Study on the Synthesis and Bioactivity of Diosgenin Antitumor Derivatives

doi:10.6023/cjoc201711016

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (4): 919-925.DOI: 10.6023/cjoc201711016 Previous Articles Next Articles

Articles

薯蓣皂苷元抗肿瘤衍生物的合成及其生物活性的研究

罗卓玛^a, 胡越高^a, 王璐红^b, 尹祥健^c, 马晓东^b, 杨鸿均^a, 赵志刚^a

a 西南民族大学化学与环境保护工程学院成都 610041;
b 大连医科大学药学院大连 116044;
c 四川川大华西药业股份有限公司成都 610014

收稿日期:2017-11-08 修回日期:2018-01-05 发布日期:2018-01-18
通讯作者: 杨鸿均 E-mail:yanghj@swun.cn
基金资助:
国家自然科学基金（No.21602083）、西南民族大学研究生创新型科研（No.CX2016SZ045）、四川省教育厅研究（No.15ZB0487）资助项目.

Study on the Synthesis and Bioactivity of Diosgenin Antitumor Derivatives

Luo Zhuoma^a, Hu Yuegao^a, Wang Luhong^b, Yin Xiangjian^c, Ma Xiaodong^b, Yang Hongjun^a, Zhao Zhigang^a

a College of Chemistry and Environmental Protection Engineering, Southwest University for Nationalities, Chengdu 610041;
b College of Pharmacy, Dalian Medical University, Dalian 116044;
c Sichuan Chuanda Huaxi Pharmaceutical Co., Ltd., Chengdu 610014

Received:2017-11-08 Revised:2018-01-05 Published:2018-01-18
Contact: 10.6023/cjoc201711016 E-mail:yanghj@swun.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21602083), the Southwest University for Nationalities Graduate Student Innovative Project (No. CX2016SZ045), and the Sichuan Provincial Department of Education Research Project (No. 15ZB0487).

1. Study on the Synthesis and Bioactivity of Diosgenin Antitumor Derivatives.PDF(2015KB)

Abstract

Nine novel diosgenin derivatives were designed and synthesized by using diosgenin as a precursor. Their structures were identified by ¹H NMR, ¹³C NMR, IR and HRMS. Antitumor activity (A549, A431, H1975, HCT-116, Aspc-1, Ramos) and cytotoxicity (HBE, LO-2) were measured for all derivatives using thiazolyl blue tetrazolium bromide (MTT). The results show that most diosgenin derivatives have significant anti-tumor activity and low cytotoxicity.

Key words: diosgenin, derivative, antitumor activity, amide

Cite this article

Luo Zhuoma, Hu Yuegao, Wang Luhong, Yin Xiangjian, Ma Xiaodong, Yang Hongjun, Zhao Zhigang. Study on the Synthesis and Bioactivity of Diosgenin Antitumor Derivatives[J]. Chin. J. Org. Chem., 2018, 38(4): 919-925.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Tang, S. R.; Yang, R. T.; Pan, F. S. J. Plant. Resour. Environ. 2007, 16, 64(in Chinese). (唐世荣, 杨如同, 潘福生, 植物资源与环境学报, 2007, 16, 64.)
[2] Sun, Q.; Ju, Y.; Zhao, Y. F. Chin. Tradit. Herb. Drugs 2002, 33, 276(in Chinese). (孙麒, 巨勇, 赵玉芬, 中草药, 2002, 33, 276.)
[3] Mattew, J. K.; Mary, L. T.; Jing, Z. H. Bioorg. Med. Chem. 2008, 16, 3209.
[4] Liu, C.; Wang, Z. Z.; Zheng, W. West China J. Pharm. Sci. 2009, 24, 483(in Chinese). (刘超, 王珍珍, 郑微, 华西药学杂志, 2009, 24, 483.)
[5] Yue, L.; Chen, L.; Kou, J. P. Chin. J. Clin. Pharmacol. Ther. 2010, 15, 233(in Chinese). (岳蕾, 陈玲, 寇俊萍, 中国临床药理学与治疗学, 2010, 15, 233.)
[6] Zeng, C. L.; Gen, Q.; Wu, Y. K. West China J. Pharm. Sci. 2011, 26, 423(in Chinese). (曾春玲, 耿倩, 吴亚克, 华西药学杂志, 2011, 26, 423.)
[7] Wang, B.; Chun, J.; Liu, Y. Org. Biomol. Chem. 2012, 10, 8822.
[8] Wang, Y.; Pan, K.; Chang, T. J. Nat. Prod. 2011, 74, 580.
[9] Yayoi, T.; Naoko, K.; Akinori, H. Steroids 2009, 74, 504.
[10] Wang, L. J.; Wang, Y.; Chen, S. W. China J. Chin. Mater. Med. 2002, 27, 777(in Chinese). (王丽娟, 王岩, 陈声武, 中国中药杂志, 2002, 27, 777.)
[11] Cecile, C.; Bertrand, L. Cell Res. 2004, 14, 188.
[12] Huo, R.; Zhou, Q. L.; Wang, B. X. Acta Pharmacol. Sin. 2004, 25, 1077.
[13] Fu, W. W.; Wu, Y, K.; Fan, J. Z. West China J. Pharm. Sci. 2010, 25, 658(in Chinese). (傅微微, 吴亚克, 范举正, 华西药学杂志, 2010, 25, 658.)
[14] Liao, P. F.; Dong, J. H.; Fan, J. Z. West China J. Pharm. Sci. 2013, 28, 364(in Chinese). (廖鹏飞, 董江红, 范举正, 华西药学杂志, 2013, 28, 364.)
[15] Wu, Y. K.; He, G.; Fu, W. W. West China J. Pharm. Sci. 2012, 27, 22(in Chinese). (吴亚克, 何谷, 傅微微, 华西药学杂志, 2012, 27, 22.)
[16] Dong, J. H.; He, G.; Wu, Y. K. Chin. Pharmacol. Bull. 2012, 47, 1407(in Chinese). (董江红, 何谷, 吴亚克, 中国药学杂志, 2012, 47, 1407.)
[17] Zhang, H. B.; Yang, X. D.; Qin, C.; Liu, Y. L.; Li, L.; Liu, J. P. CN 1876672, 2006.
[18] Zhang, R.; Guo, X. R.; He, Y.; Huang, W. West China J. Pharm. Sci. 2013, 28, 229(in Chinese). (张瑞, 郭秀蓉, 何杨, 黄文, 华西药学杂志, 2013, 28, 229.)
[19] Ding, X. Y.; He, G.; Jiang, H. P. West China J. Pharm. Sci. 2012, 46, 539(in Chinese). (丁晓勇, 何谷, 蒋红平, 药学学报, 2012, 46, 539.)
[20] Geng, Q.; Zeng, C. L.; Fu, W. W. West China J. Pharm. Sci. 2009, 24, 475(in Chinese). (耿倩, 曾春玲, 傅微微, 华西药学杂志, 2009, 24, 475.)
[21] Lu, L. H.; Wu, D. S.; Peng, L. F.; Xu, M.; Lu, X. P.; Mei, S. X. J. Yunnan Univ. (Nat. Sci. Ed.) 2015, 37, 415(in Chinese). (陆礼和, 吴德松, 彭玲芳, 徐明, 陆雪萍, 梅双喜, 云南大学学报(自然科学版), 2015, 37, 415.)
[22] Zheng, W.; Jiang, H. P.; Wu, Y. K. West China J. Pharm. Sci. 2011, 26, 107(in Chinese). (郑微, 蒋红平, 吴亚克, 华西药学杂志, 2011, 26, 107.)
[23] Fu, X. L.; Han, Y. M.; Zhang, S. J. Drugs Clin. 2011, 26, 46(in Chinese). (付晓丽, 韩英梅, 张士俊, 现代药物与临床, 2011, 26, 46.)
[24] Fan, L. H.; Cui, J. G.; Gan, C. F.; Su, S. Y. Chem. Res. Appl. 2012, 24, 8(in Chinese). (范良华, 崔建国, 甘春芳, 苏绍烊, 化学研究与应用, 2012, 24, 8.)
[25] Fujii, N.; Mallari, J. P.; Hansell, E. J. Bioorg. Med. Chem. Lett. 2005, 15, 121.
[26] Renard, D.; Perruchon, J.; Giera, M. Bioorg. Med. Chem. 2009, 17, 8123.
[27] Stulov, S. V.; Zavialova, M. G.; Mehtiev, A. R. Bioorg. Med. Chem. Lett. 2010, 20, 5495.
[28] Handratta, V. D.; Vasaitis, T. S.; Njar, V. C. O. J. Med. Chem. 2005, 48, 2972.
[29] Banday, A. H.; Mir, B. P.; Lone, I. H. Steroids 2010, 75, 805.
[30] Xie, W. G.; Peng, H. R.; Zalkow, L. H. Bioorg. Med. Chem. 2000, 8, 699.
[31] Burbiel, J.; Bracher, F. Steroids 2003, 68, 587.
[32] Lian, P.; Li, L. L.; Geng, C. R.; Zhen, X. C.; Fu, W. J. Chem. Inf. Model. 2015, 55, 1616.
[33] Wang, Q. Q. M.S. Thesis, Anhui Medical University, Hefei, 2016(in Chinese). (王欠欠, 硕士论文, 安徽医科大学, 合肥, 2016.)
[34] Ai, Y. S.; Liu, L. Q.; Xu, C. H.; Chen, H. T.; Sun, X. X. Her. Med. 2015, 24, 626(in Chinese). (艾又生, 刘力强, 徐楚鸿, 陈华庭, 孙小香, 医药导报, 2015, 24, 626.)

薯蓣皂苷元抗肿瘤衍生物的合成及其生物活性的研究

Study on the Synthesis and Bioactivity of Diosgenin Antitumor Derivatives

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yang Li, Yanan Dong, Yuehui Li. Efficient Synthesis of Nitrile Compounds through Amide Conversion via N-Boroamide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 638-643.
[2]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[3]	Baochang Gao, Yu Shi, Yuan Tian, Zhiguo Zhang, Jingru Zhang, Yufeng Sun, Guoliang Mao, Lingyan Dai. Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 644-649.
[4]	Suyan Tao, Zixin Xiang, Junjie Bai, Xiao Wan, Xiaobing Wan. Amide Hydrolysis Reaction Using tert-Butyl Nitrite [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 550-560.
[5]	Gangzhong Jiang, Jiaxing Lin, Xiaoguang Bao, Xiaobing Wan. Isoamyl Nitrite Activated Primary Sulfonamide to Sulfonyl Bromide and Sulfonyl Chloride [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 533-549.
[6]	Lijun Xu, Zongjun Li, Fushe Han, Xiang Gao. N,N-Dimethylformamide-Promoted Synthesis of Fullerene-Fused Oxazoline Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 242-250.
[7]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[8]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[9]	Zhiyou Huang, Ping Yang, Bo He, Wenxia Ou, Siyu Yuan. Design and Synthesis of Morpholine Sulfonamide Compound and Its Inhibition on Soybean Seed Germination [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 309-315.
[10]	Jing Tang, Wenkun Luo, Jun Zhou. Advances in the Synthesis of Azaspiro[4.5]trienones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3006-3034.
[11]	Wenfeng Bei, Jian Pan, Dongmei Ran, Yilin Liu, Zhen Yang, Ruokun Feng. Cobalt-Catalyzed [4+2] Annulation of Indole Carboxamide with Diynes and Monoacetylene: Direct Access to γ-Carbolinones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3226-3238.
[12]	Xiaoke Zhang, Xiangru Zheng, Chaoyong Wang. Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3180-3187.
[13]	Xuedan Wu, Ruixiang Xu, Xiaolong Fang, Kehua Zhang, Jie Jin. Design and Synthesis of N-Tetrazole and N-Oxadiazole Heterocyclic Derivatives of Sinomenine [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2506-2518.
[14]	Panxing Pang, Rong Ning, Chuang Zhu, Wenjie Huang, Xianli Ma, Caina Jiang, Fangyao Li, Xiaoqun Zhou. Synthesis and in Vitro Antitumor Activity of Matrine Semicarbazide Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2126-2135.
[15]	Lixing Sun, Tingting Sun, Haiqing Wang, Shufang Wu, Xiaoye Wang, Tianya Liu, Yuchen Zhang. Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2178-2188.