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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