Limits...
Microwave-assisted preparation and antimicrobial activity of O-alkylamino benzofurancarboxylates.

Ostrowska K, Hejchman E, Wolska I, Kruszewska H, Maciejewska D - Monatsh. Chem. (2013)

Bottom Line: Their in-vitro antimicrobial properties were assessed.Inhibition by the compounds of the growth of antibiotic-susceptible standards and clinically isolated strains of Gram-positive and Gram-negative bacteria, yeasts, and a human fungal pathogen was moderate to significant.The molecular and crystal structures of 2-(N,N-diethylamino)ethyl 6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylate were established by single-crystal X-ray diffraction. .

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha, 02097 Warsaw, Poland.

ABSTRACT

Abstract: A series of derivatives of 2 and 3-benzofurancarboxylates were synthesized under microwave-assisted conditions. Their in-vitro antimicrobial properties were assessed. Inhibition by the compounds of the growth of antibiotic-susceptible standards and clinically isolated strains of Gram-positive and Gram-negative bacteria, yeasts, and a human fungal pathogen was moderate to significant. Methyl 5-bromo-7-[2-(N,N-diethylamino)ethoxy]-6-methoxy-2-benzofurancarboxylate hydrochloride was identified as the most active compound (MIC 3-12 × 10(-3) μmol/cm(3) against Gram-positive bacteria; MIC 9.4 × 10(-2) μmol/cm(3) against Candida and Aspergillus brasiliensis). The molecular and crystal structures of 2-(N,N-diethylamino)ethyl 6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylate were established by single-crystal X-ray diffraction.

Graphical abstract: .

No MeSH data available.


Related in: MedlinePlus

Schematic diagram of molecule 1c showing the labeling scheme and the disordered2-(N,N-diethylamino)ethyl substituent
© Copyright Policy - OpenAccess
Related In: Results  -  Collection


getmorefigures.php?uid=PMC4495853&req=5

Fig3: Schematic diagram of molecule 1c showing the labeling scheme and the disordered2-(N,N-diethylamino)ethyl substituent

Mentions: The molecular and crystal structure of 1c inthe solid state were analyzed by single-crystal X-ray diffraction. The molecularstructure with the atomic numbering scheme is illustrated in Fig. 3 (the drawings were performed with Mercury software[16]). The results indicate thatthe compound crystallizes in the monoclinic space group P 21/nwith one molecule in the asymmetric unit. Selected bond lengths, bond angles, andtorsion angles are listed in Table 3. Thebenzofuran moiety is nearly planar with a maximum deviation of 0.020(1) Å for C3a.The C8, C9, C10, O16, O17, and O18 atoms are almost coplanar with the two-ringframework (the appropriate torsion angles are given in Table 3). The orientation of the substituent at C3 relativeto the benzofuran ring can be described by the torsion angle C2–C3–C9–O19 of−0.2(3)°. For the (N,N-diethylamino)ethyl fragment we observed structural disorder as aresult of conformational freedom and from X-ray data we found alternativepositions of the C12 and C13 atoms. Strong intramolecular hydrogen bonding ispresent between O16 and O17 atoms (Fig. 3;Table 4). The angle between the bestplanes of the benzofuran moiety and the C5/O17/H17A/O16/C10/C6 ring is only1.56(6)°. Moreover the weak C4–H4A···O18 and C11–H11···O18 interactions stabilizethe conformation of the molecule.Fig. 3


Microwave-assisted preparation and antimicrobial activity of O-alkylamino benzofurancarboxylates.

Ostrowska K, Hejchman E, Wolska I, Kruszewska H, Maciejewska D - Monatsh. Chem. (2013)

Schematic diagram of molecule 1c showing the labeling scheme and the disordered2-(N,N-diethylamino)ethyl substituent
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4495853&req=5

Fig3: Schematic diagram of molecule 1c showing the labeling scheme and the disordered2-(N,N-diethylamino)ethyl substituent
Mentions: The molecular and crystal structure of 1c inthe solid state were analyzed by single-crystal X-ray diffraction. The molecularstructure with the atomic numbering scheme is illustrated in Fig. 3 (the drawings were performed with Mercury software[16]). The results indicate thatthe compound crystallizes in the monoclinic space group P 21/nwith one molecule in the asymmetric unit. Selected bond lengths, bond angles, andtorsion angles are listed in Table 3. Thebenzofuran moiety is nearly planar with a maximum deviation of 0.020(1) Å for C3a.The C8, C9, C10, O16, O17, and O18 atoms are almost coplanar with the two-ringframework (the appropriate torsion angles are given in Table 3). The orientation of the substituent at C3 relativeto the benzofuran ring can be described by the torsion angle C2–C3–C9–O19 of−0.2(3)°. For the (N,N-diethylamino)ethyl fragment we observed structural disorder as aresult of conformational freedom and from X-ray data we found alternativepositions of the C12 and C13 atoms. Strong intramolecular hydrogen bonding ispresent between O16 and O17 atoms (Fig. 3;Table 4). The angle between the bestplanes of the benzofuran moiety and the C5/O17/H17A/O16/C10/C6 ring is only1.56(6)°. Moreover the weak C4–H4A···O18 and C11–H11···O18 interactions stabilizethe conformation of the molecule.Fig. 3

Bottom Line: Their in-vitro antimicrobial properties were assessed.Inhibition by the compounds of the growth of antibiotic-susceptible standards and clinically isolated strains of Gram-positive and Gram-negative bacteria, yeasts, and a human fungal pathogen was moderate to significant.The molecular and crystal structures of 2-(N,N-diethylamino)ethyl 6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylate were established by single-crystal X-ray diffraction. .

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha, 02097 Warsaw, Poland.

ABSTRACT

Abstract: A series of derivatives of 2 and 3-benzofurancarboxylates were synthesized under microwave-assisted conditions. Their in-vitro antimicrobial properties were assessed. Inhibition by the compounds of the growth of antibiotic-susceptible standards and clinically isolated strains of Gram-positive and Gram-negative bacteria, yeasts, and a human fungal pathogen was moderate to significant. Methyl 5-bromo-7-[2-(N,N-diethylamino)ethoxy]-6-methoxy-2-benzofurancarboxylate hydrochloride was identified as the most active compound (MIC 3-12 × 10(-3) μmol/cm(3) against Gram-positive bacteria; MIC 9.4 × 10(-2) μmol/cm(3) against Candida and Aspergillus brasiliensis). The molecular and crystal structures of 2-(N,N-diethylamino)ethyl 6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylate were established by single-crystal X-ray diffraction.

Graphical abstract: .

No MeSH data available.


Related in: MedlinePlus