91349-99-4

Upstream product

• 462-08-8 pyridin-3-ylamine 
• 110-13-4 2,5-hexanedione 
• 625-86-5 2,5-dimethylfuran 
• 2530-26-9 3-nitropyridine 

Downstream Products

• 35711-47-8 2,5-dimethyl-1-(pyridin-3-yl)-1H-pyrrole-3-carbaldehyde 

Relevant academic research and scientific papers

One-pot synthesis of cyclohexylamine and: N -aryl pyrroles via hydrogenation of nitroarenes over the Pd0.5Ru0.5-PVP catalyst

The direct synthesis of cyclohexylamine via the hydrogenation of nitrobenzene over monometallic (Pd, Ru or Rh) and bimetallic (PdxRu1-x) catalysts was studied. The Pd0.5Ru0.5-PVP catalyst was the most effective catalyst for this reaction. The catalyst can be reused and applied for the synthesis of N-aryl pyrroles and quinoxalines from nitrobenzenes.

Cascade Synthesis of Pyrroles from Nitroarenes with Benign Reductants Using a Heterogeneous Cobalt Catalyst

A bifunctional 3d-metal catalyst for the cascade synthesis of diverse pyrroles from nitroarenes is presented. The optimal catalytic system Co/NGr-C@SiO2-L is obtained by pyrolysis of a cobalt-impregnated composite followed by subsequent selective leaching. In the presence of this material, (transfer) hydrogenation of easily available nitroarenes and subsequent Paal–Knorr/Clauson-Kass condensation provides >40 pyrroles in good to high yields using dihydrogen, formic acid, or a CO/H2O mixture (WGSR conditions) as reductant. In addition to the favorable step economy, this straightforward domino process does not require any solvents or external co-catalysts. The general synthetic utility of this methodology was demonstrated on a variety of functionalized substrates including the preparation of biologically active and pharmaceutically relevant compounds, for example, (+)-Isamoltane.

ANDROGEN RECEPTOR ANTAGONISTS

Compounds that inhibit the androgen receptor, pharmaceutical compositions comprising one or more of the compounds, as well as methods of treating cancer using such compounds are described.

Easy-To-Synthesize Spirocyclic Compounds Possess Remarkable in Vivo Activity against Mycobacterium tuberculosis

Society urgently needs new, effective medicines for the treatment of tuberculosis. To kick-start the required hit-to-lead campaigns, the libraries of pharmaceutical companies have recently been evaluated for starting points. The GlaxoSmithKline (GSK) library yielded many high-quality hits, and the associated data were placed in the public domain to stimulate engagement by the wider community. One such series, the spiro compounds, are described here. The compounds were explored by a combination of traditional in-house research and open source methods. The series benefits from a particularly simple structure and a short associated synthetic chemistry route. Many members of the series displayed striking potency and low toxicity, and highly promising in vivo activity in a mouse model was confirmed with one of the analogues. Ultimately the series was discontinued due to concerns over safety, but the associated data remain public domain, empowering others to resume the series if the perceived deficiencies can be overcome.

Direct Synthesis of Pyrroles via Heterogeneous Catalytic Condensation of Anilines with Bioderived Furans

Given the wide applications of pyrroles in agriculture, pharmaceuticals, and supramolecular and materials chemistry, a mild and eco-friendly route to produce functionalized pyrroles from bioderived feedstocks is highly desirable. Described herein is a mild and convenient synthesis of pyrroles via direct condensation of an equimolar amount of structurally diverse anilines with biobased furans catalyzed by a simple and efficient solid acid H form zeolite Y catalyst. The protocol tolerates a large variety of functional groups and offers a general and versatile method for scale-up synthesis of a variety of N-substituted pyrrole compounds. Most importantly, the bioactive pyrrole-derived drug pyrvinium, which has lately been confirmed as highly effective in curing colon cancer, can be obtained by this method.

Discovery and structure-activity relationships of pyrrolone antimalarials

In the pursuit of new antimalarial leads, a phenotypic screening of various commercially sourced compound libraries was undertaken by the World Health Organisation Programme for Research and Training in Tropical Diseases (WHO-TDR). We report here the detailed characterization of one of the hits from this process, TDR32750 (8a), which showed potent activity against Plasmodium falciparum K1 (EC50 ～ 9 nM), good selectivity (>2000-fold) compared to a mammalian cell line (L6), and significant activity against a rodent model of malaria when administered intraperitoneally. Structure-activity relationship studies have indicated ways in which the molecule could be optimized. This compound represents an exciting start point for a drug discovery program for the development of a novel antimalarial.

Paal-Knorr pyrrole synthesis using recyclable amberlite IR 120 acidic resin: A green approach

Amberlite IR 120 acidic resin, a polymer matrix, has been demonstrated as a catalyst for Paal-Knorr condensation of 2,5-hexadione with primary amines under solvent-free conditions. This is an efficient, mild, and green methodology for N-substituted pyrrole derivatives. Copyright Taylor & Francis Group, LLC.

NOVEL QUINOLINIUM SALTS AND DERIVATIVES

The present invention relates generally to the synthesis of novel quinolinium salts and derivative compounds. Such salts and compounds are useful for inhibiting the growth of cancer cells.

Study of the Mannich reaction: β-amino-methylation of N-aryl and N-azaheteroaryl-substituted 2,5-dimethylpyrroles, compounds with potential biological activity

Owing to the increasing need of drugs for the treatment of a variety of fungal and bacterial opportunistic infections, a study has been started with the aim of synthesizing structures amenable to a number of easy-to-perform structural modifications in order to meet the requirement of bypassing resistance phenomena. This paper reports on the synthesis of several N-(α-azaheteroaryl)-substituted 2,5-dimethyl-pyrroles bearing in one β-position (or in both β-positions) aminomethyl groups, introduced via a Mannich reaction. Electronic and steric effects by the N-(azaheteroaryl) substituents and the 2- and 5-methyl groups on the course of the Mannich reaction are discussed along with the results of in vitro tests against many Candida species, some bacteria, and several pathogenic plant fungi.