53842-16-3

Basic information

• Product Name: 1H-Pyrrole, 2-(4-chlorophenyl)-5-methyl-1-phenyl-
• CAS NO: 53842-16-3
• Molecular Formula: C17H14ClN
• Molecular Weight: 267.758
• Mol File: 53842-16-3.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole, 2-(4-chlorophenyl)-5-methyl-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole, 2-(4-chlorophenyl)-5-methyl-1-phenyl-(53842-16-3)
• EPA Substance Registry System: 1H-Pyrrole, 2-(4-chlorophenyl)-5-methyl-1-phenyl-(53842-16-3)

Safety Data

• Hazardous Substances Data: 53842-16-3(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 1679-18-1 4-Chlorophenylboronic acid 
• 78-94-4 methyl vinyl ketone 
• 62-53-3 aniline 
• 104-88-1 4-chlorobenzaldehyde 
• 53842-12-9 1-(p-chlorophenyl)-1,4-pentanedione 

Downstream Products

• 146204-64-0 [5-(4-Chloro-phenyl)-2-methyl-1-phenyl-1H-pyrrol-3-ylmethyl]-dimethyl-amine 
• 146204-44-6 1-[5-(4-Chloro-phenyl)-2-methyl-1-phenyl-1H-pyrrol-3-ylmethyl]-4-methyl-piperazine 
• 146204-54-8 5-(4-Chloro-phenyl)-2-methyl-1-phenyl-3-pyrrolidin-1-ylmethyl-1H-pyrrole 

Relevant articles and documents

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.

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.

Ruthenium-catalysed conversion of 1,4-alkynediols into pyrroles

Various 1,2,5-substituted pyrroles have been synthesised from 1,4-alkynediols using a ruthenium catalysed isomerisation to give the corresponding 1,4-dicarbonyl compounds, which undergo in situ cyclisation to pyrroles in the presence of amine.