Synthesis, Crystal Structure and Antiproliferative Activity of 2,2-Dimethyl-4-oxochroman-3-yl morpholine-4-carbodithioate
黄伟;佘能芳
1.华中师范大学化学学院
2.江苏先声药业有限公司
3.南京大学
Synthesis, Crystal Structure and Antiproliferative Activity of 2,2-Dimethyl-4-oxochroman-3-yl morpholine-4-carbodithioate
HUANG Wei;SHE Neng-Fang
a (Key Laboratory of Pesticide and Chemical Biology of Ministry of Education of China, College of Chemistry, Central China Normal University, Wuhan 430079, China)
b (Jiangsu Key Laboratory of Molecular Targeted Antitumor Drug Research, Jiangsu Simcere Pharmaceutical Co., Ltd, Nanjing 210042, China)
c (Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, China)
摘要The crystal structure of the new title compound 2,2-dimethyl-4-oxochroman-3-yl- morpholine-4-carbodithioate (C16H19NO3S2, Mr = 337.44) has been prepared and determined by single-crystal X-ray diffraction. The crystal is of triclinic, space group Pī with α = 9.5518(7), b = 9.7172(7), c = 11.0220(8) Å, α = 67.08(1), β = 74.66(1), γ = 61.31(1)°, V = 822.72(10) Å3, Z = 2, Dc = 1.362 g/cm3, F(000) = 356, μ = 0.092 mm-1, MoKa radiation (λ = 0.71073), R = 0.0515 and wR = 0.1389 for 2623 observed reflections with I > 2σ(I). X-ray diffraction analysis reveals that the chroman ring adopts a half-chair conformation while the morpholine ring shows a chair conformation. Intramolecular and intermolecular C–H···S and C–H···O hydrogen bonds together with π-π interations are found in the structure. The result of MTT assay shows the title compound displays good antiproliferative activity against two human cancer cell lines.
Abstract：The crystal structure of the new title compound 2,2-dimethyl-4-oxochroman-3-yl- morpholine-4-carbodithioate (C16H19NO3S2, Mr = 337.44) has been prepared and determined by single-crystal X-ray diffraction. The crystal is of triclinic, space group Pīwith α = 9.5518(7), b = 9.7172(7), c = 11.0220(8) Å, α = 67.08(1), β = 74.66(1), γ = 61.31(1)°, V = 822.72(10) Å3, Z = 2, Dc = 1.362 g/cm3, F(000) = 356, μ = 0.092 mm-1, MoKa radiation (λ = 0.71073), R = 0.0515 and wR = 0.1389 for 2623 observed reflections with I > 2σ(I). X-ray diffraction analysis reveals that the chroman ring adopts a half-chair conformation while the morpholine ring shows a chair conformation. Intramolecular and intermolecular C–H···S and C–H···O hydrogen bonds together with π-π interations are found in the structure. The result of MTT assay shows the title compound displays good antiproliferative activity against two human cancer cell lines.
基金资助:Project supported by the National Natural Science Foundation of China (No. 21272086), China Postdoctoral Science Foundation (No. 2012T50475), and the Natural Science Foundation of Jiangsu Province (No. BK2011086)
通讯作者:
佘能芳
E-mail: nfshe@mail.ccnu.edu.cn
作者简介: 佘能芳： nfshe@mail.ccnu.edu.cn
引用本文:
黄伟;佘能芳. Synthesis, Crystal Structure and Antiproliferative Activity of 2,2-Dimethyl-4-oxochroman-3-yl morpholine-4-carbodithioate[J]. 结构化学, 2013, 32(9): 1357-1361.
HUANG Wei;SHE Neng-Fang. Synthesis, Crystal Structure and Antiproliferative Activity of 2,2-Dimethyl-4-oxochroman-3-yl morpholine-4-carbodithioate. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2013, 32(9): 1357-1361.
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