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Two biologically active thiophene-3-carboxamide derivatives

Vasu, * and Nirmala, KA and Choudhury, AR and Mohan, S and Saravanan, J and Narasimhamurthy, T (2003) Two biologically active thiophene-3-carboxamide derivatives. In: Acta Crystallographica Section C: Crystal Structure Communications, 59 (12). o676-o678.


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$The\hspace{5mm}two\hspace{5mm}title\hspace{5mm}compound,$ $2-(\lbrace (1Z)-[4-(dimethylamino)-phenyl]methylene\rbrace amino)-4,5-dimethyl-N-(2-methylphenyl)thiophene-3-carboxamide},\hspace{5mm}C_{23}H_{25}N_{3}OS,\hspace{5mm}(I),\hspace{5mm}and\hspace{5mm}2- \lbrace ((1E)-[4-(dimethylamino)phenyl \rbrace methylene}amino)-N-(4-methylphenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide,\hspace{5mm}C_{25}H_{27}N_{3}OS$, (II), show antibacterial and antifungal activities. The asymmetric unit of (II) contains two crystallographically independent molecules. The o-toluidine ring in (I) lies gauche with respect to the thiophene ring. In (II), the p-toluidine ring is coplanar with the thiophene ring in one molecule, but is tilted from it in the other molecule. Neither structure exhibits any significant intermolecular interactions, but in both, an intramolecular $N-H{\cdot\cdot\cdot}N$ hydrogen bond forms a pseudo-six-membered ring, thus locking the molecular conformation and removing conformational flexibility.

Item Type: Journal Article
Publication: Acta Crystallographica Section C: Crystal Structure Communications
Publisher: Blackwell
Additional Information: Copyright for this article belongs to Blackwell Publishing.
Department/Centre: Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Division of Information Sciences (Doesn't exist now) > BioInformatics Centre
Date Deposited: 11 Jan 2007
Last Modified: 19 Sep 2010 04:23
URI: http://eprints.iisc.ac.in/id/eprint/5173

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