119673-50-6

Basic information

• Product Name: 1-(4-FLUORO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE-3-CARBALDEHYDE
• Synonyms: 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde(SALTDATA: FREE)
• CAS NO: 119673-50-6
• Molecular Formula: C₁₃H₁₂FNO
• Molecular Weight: 217.24
• Mol File: 119673-50-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 337.1°C at 760 mmHg
• Flash Point: 157.7°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 0.000108mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: 1-(4-FLUORO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-FLUORO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE-3-CARBALDEHYDE(119673-50-6)
• EPA Substance Registry System: 1-(4-FLUORO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE-3-CARBALDEHYDE(119673-50-6)

Safety Data

• Hazardous Substances Data: 119673-50-6(Hazardous Substances Data)

Usage

General Description

1-(4-Fluoro-phenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde is a chemical compound with the molecular formula C13H12FNO. It is a pyrrole derivative with a substituted phenyl and a carbaldehyde group. 1-(4-FLUORO-PHENYL)-2,5-DIMETHYL-1H-PYRROLE-3-CARBALDEHYDE is commonly used in organic synthesis and medicinal chemistry as a building block for the production of various pharmaceutical and agrochemical products. Its properties and reactivity make it a valuable intermediate in the synthesis of diverse organic compounds. Additionally, it exhibits potential biological activities, making it a subject of interest for drug discovery and development.

InChI:InChI=1/C13H12FNO/c1-9-7-11(8-16)10(2)15(9)13-5-3-12(14)4-6-13/h3-8H,1-2H3

Upstream product

• 371-40-4 4-fluoroaniline 
• 110-13-4 2,5-hexanedione 
• 54609-08-4 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 890235-83-3 C₁₈H₁₈FN₃OS 
• 292873-75-7 (2Z, 5Z)-3-cyclohexyl-5-((1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-2-(phenylimino)thiazolidin-4-one 
• 1428183-48-5 C₂₁H₂₁FN₂O₃ 

Relevant articles and documents

Design and Synthesis of 1-((1,5-Bis(4-chlorophenyl)-2-methyl-1H-pyrrol-3-yl)methyl)-4-methylpiperazine (BM212) and N-Adamantan-2-yl-N′-((E)-3,7-dimethylocta-2,6-dienyl)ethane-1,2-diamine (SQ109) Pyrrole Hybrid Derivatives: Discovery of Potent Antitubercular Agents Effective against Multidrug-Resistant Mycobacteria

Novel pyrroles have been designed, synthesized, and evaluated against mycobacterial strains. The pyrroles have originally been designed as hybrids of the antitubercular drugs BM212 (1) and SQ109 (2), which showed common chemical features with very similar topological distribution. A perfect superposition of the structures of 1 and 2 revealed by computational studies suggested the introduction of bulky substituents at the terminal portion of the pyrrole C3 side chain and the removal of the C5 aryl moiety. Five compounds showed high activity toward Mycobacterium tuberculosis, while 9b and 9c were highly active also against multidrug-resistant clinical isolates. Compound 9c showed low eukaryotic cell toxicity, turning out to be an excellent lead candidate for preclinical trials. In addition, four compounds showed potent inhibition (comparable to that of verapamil) toward the whole-cell drug efflux pump activity of mycobacteria, thus turning out to be promising multidrug-resistance-reversing agents.

Synthesis, structure and in vitro anti-trypanosomal activity of non-toxic arylpyrrole-based chalcone derivatives

With an intention of identifying chalcone derivatives exhibiting anti-protozoal activity, a cohort of relatively unexplored arylpyrrole-based chalcone derivatives were synthesized in moderate to good yields. The resultant compounds were evaluated in vitro for their potential activity against a cultured Trypanosoma brucei brucei 427 strain. Several compounds displayed mostly modest in vitro anti-trypanosomal activity with compounds 10e and 10h emerging as active candidates with IC50 values of 4.09 and 5.11 μM, respectively. More importantly, a concomitant assessment of their activity against a human cervix adenocarcinoma (HeLa) cell line revealed that these compounds are non-toxic.

Discovery and optimisation studies of antimalarial phenotypic hits

There is an urgent need for the development of new antimalarial compounds. As a result of a phenotypic screen, several compounds with potent activity against the parasite Plasmodium falciparum were identified. Characterization of these compounds is discussed, along with approaches to optimise the physicochemical properties. The in vitro antimalarial activity of these compounds against P. falciparum K1 had EC50 values in the range of 0.09e29 mM, and generally good selectivity (typically >100-fold) compared to a mammalian cell line (L6). One example showed no significant activity against a rodent model of malaria, and more work is needed to optimise these compounds.