Two biologically active thiophene-3-carboxamide derivatives.
The compounds 2-[[(E)-(4-methoxyphenyl)methylene]amino]-N-(3-methylphenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, C24H24N2O2S, (I), and N-(4-methylphenyl)-2-[[(E)-(4-methylphenyl)methylene]amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, C24H24N2OS, (II), show antibacterial and antifungal activities. The m-toluidine ring in (I) and the p-toluidine ring in (II) are coplanar with their respective thiophene rings. In (I), an intermolecular C-H...O hydrogen bond is present, whereas (II) does not exhibit any significant intermolecular interactions. However, in both compounds, an intramolecular N-H.N hydrogen bond forms a pseudo-six-membered ring, thus locking the molecular conformation and eliminating conformational flexibility.
Vasu
Vivekananda Degree College, Bangalore 560 055, Karnataka, India.
Nirmala
K A
KA
Chopra
Deepak
D
Mohan
S
S
Saravanan
J
J
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry*
D000577:Amides; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D013876:Thiophenes