the references tebuconazole and bixafen towards some multidrug-resistant strains. Two dozen of derivatives have been obtained for each series and allowed to establish early structure-activity relationships useful for the development of next generation of γ-lactam derivatives with improved efficacy.

N-Heterocyclic carbene triazolium salts containing brominated aromatic motifs: Features and synthetic protocol

In this work, we provide a brief overview of the role of N-aryl substituents on triazolium N-heterocyclic carbene (NHC) catalysis. This synopsis provides context for the disclosed synthetic protocol for new chiral N-heterocyclic carbene (NHC) triazolium salts with brominated aromatic motifs. Incorporating brominated aryl rings into NHC structures is challenging, probably due to the substantial steric and electronic influence these substituents exert throughout the synthetic protocol. However, these exact characteristics make it an interesting N-aryl substituent, because the electronic and steric diversity it offers could find broad use in organometallic- A nd organo-catalysis. Following the synthetic reaction by NMR guided the extensive modification of a known protocol to enable the preparation of these challenging NHC pre-catalysts.

Discovery of AZD4573, a Potent and Selective Inhibitor of CDK9 That Enables Short Duration of Target Engagement for the Treatment of Hematological Malignancies

A CDK9 inhibitor having short target engagement would enable a reduction of Mcl-1 activity, resulting in apoptosis in cancer cells dependent on Mcl-1 for survival. We report the optimization of a series of amidopyridines (from compound 2), focusing on properties suitable for achieving short target engagement after intravenous administration. By increasing potency and human metabolic clearance, we identified compound 24, a potent and selective CDK9 inhibitor with suitable predicted human pharmacokinetic properties to deliver transient inhibition of CDK9. Furthermore, the solubility of 24 was considered adequate to allow i.v. formulation at the anticipated effective dose. Short-term treatment with compound 24 led to a rapid dose- and time-dependent decrease of pSer2-RNAP2 and Mcl-1, resulting in cell apoptosis in multiple hematological cancer cell lines. Intermittent dosing of compound 24 demonstrated efficacy in xenograft models derived from multiple hematological tumors. Compound 24 is currently in clinical trials for the treatment of hematological malignancies.

METALLOENZYME INHIBITOR COMPOUNDS

Provided are compounds having HDAC6 modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by HDAC6.

Propionic Acid Derivatives and Methods of Use Thereof

Provided herein are compounds and pharmaceutical compositions of formula I where R1, R2, R3, R4, R5 and R6 are as described herein. Also provided pharmaceutically acceptable salts or stereoisomers of these compounds. In addition methods are provided for inhibiting the binding of an integrin to treat various pathophysiological conditions.

Carboranes as Aryl Mimetics in Catalysis: A Highly Active Zwitterionic NHC-Precatalyst

Modern catalysis takes advantage of aryl-based interactions to tune and control reactions. In the design of N-heterocyclic-carbene catalysts, both the electronic and steric nature of the nitrogen substituents play a crucial role. Although hydrocarbon-based systems and especially aryl residues have contributed considerably to overcome multifaceted catalytic challenges, the unique properties of carborane moieties, including delocalized charge, potential planar chirality, and well-known thermodynamic stability, offer unprecedented opportunities to develop new catalysts while being employed as aryl mimetics. We report a straightforward synthetic route to a novel zwitterionic triazolium-based N-heterocyclic carbene (NHC) precatalyst bearing a 7,8-dicarba-nido-undecaboranyl substituent. The catalyst's excellent activity and its broad applicability are demonstrated in a wide range of organocatalytic transformations. Comparison of the performance with known N-aryl NHC catalysts offers preliminary insights into the stereoelectronic nature of this nido-carboranyl substituent.

Synthesis of [1,2-A]-fused tricyclic dihydroquinolines by palladiumcatalyzed intramolecular C-N cross-coupling of polarized heterocyclic enamines

A simple methodology for [1,2-A]-fused tricyclic dihydroquinolines is established. The key ste of the methodology is an intramolecular Buchwald-Hartwig amination reaction of suitabl halogenated (both bromo and chloro) cyclic enaminoketones, enaminoesters and enaminonitrile with various ring size (from five-to seven-membered). Optimal reaction conditions (palladiu source, base, ligand) depend on the ring size of the starting enamine, giving 65-98% yield of th tricyclic product. A treatment of the products with perchloric acid gives respective quinoliniu perchlorates.

Chemical Compounds

Provided are a series of novel pyridine or pyrimidine derivatives which inhibit CDK9 and may be useful for the treatment of hyperproliferative diseases. In particular the compounds are of use in the treatment of proliferative disease such as cancer including hematological malignancies such as acute myeloid leukemia, multiple myeloma, chronic lymphocytic leukemia, diffuse large B cell lymphoma, Burkitt's lymphoma, follicular lymphoma and solid tumors such as breast cancer, lung cancer, neuroblastoma and colon cancer.

NITROGENATED HETEROCYCLIC COMPOUND

The present invention provides a compound having a PDE2A selective inhibitory action, which is useful as an agent for the prophylaxis or treatment of schizophrenia, Alzheimer's disease and the like. The present invention is a compound represented by the formula (1): wherein each symbol is as described in the specification, or a salt thereof.