Jing-Song Lv

Design, synthesis and evaluation of clinafloxacin triazole hybrids as a new type of antibacterial and antifungal agents

A series of clinafloxacin triazole hybrids as a new type of antibacterial and antifungal agents were synthesized for the first time and screened for their antimicrobial efficacy against four Gram-positive bacteria, four Gram-negative bacteria and two fungi by two fold serial dilution technique. The bioactive assay indicated that most of the target compounds displayed broad antimicrobial spectrum and good antibacterial and antifungal activities with low MIC values ranging from 0.25 to 2 μg/mL against all the tested strains which exhibited comparable or even better efficiency in comparison with the reference drugs Chloramphenicol, Clinafloxacin and Fluconazole, respectively. Notably, some synthesized clinafloxacin triazoles showed stronger efficacy against methicillin-resistant Staphylococcus aureus than their parent Clinafloxacin.

1,2,3-Triazole-derived naphthalimides as a novel type of potential antimicrobial agents: synthesis, antimicrobial activity, interaction with calf thymus DNA and human serum albumin.

A series of 1,2,3-triazole-derived naphthalimides as a novel type of potential antimicrobial agents were synthesized and characterized by IR, NMR and HRMS spectra. All the new compounds were screened for their antimicrobial activity against four Gram-positive bacteria, four Gram-negative bacteria and three fungi. Bioactive assay manifested that 3,4-dichlorobenzyl compound 9e and its corresponding hydrochloride 11e showed better anti-Escherichia coli activity than Norfloxacin and Chloromycin. Preliminary research revealed that compound 9e could effectively intercalate into calf thymus DNA to form compound 9e-DNA complex which might block DNA replication and thus exert antimicrobial activities. Human serum albumin could effectively store and carry compound 9e by electrostatic interaction.

Heterocyclic Naphthalimides as New Skeleton Structure of Compounds with Increasingly Expanding Relational Medicinal Applications

Naphthalimide compounds are an important type of nitrogen-containing aromatic heterocycles with cyclic double imides and the naphthalene framework. This π-deficient large conjugated planar structure enables naphthalimide derivatives to readily interact with various biological cations, anions, small molecules and macromolecules such as DNAs, enzymes and recetors in living organism via noncovalent bonds, therefore exhibiting extensive potentiality in relatively medicinal applications. Currently, some naphthalimides as anticancer agents have entered into clinical trials and other naphthalimide-based medicinal developments as potential drugs for treatment of various diseases are actively and unprecedentedly expanding. Naphthalimide-derived artificial ion receptors, fluorescent probes and cell imaging agents are being overwhelmingly investigated and have a diversity of potential applications in real-time detecting ions and biomolecules, understanding biological processes and determining pharmacological and pharmacokinetic properties. All the above mentions have strongly implied that naphthalimide-based derivatives as new skeleton structure of compounds possess increasingly expanding relational medicinal applications, and the related research is becoming a quite attractive active topic and newly rising highlight. Combining with our research and referring other works from literature, this work systematically reviews the current research and development of heterocyclic naphthalimides as anticancer, antibacterial, antifungal, antiviral, anti-inflammatory, antidepressant agents as well as artificial cation and anion receptors, diagnostic agents and pathologic probes, and cell imaging agents for biologically important species. Some rational design strategies, structure-activity relationships and action mechanisms are discussed. The perspectives of the future development of naphthalimide-based medicinal chemistry are also presented.

Synthesis and biological evaluation of Schiff base-linked imidazolyl naphthalimides as novel potential anti-MRSA agents

A series of novel Schiff base-linked imidazole naphthalimides were developed and their antimicrobial behavior demonstrated that compound 9i could effectively inhibit the growth of some tested strains, especially for MRSA (MIC = 0.003 μmol mL−1), which was superior to the reference drugs. Bacterial membrane permeabilization, bacterial resistance and time-kill kinetic assays of compound 9i against MRSA manifested that it was able to permeate the cell membrane, rapidly kill the tested strains and stall the development of bacterial resistance. Preliminary research revealed that compound 9i could form a stable complex with calf thymus DNA by intercalation mode. These results suggested that compound 9i could serve as a promising anti-MRSA candidate.

N-[4-(Azetidin-1-ylsulfon­yl)phen­yl]-N-(2,4-difluoro­benz­yl)acetamide

In the title molecule, C18H18F2N2O3S, the dihedral angle between the benzene rings is 79.40 (11)°. The 2,4-difluorobenzyl and azetidine fragments adopt a trans arrangement relative to the central benzene ring. In the crystal, weak C—H⋯O hydrogen bonds connect molecules into a two-dimensional network parallel to (001).

(Z)-1-(2,4-Difluoro­phen­yl)-3-(4-fluoro­phen­yl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one

In the title molecule, C17H10F3N3O, the C=C bond connecting the triazole ring and 4-fluorophenyl groups adopts a Z conformation. The triazole ring forms dihedral angles of 15.3 (1) and 63.5 (1)°, with the 2,4-difluoro-substituted and 4-fluoro-substituted benzene rings, respectively. The dihedral angle between the two benzene rings is 51.8 (1)°.

1H-1,2,4-Triazol-4-ium (3,4-dichloro-phen-yl)methane-sulfonate.

In the title molecular salt, C2H4N3 +·C7H5Cl2O3S−, C—C—S angle [112.25 (18)°] deviates slightly from that expected for ideal sp 3-hybridization geometry. In the crystal, the components are linked by N—H⋯O and bifurcated N—H⋯(O,O) hydrogen bonds into chains parallel to [110].

6-Bromo-2-(diprop-2-ynyl­amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione

The asymmetric unit of the title compound, C18H11BrN2O2, contains two independent molecules in which the prop-2-ynylamino groups have different mutual orientations. In one molecule, the Br atom is disordered over two positions, with refined occupancies of 0.742 (2) and 0.258 (2).

(Z)-1,3-Bis(4-chloro­phen­yl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one

In the title molecule, C17H11Cl2N3O, the C=C bond connecting the triazole and 4-chlorophenyl groups adopts a Z geometry. The dihedral angles formed by the triazole ring and the 4-chloro substituted benzene rings are 67.3 (1) and 59.1 (1)°. The dihedral angle between the two benzene rings is 73.5 (1)°.

9-(4-Bromo­but­yl)-9H-carbazole

In the title compound, C16H16BrN, the bromobutyl group lies on one side of the carbazole ring plane and has a zigzag shape. The dihedral angle between the two benzene rings is 0.55°. In the crystal, molecules are connected by van der Waals interactions.