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Synthesis, spectral and solid state characterization of a new bioactive hydrazine bridged cyclic diphosphonium compound.

ABSTRACT: The facile preparation of a racemic hydrazine bridged diphosphonium compound possessing a ring system analogous to bicyclo[3.3.2]decane is reported. Although the reaction yield is low, the structure of the compound, which possesses an eight-membered ring, two phosphonium cationic centers, a biimino bridge, molecular chirality and two fused aromatic rings locked into roughly perpendicular planes is unusual. The compound displays substantial biological activity in the brine shrimp test and cleaves plasmid DNA.

SUBMITTER: Milenkovic M

PROVIDER: S-EPMC6268038 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

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Synthesis, spectral and solid state characterization of a new bioactive hydrazine bridged cyclic diphosphonium compound.

Milenković Milica M Warżajtis Beata B Rychlewska Urszula U Radanović Dušanka D Anđelković Katarina K Božić Tatjana T Vujčić Miroslava M Sladić Dušan D

Molecules (Basel, Switzerland) 20120302 3

The facile preparation of a racemic hydrazine bridged diphosphonium compound possessing a ring system analogous to bicyclo[3.3.2]decane is reported. Although the reaction yield is low, the structure of the compound, which possesses an eight-membered ring, two phosphonium cationic centers, a biimino bridge, molecular chirality and two fused aromatic rings locked into roughly perpendicular planes is unusual. The compound displays substantial biological activity in the brine shrimp test and cleaves ...[more]

PMID: 22388967

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Project description:A novel Schiff base derivative of 4-aminoantipyrine, that is, (E)-4-(2-methoxybenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (MBA-dMPP), was synthesized and characterized by FT-IR, 1H-NMR, and EI-MS. Single-crystal X-ray diffraction data revealed MBA-dMPP adopts a trans configuration around its central C=N double bond, and forms orthorhombic crystals. XRD revealed that MBA-dMPP possess two different planes, in which the pyrazolone and benzylidene groups attached to C9 of the pyrazolone ring are almost coplanar and the phenyl ring connected to the N1 atom of the pyrazolone moiety lies in another plane. The intermolecular, host-guest C-H…O, C-H…N, and C-H…C van der Waals interactions were found to form a 3D network and confer stability to the MBA-dMPP crystal structure. The quantitative and qualitative solid state behaviors of MBA-dMPP were subjected to 3D Hirshfeld surface analysis and 2D fingerprint plotting. Reciprocal H…H contacts contributed most (52.9 %) to the Hirshfeld surface, followed by C…H/H…C contacts (30.2 %), whereas, O…H/H…O and N…H/H…N interactions contributed 15.5 % to the Hirshfeld surface. Electrostatic potentials were mapped over the Hirshfeld surface to analyze electrostatic complementarities within the MBA-dMPP crystal. In addition, geometrical descriptors were also analyzed to the extent of surface interactions. MBA-dMPP was also investigated for in vitro antibacterial activity against Gram-positive and Gram-negative bacterial strains, and showed highest activity against Bacillus cereus (MIC = 12.5 μg mL-1) and Salmonellatythimurium (MIC = 50 μg mL-1). In silico screening was conducted by docking MBA-dMPP on the active site of S12 bacterial protein (an important therapeutic target of antibacterial agents) and its binding properties were compared with those of ciprofloxacin. Moreover, a field points map of MBA-dMPP ligand was studied to determine electrostatic and van der Waals forces, hydrophobic potentials, and positions involved in ligand-receptor interactions. Finally, the torsion energies of crystal structure and optimized and bioactive conformers of MBA-dMPP were compared to predict its bioactive conformation.

Dataset Information

Synthesis, spectral and solid state characterization of a new bioactive hydrazine bridged cyclic diphosphonium compound.

Publications

Synthesis, spectral and solid state characterization of a new bioactive hydrazine bridged cyclic diphosphonium compound.

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