Synthesis, supramolecularity and in vitro antimicrobial activity of 3a,8a-dihydroxy-2-thioxo-1,3,3a,

Abstract The solid-state structure of 3a,8a-dihydroxy-2-thioxo-1,3,3a,8a-tetrahydroindeno[1,2- d ]imidazol-8(2 H )-one (3) was determined using X-ray single crystal technique. Its non-covalent interactions were analyzed carefully in terms of crystal engineering and supramolecular chemistry. Multiple sulfur–hydrogen and oxygen–hydrogen interactions are present in the structure, most commonly involving bifurcated H⋯S⋯H motifs which resulted in formation interesting centrosymmetric dimmers. This compound demonstrated comparable antimicrobial activity to that of clinically used antimicrobial agents against selected microorganisms.

[1]  M. Messali,et al.  A Dinitrodiphenyldiquinoline Host for Selective Inclusion of Polar Guests , 2006 .

[2]  G. Kaupp,et al.  Quantitative reaction cascades of ninhydrin in the solid state. , 2002, Chemistry.

[3]  Rangappa S. Keri,et al.  Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles. , 2009, European journal of medicinal chemistry.

[4]  M. R. Matteo,et al.  Benzimidazole derivatives with atypical antiinflammatory activity. , 1987, Journal of medicinal chemistry.

[5]  D. MacNicol,et al.  Symmetry in the Evolution of Host Design , 1997 .

[6]  G. Desiraju Crystal engineering. From molecules to materials , 2003 .

[7]  Gautam R. Desiraju,et al.  Crystal engineering : the design of organic solids , 1989 .

[8]  D. Craig,et al.  The Pi – Halogen Dimer (PHD) Interaction: A Versatile New Construction Unit for Crystal Engineering , 2005 .

[9]  D. Craig,et al.  Anomalous Inclusion Behavior Shown by a Thia-Bridged Diquinoline Derivative , 2010 .

[10]  D. Craig,et al.  An oxa-bridged tetrahalo aryl lattice inclusion host , 2003 .

[11]  Hanan M. Refaat Synthesis and anticancer activity of some novel 2-substituted benzimidazole derivatives. , 2010, European journal of medicinal chemistry.

[12]  Gerhard M. J. Schmidt,et al.  Photodimerization in the solid state , 1971 .

[13]  T. Inoue,et al.  Synthesis of benzimidazole derivatives as antiallergic agents with 5-lipoxygenase inhibiting action. , 1999, Chemical & pharmaceutical bulletin.

[14]  Gautam R. Desiraju,et al.  Designer crystals: intermolecular interactions, network structures and supramolecular synthons , 1996 .

[15]  D. Craig,et al.  Role of Double C-HN Weak Hydrogen Bonding Motifs in N -Heteroaromatic Inclusion Chemistry , 2004 .

[16]  J. Eloff A Sensitive and Quick Microplate Method to Determine the Minimal Inhibitory Concentration of Plant Extracts for Bacteria , 1998, Planta medica.

[17]  D. Craig,et al.  Interlocking molecular grid lattices involving weak assembly forces , 2002 .

[18]  E. Buyukbingol,et al.  A study on the antioxidant capacities of some benzimidazoles in rat tissues. , 1998, Chemico-biological interactions.

[19]  M. Doble,et al.  Experimental and QSAR studies on antimicrobial activity of benzimidazole derivatives. , 2008, Chemical & pharmaceutical bulletin.

[20]  Gautam R. Desiraju,et al.  The Weak Hydrogen Bond: In Structural Chemistry and Biology , 1999 .

[21]  A. Chimirri,et al.  Anti-HIV agents II. Synthesis and in vitro anti-HIV activity of novel 1H,3H-thiazolo[3,4-a]benzimidazoles. , 1991, Farmaco.

[22]  R. Tan,et al.  New edge–edge packing motifs present in the crystal structures of a thia-bridged tetrabromo aryl host , 2005 .

[23]  D. Craig,et al.  The Janus-like behaviour of sulfur in substituted diquinoline inclusion crystal structures , 2008 .

[24]  Gautam R. Desiraju,et al.  Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis , 1995 .

[25]  Rangappa S. Keri,et al.  Derivatives of benzimidazole pharmacophore: synthesis, anticonvulsant, antidiabetic and DNA cleavage studies. , 2010, European journal of medicinal chemistry.

[26]  Gautam R. Desiraju,et al.  The C-h···o hydrogen bond:  structural implications and supramolecular design. , 1996, Accounts of chemical research.

[27]  D. MacNicol,et al.  An efficient synthesis of hexa-substituted benzenes and the discovery of a novel host conformation for hexakis (β-naphthylthio) benzene ☆ , 1982 .

[28]  S. Pricl,et al.  Antiviral activity of benzimidazole derivatives. II. Antiviral activity of 2-phenylbenzimidazole derivatives. , 2010, Bioorganic & medicinal chemistry.