Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (5): 1606-1619.DOI: 10.6023/cjoc202311020 Previous Articles Next Articles
ARTICLES
许芹芳a, 胡健灵a, 刘园林a, 张超a, 李明月a, 彭姝羚a, 刘志军a,b, 陈河如a,c,d,*()
收稿日期:
2023-11-22
修回日期:
2023-12-20
发布日期:
2024-01-18
基金资助:
Qinfang Xua, Jianling Hua, Yuanlin Liua, Chao Zhanga, Mingyue Lia, Shuling Penga, Zhijun Liua,b, Heru Chena,c,d()
Received:
2023-11-22
Revised:
2023-12-20
Published:
2024-01-18
Contact:
*E-mail: Supported by:
Share
Qinfang Xu, Jianling Hu, Yuanlin Liu, Chao Zhang, Mingyue Li, Shuling Peng, Zhijun Liu, Heru Chen. Design, Syntheses of Novel Triazenes with Better Druggability and the Investigation on Their Anti-tumor Activities[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1606-1619.
Cell line | Inhibition rate/% | ||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
4a | 4b | 4c | 4d | 4e | 4f | 4g | 4h | 4i | 4j | 4k | |
HepG-2 | 50.8 36.2 | 27.3 13.4 | 63.4 50.3 | 18.6 5.3 | 45.1 22.7 | 32.2 23.8 | 28.2 8.6 | 37.7 8.9 | -8.2 -2.4 | 1.8 7.1 | -8.3 -2.5 |
MDA-MB-231 | -22.5 -47.5 | 15.8 -1.1 | 17.8 1.2 | -0.4 -8.3 | 14.1 23.5 | 28.1 17.5 | 16.1 9.6 | 26.4 5.3 | 14.8 -19.3 | 14.5 -7.2 | 1.2 -11.6 |
PC-3 | 36.9 32.1 | 5.5 9.3 | -16.2 2.3 | 7.1 -1.4 | -18.8 11.5 | -17.1 -10.0 | -16.5 -21.0 | 17.4 6.5 | 1.9 -8.8 | 18.7 2.4 | 19.7 -2.0 |
SW620 | -20.7 -17.5 | 13.0 6.5 | 5.4 -5.0 | 0.9 0.0 | 6.5 2.2 | -13.8 -6.8 | -9.3 5.0 | 15.1 17.8 | 11.1 -3.3 | 3.4 -3.3 | 21.8 2.9 |
U87 | 42.4 16.9 | 17.9 7.7 | 39.0 28.4 | 16.2 -15.4 | 19.1 13.2 | 17.1 1.5 | -43.6 -29.0 | 19.2 -16.6 | 8.4 6.0 | 17.9 -9.1 | 17.1 -12.1 |
A375 | 14.3 -7.3 | 28.2 2.6 | 9.9 5.8 | 8.1 0.0 | 18.3 -3.9 | 11.5 -8.2 | 39.1 15.6 | 36.8 14.3 | 29.4 16.7 | 3.7 -18.4 | 6.4 2.8 |
Cell line | Inhibition rate/% | ||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
4a | 4b | 4c | 4d | 4e | 4f | 4g | 4h | 4i | 4j | 4k | |
HepG-2 | 50.8 36.2 | 27.3 13.4 | 63.4 50.3 | 18.6 5.3 | 45.1 22.7 | 32.2 23.8 | 28.2 8.6 | 37.7 8.9 | -8.2 -2.4 | 1.8 7.1 | -8.3 -2.5 |
MDA-MB-231 | -22.5 -47.5 | 15.8 -1.1 | 17.8 1.2 | -0.4 -8.3 | 14.1 23.5 | 28.1 17.5 | 16.1 9.6 | 26.4 5.3 | 14.8 -19.3 | 14.5 -7.2 | 1.2 -11.6 |
PC-3 | 36.9 32.1 | 5.5 9.3 | -16.2 2.3 | 7.1 -1.4 | -18.8 11.5 | -17.1 -10.0 | -16.5 -21.0 | 17.4 6.5 | 1.9 -8.8 | 18.7 2.4 | 19.7 -2.0 |
SW620 | -20.7 -17.5 | 13.0 6.5 | 5.4 -5.0 | 0.9 0.0 | 6.5 2.2 | -13.8 -6.8 | -9.3 5.0 | 15.1 17.8 | 11.1 -3.3 | 3.4 -3.3 | 21.8 2.9 |
U87 | 42.4 16.9 | 17.9 7.7 | 39.0 28.4 | 16.2 -15.4 | 19.1 13.2 | 17.1 1.5 | -43.6 -29.0 | 19.2 -16.6 | 8.4 6.0 | 17.9 -9.1 | 17.1 -12.1 |
A375 | 14.3 -7.3 | 28.2 2.6 | 9.9 5.8 | 8.1 0.0 | 18.3 -3.9 | 11.5 -8.2 | 39.1 15.6 | 36.8 14.3 | 29.4 16.7 | 3.7 -18.4 | 6.4 2.8 |
细胞株 | IC50 a/(μmol•L-1) | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
DTIC | 6a | 6b | 6c | 6d | 6e | 6f | 6g | 6h | 6i | 6j | 6k | |
HepG-2 | >200b | 86.7±1.5 | >200b | >200b | >200b | 45.4±2.9 | 100~200 | 21.6±2.9 | 45.1±1.6 | 100~200 | 100~200 | >200b |
C6 | >200b | 31.4±1.2 | >200b | >200b | >200b | 4.2±1.5 | 28.2±0.9 | 3.6±2.1 | 20.5±1.5 | 31.9±7.1 | 27.1±2.3 | >200b |
SW620 | >200b | 20.4±0.4 | >200b | >200b | >200b | 12.1±0.4 | 23.0±2.6 | 5.8±0.6 | 13.4±3.8 | 35.1±8.5 | 42.9±0.9 | >200b |
PC-3 | >200b | 32.2±7.5 | >200b | >200b | >200b | 5.8±0.9 | 60.6±2.2 | 7.0±0.3 | 36.4±0.8 | 100~200 | 90.8±1.3 | >200b |
B16 | >200b | 64.4±6.2 | >200b | >200b | >200b | 100~200 | 53.6±3.6 | 9.4±0.1 | 13.8±3.1 | 10.5±0.4 | 16.8±0.4 | >200b |
A549 | >200b | 100~200 | >200b | >200b | >200b | 33.8±4.6 | 100~200 | 13.7±1.6 | 39.5±1.4 | 74.4±2.1 | >200b | >200b |
细胞株 | IC50 a/(μmol•L-1) | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
DTIC | 6a | 6b | 6c | 6d | 6e | 6f | 6g | 6h | 6i | 6j | 6k | |
HepG-2 | >200b | 86.7±1.5 | >200b | >200b | >200b | 45.4±2.9 | 100~200 | 21.6±2.9 | 45.1±1.6 | 100~200 | 100~200 | >200b |
C6 | >200b | 31.4±1.2 | >200b | >200b | >200b | 4.2±1.5 | 28.2±0.9 | 3.6±2.1 | 20.5±1.5 | 31.9±7.1 | 27.1±2.3 | >200b |
SW620 | >200b | 20.4±0.4 | >200b | >200b | >200b | 12.1±0.4 | 23.0±2.6 | 5.8±0.6 | 13.4±3.8 | 35.1±8.5 | 42.9±0.9 | >200b |
PC-3 | >200b | 32.2±7.5 | >200b | >200b | >200b | 5.8±0.9 | 60.6±2.2 | 7.0±0.3 | 36.4±0.8 | 100~200 | 90.8±1.3 | >200b |
B16 | >200b | 64.4±6.2 | >200b | >200b | >200b | 100~200 | 53.6±3.6 | 9.4±0.1 | 13.8±3.1 | 10.5±0.4 | 16.8±0.4 | >200b |
A549 | >200b | 100~200 | >200b | >200b | >200b | 33.8±4.6 | 100~200 | 13.7±1.6 | 39.5±1.4 | 74.4±2.1 | >200b | >200b |
细胞株 | IC50a/(μmol•L-1) | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
DTIC | 6a | 6b | 6c | 6d | 6e | 6f | 6g | 6h | 6i | 6j | 6k | |
HepG-2 | >200b | 22.6±3.4 | >200b | >200b | >200b | 20.3±4.1 | 31.1±1.0 | 14.1±2.5 | 23.1±3.7 | 41.4±5.3 | 53.8±1.1 | >200b |
C6 | >200b | 22.7±0.1 | >200b | >200b | >200b | 4.0±0.4 | 30.1±0.8 | 9.1±0.3 | 21.7±0.6 | 35.7±5.9 | 18.7±1.3 | >200b |
SW620 | >200b | 16.5±1.8 | >200b | >200b | >200b | 16.4±2.0 | 24.9±4.2 | 4.8±0.2 | 11.6±0.5 | 42.9±4.6 | 36.7±0.4 | >200b |
PC-3 | >200b | 100~200 | >200b | >200b | >200b | 4.5±0.6 | 29.3±1.1 | 5.7±0.4 | 28.1±1.9 | 100~200 | 49.2±1.0 | >200b |
B16 | >200b | 20.6±2.4 | >200b | >200b | >200b | 100~200 | 28.1±1.2 | 5.8±0.2 | 16.5±6.8 | 18.4±5.7 | 18.3±0.2 | >200b |
A549 | >200b | 57.0±4.0 | >200b | >200b | >200b | 19.3±2.0 | 64.5±0.4 | 18.7±1.2 | 30.4±1.0 | 44.4±1.7 | >200b | >200b |
细胞株 | IC50a/(μmol•L-1) | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
DTIC | 6a | 6b | 6c | 6d | 6e | 6f | 6g | 6h | 6i | 6j | 6k | |
HepG-2 | >200b | 22.6±3.4 | >200b | >200b | >200b | 20.3±4.1 | 31.1±1.0 | 14.1±2.5 | 23.1±3.7 | 41.4±5.3 | 53.8±1.1 | >200b |
C6 | >200b | 22.7±0.1 | >200b | >200b | >200b | 4.0±0.4 | 30.1±0.8 | 9.1±0.3 | 21.7±0.6 | 35.7±5.9 | 18.7±1.3 | >200b |
SW620 | >200b | 16.5±1.8 | >200b | >200b | >200b | 16.4±2.0 | 24.9±4.2 | 4.8±0.2 | 11.6±0.5 | 42.9±4.6 | 36.7±0.4 | >200b |
PC-3 | >200b | 100~200 | >200b | >200b | >200b | 4.5±0.6 | 29.3±1.1 | 5.7±0.4 | 28.1±1.9 | 100~200 | 49.2±1.0 | >200b |
B16 | >200b | 20.6±2.4 | >200b | >200b | >200b | 100~200 | 28.1±1.2 | 5.8±0.2 | 16.5±6.8 | 18.4±5.7 | 18.3±0.2 | >200b |
A549 | >200b | 57.0±4.0 | >200b | >200b | >200b | 19.3±2.0 | 64.5±0.4 | 18.7±1.2 | 30.4±1.0 | 44.4±1.7 | >200b | >200b |
Compd. | Safety index | ||||
---|---|---|---|---|---|
HepG-2 | C6 | SW620 | PC-3 | B16 | |
DTIC | <1.5 | <1.5 | <1.5 | <1.5 | 1.5a |
6e | 1.2 | 12.8 | 4.5 | 9.4 | <0.2 |
6g | 1.0 | 5.9 | 3.7 | 3.1 | 2.3 |
6h | 1.7 | 3.8 | 5.8 | 2.1 | 5.6 |
6i | <0.2 | 5.0 | 4.6 | <0.2 | 15.2 |
Compd. | Safety index | ||||
---|---|---|---|---|---|
HepG-2 | C6 | SW620 | PC-3 | B16 | |
DTIC | <1.5 | <1.5 | <1.5 | <1.5 | 1.5a |
6e | 1.2 | 12.8 | 4.5 | 9.4 | <0.2 |
6g | 1.0 | 5.9 | 3.7 | 3.1 | 2.3 |
6h | 1.7 | 3.8 | 5.8 | 2.1 | 5.6 |
6i | <0.2 | 5.0 | 4.6 | <0.2 | 15.2 |
Compd. | Safety index | ||||
---|---|---|---|---|---|
HepG-2 | C6 | SW620 | PC-3 | B16 | |
DTIC | <1.4 | <1.4 | <1.4 | <1.4 | 1.4a |
6e | 1.7 | 8.5 | 2.1 | 7.6 | <0.2 |
6g | 1.1 | 1.7 | 3.2 | 2.7 | 2.7 |
6h | 2.7 | 2.9 | 5.4 | 2.2 | 3.8 |
6i | 3.8 | 4.4 | 3.6 | <0.2 | 8.5 |
Compd. | Safety index | ||||
---|---|---|---|---|---|
HepG-2 | C6 | SW620 | PC-3 | B16 | |
DTIC | <1.4 | <1.4 | <1.4 | <1.4 | 1.4a |
6e | 1.7 | 8.5 | 2.1 | 7.6 | <0.2 |
6g | 1.1 | 1.7 | 3.2 | 2.7 | 2.7 |
6h | 2.7 | 2.9 | 5.4 | 2.2 | 3.8 |
6i | 3.8 | 4.4 | 3.6 | <0.2 | 8.5 |
Compd. | coil phase/(μg•mL-1) | caqueous phase/(μg•mL-1) | P | lg P |
---|---|---|---|---|
DTIC | 205.4 | 112.4 | 1.8 | 0.3 |
6e | 845.4 | 0.3 | 2633.8 | 3.4 |
6g | 1539.3 | 0.2 | 7975.8 | 3.9 |
6h | 1784.3 | 0.2 | 7965.7 | 3.9 |
6i | 732.9 | 0.4 | 1720.4 | 3.2 |
Compd. | coil phase/(μg•mL-1) | caqueous phase/(μg•mL-1) | P | lg P |
---|---|---|---|---|
DTIC | 205.4 | 112.4 | 1.8 | 0.3 |
6e | 845.4 | 0.3 | 2633.8 | 3.4 |
6g | 1539.3 | 0.2 | 7975.8 | 3.9 |
6h | 1784.3 | 0.2 | 7965.7 | 3.9 |
6i | 732.9 | 0.4 | 1720.4 | 3.2 |
[1] |
Griess, P. Justus Liebigs Ann. Chem. 1862, 121, 258.
|
[2] |
Connors, T. A.; Goddard, P. M.; Merai, K.; Ross, W. C. J.; Wilman, D. E. V. Biochem. Pharmacol. 1976, 25, 241.
pmid: 1267820 |
[3] |
Clarke, D. A.; Barclay, R. K.; Stock, C. C.; Rondestvedt, C. S. Jr. Proc. Soc. Expt. Biol. Med. 1955, 90, 484.
|
[4] |
Shealy, Y. F.; Krauth, C. A.; Montgomery, J. A. J. Org. Chem. 1962, 27, 2150.
|
[5] |
Wexler, P. In Encyclopedia of Toxicology, 3rd ed., Ed.: Andrea, M., Academic Press, Lundon, 2014, pp. 1132-1134.
|
[6] |
Ege, G.; Gilbert, K. Tetrahedron Lett. 1979, 20, 4253.
|
[7] |
Clark, A. S.; Deans, B.; Stevens, M. F. G.; Tisdale, M. J.; Wheelhouse, R. T.; Denny, B. J.; Hartley, J. A. J. Med. Chem. 1995, 38, 1493.
pmid: 7739008 |
[8] |
Saunders, P. P.; Schultz, G. A. Biochem. Pharmacol. 1970, 19, 911.
pmid: 4994358 |
[9] |
Skibba, J. L.; Beal, D. D.; Ramirez, G.; Bryan, G. T. Cancer Res. 1970, 30, 147.
pmid: 5441073 |
[10] |
Denny, B. J.; Wheelhouse, R. T.; Stevens, M. F.; Tsang, L. L.; Slack, J. A. Biochemistry 1994, 33, 9045.
doi: 10.1021/bi00197a003 pmid: 8049205 |
[11] |
Lei, Q.; Zhang, S. Y.; Liu, M. L.; Li, J.; Zhang, X.; Long, Y. Mol. Diversity 2017, 21, 957.
|
[12] |
Wei, G. P.; Zhang, X.; Lei, Q.; Xu, M.; Zhang, M. Q.; Long, Y. Chin. J. Org. Chem. 2018, 38, 2137 (in Chinese).
|
( 魏光璞, 张茜, 雷强, 徐淼, 张明千, 龙跃, 有机化学, 2018, 38, 2137.)
doi: 10.6023/cjoc201802013 |
|
[13] |
Ge, Y.; Ren, T.; Cui, X.; Zhao, L. J.; Zhong, R. G. Chem. Reagents 2018, 40, 707 (in Chinese).
|
( 葛瑶, 任婷, 崔鑫, 赵丽娇, 钟儒刚, 化学试剂, 2018, 40, 707.)
|
|
[14] |
Matheson, S. L.; Mcnamee, J. P.; Wang, T. Q.; Alaoui-Jamali, M. A.; Tari, M. A.; Jean-Claude, B. J. J. Pharmacol. Exp. Ther. 2004, 311, 1163.
|
[15] |
Monteiro, A. S.; Almeida, J.; Cabral, G.; Severino, P.; Videira, P. A.; Sousa, A.; Nunes, R.; Pereira, J. D.; Francisco, A. P.; Jesus Perry, M.; Mendes, E. Eur. J. Med. Chem. 2013, 70, 1.
doi: 10.1016/j.ejmech.2013.09.040 pmid: 24125877 |
[16] |
Lei, Q.; Qin, S.; Feng, C.; Li, P.; Zhang, X.; Long, Y. Chin. J. Org. Chem. 2016, 36, 406 (in Chinese).
|
( 雷强, 秦上尚, 冯翠宁, 李佩佩, 张茜, 龙跃, 有机化学, 2016, 36, 406.)
doi: 10.6023/cjoc201507004 |
|
[17] |
Zhang, M.; Liu, B.; Lei, Q.; Yan, J.; Zhao, Z.; Long, Y. Chin. J. Org. Chem. 2019, 39, 1064 (in Chinese).
|
( 张明千, 刘斌凯, 雷强, 颜景东, 赵中玉, 龙跃, 有机化学, 2019, 39, 1064.)
doi: 10.6023/cjoc201809003 |
|
[18] |
Chen, Y.; Zhang, M.; Li, Z.; Luo, D.; Li, L.; Yu, T.; Long, Y. Chin. J. Org. Chem. 2019, 39, 3283 (in Chinese).
|
( 陈彦君, 张明千, 李子秋, 罗德福, 李龙辉, 俞婷婷, 龙跃, 有机化学, 2019, 39, 3283.)
doi: 10.6023/cjoc201905035 |
|
[19] |
Chen, Z. X.; Riggs, A. D. J. Biol. Chem. 2011, 286, 18347.
|
[20] |
Jin, J.; Gong, J.; Yin, T.; Lu, Y.; Xia, J.; Xie, Y.; Di, Y.; He, L.; Guo, J. Eur. J. Pharm. 2011, 654, 17.
|
[21] |
Xiao, Q. W.; Lu, Y. F.; Chen, X. P. Ind. J. Pharm. Sci. 2020, 82, 361.
|
[22] |
Chen, M.; Su, D.; Xu, H.; Ai, Z.; Wang, R.; Chai, X.; Luo, W.; Yang, M.; Liu, Y.; Song, Y. Chin. Arch. Traditional Chin. Med. 2022, 40, 191 (in Chinese).
|
( 陈梦莹, 苏丹, 徐焕华, 艾志福, 王瑞英, 柴晓燕, 罗湾湾, 杨明, 刘亚丽, 宋永贵, 中华中医药学刊, 2022, 40, 191.)
|
|
[23] |
Teramoto, S. Int. J. Chronic Obstruct. Pulm. Dis. 2022, 17, 1453.
|
[24] |
Al Jamal, M.; Al Bathish, M.; Gazy, A. Pharmacia 2023, 70, 299.
|
[25] |
Losada-Barreiro, S.; Paiva-Martins, F.; Bravo-Diaz, C. Antioxidants 2023, 12, 828.
|
[26] |
Qiao, Y.; Xia, S.; Ma, P. Chem. Eng. Data 2008, 53, 280.
|
[27] |
Kolar, G. F. Z. Naturforsch.,B: Anorg. Chem., Org. Chem.,Biochem., Biophys., Biol. 1972, 27, 1183.
|
[28] |
Voronin, V. G.; Pleshkova, A. P.; Ermakov, A. I.; Petrova, I. D.; Karaseva, N. F.; Zelenova, V. P. Zh. Org. Khim. 1979, 15, 63.
|
[29] |
Liu, J.; Zhang, B.; Sun, J.; Chen, Y. Chin. J. Pharm. 1984, 9, 20 (in Chinese).
|
( 刘纪云, 张葆珣, 孙家莉, 陈奕, 中国医药工业杂志, 1984, 9, 20.)
|
|
[30] |
Wilman, D. E. V.; Cox, P. J.; Goddard, P. M.; Hart, L. I.; Merai, K.; Newell, D. R. J. Med. Chem. 1984, 27, 870.
pmid: 6737430 |
[31] |
Freimanis, J.; Markava, E.; Matisova, G.; Gerca, L.; Muzikante, I.; Rutkis, M.; Silinsh, E. Langmuir 1994, 10, 3311.
|
[32] |
Wilman, D. E. V.; Goddard, P. M.; Heales, B. E. J. Med. Chem. 1991, 2, 101.
|
[33] |
Dunn, W. J. 3rd.; Greenberg, M. J. J. Pharm. Sci. 1977, 66, 1416.
|
[1] | Yumei Zhong, Xiaoying Zou, Xiaoya Zhuo, Yihan Wang, Jiayi Shen, Lüyin Zheng, Wei Guo. Design, Synthesis and in vitro Anti-Cancer Activity of Novel Ethyl 4-Oxo-2-iminothiazolidin-5-ylidene Acetates [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1452-1461. |
[2] | Ruijia Chen, Cong Zhou, Xiwen Pang, Jiajun Liu, Yucheng Gu, Jianwen Liu, Zhong Li. Design, Synthesis, Anti-cancer Activities and Computational Analysis of Novel Diamides Conformationally Restricted by Cyclopropane [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 277-292. |
[3] | Yan Longjia, Li Yongliang, Deng Minggao, Chen Anchao, Du Zhiyun, Dong Changzhi, Chen Huixiong. Design, Synthesis and Biological Activities of Compounds Containing 1,3,4-Oxadiazole or 1,3,4-Thiadiazole [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 731-739. |
[4] | Zhang Chao, Liu Zhijun, Li Yanbing, He Yepu, Lin Xiaohong, Chen Heru. Environment-Friendly Synthesis of Targeted Anticancer Drug N-(N'-Carbobenzoxyglycylprolyl)procarbazine (Z-GP-Pcb) and the Evaluation of Its Activity to Penetrate Blood-Brain Barrier [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 536-540. |
[5] | Dai Yi, Zhong Fei. Advances in the Study of Structural Modification and Biological Activities of Oridonin [J]. Chin. J. Org. Chem., 2017, 37(7): 1701-1713. |
[6] | Yu Jiangfan, Feng Ruokun, Yang Zhen. Synthetic Studies toward Neopeltolide:A Potent Anti-cancer Natural Product [J]. Chin. J. Org. Chem., 2017, 37(10): 2526-2543. |
[7] | Lei Qiang, Qin Shangshang, Feng Cuining, Li Peipei, Zhang Xi, Long Yue. Synthesis and Biological Activities of 1,3,4-Oxadiazole Triazene Derivatives [J]. Chin. J. Org. Chem., 2016, 36(2): 406-411. |
[8] | Zhang Wei, Liu Guoyun, Yin Ruwen, Li Yingxia. Research Progress of Apratoxin A:A Marine Cyclicdepsipeptide with Significant Anti-cancer Activity [J]. Chin. J. Org. Chem., 2014, 34(3): 475-484. |
[9] | Xiao Fanhua, Wu Fanhong. Process Optimization for the Synthesis of Disodium Combretastatin A-4 Phosphate [J]. Chin. J. Org. Chem., 2013, 33(07): 1564-1567. |
[10] | Tang Chu, Chen Yu, Bai Shun, Yang Guangzhong. Advances in the Study of Structural Modification and Biological Activities of Oleanolic Acid [J]. Chin. J. Org. Chem., 2013, 33(01): 46-65. |
[11] | Nan Guangming, Zhou Jun. Study on Lewis Acid Induced the Stille Cross-Coupling Reactions of Aryltriazenes as Substrates [J]. Chin. J. Org. Chem., 2012, 32(9): 1695-1699. |
[12] | ZHAO Long-Xuan, TIAN Ming-Zhu, JIN Li-Ji, HE Xing-Long, SHEN Ping, ZHANG Xiao-Cui, YANG Jun-Wei. Synthesis and Characterization of Derivatives of Asiatic Acid and Primary Study on Anti-cancer Activity [J]. Chin. J. Org. Chem., 2011, 31(05): 646-652. |
[13] | MA, Zhi-Hong*,a ; LIN, Jinb. Progress in Synthesis and Application of Fulvene [J]. Chin. J. Org. Chem., 2008, 28(10): 1707-1714. |
[14] | XIAO Fan-hua, WU Fan-hong. The process optimization for the synthesis of disodium Combretastatin A-4 phosphate [J]. Chin. J. Org. Chem., 0, (0): 0-0. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||