CRYSTAL STRUCTURES AND ANTIBACTERIAL ACTIVITY OF HYDRAZONE DERIVATIVES FROM 1H-INDOL-3-ACETOHYDRAZIDE
F. Zhi1, N. Shao2, Q. Wang2, Y. Zhang2, R. Wang1, Y. Yang2
1Modern Medical Research Center, Third Affiliated Hospital of Suzhou University, Changzhou, P. R. China 2Department of Neurosurgery, Third Affiliated Hospital of Suzhou University, Changzhou, P. R. China yangyilin_szu@126.com
Ключевые слова: hydrazone derivative, synthesis, X-ray diffraction, antibacterial activity
Страницы: 155-161
Аннотация
A series of three new hydrazone derivatives C22H19N3O2 (1), C17H13ClN4O3 (2), and C21H24N4O2⋅CH4O (3) obtained by the condensation of 1H-indol-3-acetohydrazide with 2-methoxynaphthaldehyde, 2-chloro-5-nitrobenzaldehyde, and 4-diethylaminosalicylaldehyde, respectively, in methanol, ia prepared. The compounds are characterized by elemental analysis, IR spectra, 1H NMR spectra, and single crystal X-ray diffraction. Compound 1crystallizes in the monoclinic space group P21/n with unit cell dimensions a = 17.740(2) Å,b = 5.621(1) Å, c = 18.573(3) Å, β = 92.659(2)°, V = 1850.0(6) Å3, Z = 4, R1 = 0.0610 andwR2 = 0.1155. Compound 2 crystallizes in the monoclinic space group C2/c with unit cell dimensions a = 29.178(2) Å, b = 8.195(1) Å, c = 14.372(1) Å, Å = 109.446(2)°, V = 3240.5(5) Å3, Z = 8, R1 = 0.0452 and wR2 = 0.1028. Compound 3 crystallizes in the monoclinic space group Pc with unit cell dimensions a = 6.579(1) Å, b = 15.112(2) Å, c = 10.676(2) Å, Å = 90.030(2)°, V = 1061.4(3) Å3, Z = 2, R1 = 0.0535 and wR2 = 0.1123. The single crystal X-ray structural determination reveals that the molecules of the compounds are much twisted due to the lack of efficient conjugation. Preliminary biological tests indicate that the compounds are effective antibacterial material.
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