Synthesis and Antitumor Activity of 2-[1-(2-Formylamido-3-phenylpropionyloxy)alkyl]-1,4- dihydroxy-9,10-anthraquinone Derivatives

高等学校化学研究 ›› 2012, Vol. 28 ›› Issue (6): 971-975.

Synthesis and Antitumor Activity of 2-[1-(2-Formylamido-3-phenylpropionyloxy)alkyl]-1,4- dihydroxy-9,10-anthraquinone Derivatives

JIN Li-li, JIN Guang-zhu

College of Pharmacy, Yanbian University, Yanji 133002, P. R. China

收稿日期:2012-03-14 修回日期:2012-08-06 出版日期:2012-11-25 发布日期:2012-11-09
通讯作者: JIN Guang-zhu E-mail:gzjin@ybu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.30360119).

Synthesis and Antitumor Activity of 2-[1-(2-Formylamido-3-phenylpropionyloxy)alkyl]-1,4- dihydroxy-9,10-anthraquinone Derivatives

JIN Li-li, JIN Guang-zhu

College of Pharmacy, Yanbian University, Yanji 133002, P. R. China

Received:2012-03-14 Revised:2012-08-06 Online:2012-11-25 Published:2012-11-09
Contact: JIN Guang-zhu E-mail:gzjin@ybu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.30360119).

摘要/Abstract

摘要：

A series of 2-[1-(2-formylamido-3-phenylpropionyloxy)alkyl]-1,4-dihydroxy-9,10-anthraquinone(2-FPADHAQ) derivatives was designed and synthesized. Their antitumor activities were tested against L1210 tumor cells and P388 mouse leukemic tumor cells in vitro and in ICR mice bearing sarcoma 180 cells in vivo. Overall, the introduction of 2-formylamido-3-phenyl-propanoic acid(2-FPPA) into the C-2-alkyl side chain C′-1 hydroxy group in 2-(1-hydroxyalkyl)-1,4-dihydroxy-9,10-anthraquinones(2-HDHAQ) enhanced the antitumor activity compared with the starting materials. 2-FPADHAQ with alkyl chains longer than the pentyl group had negligible activity, whereas compounds 2b, 2c, 2d and 2epossessing shorter chains demonstrated moderate cytotoxic activity[50% effective dose(ED₅₀) of L1210 and P388 are 2.61-4.75 and 5.84-8.74 μg/mL], whereas compound 2l with an aromatic system showed strong cytotoxic activity. T/C(%) values[(average survival days in the test group)/(average survival days in the control group)×100%] also show that the introduction of 2-FPPA into the side chain of 2-HDHAQ enhanced antitumor activity. These data suggest that the introduction of an amino acid into the starting material may increase its affinity for DNA or its selectivity for proliferating cancer cells.

关键词: Anthraquinone, Antitumor, Cytotoxicity, Phenylalanine

Abstract:

Key words: Anthraquinone, Antitumor, Cytotoxicity, Phenylalanine

JIN Li-li, JIN Guang-zhu. Synthesis and Antitumor Activity of 2-[1-(2-Formylamido-3-phenylpropionyloxy)alkyl]-1,4- dihydroxy-9,10-anthraquinone Derivatives[J]. 高等学校化学研究, 2012, 28(6): 971-975.

JIN Li-li, JIN Guang-zhu. Synthesis and Antitumor Activity of 2-[1-(2-Formylamido-3-phenylpropionyloxy)alkyl]-1,4- dihydroxy-9,10-anthraquinone Derivatives[J]. Chemical Research in Chinese Universities, 2012, 28(6): 971-975.

[1]	Ghadah F. ALJOHANI, Fatma A. A. EL-HAG, Mohamed S. BEKHEIT, Ewies F. EWIES, May A. EL-MANAWATY. An Efficient One-pot Synthesis of Certain Stereoselective Spiro[pyrazole-4,5'-isoxazoline]-5-one Derivatives: In vitro Evaluation of Antitumor Activities,Molecular Docking and In silico ADME Predictions[J]. 高等学校化学研究, 2022, 38(4): 1073-1082.
[2]	YU Fangyuan, WANG Kai, WANG Chuan, HE Xinxia, LIAO Yang, ZHAO Shilin, MAO Hui, LI Xiaoting, MA Jun. Anthraquinone Covalently Modified Carbon Nanotubes for Efficient and Steady Electrocatalytic H₂O₂ Generation[J]. 高等学校化学研究, 2020, 36(6): 1332-1338.
[3]	ZHANG Xiulan, ZHANG Huan, LIU Jingbo, XIONG Lixia, LI Zhengming. Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH₃-1H-Pyrazole[J]. 高等学校化学研究, 2020, 36(5): 829-834.
[4]	ZHANG Xiulan, ZHANG Huan, MA Jinlong, YU Shujing, LI Zhengming. Design, Synthesis and Biological Activities of Novel N-Aryl-1H-pyrazole-5-carboxylate Derivatives[J]. 高等学校化学研究, 2020, 36(5): 853-858.
[5]	PENG Xiaoyu, ZHAO Anran, HUANG Kelin, HU Tingju, LIU Buming, HUANG Yan, CHEN Hailan, CHAI Ling, LIN Cuiwu. Synthesis of Caffeic Acid Sulphonamide Derivatives and Preliminary Exploration of Their Biological Applications[J]. 高等学校化学研究, 2020, 36(5): 795-803.
[6]	TANG Xu, DU Zhijun, WU Guojie, HAN Fushe. Synthesis of P-Stereogenic Diarylphosphinamides as Novel Inhibitors of Melanoma[J]. 高等学校化学研究, 2019, 35(5): 812-816.
[7]	GUAN Shuwen, YU Xiaoxuan, LI Junyang, XU Heng, HAN Wenzhao, SHI Guannan, XU Jia, WANG Liping. Delivery of Survivin siRNA Using Cationic Diphenylalanine Vesicles[J]. 高等学校化学研究, 2019, 35(3): 434-439.
[8]	TIAN Ye, YU Simiao, CAI Lude, GONG Guowei, WU Guodong, QI Hongxia, ZHAO Yanfang, QIN Mingze. Synthesis and Antitumor Activity of Sorafenib Analogs Containing a Tetrazole Moiety[J]. 高等学校化学研究, 2019, 35(1): 41-46.
[9]	CHU Chenliang, CUI Ting, LI Sida, ZHAN Ruoting, GAO Youheng. Structure and Activity of a New Sapogenin from Chlorophytum laxum R. Br.[J]. 高等学校化学研究, 2018, 34(5): 732-735.
[10]	XU Qihao, YU Shujia, CAI Yijun, YANG Jinyu, ZHAO Linxiang, LIU Dan. Design, Synthesis and Biological Evaluation of Novel Selective Thiol-based Histone Deacetylase(HDAC) VI InhibitorsBearing Indeno[1,2-c]pyrazole or Benzoindazole Scaffold[J]. 高等学校化学研究, 2018, 34(1): 75-83.
[11]	YANG Jiajia, WANG Meng, LI Xia, FAN Ningning, XUE Liangmin, LI Hao, TIAN Chao, WANG Xiaowei, LIU Junyi, ZHANG Zhili. Syntheses and Antiproliferative Evaluation of 6-Thienyl, 6-Polyphenyl Aryl and 6-Naphthyl Derivatives of 2,4-Diaminopyrido[3,2-d]pyramidine as Non-classical Antifolate Targeting DHFR[J]. 高等学校化学研究, 2017, 33(4): 559-568.
[12]	LI Yongqing, XIAO Ran, LIU Zonglai, LIANG Xiujuan, FENG Wei. Cytotoxicity of NiO Nanoparticles and Its Conversion Inside Chlorella vulgaris[J]. 高等学校化学研究, 2017, 33(1): 107-111.
[13]	LI Hongshuang, WANG Xinran, DUAN Guiyun, XIA Chengcai, XIAO Yuliang, LI Furong, GE Yanqing, YOU Guirong, HAN Junfen, FU Xiaopan, TAN Shanhui, WANG Rongwei. Synthesis, Antitumor Activity and Preliminary Structure-activity Relationship of 2-Aminothiazole Derivatives[J]. 高等学校化学研究, 2016, 32(6): 929-937.
[14]	LI Fengran, LIU Yang, WANG Shuai, WEI Gaofei, CHENG Maosheng. Synthesis and Tumor Cytotoxicity of Novel 1, 2, 3-Triazole-substituted 3-Oxo-oleanolic Acid Derivatives[J]. 高等学校化学研究, 2016, 32(6): 938-942.
[15]	CHEN Qing, LIN Jianhong, ZHAO Dan, ZHU Xuan. Isolation and Stucture Elucidation of Diterpenes from Wedelia prostrata and Their Cytotoxicity Activities[J]. 高等学校化学研究, 2016, 32(5): 792-796.

Synthesis and Antitumor Activity of 2-[1-(2-Formylamido-3-phenylpropionyloxy)alkyl]-1,4- dihydroxy-9,10-anthraquinone Derivatives

Synthesis and Antitumor Activity of 2-[1-(2-Formylamido-3-phenylpropionyloxy)alkyl]-1,4- dihydroxy-9,10-anthraquinone Derivatives

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价