Synthesis, Crystal Structure and Biological Activity of Dimethyl 1-Methyl-1,4-dihydroquinoline-3,4-dicarboxylate and Tetramethyl Pyrrolo-[1,2-a] quinoline-2,3,4,5-tetracarboxylate

The target compounds 3 (C14H15NO4) and 4 (C20H17NO8) were synthesized and structurally determined by single-crystal X-ray diffraction. The crystal of 3 is in the monoclinic system, space group P2(1)/c with a = 7.3017(3), b = 7.8737(5), c = 22.4227(11) angstrom, beta = 94.837(5)degrees, C14H15NO4, Mr = 261.27, D-c = 1.351 g/cm(3), V = 1284.51(11) angstrom(3), Z = 4, F(000) = 552, mu(MoKa) = 0.828 mm(-1), T = 289.12(10) K, 2236 independent reflections with 1827 observed ones (I > 2 sigma(I)), R = 0.0515 and wR = 0.1394 with GOF = 1.044 (R = 0.0605 and wR = 0.1548 for all data). The crystal of compound 4 is in the monoclinic system, space group P2(1)/1c with a = 7.1269(3), b = 12.6518(6), c = 20.7540(8) angstrom, beta = 96.941(4)degrees, C20H17NO8, M-r = 399.35, D-c = 1.428 g/cm(3), V = 1857.61(14) angstrom(3), Z = 4, F(000) = 832.0, mu(MoKa) = 0.950 mm(-1), T = 288.81(10) K, 3216 independent reflections with 2253 observed ones (I > 2 sigma(I)), R = 0.0612 and wR = 0.1548 with GOF = 1.055 (R = 0.0824 and wR = 0.1790 for all data). The skeleton of 1,4-dihydroquinoline 3 is noncoplanar, while pyrrolo[1,2-a]-quinoline 4 owns a coplanar frame structure. One-dimensional interaction model of compound 4 was formed by the one kind of pi -pi interaction between the two adjacent molecules at upper and lower levels. And the inhibition to the strand transfer process of HIV-1 integrase of the title compounds was also evaluated.