Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2723-2734.DOI: 10.6023/cjoc202012047 Previous Articles Next Articles
ARTICLES
李宁波a,b,c,*(), 续立a, 马榕a, 范琪a, 李波b, 乔洁a,b, 郭睿a,c,*(), 许新华d
收稿日期:
2020-12-28
修回日期:
2021-03-30
发布日期:
2021-04-16
通讯作者:
李宁波, 郭睿
基金资助:
Ningbo Lia,b,c(), Li Xua, Rong Maa, Qi Fana, Bo Lib, Jie Qiaoa,b, Rui Guoa,c(), Xinhua Xud
Received:
2020-12-28
Revised:
2021-03-30
Published:
2021-04-16
Contact:
Ningbo Li, Rui Guo
Supported by:
Share
Ningbo Li, Li Xu, Rong Ma, Qi Fan, Bo Li, Jie Qiao, Rui Guo, Xinhua Xu. Synthesis and Antitumor Activities of Novel Organic Sulfur (Selenium) Tegafur Derivatives[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2723-2734.
Entry | Cat./mol% | Zn dust/ mmol | Solvent | Time/h | Yieldb/% |
---|---|---|---|---|---|
1 | 5 | 0 | THF | 12 | 0 |
2 | 0 | 1 | THF | 12 | 0 |
3 | 5 | 1 | THF | 4 | 82 |
4 | 5 | 1.2 | THF | 4 | 94 |
5 | 7 | 1.2 | THF | 4 | 93 |
6 | 5 | 1.5 | THF | 4 | 94 |
6 | 5 | 1.2 | THF | 1 | 94 |
7 | 5 | 1.2 | THF | 0.5 | 73 |
8 | 5 | 1.2 | CH3CN | 1 | 72 |
9 | 5 | 1.2 | CH2Cl2 | 1 | 47 |
10 | 5 | 1.2 | DMF | 1 | 68 |
11 | 5 | 1.2 | Toluene | 1 | 26 |
Entry | Cat./mol% | Zn dust/ mmol | Solvent | Time/h | Yieldb/% |
---|---|---|---|---|---|
1 | 5 | 0 | THF | 12 | 0 |
2 | 0 | 1 | THF | 12 | 0 |
3 | 5 | 1 | THF | 4 | 82 |
4 | 5 | 1.2 | THF | 4 | 94 |
5 | 7 | 1.2 | THF | 4 | 93 |
6 | 5 | 1.5 | THF | 4 | 94 |
6 | 5 | 1.2 | THF | 1 | 94 |
7 | 5 | 1.2 | THF | 0.5 | 73 |
8 | 5 | 1.2 | CH3CN | 1 | 72 |
9 | 5 | 1.2 | CH2Cl2 | 1 | 47 |
10 | 5 | 1.2 | DMF | 1 | 68 |
11 | 5 | 1.2 | Toluene | 1 | 26 |
Compd. | IC50+SD/(μmol•L–1) | |
---|---|---|
HCT-116 | SGC-7901 | |
Tegafur | 861.13±15.34 | 1000.42±10.89 |
5a | 518.74±4.38 | 610.82±6.86 |
5b | 223.15±2.09 | 445.23±4.70 |
5c | 389.53±3.79 | 398.80±4.52 |
5d | 217.06±1.74 | 242.16±2.10 |
5e | 994.99±4.57 | 883.61±1.69 |
5f | 176.72±3.16 | 265.08±2.68 |
5g | 447.89±3.94 | 458.44±3.15 |
5h | 1058.44±6.91 | 501.28±7.84 |
5i | 246.49±12.71 | 238.43±1.53 |
5j | 729.13±3.75 | 348.14±6.50 |
5k | 142.07±7.77 | 240.11±4.66 |
5l | 224.91±4.88 | 274.50±3.32 |
5m | 252.36±3.88 | 290.93±6.12 |
5n | 308.94±5.90 | 258.75±2.19 |
5o | 601.26±5.80 | 1115.76±4.05 |
5p | 428.59±3.78 | 744.04±2.73 |
5q | 352.59±2.62 | 771.33±5.50 |
5r | 290.06±3.49 | 604.25±4.03 |
5s | 135.34±1.88 | 226.97±3.86 |
5t | 392.60±2.03 | 405.85±3.91 |
5u | 239.64±2.40 | 235.93±4.34 |
5v | 223.40±2.97 | 197.35±2.16 |
5w | 224.85±4.32 | 230.69±3.62 |
5x | 200.62±2.92 | 247.33±3.43 |
5y | 198.56±3.30 | 335.06±5.65 |
Compd. | IC50+SD/(μmol•L–1) | |
---|---|---|
HCT-116 | SGC-7901 | |
Tegafur | 861.13±15.34 | 1000.42±10.89 |
5a | 518.74±4.38 | 610.82±6.86 |
5b | 223.15±2.09 | 445.23±4.70 |
5c | 389.53±3.79 | 398.80±4.52 |
5d | 217.06±1.74 | 242.16±2.10 |
5e | 994.99±4.57 | 883.61±1.69 |
5f | 176.72±3.16 | 265.08±2.68 |
5g | 447.89±3.94 | 458.44±3.15 |
5h | 1058.44±6.91 | 501.28±7.84 |
5i | 246.49±12.71 | 238.43±1.53 |
5j | 729.13±3.75 | 348.14±6.50 |
5k | 142.07±7.77 | 240.11±4.66 |
5l | 224.91±4.88 | 274.50±3.32 |
5m | 252.36±3.88 | 290.93±6.12 |
5n | 308.94±5.90 | 258.75±2.19 |
5o | 601.26±5.80 | 1115.76±4.05 |
5p | 428.59±3.78 | 744.04±2.73 |
5q | 352.59±2.62 | 771.33±5.50 |
5r | 290.06±3.49 | 604.25±4.03 |
5s | 135.34±1.88 | 226.97±3.86 |
5t | 392.60±2.03 | 405.85±3.91 |
5u | 239.64±2.40 | 235.93±4.34 |
5v | 223.40±2.97 | 197.35±2.16 |
5w | 224.85±4.32 | 230.69±3.62 |
5x | 200.62±2.92 | 247.33±3.43 |
5y | 198.56±3.30 | 335.06±5.65 |
[1] |
Tsuboi, M.; Hamada, C.; Kato, H.; Ohta, M. Chemotherapy 2017, 62,357.
doi: 10.1159/000479084 |
[2] |
Ranieri, G.; Marech, I.; Porcelli, M. Giotta, F.; Palmiotti, G.; Laricchia, G.; Fazio, V.; Gadaleta,C. D. Oncotarget 2018, 9,8197.
doi: 10.18632/oncotarget.v9i8 |
[3] |
Longleyd, B.; Harkin,D. P.; Johnston,P. G. Nat. Rev. Cancer 2003, 3,330.
doi: 10.1038/nrc1074 |
[4] |
Broto, M.; Mccabe, R.; Galve, R.; Marco,M. P. Analyst 2017, 142,2404.
doi: 10.1039/C7AN00418D |
[5] |
Arias,J. L.; Sáez-Fernández, E.; López-Viota, M.; Biedma-Ortiz,R. A.; Ruiz,M. A. Med. Chem. 2012, 8,516.
doi: 10.2174/157340612801216373 |
[6] |
Boisdron-celle, M.; Capitain, O.; Faroux, R.; Borg, C.; Metges,J. P.; Galais,M. P.; Kaassis, M.; Bennouna, J.; Bouhier-leporrier, O.; Francois, E.; Baumgaertner, I.; Guerin-Meyer, V.; Cojocarasu, O.; Roemer-Becuwe, C.; Stampfli, C.; Rosenfeld, L.; Lecompte, T.; Berger, V.; Morel, A.; Gamelin, E. Semin. Oncol. 2017, 44,13.
doi: 10.1053/j.seminoncol.2017.02.008 |
[7] |
Zhang,Y. -X.; Dai,G. -F.; Wang, L.; Tao,J. -C. Bioorg. Med. Chem. Lett. 2007, 17,1613.
doi: 10.1016/j.bmcl.2006.12.092 |
[8] |
Tian,Z. Y.; Xie,S. Q.; Zhao, J.; Gao,W. -Y.; Wang,C. J. J. Henan Univ. 2008, 28,469 (in Chinese).
|
( 田智勇, 谢松强, 赵瑾, 高文远, 王超杰, 河南大学学报, 2008, 28,469.)
|
|
[9] |
Xiao,K. Y.; Dai, Y. Shi,W. Q.; Li,J. Z.; Li, Y.; Yin,S. F. Chin. J. Org. Chem. 2012, 32,169 (in Chinese).
doi: 10.6023/cjoc1107042 |
( 肖克毅, 戴亚, 石万棋, 李剑忠, 李颖, 尹述凡, 有机化学, 2012, 32,169.)
|
|
[10] |
Liu,W. Q.; Tao,L. M.; Zang,Z. L.; Li,Y. H.; Xu,X. H. Chin. J. Synth. Chem. 2009, 17,64 (in Chinese).
|
( 刘文奇, 陶李明, 臧中林, 李银辉, 许新华, 合成化学, 2009, 17,64.)
|
|
[11] |
Qin,S. H.; Liu,A. Q.; Yu,S. H.; Wang,F. L. Chin. Pharmacol. Bull. 2013, 29,145 (in Chinese).
|
( 秦三海, 刘爱芹, 于胜海, 王凤玲, 中国药理学通报, 2013, 29,145.)
|
|
[12] |
Liu,Y. M.; Lee,H. Y.; Lai,M. J.; Pan,S. L.; Huang,H. L.; Kuo,F. C.; Chen,M. C.; Liou,J. P. Org. Biomol. Chem. 2015, 13,10226.
doi: 10.1039/C5OB01509J |
[13] |
Kasprzak, A.; Koszytkowska-Stawińska, M.; Nowicka,A. M.; Buchowicz, W.; Poplawska, M. J. Org. Chem. 2019, 84,15900.
doi: 10.1021/acs.joc.9b02353 |
[14] |
Rich,T. A.; Shepard,R. C.; Mosley,S. T. J. Clin. Oncol. 2004, 22,2214.
doi: 10.1200/JCO.2004.08.009 |
[15] |
Wu,L. Q.; Yang,X. J.; Peng,Q. J. Sun,G. F. Eur. J. Med. Chem. 2017, 127,599.
doi: 10.1016/j.ejmech.2017.01.021 |
[16] |
Liu,W. Q.; Yin,X. H.; Zang,Z. L.; Yu,X. F.; Tao,L. M.; Li,Y. J. Xu,X. H. Chin. J. Org. Chem. 2009, 29,2021 (in Chinese).
|
( 刘文奇, 尹显洪, 臧中林, 余晓芬, 陶李明, 李言杰, 许新华, 有机化学, 2009, 29,2021.)
|
|
[17] |
He,W. B.; Gao,L. Q.; Chen,X. J.; Wu,Z. L.; Huang, Y.; Cao, Z.; Xu,X. H. He,W. -M. Chin. Chem. Lett. 2020, 31,1895.
doi: 10.1016/j.cclet.2020.02.011 |
[18] |
Wu, Y.; Lin,Y. -W.; He,W. -M. Chin. Chem. Lett. 2020, 31,2999.
doi: 10.1016/j.cclet.2020.09.005 |
[19] |
Wu, C.; Xiao,H. J.; Wang,S. W.; Tang,M. S.; Tang,Z. L.; Xia, W.; Li,W. F.; Cao, Z.; He,W. -M. ACS Sustainable Chem. Eng. 2019, 7,2169.
doi: 10.1021/acssuschemeng.8b04877 |
[20] |
Madhunapantula,S. V.; Desai, D.; Sharma, A.; Huh,S. J.; Amin, S.; Robertson,G. P. Mol. Cancer Ther. 2008, 7,1297.
doi: 10.1158/1535-7163.MCT-07-2267 |
[21] |
Sun,C. L.; Sun,X. N.; Pu,Y. X.; Li,C. Y.; Sun,L. J.; Wang, J.; Li,Y. Z. Chin. J. Org. Chem. 2017, 37,440 (in Chinese).
doi: 10.6023/cjoc201607024 |
( 孙成路, 孙晓娜, 蒲雨昕, 李传银, 孙丽杰, 王静, 李益政, 有机化学, 2017, 37,440.)
|
|
[22] |
Wang,L. X.; Li,N. B.; Wang,H. J.; Liu, W.; Diao,H. P.; Xu,X. H. Chin. J. Org. Chem. 2019, 39,1802 (in Chinese).
doi: 10.6023/cjoc201812033 |
( 王灵晓, 李宁波, 王浩江, 刘文, 刁海鹏, 许新华, 有机化学, 2019, 39,1802.)
|
|
[23] |
Chen,J. -Y.; Zhong,C. -T.; Gui,Q. -W.; Zhou,Y. -M.; Fang,Y. -Y.; Liu,K. -J.; Lin,Y. -W.; Cao, Z.; He,W. -M. Chin. Chem. Lett. 2021, 32,475.
doi: 10.1016/j.cclet.2020.09.034 |
[24] |
Zang,Z. L.; Liu,S. Q.; Chen, X.; Li,Y. J.; Zhou, B.; Xu,X. H. Acta Pham. Sin. 2006, 41,1184 (in Chinese).
|
( 臧中林, 刘少琼, 陈雄, 李言杰, 周冰, 许新华, 药学学报 2006, 41,1184.)
|
|
[25] |
Deng,X. H.; Xia, X.; Shao,L. L.; Zang,Z. L.; Li,Y. J.; Xu,X. H. Chin. J. Synth. Chem. 2008, 16,285 (in Chinese).
|
( 邓新华, 夏湘, 邵玲玲, 臧中林, 李言杰, 许新华, 合成化学, 2008, 16,282.)
|
|
[26] |
Wang,L. X.; Qiao, J.; Wei,J. C.; Liang,Z. W.; Xu,X. H.; Li,N. B. Tetrahedron 2020, 76,130750.
doi: 10.1016/j.tet.2019.130750 |
[27] |
Yu,A. H.; Xu,X. H. Chem. Reagents 2020, 42,1370 (in Chinese).
|
( 喻爱和, 许新华, 化学试剂 2020, 42,1370.)
|
[1] | 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. |
[2] | 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. |
[3] | Kanghui Duan, Junlong Tang, Wanqing Wu. Recent Advances in the Synthesis of Fused Heterocyclic Compounds and Their Antitumor Activities [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 826-854. |
[4] | Weiqin Liu, Lihui Shao, Chengpeng Li, Yayu Zou, Haitao Long, Yan Li, Qiangsheng Ge, Zhenchao Wang, Guiping Ouyang. Synthesis and Antitumor Activity of 3-Hydrazone Quinazolinone Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 214-222. |
[5] | Jing Zhao, Zhe Jin, Run Wang, Xin'geng Zhang, Yingmei Han, Chun Hu, Xiaoping Liu, Chuanming Zhang, Liping Jin. Design, Synthesis and Anticancer Activity of 2-((Pyridin- 2-ylmethyl)thio)-1H-benzimidazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2172-2183. |
[6] | Dongyan Hu, Guangtian Han, Xi'an Li, Huazhong Ren, Lirong Yue, Li Guo, Jiafu Feng. Synthesis and Evaluation in vitro of Novel Harmine Derivatives as Anticancer Activity Agents [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1863-1871. |
[7] | Lu Xue, Lihua Zhang, Chengyu Zhang, Xin Zhao, Weifan Dang, Zhaoxin Wang, Chunhua Wang, Tongchuan Suo, Xiaohui Yan. Discovery of Tiancimycin Congeners from Streptomyces sp. CB03234-S [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1241-1247. |
[8] | Honglin Dai, Xiaojie Si, Lingling Chi, Hao Wang, Chao Gao, Zhengjie Wang, Limin Liu, Jiajie Ma, Fuqiang Yu, Hongmin Liu, Yu Ke, Qiurong Zhang. Synthesis and Antitumor Activity Evaluation of 2,4,6-Trisubstituted Quinazoline Derivatives Containing Thiazole Structure [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3853-3862. |
[9] | Lijun Yin, Chaoqun Li, Xiaoxia Wu, Guangsen Xu, Zhiying Li, Yuemao Shen. Synthesis of (E)-N-(4-Styrene) Acrylamides for DNA Topoisomerase IIα Inhibitors and Antitumor Agents [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 293-301. |
[10] | Zhengjie Wang, Honglin Dai, Xiaojie Si, Chao Gao, Limin Liu, Luye Zhang, Yang Zhang, Yadan Song, Peirong Zhao, Jiaxin Zheng, Yu Ke, Hongmin Liu, Qiurong Zhang. Synthesis and Antitumor Activity of 2,4,6-Trisubstituted Novel Quinazoline Derivatives Containing Trifluoromethyl [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 249-256. |
[11] | Shenghui Wang, Yongfeng Guan, Xiujuan Liu, Xinying Yuan, Guangxi Yu, Yinru Li, Yanbing Zhang, Jian Song, Wen Li, Saiyang Zhang. Design, Synthesis and Anticancer Activity Studies of Novel Quinoline-Indole Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3617-3624. |
[12] | Jiaoli Ma, Penghu Guo, Jing Li, Xincheng Liao, Huicheng Cheng. Synthesis and Antitumor Activity of Amide Derivatives Containing 1,3,4-Thiadiazole and Pyrazole Moieties [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3214-3222. |
[13] | Yinghao Liu, Fangxia Lin, Yinfeng Tan, Jingyu Yang, Bin Zhang, Xueming Zhou, Xinming Song. Three New Phenanthraquinones from the Root of Dendrobium nobile [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2112-2115. |
[14] | Yuxun Zhao, Yunyun Wang, Chenglong Zhang, Xu Xu, Shifa Wang. Synthesis of Novel Camphor Sulfamoxime Ether Derivatives and Its Application in Antitumor Activity [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1224-1233. |
[15] | Jing Cong, Fang Fang, Liangmin Xue, Meng Wang, Chao Tian, Xiaowei Wang, Junyi Liu, Zhili Zhang. Synthesis and Antitumor Activity of Novel Pyrimidine Monocyclic Nonclassical Antifolates [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 776-787. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||