BIOMAT Database Logo BIOMAT Database Logo

Researches on antibacterial and antifungal agents. IX--Pyrrole analogues of bifonazole with potent antifungal activities. 1988

S Massa, and G Stefancich, and F Corelli, and R Silvestri, and S Panico, and M Artico, and N Simonetti
Dipartimento di Studi Farmaceutici, Università degli Studi di Roma La Sapienza, Italy.

The synthesis and antifungal activities of pyrrole analogues of bifonazole are reported. Reduction of 4-nitrobenzophenone to the corresponding alcohol, reaction with phosphorus tribromide of the latter compound and condensation of the bromonitroderivative with imidazole led to 1-[alpha-(4-nitrophenyl)-4'-benzyl]-1H-imidazole. Hydrogenation of the nitro group to amino and reaction with 2,5-dimethoxytetrahydrofuran according to the Clauson-Kaas procedure afforded the pyrrole analogue of bifonazole. This compound and the related chloroderivative were also prepared by a similar pathway starting from 4-(1H-pyrrol-1-yl)benzophenone and its 4'-chloroderivative. Microbiological screening against Candida albicans and Candida spp showed 1-(alpha-[4-(1H-pyrrol-1-yl)phenyl]benzyl)-1H-imidazole to be the most active compound among the tested derivatives.

UI MeSH Term Description Entries
D007093 Imidazoles Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D008826 Microbial Sensitivity Tests Any tests that demonstrate the relative efficacy of different chemotherapeutic agents against specific microorganisms (i.e., bacteria, fungi, viruses). Bacterial Sensitivity Tests,Drug Sensitivity Assay, Microbial,Minimum Inhibitory Concentration,Antibacterial Susceptibility Breakpoint Determination,Antibiogram,Antimicrobial Susceptibility Breakpoint Determination,Bacterial Sensitivity Test,Breakpoint Determination, Antibacterial Susceptibility,Breakpoint Determination, Antimicrobial Susceptibility,Fungal Drug Sensitivity Tests,Fungus Drug Sensitivity Tests,Sensitivity Test, Bacterial,Sensitivity Tests, Bacterial,Test, Bacterial Sensitivity,Tests, Bacterial Sensitivity,Viral Drug Sensitivity Tests,Virus Drug Sensitivity Tests,Antibiograms,Concentration, Minimum Inhibitory,Concentrations, Minimum Inhibitory,Inhibitory Concentration, Minimum,Inhibitory Concentrations, Minimum,Microbial Sensitivity Test,Minimum Inhibitory Concentrations,Sensitivity Test, Microbial,Sensitivity Tests, Microbial,Test, Microbial Sensitivity,Tests, Microbial Sensitivity
D011758 Pyrroles Azoles of one NITROGEN and two double bonds that have aromatic chemical properties. Pyrrole
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D000935 Antifungal Agents Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. Anti-Fungal Agents,Antifungal Agent,Fungicides, Therapeutic,Antibiotics, Antifungal,Therapeutic Fungicides,Agent, Antifungal,Anti Fungal Agents,Antifungal Antibiotics
D055598 Chemical Phenomena The composition, structure, conformation, and properties of atoms and molecules, and their reaction and interaction processes. Chemical Concepts,Chemical Processes,Physical Chemistry Concepts,Physical Chemistry Processes,Physicochemical Concepts,Physicochemical Phenomena,Physicochemical Processes,Chemical Phenomenon,Chemical Process,Physical Chemistry Phenomena,Physical Chemistry Process,Physicochemical Phenomenon,Physicochemical Process,Chemical Concept,Chemistry Process, Physical,Chemistry Processes, Physical,Concept, Chemical,Concept, Physical Chemistry,Concept, Physicochemical,Concepts, Chemical,Concepts, Physical Chemistry,Concepts, Physicochemical,Phenomena, Chemical,Phenomena, Physical Chemistry,Phenomena, Physicochemical,Phenomenon, Chemical,Phenomenon, Physicochemical,Physical Chemistry Concept,Physicochemical Concept,Process, Chemical,Process, Physical Chemistry,Process, Physicochemical,Processes, Chemical,Processes, Physical Chemistry,Processes, Physicochemical

Related Publications

S Massa, and G Stefancich, and F Corelli, and R Silvestri, and S Panico, and M Artico, and N Simonetti
Researches on antibacterial and antifungal agents, XIV: Thiophene analogues of bifonazole.
April 1992, Archiv der Pharmazie,
S Massa, and G Stefancich, and F Corelli, and R Silvestri, and S Panico, and M Artico, and N Simonetti
Researches on antibacterial and antifungal agents, XII: Analogues of bifonazole with two imidazole moieties and related azoles.
May 1990, Archiv der Pharmazie,
S Massa, and G Stefancich, and F Corelli, and R Silvestri, and S Panico, and M Artico, and N Simonetti
Antifungal agents. VIII. Synthesis and antifungal activities of bipyrryl analogues of bifonazole.
April 1994, Farmaco (Societa chimica italiana : 1989),
S Massa, and G Stefancich, and F Corelli, and R Silvestri, and S Panico, and M Artico, and N Simonetti
Antibacterial and antifungal agents. XV. Synthesis and antifungal activity of structural analogues of bifonazole and ketoconazole.
November 1992, Archiv der Pharmazie,
S Massa, and G Stefancich, and F Corelli, and R Silvestri, and S Panico, and M Artico, and N Simonetti
Synthesis, antibacterial and antifungal activities of bifonazole derivatives.
June 2011, Archiv der Pharmazie,
S Massa, and G Stefancich, and F Corelli, and R Silvestri, and S Panico, and M Artico, and N Simonetti
Amphiphilic Tobramycin Analogues as Antibacterial and Antifungal Agents.
August 2015, Antimicrobial agents and chemotherapy,
S Massa, and G Stefancich, and F Corelli, and R Silvestri, and S Panico, and M Artico, and N Simonetti
Antifungal agents, Part 11. Biphenyl analogues of naftifine: synthesis and antifungal activities.
September 1995, Archiv der Pharmazie,
S Massa, and G Stefancich, and F Corelli, and R Silvestri, and S Panico, and M Artico, and N Simonetti
Recent development of potent analogues of oxazolidinone antibacterial agents.
February 2013, Bioorganic & medicinal chemistry,
S Massa, and G Stefancich, and F Corelli, and R Silvestri, and S Panico, and M Artico, and N Simonetti
Azole Derivatives: Recent Advances as Potent Antibacterial and Antifungal Agents.
January 2023, Current medicinal chemistry,
S Massa, and G Stefancich, and F Corelli, and R Silvestri, and S Panico, and M Artico, and N Simonetti
Research on antibacterial and antifungal agents. IX--Synthesis and microbiological activity of new N-arylpyrroles.
January 1991, Farmaco (Societa chimica italiana : 1989),
Copied contents to your clipboard!