Synthesis and Characterization of 8-Chloro-7-(4-(3-chloropropanoyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

摘要

A new compound 8-chloro-7-(4-(3-chloropropanoyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid(II, C_(20)H_(20)Cl_2FN_3O_4, Mr = 456.08) was synthesized and characterized by 1H NMR, 13 C NMR, HR MS and single-crystal X-ray diffraction. X-ray powder diffraction(XRPD), thermal stabilities, UV-Vis spectrum, photoluminescent properties and absolute quantum yield of compound II were also investigated. The structure demonstrates that the crystal belongs to the triclinic system, space group P1 with a = 7.7339(3), b = 10.2396(5), c = 15.9076(8) ?, α = 76.517(4), β = 77.609(4), γ = 80.320(4)°, V = 1187.22(9) ?3, Z = 2, Dc = 1.514 g/mm3, μ = 4.901 mm-1, F(000) = 556.0, R = 0.0534 and w R = 0.1447(I > 2σ(I)). The result reveals that fluoroquionolone moiety in this structure stacks with π×××π interactions to generate an infinite 1D chain, which can stabilize the whole framework of compound II. Delightfully, preliminary antibacterial activity in vitro against 4 cell strains uncovers that compound II has almost equal strong activity in comparison with Clinafloxacin, but stronger than Norfloxacin. These outcomes provide important information for further exploration of the structure-activity relationship(SAR) of compound II derivatives or analogs.