Progress in Synthesis and Antagonistic Activities towards PAFR and GlyR of Ginkgolide Derivatives and Analogs

doi:10.6023/cjoc201209028

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (06): 1263-1272.DOI: 10.6023/cjoc201209028 Previous Articles Next Articles

Reviews

银杏内酯衍生物和类似物的合成及PAFR和GlyR拮抗活性研究进展

惠爱玲^a, 吴泽宇^a, 袁媛^a, 周安^b, 潘见^a

a 合肥工业大学天然药物研究所合肥 230009;
b 安徽中医学院安徽省中药研究与开发重点实验室合肥 230038

收稿日期:2012-09-20 修回日期:2012-12-19 发布日期:2012-12-25
通讯作者: 惠爱玲 E-mail:haling@mail.ustc.edu.cn
基金资助:
安徽省科技计划(No.11010401025)资助项目.

Progress in Synthesis and Antagonistic Activities towards PAFR and GlyR of Ginkgolide Derivatives and Analogs

Hui Ailing^a, Wu Zeyu^a, Yuan Yuan^a, Zhou An^b, Pan Jian^a

a Institute of Natural Medicine, Hefei University of Technology, Hefei 230009;
b Anhui Province Key Laboratory of Research and Development of Chinese Medicine, Anhui University of Traditional Chinese Medicine, Hefei 230038

Received:2012-09-20 Revised:2012-12-19 Published:2012-12-25
Supported by:
Project supported by the Science and Technology Project of Anhui Province (No.11010401025).

Ginkgolides are diterpene trilactones with a cage-like skeleton consisting of six five-membered rings and a unique t-Bu group from Ginkgo biloba tree.Many studies have demonstrated that they are highly potent and selective antagonists of platelet activating factor receptor (PAFR) and glycine receptor (GlyR).Ginkgolide skeleton modifications may conduce to physiological activities variation.Therefore, many ginkgolide derivatives and analogs have been synthesized for the optimal antagonistic activities towards PAFR or GlyR.This review covers the structure-activity relationship studies of ginkgolide derivatives and analogs.

Key words: ginkgolide derivatives, ginkgolide analogs, platelet activating factor receptor, glycine receptor, structure-activity relationship

Cite this article

Hui Ailing, Wu Zeyu, Yuan Yuan, Zhou An, Pan Jian. Progress in Synthesis and Antagonistic Activities towards PAFR and GlyR of Ginkgolide Derivatives and Analogs[J]. Chin. J. Org. Chem., 2013, 33(06): 1263-1272.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Braquet, P.; Spinnewyn, B.; Braquet, M.Blood Vessels 1985, 16, 558. (b) Braquet, P.; Drieu, K.; Etienne, A.Actual.Chim.Ther. 1986, 13, 237.
[2] (a) Kondratskaya, E.L.; Lishko, P.V.; Chatterjee, S.S.; Krishtal, O.A.Neurochem.Int. 2002, 40, 647. (b) Kondratskayaand, E.L.; Krishtal, O.A.Neurophysiology 2002, 34, 155. (c) Jaracz, S.; Nakanishi, K.; Jensen, A.A.; Strφmgaard, K.Chem.Eur.J. 2004, 10, 1507. (d) Jensen, A.A.; Begum, N.; Vogensen, S.B.; Knapp, K.M.; Gundertofte, K.; Dzyuba, S.V.; Ishii, H.; Nakanishi, K.; Kristiansen, U.; Strφmgaard, K.J.Med.Chem. 2007, 50, 1610.
[3] Ivic, L.; Sands, T.T.J.; Fishkin, N.; Nakanishi, K.; Kriegstein, A.R.; Strφmgaard, K.J.Biol.Chem. 2003, 278, 49279.
[4] (a) Corey, E.J.; Kang, M.; Desai, M.C.; Ghosh, A.K.; Houpis, J.N.J.Am.Chem.Soc. 1988, 110, 649. (b) Corey, E.J.; Gavai, A.V.Tetrahedron Lett. 1988, 29, 3201. (c) Crimmins, M.T.; Pace, J.M.; Nantermet, P.G.; Kim-Meade, A.S.; Thomas, J.B.; Watterson, S.H.; Wagman, A.S.J.Am.Chem.Soc. 1999, 121, 10249.(d) Wu, Y.L.; He, Z.L.Highlights of Total Synthesis of Natural Products: Terpenes, Science Press, Beijing, 2010, pp.457～468 (in Chinese) (吴毓林, 何子乐, 天然产物全合成荟萃——萜类, 科学出版社, 北京, 2010, pp.457～468.)
[5] (a) Corey, E.J.; Gavai, A.V.Tetraheron Lett. 1989, 30, 6959.(b) Corey, E.J.; Rao, K.S.Tetrahedron Lett. 1991, 32, 4623.
[6] Braquet, P.; Esanu, A.GB 2211841, 1989[Chem.Abstr. 1990, 112, 76805].
[7] (a) Park, H.K.; Lee, S.K.; Park, P.U.; Kwak, W.J.WO 9306107, 1993[Chem.Abstr. 1993, 119, 138985]. (b) Park, P.U.; Pyo, S.; Lee, S.K.; Sung, J.H.; Kwak, W.J.; Park, H.K.; Cho, Y.B.; Ryu, G.H.; Kim, T.S.WO 9518131, 1995[Chem.Abstr.1995, 123, 314213]. (c) Park, P.U.; Pyo, S.; Lee, S.K.; Sung, J.H.; Kwak, W.J.; Park, H.K.; Cho, Y.B.; Ryu, G.H.; Kim, T.S.US 5541183, 1996 [Chem.Abstr. 1995, 123, 314213].
[8] Xu, R.S.Natural Products Chemistry, Science Press, Beijing, 2003, pp.397～409 (in Chinese).(徐任生, 天然产物化学, 科学出版社, 北京, 2003, pp.397～409.)
[9] Chen, J.Z.; Hu, L.H.; Jiang, H.L.The Fifth China—Japan Joint Symposium on Drug Design and Development, Chengdu, 1997, pp.81～82.
[10] Chen, J.Z.; Chen, K.X.; Jiang, H.L.; Gu, J.D.; Zhu, W.L.; Hu, Z.J.; Ji, R.Y.Sci.China, Ser.B 1998, 28, 316 (in Chinese). (陈建忠, 陈凯先, 蒋华良, 顾建德, 朱维良, 胡增建, 嵇汝运, 中国科学(B辑), 1998, 28, 316.)
[11] Chen, J.Z.; Hu, L.H.; Jiang, H.L.; Gu, J.D.; Zhu, W.L.; Chen, Z.L.; Chen, K.X.; Ji, R.Y.Bioorg.Med.Chem.Lett. 1998, 8, 1291.
[12] (a) Hu.L.H.; Chen, Z.L.; Xie, Y.Y.; Jiang, Y.Y.; Zhen, H.W.J.Asian Nat.Prod.Res. 2000, 2, 103. (b) Hu, L.H.; Chen, Z.L.; Xie, Y.Y.J.Asian Nat.Prod.Res. 2001, 3, 219.
[13] Hu, L.H.; Chen, Z.L.; Chen, X.F.; Xie, Y.Y.Pure Appl.Chem. 1999, 71, 1153.
[14] Hu, L.H.; Chen, Z.L.; Xie, Y.Y.; Jiang, Y.Y.; Zhen, H.W.Bioorg.Med.Chem. 2000, 8, 1515.
[15] Klebe, G.; Abraham, U.; Mietzner, T.J.Med.Chem. 1994, 37, 4130.
[16] Tong, W.; Lowis, D.R.; Perkins, R.; Chen, Y.; Welsh, W.J.; Goddette, D.W.; Heritage, T.W.; Sheehan, D.M.J.Chem.Inf.Comput.Sci. 1998, 38, 669.
[17] Zhu, W.L.; Chen, G.; Hu, L.H.; Luo, X.M.; Gui, C.S.; Luo, C.; Puah, C.M.; Chen, K.X.; Jiang, H.L. Bioorg.Med.Chem.2005, 13, 313.
[18] Strφmgaard, K.; Saito, D.R.; Shindou, H.; Ishii, S.; Shimizu, T.; Nakanishi, K.J.Med.Chem. 2002, 45, 4038.
[19] Jaracz, S.; Strφmgaard, K.; Nakanishi, K.J.Org.Chem. 2002, 67, 4623.
[20] Vogensen, S.B.; Strφmgaard, K.; Shindou, H.; Jaracz, S.; Suehiro, M.; Ishii, S.; Shimizu, T.; Nakanishi, K.J.Med.Chem. 2003, 46, 601.
[21] Strφmgaard, K.; Suehiro, M.; Nakanishi, K.Bioorg.Med.Chem.Lett. 2004, 14, 5673.
[22] Tanaka, K.; Kester, K.D.; Berova, N.; Nakanishi, K.Tetrahedron Lett. 2005, 46, 531.
[23] Tanaka, K.; Pimentel, M.; Berova, N.; Nakanishi, K.Bull.Chem.Soc.Jpn. 2005, 78, 1843.
[24] Ishii, H.; Dzyuba, S.V.; Nakanishi, K.Org.Biomol.Chem. 2005, 3, 3471.
[25] (a) Strφmgaard, K.; Nakanishi, K.Angew.Chem., Int.Ed.Engl. 2004, 43, 1640. (b) Nakanishi, K.Bioorg.Med.Chem. 2005, 13, 4987. (c) Dzyuba, S.V.; Bolshakov, S.; Li, J.; Nakanishi, K.Heterocycles 2005, 66, 743.
[26] Kato, E.; Howitt, R.; Dzyuba, S.V.; Nakanishi, K.Org.Biomol.Chem.2007, 5, 3758.
[27] Pietri, S.; Liebgott, T.; Finet, J.-P.; Culcasi, M.; Billottet, L.; Bernard-Henriet, C.Drug Dev.Res. 2001, 54, 191.
[28] Suehiro, M.; Simpson, N.R.; van Heertum, R.J.Labelled Compd.Radiopharm. 2004, 47, 485.
[29] Guo, C.J.; Ren, Y.; Qin, Y.L.; Zhang, Q.J.Asian Nat.Prod.Res. 2008, 10, 989.
[30] Liu, C.D.; Pan, S.H.; Mao, L.S.; Gu, P.C.; Wei, M.; Xu, H.Q.Chin.J.Nat.Med.2009, 7, 301.
[31] Deng, Y.; Fang, W.R.; Li, Y.M.; Cen, J.; Fang, F.; Lv, P.; Gong, S.B.; Mao, L.S.Eur.J.Pharmacol. 2009, 616, 43.
[32] (a) Wu, Z.Y.; Pan, J.; Yuan, Y.; Hui, A.L.; Yang, Y.; Zhou, A.; Tao, M.; Zhou, X.J. Med.Chem.Res. 2012, 21, 4028.(b) Pan, J.; Wu, Z.Y.; Yuan, Y.; Hui, A.L.; Yang, Y.Lat.Am.J.Pharm.2011, 30, 1167.(c) Pan, J.; Wu, Z.Y.; Hui, A.L.; Tao, M.Lishizhen Med.Mater.Med.Res. 2011, 22, 2397 (in Chinese).(潘见, 吴泽宇, 惠爱玲, 陶敏, 时珍国医国药, 2011, 22, 2397.) (d) Pan, J.; Yuan, Y.; Hui, A.L.; Zhou, A.; Wu, Z.Y.Chin.Pharm.Bull.2012, 28, 1435 (in Chinese).(潘见, 袁媛, 惠爱玲, 周安, 吴泽宇, 中国药理学通报, 2012, 28, 1435.) (e) Yuan, Y.; Pan, J.; Wu, Z.Y.; Hui, A.L.; Zhou, A.J.Chromatogr.Sci. 2012, 51, 266.(f) Chen, Y.Ph.D.Dissertation, Hefei University of Technology, Hefei, 2009 (in Chinese).(陈彦, 博士论文, 合肥工业大学, 合肥, 2009.) (g) Wu, Z.Y. Ph.D.Dissertation, Hefei University of Technology, Hefei, 2012 (in Chinese).(吴泽宇, 博士论文, 合肥工业大学, 合肥, 2012.) (h) Zhou, X.J. M.S.Thesis, Hefei University of Technology, Hefei, 2012 (in Chinese).(周小健, 硕士论文, 合肥工业大学, 合肥, 2012.)

银杏内酯衍生物和类似物的合成及PAFR和GlyR拮抗活性研究进展

Progress in Synthesis and Antagonistic Activities towards PAFR and GlyR of Ginkgolide Derivatives and Analogs

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Haibo Huo, Guixia Li, Shijun Wang, Chun Han, Baojun Shi, Jian Li. Novel γ-Carboline Derivatives as Antibacterial Agents: Synthesis and Antibacterial Evaluation [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 204-215.
[2]	Xin Zuo, Shinuo Xu, Zhongyang Chen, Jianfeng Yan, Yaofeng Yuan. Research Progress of Electron Transport Properties in Ferrocene- Containing Single-Molecule Junctions [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2313-2322.
[3]	Jinyan He, Fuyun Tian, Qingqing Wu, Yueming Zheng, Yuting Chen, Haiyan Xu, Zhengsheng Jin, Li Zhan, Xinqiang Cheng, Yueling Gu, Zhaobing Gao, Guilong Zhao. Design, Synthesis and Bioactivity of [3.3.3]Propellane-Based Voltage-Gated Calcium Channel α2δ Subunit Ligands [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2226-2238.
[4]	Xingzhou Liu, Mingjia Yu, Jianhua Liang. Research Progress on the Synthesis of Protoberberine Skeleton and Its Anti-inflammatory Activity [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1325-1340.
[5]	Rong Zhang, Xiang Gao, Lingling Chen, Fajun Nan. Discovery and Structure-Activity Relationship Studies of Thiazole- Oxazole Tandem Heterocyclic RNA Splicing Inhibitors [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2925-2939.
[6]	Ming Cai, Liang Shao, Fan Yang, Jihong Zhang, Fei Yu. Design, Synthesis of Pentacyclic Triterpenoid Glucose Conjugate and in vitro Activity against Influenza Virus [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1453-1462.
[7]	Siyu Zhu, Xinyu Huo, Qin Ma, Wei Chen, Jie Zhang, Liang Guo. Design, Synthesis, and Antitumor Activity of β-Carboline-Benzimidazole Hybrids [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1129-1135.
[8]	Yuanfang Kong, Bin Yang, Yan Zhuang, Jingyu Zhang, Demei Sun, Chunhong Dong. Research Progress on the Synthesis and Structure-Activity Relationship of Five Hypoglycemic Active Heterocycles Based on Dipeptidyl Peptidase 4 (DPP-4) Target Design [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 770-784.
[9]	Yan Zeng, Lifei Nie, Chao Niu, Aytilla Mamatjan, Khurshed Bozorov, Jiangyu Zhao, Haji Akber Aisa. Synthesis and Biological Activities of Dihydrooxazolo[5,4-d]-pyrrolo[1,2-a]pyrimidinones [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 543-556.
[10]	Wei Wang, Furan Wu, Yidan Ma, Dan Xu, Gong Xu. Study on Synthesis and Antifungal Activity of Novel Benzamides Containing Substituted Pyrazole Unit [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 607-618.
[11]	Lijie Yu, Bo Feng, Zhijia Wang, Lixin Gao, Chun Zhang, Rajendran Satheeshkumar, Jia Li, Yubo Zhou, Wenlong Wang. Synthesis of 5-Phenyl-1,3,4-thiadiazole Derivatives and Their Biochemical Evaluation against Src Homology 2 Domain-Containing Protein Tyrosine Phosphatase 1 (SHP1) [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3097-3105.
[12]	Hang Liu, Shuyun Zhang, Huan Li, Yan Zhang, Zhengming Li, Baolei Wang. Synthesis and Biological Activities of Novel 8-((3,4,4-Trifluorobut-3-en-1-yl)thio)-substituted Methylxanthines and Their Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2091-2098.
[13]	Ding Ma, Junli Ao, Naifeng Hu, Guangxin Liang. Progress in Biological Activity and Synthesis of Nematode Hatching Pheromone Glycinoeclepin A [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 553-566.
[14]	Yue Sun, Liang Guo, Wenxi Fan, Wei Chen, Jie Zhang, Bin Dai. Synthesis, Crystal Structure and Antitumor Activity of Novel 5-Chloro-β-carboline Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 400-406.
[15]	Shao Lihui, Gan Yiyuan, Hou Mi, Tao Shilin, Zhang Liqiong, Wang Zhenchao, Ouyang Guiping. Design, Synthesis and Biological Activity of Quinazolinone Derivatives Containing Hydrazone Structural Units [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1975-1982.