3771-57-1

Upstream product

• 62-53-3 aniline 
• 583-05-1 1-phenylpentane-1,4-dione 
• 201230-82-2 carbon monoxide 
• 78-94-4 methyl vinyl ketone 
• 98-80-6 phenylboronic acid 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 3240-29-7 1-Phenylpent-4-en-1-one 
• 98-95-3 nitrobenzene 
• 52313-46-9 ethyl 2-acetyl-4-oxo-4-phenylbutanoate 
• 123-76-2 levulinic acid 
• 4553-59-7 2-anilino-2-phenylacetonitrile 

Downstream Products

• 102237-56-9 1-(2-methyl-1,5-diphenyl-pyrrol-3-yl)-propan-1-one 
• 102665-34-9 (2-methyl-1,5-diphenyl-pyrrol-3-yl)-phenyl ketone 
• 53068-11-4 3,4-dibenzoyl-2-methyl-1,5-diphenyl-pyrrole 
• 102882-94-0 (4-methoxy-phenyl)-(2-methyl-1,5-diphenyl-pyrrol-3-yl)-ketone 
• 115916-21-7 3,4-bis-(4-methoxy-benzoyl)-2-methyl-1,5-diphenyl-pyrrole 
• 96757-78-7 1-(2-methyl-1,5-diphenyl-1H-pyrrol-3-yl)ethanone 
• 102479-02-7 3,4-diacetyl-2-methyl-1,5-diphenyl-pyrrole 
• 102028-13-7 2-methyl-1,5-diphenyl-pyrrole-3-carbaldehyde 
• 146204-49-1 1-Methyl-4-(2-methyl-1,5-diphenyl-1H-pyrrol-3-ylmethyl)-piperazine 
• 120945-13-3 1,4-bis-(4-methoxy-phenyl)-5-methyl-6,7-diphenyl-6H-pyrrolo[3,4-d]pyridazine 
• 122493-42-9 5-methyl-1,4,6,7-tetraphenyl-6H-pyrrolo[3,4-d]pyridazine 
• 114380-54-0 1,4,5-trimethyl-6,7-diphenyl-6H-pyrrolo[3,4-d]pyridazine 
• 146204-67-3 Dimethyl-(2-methyl-1,5-diphenyl-1H-pyrrol-3-ylmethyl)-amine 
• 146204-59-3 2-Methyl-1,5-diphenyl-3-pyrrolidin-1-ylmethyl-1H-pyrrole 

Relevant academic research and scientific papers

Design, synthesis and in-vitro anti-cancer evaluation of novel derivatives of 2-(2-methyl-1,5-diaryl-1h-pyrrol-3-yl)-2-oxo-n-(pyridin-3-yl)acetamide

Objective: Several anti-tubulin agents were introduced for the cancer treatment so far. Despite successes in the treatment of cancer, these agents cause toxic side effects, including peripheral neuropathy. Comparing anti-tubulin agents, indibulin seemed to cause minimal peripheral neuropathy, but its poor aqueous solubility and other potential clinical problems have led to its remaining in a preclinical stage. Methods: Herein, indibulin analogues were synthesized and evaluated for their in vitro anti-cancer activity using MTT assay (on the MCF-7, T47-D, MDA-MB231 and NIH-3T3 cell lines), annexin V/PI staining assay, cell cycle analysis, anti-tubulin assay and caspase 3/7 activation assay. Results: One of the compounds, 4a, showed good anti-proliferative activity against MCF-7 cells (IC50: 7.5 μM) and low toxicity on a normal cell line (IC50 > 100μM). All of the tested compounds showed lower cytotoxicity on normal cell line in comparison to reference compound, indibulin. In the annexin V/PI staining assay, induction of apoptosis in the MCF-7 cell line was observed. Cell cycle analysis illustrated an increasing proportion of cells in the sub-G-1 phase, consistent with an increasing proportion of apoptotic cells. No increase in G2/M cells was observed, consistent with the absence of anti-tubulin activity. A caspase 3/7 assay protocol showed that apoptosis induction by more potent compounds was due to activation of caspase 3. Conclusion: newly synthesized compounds exerted acceptable anticancer activity and further investigation of current scaffold would be beneficial.

A fluorescent target-guided Paal-Knorr reaction

It has become increasingly apparent that high-diversity chemical reactions play a significant role in the discovery of bioactive small molecules. Here, we describe an expanse of this paradigm, combining a ‘target-guided synthesis’ concept with Paal-Knorr chemistry applied to the preparation of fluorescent ligands for human prostaglandin-endoperoxide synthase (COX-2).

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.

Synthesis and anti-breast cancer activity of novel indibulin related diarylpyrrole derivatives

Background: During recent years, a number of anti-tubulin agents were introduced for treatment of diverse types of cancer. Despite their potential in the treatment of cancer, drug resistance and adverse toxicity, such as peripheral neuropathy, are some of the negative effects of anti-tubulin agents. Among anti-tubulin agents, indibulin was found to cause minimal peripheral neuropathy. Thus far, however, indibulin has not entered clinical usage, caused in part by its poor aqueous solubility and other developmental problems in preclinical evaluation. Objectives: With respect to need for finding potent and safe anticancer agents, in our current research work, we synthesized several indibulin-related diarylpyrrole derivatives and investigated their anti-cancer activity. Methods: Cell cultur studies were perfomred using the MTT cell viability assay on the breast cancer cell lines MCF-7, T47-D, and MDA-MB231 and also NIH-3?T3 cells as representative of a normal cell line. The activity of some of the synthesized compounds for tubulin interaction was studied using colchicine binding and tubulin polymerization assays. The annexin V-FITC/PI method and flow cytometric analysis were used for studying apoptosis induction and cell cycle distribution. Results and conclusion: Two of the synthesized compounds, 4f and 4?g, showed high activity on the MDA-MB231 cell line (IC50?= 11.82 and 13.33?μM, (respectively) and low toxicity on the normal fibroblast cells (IC50?> 100?μM). All of the tested compounds were more potent on T47-D cancer cells and less toxic on NIH-3?T3 normal cells in comparison to reference compound, indibulin. The tubulin polymerization inhibition assay and [3H]colchicine binding assay showed that the main mechanism of cell death by the potent synthesized compounds was not related to an interaction with tubulin. In the annexin V/PI staining assay, the induction of apoptosis in the MCF-7 and MDA-MB231 cell lines was observed. Cell cycle analysis illustrated an increased percentage of sub-G-1 cells in the MDA-MB231 cell line as a further indication of cell death through induction of apoptosis. [Figure not available: see fulltext.].

One-pot synthesis of 2-methyl-1,5-diaromatic-1H-pyrroles from styrene, acetone and arylamines using TBHP, copper(II) trifluoromethanesulfonate and sulfamic acid

The one-pot copper/manganese co-catalyzed heterocyclization of arylamine derivatives with styrene and acetone to produce a series of 2-methyl-1,5-diaromatic-1H-pyrroles was investigated. The described reaction combines 1,4-dicarbonyl synthesis and Paal-Knorr type condensation reactions.

Greener Paal-Knorr Pyrrole Synthesis by Mechanical Activation

A straightforward and solventless synthesis of pyrroles was developed by using mechanochemical activation and a biosourced organic acid as the catalyst. Relative to traditional Paal-Knorr methodologies, various N-substituted pyrroles were obtained in very short reaction times. By reaction with unreactive diketones, desymmetrized aliphatic and aromatic compounds were also synthesized.

Efficient synthesis of substituted pyrroles through Pd(OCOCF3)2-catalyzed reaction of 5-hexen-2-one with primary amines

An efficient and facile Pd(OCOCF3)2-catalyzed one-pot cascade protocol has been developed for the synthesis of multiple substituted pyrroles in good to excellent yields. Unlike the reported method starting from the 2-alkenal-1,3-carbonyl compounds, the process utilizes the less reactive 5-hexen-2-one and the method has great potential as a complement to the current developed methods.

Organic synthesis in deep eutectic solvents: Paal-Knorr reactions

Deep eutectic solvents (the combination of either urea or glycerol with choline chloride) are effective solvents/catalysts for Paal-Knorr reactions to form pyrroles of furans. The reaction conditions are quite mild and do not require the addition of an additional Bronsted or Lewis acid catalyst. Given the inexpensive, non-toxic, and recyclable nature of the DES, these reaction conditions are simple and highly environmentally friendly.

Indium-mediated one-pot pyrrole synthesis from nitrobenzenes and 1,4-diketones

One-pot reduction-triggered heterocyclizations of nitrobenzene derivatives with 1,4-diketones were investigated. In the presence of indium/AcOH in toluene at 80 C, reaction of nitrobenzenes with 2,5-hexadione produced moderate to excellent yields (40-98%)

Xanthan sulfuric acid as an efficient, green, biodegradable, and recyclable solid acid catalyst for one-pot synthesis of N-substituted pyrroles under solvent-free conditions at room temperature

A new, green, and efficient method for synthesis of a variety of N-substituted pyrroles from condensation reactions of 2,5-hexanedione with amines or diamines using xanthan sulfuric acid as a biosupported and reusable ecofriendly catalyst under solvent-free conditions at room temperature is described. The use of a nontoxic, inexpensive, easily available, and reusable biosupported proton source catalyst under solvent-free conditions makes this protocol practical, environmentally friendly, and economically attractive.