Citation: Xue-Mei XU, Zai-Gang LUO, Xin-Xin HAN, Qian-Nan LIU, Rui LI. 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[J]. Chinese Journal of Structural Chemistry, ;2020, 39(7): 1271-1276. doi: 10.14102/j.cnki.0254–5861.2011–2615 shu

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

College of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, China

Corresponding author: Zai-Gang LUO, luozi139@163.com
Received Date: 23 September 2019
Accepted Date: 18 March 2020

Fund Project: the Natural Science Research Projects in Colleges and Universities of Anhui Province KJ2019A0116Natural Science Foundation of Anhui Province 1608085MB38

Figures(3)

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 P2₁/c with a = 7.3017(3), b = 7.8737(5), c = 22.4227(11) Å, β = 94.837(5)°, C₁₄H₁₅NO₄, M_r = 261.27, D_c = 1.351 g/cm³, V = 1284.51(11) Å³, Z = 4, F(000) = 552, µ(MoKa) = 0.828 mm^–1, T = 289.12(10) K, 2236 independent reflections with 1827 observed ones (I > 2σ(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 P2₁/c with a = 7.1269(3), b = 12.6518(6), c = 20.7540(8) Å, β = 96.941(4)°, C₂₀H₁₇NO₈, M_r = 399.35, D_c = 1.428 g/cm³, V = 1857.61(14) Å³, Z = 4, F(000) = 832.0, µ(MoKa) = 0.950 mm^–1, T = 288.81(10) K, 3216 independent reflections with 2253 observed ones (I > 2σ(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 π-π 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.
- 1,4-dihydroquinoline,
- pyrrolo[1,2-a]quinoline,
- synthesis,
- crystal structure,
- HIV-1 integrase
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