期刊文献+

Synthesis and Crystal Structure of (E)-2-(1-(2-Hydroxy-4-methoxyphenyl)ethylideneamino)-3-(4-hydroxyphenyl)methyl Propionate

Synthesis and Crystal Structure of (E)-2-(1-(2-Hydroxy-4-methoxyphenyl)ethylideneamino)-3-(4-hydroxyphenyl)methyl Propionate
下载PDF
导出
摘要 (E)-2-(1-(2-Hydroxy-4-methoxyphenyl)ethylideneamino)-3-(4-hydroxyphenyl)methyl propionate (C22H27O6N, Mr = 401.45) has been synthesized by a condensation reaction of paeonol with tyrosin methyl ester hydrochloride, and its structure was determined by IR, NMR, HR MS and X-ray single-crystal diffraction. The crystal belongs to the monoclinic system, space group P21/c, with a = 11.91291(15), b = 9.49947(12), c = 19.8727(3) , β = 106.1104(15)°, V = 2160.60(5)3, Z = 4, Dc = 1.234 g/cm3, μ = 0.739 mm-1, F(000) = 856, R = 0.0466 and wR = 0.1461 for 3859 observed reflections with (Ⅰ〉 2σ(Ⅰ)). In the crystal structure, the title compound is constructed by a centrosymmetric dimmer unit composed of a pair of π-π stacking enantiomers, and such units are linked by intermolecular O(5)-H(5)…O(1) and intramolecular N(1)-H(1)…O(1) hydrogen bonds. (E)-2-(1-(2-Hydroxy-4-methoxyphenyl)ethylideneamino)-3-(4-hydroxyphenyl)methyl propionate (C22H27O6N, Mr = 401.45) has been synthesized by a condensation reaction of paeonol with tyrosin methyl ester hydrochloride, and its structure was determined by IR, NMR, HR MS and X-ray single-crystal diffraction. The crystal belongs to the monoclinic system, space group P21/c, with a = 11.91291(15), b = 9.49947(12), c = 19.8727(3) , β = 106.1104(15)°, V = 2160.60(5)3, Z = 4, Dc = 1.234 g/cm3, μ = 0.739 mm-1, F(000) = 856, R = 0.0466 and wR = 0.1461 for 3859 observed reflections with (Ⅰ〉 2σ(Ⅰ)). In the crystal structure, the title compound is constructed by a centrosymmetric dimmer unit composed of a pair of π-π stacking enantiomers, and such units are linked by intermolecular O(5)-H(5)…O(1) and intramolecular N(1)-H(1)…O(1) hydrogen bonds.
出处 《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 2013年第5期751-755,共5页 结构化学(英文)
基金 Supported by the National Natural Science Foundation of China (No. 21072178) Innovation Specialist Projects of Henan Province(No. 114200510023) Innovation Scientists and Technicians Troop Construction Projects of Zhengzhou City (No. 112PLJRC359)
关键词 SYNTHESIS PAEONOL crystal structure hydrogen bond synthesis, paeonol, crystal structure, hydrogen bond
  • 相关文献

参考文献17

  • 1Chou, T. C. Anti-inflanunatory and analgesic effects of paeonol in carrageenan evoked thermal typeralgesia. British J. Pharmacol. 2003, 139, 1146-1152.
  • 2Lee, B.; Shin, Y. W.; Bae, E. A.; Han, S. J.; Kim, J. S.; Kang, S. S.; Kim, D. H. Antiallergic effect of the root ofPaeonia Iactiflora and its constituents paeoniflorin and paeonol. Arch. Pharmacal Res. 2008, 31, 445-450.
  • 3Chen, B. D.; Ning, M. J.; Yang, G S. Effect of paeonol on antioxidant and immune regulatory activity in hepatocellular carcinoma rats. Molecules 2012,17,4672-4683.
  • 4Li, N.; Fan, 1. J.; Sun, G P.; Wan, X. A.; Wang, Z. G; Wu, Q. A.; Wang, H. Paeonol inhibits tumor growth in gastric cancer in vitro and in vivo. World J. Gastroenterol. 2010, 16,4483-4490.
  • 5Sun, G P.; Wang, H.; Xu, S. P.; Shen, Y. X.; Wu, Q.; Chen, Z. D.; Wei, W. Anti-tumor effects ofpaeonol in a HepA-hepatoma bearing mouse model via induction of tumor cell apoptosis and stimulation ofIL-2 and TNF-alpha production. European J. Pharmacol. 2008,584,246-252.
  • 6Du, Q.; Feng, G Z.; Shen, J.; Cui, J.; Cai, J. K. Paeonol attenuates airway inflammation and hyperresponsiveness in a murine model of ovalbumin induced asthma. Can. J. Physiol. Pharmacal. 2010, 88, 1010-1016.
  • 7Li, Y. J.; Bao, J. X.; Xu, J. w.; Murad, F.; Bian, K. Vascular dilation by paeonol-A mechanism study. Vasco Pharmacol. 2010,53, 169-176.
  • 8Xu, X. Y.; Gao, J.; Chen. J.; Li. S. Z.; Yang, X. J.; Song. H. B. Preparation and crystal structure ofpaeonol. Chin. J. Struct. Chem. 2005,24,436-438.
  • 9Tsai, Y.; Tsai, H. H.; Wu, C. P.; Tsai, F. J. Preparation, characterization and activity of the inclusion complex ofpaeonol with beta-cyclodextrin. Food Chem.2010, 120,837-841.
  • 10Qin, D. D.; Yang, Z. Y.; Zhang, F. H.; Du, B.; Wang, P.; Li, T. R. Evaluation of the antioxidant, DNA interaction and tumor cell cytotoxicity activities of copper(II) complexes with paeonol Schiff-base. Inorg. Chem. Commun. 2010, 13, 727-729.

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部