Review Article

丹参酮IIA:药理、全合成和结构修饰的研究进展

卷 29, 期 11, 2022

发表于: 14 January, 2022

页: [1959 - 1989] 页: 31

弟呕挨: 10.2174/0929867328666211108110025

价格: $65

Open Access Journals Promotions 2
摘要

丹参酮IIA是中药丹参的主要生物活性成分,因其独特的结构特征和多种良好的生物活性而得到了广泛的研究。本文就丹参酮IIA的药理学、全合成和结构修饰进行了综述。我们希望本次评审将有助于更好地了解该领域的进展,并为进一步研究丹参酮IIA提供建设性的建议。

关键词: 丹参酮IIA,药理学,合成,结构修饰,丹参,中药。

[1]
Harvey, A.L.; Edrada-Ebel, R.; Quinn, R.J. The re-emergence of natural products for drug discovery in the genomics era. Nat. Rev. Drug Discov., 2015, 14(2), 111-129.
[http://dx.doi.org/10.1038/nrd4510] [PMID: 25614221]
[2]
Chen, H.; Gao, Y.; Wang, A.; Zhou, X.; Zheng, Y.; Zhou, J. Evolution in medicinal chemistry of ursolic acid derivatives as anticancer agents. Eur. J. Med. Chem., 2015, 92, 648-655.
[http://dx.doi.org/10.1016/j.ejmech.2015.01.031] [PMID: 25617694]
[3]
Chen, H.; Gao, Y.; Wu, J.; Chen, Y.; Chen, B.; Hu, J.; Zhou, J. Exploring therapeutic potentials of baicalin and its aglycone baicalein for hematological malignancies. Cancer Lett., 2014, 354(1), 5-11.
[http://dx.doi.org/10.1016/j.canlet.2014.08.003] [PMID: 25128647]
[4]
Eder, J.; Sedrani, R.; Wiesmann, C. The discovery of first-in-class drugs: Origins and evolution. Nat. Rev. Drug Discov., 2014, 13(8), 577-587.
[http://dx.doi.org/10.1038/nrd4336] [PMID: 25033734]
[5]
Miller, L.H.; Su, X. Artemisinin: discovery from the Chinese herbal garden. Cell, 2011, 146(6), 855-858.
[http://dx.doi.org/10.1016/j.cell.2011.08.024] [PMID: 21907397]
[6]
Tian, X.H.; Wu, J.H. Tanshinone derivatives: A patent review (January 2006 - September 2012). Expert Opin. Ther. Pat., 2013, 23(1), 19-29.
[http://dx.doi.org/10.1517/13543776.2013.736494] [PMID: 23094864]
[7]
Wang, X.; Morris-Natschke, S.L.; Lee, K.H. New developments in the chemistry and biology of the bioactive constituents of Tanshen. Med. Res. Rev., 2007, 27(1), 133-148.
[http://dx.doi.org/10.1002/med.20077] [PMID: 16888751]
[8]
Liu, X.; He, H.; Huang, T.; Lei, Z.; Liu, F.; An, G.; Wen, T.; Tanshinone, I.I.A. Protects against dextran sulfate sodium- (DSS-) induced colitis in mice by modulation of neutrophil infiltration and Activation. Oxid. Med. Cell. Longev., 2016, 2016
[http://dx.doi.org/10.1155/2016/7916763]]
[9]
Shi, L.L.; Liu, D.M.; Zhu, H.; Chen, M.; Zou, X.P. Anti-inflammatory effect and mechanism of Sodium Tanshinone IIA Sulfonate on acute necrotizing pancreatitis associated lung injury in rats. Clin. J. Gastroenterol., 2014, 19(6), 332-335.
[10]
Baillie, A.C.; Thomson, R.H. Naturally occurring quinones. Part XI. The tanshinones. J. Chem. Soc. C: Org., 1968, (1), 48-52.
[http://dx.doi.org/10.1039/j39680000048]
[11]
Weng, X.C.; Gordon, M.H. Antioxidant activity of quinones extracted from tanshen (Salvia miltiorrhiza Bunge). J. Agric. Food Chem., 1992, 40(8), 1331-1336.
[http://dx.doi.org/10.1021/jf00020a007]
[12]
Park, J.W.; Floyd, R.A. Lipid peroxidation products mediate the formation of 8-hydroxydeoxyguanosine in DNA. Free Radic. Biol. Med., 1992, 12(4), 245-250.
[http://dx.doi.org/10.1016/0891-5849(92)90111-S] [PMID: 1315708]
[13]
Shen, Q.K.; Deng, H.; Wang, S.B.; Tian, Y.S.; Quan, Z.S. Synthesis, and evaluation of in vitro and in vivo anticancer activity of 14-substituted oridonin analogs: A novel and potent cell cycle arrest and apoptosis inducer through the p53-MDM2 pathway. Eur. J. Med. Chem., 2019, 173, 15-31.
[http://dx.doi.org/10.1016/j.ejmech.2019.04.005] [PMID: 30981113]
[14]
Newman, D.J.; Cragg, G.M. Natural products as sources of new drugs from 1981 to 2014. J. Nat. Prod., 2016, 79(3), 629-661.
[http://dx.doi.org/10.1021/acs.jnatprod.5b01055] [PMID: 26852623]
[15]
Feng, X.; Zhang, X.X.; Feng, T.J.; Chi, D. Antitumor effect of Tanshinone IIA submicron emulsion and effect on its reversal of multidrug resistance in SMMC-7721/VCR tumor. Zhongguo Lin Chuang Yao Li Xue Za Zhi, 2017, 33(05), 427-430.
[16]
Wang, X.; Wei, Y.; Yuan, S.; Liu, G.; Lu, Y.; Zhang, J.; Wang, W. Potential anticancer activity of tanshinone IIA against human breast cancer. Int. J. Cancer, 2005, 116(5), 799-807.
[http://dx.doi.org/10.1002/ijc.20880] [PMID: 15849732]
[17]
Feng, J.H.; Zheng, T.; Hou, Z.H.; Lv, C.; Wei, Y.B. Study on anti-tumor and anti-angiogenic activity of cryptotanshinone. Chinese J. Biochem. Pharmaceut, 2017, 37(3), 30-33.
[18]
Yan, X.H.; Song, Y. Mechanism of antitumor activity of Tanshinone I on Human Gastric Cancer MGC-803 cells. J. Tradit. Chin. Med., 2016, 43(11), 2337-2339.
[19]
Liang, Y.; Yang, Y.; Yuan, S.; Meng, W.; Liu, T.; Jia, Y. Acute promyelocytic leukemia cell differentiation induced by tanshinone II A and its molecular mechanism. Zhonghua Xue Ye Xue Za Zhi, 2000, 21(1), 23-26.
[PMID: 11876956]
[20]
Liu, W.; Zhou, J.; Geng, G.; Shi, Q.; Sauriol, F.; Wu, J.H. Antiandrogenic, maspin induction, and antiprostate cancer activities of tanshinone IIA and its novel derivatives with modification in ring A. J. Med. Chem., 2012, 55(2), 971-975.
[http://dx.doi.org/10.1021/jm2015292] [PMID: 22175694]
[21]
Zhang, P.; Pei, Y.; Qi, Y.; Piao, B.K. Influence of blood-activating drugs on adhesion and invasion of cells in lung cancer patients. Chung Kuo Chung Hsi I Chieh Ho Tsa Chih, 1999, 19(2), 103-105.
[PMID: 11783292]
[22]
Luo, H.W.; Wei, B.Y.; Liu, Q.H.; Chen, X.H.; Feng, Y. Structure-cytotoxic activity relationships of Diterpenoid Tanshinones from Salvias. Zhongguo Yaoke Daxue Xuebao, 2002, 1, 8-14.
[23]
Wang, X.; Yuan, S.; Wang, C. A preliminary study of the anti-cancer effect of tanshinone on hepatic carcinoma and its mechanism of action in mice. Zhonghua Zhong Liu Za Zhi, 1996, 18(6), 412-414.
[PMID: 9387289]
[24]
Wang, X.; Yuan, S.; Huang, R.; Song, Y. An observation of the effect of tanshinone on cancer cell proliferation by Brdu and PCNA labeling. Hua Hsi I Ko Ta Hsueh Hsueh Pao, 1996, 27(4), 388-391.
[PMID: 9389009]
[25]
Lv, C.; Zeng, H-W.; Wang, J-X.; Yuan, X.; Zhang, C.; Fang, T.; Yang, P-M.; Wu, T.; Zhou, Y-D.; Nagle, D.G.; Zhang, W-D. The antitumor natural product tanshinone IIA inhibits protein kinase C and acts synergistically with 17-AAG. Cell Death Dis., 2018, 9(2), 165.
[http://dx.doi.org/10.1038/s41419-017-0247-5] [PMID: 29416003]
[26]
Sui, H.; Zhao, J.; Zhou, L.; Wen, H.; Deng, W.; Li, C.; Ji, Q.; Liu, X.; Feng, Y.; Chai, N.; Zhang, Q.; Cai, J.; Li, Q. Tanshinone IIA inhibits β-catenin/VEGF-mediated angiogenesis by targeting TGF-β1 in normoxic and HIF-1α in hypoxic microenvironments in human colorectal cancer. Cancer Lett., 2017, 403, 86-97.
[http://dx.doi.org/10.1016/j.canlet.2017.05.013] [PMID: 28602978]
[27]
Liu, J-J.; Zhang, Y.; Lin, D-J.; Xiao, R-Z. Tanshinone IIA inhibits leukemia THP-1 cell growth by induction of apoptosis. Oncol. Rep., 2009, 21(4), 1075-1081.
[http://dx.doi.org/10.3892/or_00000326] [PMID: 19288011]
[28]
Zhang, J.; Wang, J.; Jiang, J-Y.; Liu, S-D.; Fu, K.; Liu, H-Y. Tanshinone IIA induces cytochrome c-mediated caspase cascade apoptosis in A549 human lung cancer cells via the JNK pathway. Int. J. Oncol., 2014, 45(2), 683-690.
[http://dx.doi.org/10.3892/ijo.2014.2471] [PMID: 24888720]
[29]
Yen, J-H.; Huang, S-T.; Huang, H-S.; Fong, Y-C.; Wu, Y-Y.; Chiang, J-H.; Su, Y-C. HGK-sestrin 2 signaling-mediated autophagy contributes to antitumor efficacy of Tanshinone IIA in human osteosarcoma cells. Cell Death Dis., 2018, 9(10), 1003.
[http://dx.doi.org/10.1038/s41419-018-1016-9] [PMID: 30258193]
[30]
Liu, Z.; Zhu, W.; Kong, X.; Chen, X.; Sun, X.; Zhang, W.; Zhang, R. Tanshinone IIA inhibits glucose metabolism leading to apoptosis in cervical cancer. Oncol. Rep., 2019, 42(5), 1893-1903.
[http://dx.doi.org/10.3892/or.2019.7294] [PMID: 31485631]
[31]
Bai, Y.; Zhang, L.; Fang, X.; Yang, Y. Tanshinone IIA enhances chemosensitivity of colon cancer cells by suppressing nuclear factor-κB. Exp. Ther. Med., 2016, 11(3), 1085-1089.
[http://dx.doi.org/10.3892/etm.2016.2984] [PMID: 26998041]
[32]
Chien, S.Y.; Kuo, S.J.; Chen, Y.L.; Chen, D.R.; Cheng, C.Y.; Su, C.C. Tanshinone IIA inhibits human hepatocellular carcinoma J5 cell growth by increasing Bax and caspase 3 and decreasing CD31 expression in vivo. Mol. Med. Rep., 2012, 5(1), 282-286.
[http://dx.doi.org/10.3892/mmr.2011.631] [PMID: 22002472]
[33]
Zhang, X.; Zhou, Y.; Gu, Y.E. Tanshinone IIA induces apoptosis of ovarian cancer cells in vitro and in vivo through attenuation of PI3K/AKT/JNK signaling pathways. Oncol. Lett., 2019, 17(2), 1896-1902.
[http://dx.doi.org/10.3892/ol.2018.9744] [PMID: 30675253]
[34]
Huang, C.Y.; Chiu, T.L.; Kuo, S.J.; Chien, S.Y.; Chen, D.R.; Su, C.C. Tanshinone IIA inhibits the growth of pancreatic cancer BxPC 3 cells by decreasing protein expression of TCTP, MCL 1 and Bcl xL. Mol. Med. Rep., 2013, 7(3), 1045-1049.
[http://dx.doi.org/10.3892/mmr.2013.1290] [PMID: 23358553]
[35]
He, L.; Gu, K. Tanshinone IIA regulates colorectal cancer apoptosis via attenuation of Parkin mediated mitophagy by suppressing AMPK/Skp2 pathways. Mol. Med. Rep., 2018, 18(2), 1692-1703.
[http://dx.doi.org/10.3892/mmr.2018.9087] [PMID: 29845197]
[36]
Li, X.; Li, Z.; Li, X.; Liu, B.; Liu, Z. Mechanisms of Tanshinone II a inhibits malignant melanoma development through blocking autophagy signal transduction in A375 cell. BMC Cancer, 2017, 17(1), 357.
[http://dx.doi.org/10.1186/s12885-017-3329-y] [PMID: 28532456]
[37]
Weber, C.; Noels, H. Atherosclerosis: current pathogenesis and therapeutic options. Nat. Med., 2011, 17(11), 1410-1422.
[http://dx.doi.org/10.1038/nm.2538] [PMID: 22064431]
[38]
Wang, J.; Du, P.F. Effect of Tanshinone II A and niacin on the cardiovascular function of infant obese rat. J. Prac. Med., 2014, 24(18), 3293-3295.
[39]
Long, C.L.; Wang, H.; Xiao, W.B. Hypertensive cardiovascular remodeling and the antihypertensive treatment. Bull. Acad. Mil. Med. Sci., 1997, 21(1), 63-67.
[40]
Zhang, B.B.; Cai, H. Research progress of Tanshinone IIA on ventricular remodeling. Anhui Yiyao, 2014, 18(12), 2230-2233.
[41]
Sun, D.D.; Wang, H.C.; Wang, X.B.; Luo, Y.; Jin, Z.X.; Li, Z.C.; Li, G.R.; Dong, M.Q. Tanshinone IIA: A new activator of human cardiac KCNQ1/KCNE1 (I(Ks)) potassium channels. Eur. J. Pharmacol., 2008, 590(1-3), 317-321.
[http://dx.doi.org/10.1016/j.ejphar.2008.06.005] [PMID: 18573250]
[42]
Yu, H.B.; Xu, C.Q.; Shan, H.L.; Dong, D.L.; Yang, B.F.; Lou, Y.P. Effect of tanshinone II-A on potassium currents in rat ventricular myocytes. J. Harbin Med. Uni., 2002, 36(2), 112-114.
[43]
Van Wagoner, D.R.; Pond, A.L.; Lamorgese, M.; Rossie, S.S.; McCarthy, P.M.; Nerbonne, J.M. Effects of Tanshinone IIA on peripheral blood of matrix metalloproteinase and atrial muscle tissue A1c subunit role of L-type calcium channel in rats with atrial fibrillation. Zhongguo Shiyan Fangjixue Zazhi, 2013, 19(2), 154-157.
[44]
Jun-tian, Z. The general situation and progress of the modern research of red sage root (Radix salviae miltiorrhizae). Her. Med., 2004, 23(7), 435-440.
[45]
Dong, K.; Xu, W.; Yang, J.; Qiao, H.; Wu, L. Neuroprotective effects of Tanshinone IIA on permanent focal cerebral ischemia in mice. Phytother. Res., 2009, 23(5), 608-613.
[http://dx.doi.org/10.1002/ptr.2615] [PMID: 18844253]
[46]
Lam, B.Y.; Lo, A.C.; Sun, X.; Luo, H.W.; Chung, S.K.; Sucher, N.J. Neuroprotective effects of tanshinones in transient focal cerebral ischemia in mice. Phytomedicine, 2003, 10(4), 286-291.
[http://dx.doi.org/10.1078/094471103322004776] [PMID: 12809358]
[47]
Zhang, W.J.; Feng, J.; Zhou, R.; Ye, L.Y.; Liu, H.L.; Peng, L.; Lou, J.N.; Li, C.H. Tanshinone IIA protects the human blood-brain barrier model from leukocyte-associated hypoxia-reoxygenation injury. Eur. J. Pharmacol., 2010, 648(1-3), 146-152.
[http://dx.doi.org/10.1016/j.ejphar.2010.08.040] [PMID: 20826144]
[48]
Hao, H.; Wang, G.; Cui, N.; Li, J.; Xie, L.; Ding, Z. Pharmacokinetics, absorption and tissue distribution of tanshinone IIA solid dispersion. Planta Med., 2006, 72(14), 1311-1317.
[http://dx.doi.org/10.1055/s-2006-951698] [PMID: 17024606]
[49]
Lin, T.H.; Hsieh, C.L. Pharmacological effects of Salvia miltiorrhiza (Danshen) on cerebral infarction. Chin. Med., 2010, 5(22), 22.
[http://dx.doi.org/10.1186/1749-8546-5-22] [PMID: 20565944]
[50]
Kakisawa, H.; Tateishi, M.; Kusumi, T. Synthesis of tanshinone-II and cryptotanshinone. Tetrahedron Lett., 1968, 9, 3783-3786.
[http://dx.doi.org/10.1016/S0040-4039(00)75540-7]
[51]
Danheiser, R.L.; Casebier, D.S.; Firooznia, F. Aromatic annulation strategy for the synthesis of angularly-fused diterpenoid quinones. Total synthesis of (+)-neocryptotanshinone, (-)-cryptotanshinone, tanshinone IIA, and (±)-royleanone. J. Org. Chem., 1995, 60(26), 8341-8350.
[http://dx.doi.org/10.1021/jo00131a006]
[52]
Huang, H.; Song, C.J.; Wang, Z.; Li, M.Y.; Chang, J.B. Total synthesis of tanshinone IIA. Tetrahedron Lett., 2020, 61(28), 152102.
[http://dx.doi.org/10.1016/j.tetlet.2020.152102]
[53]
Jiang, Y.Y.; Li, Q.; Lu, W.; Cai, J.C. Facile and efficient total synthesis of (±)-cryptotanshinone and tanshinone IIA. Tetrahedron Lett., 2003, 44(10), 2073-2075.
[http://dx.doi.org/10.1016/S0040-4039(03)00191-6]
[54]
Tateishi, M.; Kusumi, T.; Kakisawa, H. Synthesis of tanshinones. Tetrahedron, 1971, 27(1), 237-244.
[http://dx.doi.org/10.1016/S0040-4020(01)92414-7]
[55]
Corey, E.J.; Chaykovsky, M. Methylsulfinyl carbanion. Formation and application to organic synthesis. J. Am. Chem. Soc., 1965, 87(6), 1345-1353.
[http://dx.doi.org/10.1021/ja01084a033]
[56]
Lee, J.S.; Han, S.Y.; Kim, M.S.; Yu, C.M.; Kim, M.H.; Kim, S.H.; Min, Y.K.; Kim, B.T. Synthesis of novel chemical probes for the study of tanshinone binding proteins. Bioorg. Med. Chem. Lett., 2006, 16(18), 4733-4737.
[http://dx.doi.org/10.1016/j.bmcl.2006.07.019] [PMID: 16872829]
[57]
Dong, Y.; Morris-Natschke, S.L.; Lee, K.H. Biosynthesis, total syntheses, and antitumor activity of tanshinones and their analogs as potential therapeutic agents. Nat. Prod. Rep., 2011, 28(3), 529-542.
[http://dx.doi.org/10.1039/c0np00035c] [PMID: 21225077]
[58]
Lu, Q.; Zhang, P.; Zhang, X.; Chen, J. Experimental study of the anti-cancer mechanism of tanshinone IIA against human breast cancer. Int. J. Mol. Med., 2009, 24(6), 773-780.
[http://dx.doi.org/10.3892/ijmm_00000291] [PMID: 19885617]
[59]
Ulubelen, A.; Topcu, G.; Johansson, C.B. Norditerpenoids and diterpenoids from Salvia multicaulis with antituberculous activity. J. Nat. Prod., 1997, 60(12), 1275-1280.
[http://dx.doi.org/10.1021/np9700681] [PMID: 9428161]
[60]
Maione, F.; Cantone, V.; Chini, M.G.; De Feo, V.; Mascolo, N.; Bifulco, G. Molecular mechanism of tanshinone IIA and cryptotanshinone in platelet anti-aggregating effects: An integrated study of pharmacology and computational analysis. Fitoterapia, 2015, 100, 174-178.
[http://dx.doi.org/10.1016/j.fitote.2014.11.024] [PMID: 25497578]
[61]
Peng, Z.Y.; Chen, L.G.; Jia, H.X.; Hu, X.Q.; Cheng, S.B. Effect of tanshinone IIA on endothelial cell injured by serum of patients with hypertension. Zhongchengyao, 2012, 34(2), 199-203.
[62]
Ren, Z.H.; Tong, Y.H.; Xu, W.; Ma, J.; Chen, Y. Tanshinone II A attenuates inflammatory responses of rats with myocardial infarction by reducing MCP-1 expression. Phytomedicine, 2010, 17(3-4), 212-218.
[http://dx.doi.org/10.1016/j.phymed.2009.08.010] [PMID: 19800776]
[63]
Lu, X.L.; Cai, J.T. Research progress of anticancer effect of tanshinone IIA in vivo. Cancer Res. Clin., 2014, 26(12), 854-856.
[64]
Yao, Z.J.; Guo, Y.; Zhang, C.S.; Bao, L.; Zhang, Y.Z. Study on the sodium TanshinoneIIA Sulfonate and its synthesis technics. Nat. Prod. Res. Dev., 2009, 21(03), 506-508.
[65]
Pan, Z.G.; Zhang, J.T.; Duan, L.H.; Yang, P.S. Preparation of TanshinoneIIA derivative Phenanthro [1, 2-b]furan -10, 11- methylene-dioxy- 6, 7, 8, 9-tetrahydro-1, 6, 6-trimethyl. Contemp. Chem. Indus., 2014, 43(06), 942-944.
[66]
Bi, Y.F.; Wang, Z.J.; Guan, R.F.; Ye, Y.T.; Chen, Y.Y.; Zhang, Y.B.; Liu, H.M. Design, synthesis and vasodilative activity of tanshinone IIA derivatives. Bioorg. Med. Chem. Lett., 2012, 22(15), 5141-5143.
[http://dx.doi.org/10.1016/j.bmcl.2012.05.014] [PMID: 22765898]
[67]
Liang, B.; Yu, S.; Li, J.; Wang, F.; Liang, G.; Zhang, A.; Ding, C. Site-selective Csp 3 -H aryloxylation of natural product Tanshinone IIA and its analogues. Tetrahedron Lett., 2017, 58(19), 1822-1825.
[http://dx.doi.org/10.1016/j.tetlet.2017.03.078]
[68]
Ding, C.; Li, J.; Jiao, M.; Zhang, A. Catalyst-free sp3 C-H acyloxylation: regioselective synthesis of 1-acyloxy derivatives of the natural product tanshinone IIA. J. Nat. Prod., 2016, 79(10), 2514-2520.
[http://dx.doi.org/10.1021/acs.jnatprod.6b00370] [PMID: 27672695]
[69]
Zeng, L.W.; Zhou, C.X.; Liu, J.D.; Liu, C.H.; Mo, J.X.; Hou, A.F.; Yao, W.; Wang, Z.Z.; Gan, L.S. Design, synthesis, and antimicrobial activities of new tanshinone IIA esters. Nat. Prod. Res., 2016, 30(23), 2662-2668.
[http://dx.doi.org/10.1080/14786419.2016.1138302] [PMID: 26829106]
[70]
Sun, C.J.; Bai, D.L. Synthesis of some compounds related to Tanshinquinone. Acat. Pharm. Sin., 1985, 1, 39-43.
[PMID: 4024950]
[71]
Li, M.M.; Xia, F.; Li, C.J.; Xu, G.; Qin, H.B. Design, synthesis and cytotoxicity of nitrogen-containing tanshinone derivatives. Tetrahedron Lett., 2018, 59(1), 46-48.
[http://dx.doi.org/10.1016/j.tetlet.2017.11.046]
[72]
An, L.K.; Bu, X.Z.; Wu, H.Q.; Guo, X.D.; Ma, L.; Gu, L.Q. The reaction of tanshinones with amines. Chin. Chem. Lett., 2003, 14(6), 557-560. Available at: http://www.ccspublishing.org.cn/article/1001-8417/2003/6/557?viewType=html
[73]
Li, X.B.; Cheng, X.; Zhang, D.L.; Wu, H.Q.; Ye, J.T.; Du, J.; Huang, Z.S.; Gu, L.Q.; An, L.K. Syntheses of tanshinone anhydrides and their suppression on oxidized LDL uptake in macrophages and foam cell formation. Pharmazie, 2014, 69(3), 163-167.
[PMID: 24716403]
[74]
Xu, C.S.; Chen, L. Advances in research on total synthesis and structural modification of Tanshinone IIA and its analogues. Prog. Pharmaceut. Sci., 2013, 37(02), 58-65. Available at: http://en.cnki.com.cn/Article_en/CJFDTotal-YXJZ201302003.htm
[75]
An, L-K.; Bu, X-Z.; Wu, H-Q.; Guo, X-D.; Ma, L.; Gu, L-Q. Reaction of tanshinones with biogenic amine metabolites in vitro. Tetrahedron, 2002, 58(52), 10315-10321.
[http://dx.doi.org/10.1016/S0040-4020(02)01414-X]
[76]
Yang, R.; Liu, A.; Ma, X.; Li, L.; Su, D.; Liu, J. Sodium tanshinone IIA sulfonate protects cardiomyocytes against oxidative stress-mediated apoptosis through inhibiting JNK activation. J. Cardiovasc. Pharmacol., 2008, 51(4), 396-401.
[http://dx.doi.org/10.1097/FJC.0b013e3181671439] [PMID: 18427283]
[77]
Qian, M.K.; Yang, B.J.; Gu, W.H.; Chen, Z.X.; Chen, X.T.; Ye, X.Q. Studies on the active principles of dan shen-I, the structure of sodium tanshinone II-A sulfonate and methylene tanshinone. Acta Chimi. Sin., 1978, 36(3), 199-206. Available at: http://sioc-journal.cn/Jwk_hxxb/EN/Y1978/V36/I3/199
[78]
Jiao, M.; Ding, C.; Zhang, A. Preparation of 2-aryl derivatives of tanshinone I through a palladium-catalyzed Csp2–H activation/arylation approach. Tetrahedron Lett., 2015, 56(21), 2799-2802.
[http://dx.doi.org/10.1016/j.tetlet.2015.04.040]
[79]
Müller, K.; Faeh, C.; Diederich, F. Fluorine in pharmaceuticals: Looking beyond intuition. Science, 2007, 317(5846), 1881-1886.
[http://dx.doi.org/10.1126/science.1131943] [PMID: 17901324]
[80]
Hagmann, W.K. The many roles for fluorine in medicinal chemistry. J. Med. Chem., 2008, 51(15), 4359-4369.
[http://dx.doi.org/10.1021/jm800219f] [PMID: 18570365]
[81]
Wang, J.; Sánchez-Roselló, M.; Aceña, J.L.; del Pozo, C.; Sorochinsky, A.E.; Fustero, S.; Soloshonok, V.A.; Liu, H. Fluorine in pharmaceutical industry: Fluorine-containing drugs introduced to the market in the last decade (2001-2011). Chem. Rev., 2014, 114(4), 2432-2506.
[http://dx.doi.org/10.1021/cr4002879] [PMID: 24299176]
[82]
Dan, N.; Bhakat, S. New paradigm of an old target: An update on structural biology and current progress in drug design towards plasmepsin II. Eur. J. Med. Chem., 2015, 95, 324-348.
[http://dx.doi.org/10.1016/j.ejmech.2015.03.049] [PMID: 25827401]
[83]
Persch, E.; Dumele, O.; Diederich, F. Molecular recognition in chemical and biological systems. Angew. Chem. Int. Ed. Engl., 2015, 54(11), 3290-3327.
[http://dx.doi.org/10.1002/anie.201408487] [PMID: 25630692]
[84]
Stokes, S.S.; Gowravaram, M.; Huynh, H.; Lu, M.; Mullen, G.B.; Chen, B.; Albert, R.; O’Shea, T.J.; Rooney, M.T.; Hu, H.; Newman, J.V.; Mills, S.D. Discovery of bacterial NAD+-dependent DNA ligase inhibitors: Improvements in clearance of adenosine series. Bioorg. Med. Chem. Lett., 2012, 22(1), 85-89.
[http://dx.doi.org/10.1016/j.bmcl.2011.11.071] [PMID: 22154350]
[85]
Mykhailiuk, P.K.; Starova, V.; Iurchenko, V.; Shishkina, S.V.; Shishkin, O.V.; Khilchevskyi, O.; Zaporozhets, O. 1-Amino-4,4-difluorocyclohexanecarboxylic acid as a promising building block for drug discovery: Design, synthesis and characterization. Tetrahedron, 2013, 69(20), 4066-4075.
[http://dx.doi.org/10.1016/j.tet.2013.03.072]
[86]
Li, J.; Xue, Y.; Fan, Z.; Ding, C.; Zhang, A. Difluorination of Furonaphthoquinones. J. Org. Chem., 2017, 82(14), 7388-7393.
[http://dx.doi.org/10.1021/acs.joc.7b01064] [PMID: 28653529]
[87]
Xu, D.; Hu, H.; Guan, J.; Da, J.; Xie, Y.; Liu, Y.; Kong, R.; Song, G.; Zhou, H. Synthesis of novel tanshinone derivatives for treatment of castration-resistant prostate cancer. Chem. Biol. Drug Des., 2019, 94(3), 1656-1663.
[http://dx.doi.org/10.1111/cbdd.13567] [PMID: 31108007]
[88]
Wu, Q.; Zheng, K.; Huang, X.; Li, L.; Mei, W. Tanshinone-IIA-based analogues of imidazole alkaloid act as potent inhibitors to block breast cancer invasion and metastasis in vivo. J. Med. Chem., 2018, 61(23), 10488-10501.
[http://dx.doi.org/10.1021/acs.jmedchem.8b01018] [PMID: 30398868]
[89]
Komodziński, K.; Lepczyńska, J.; Ruszkowski, P.; Milecki, J.; Skalski, B. Biological evaluation of an imidazole-fused 1,3,5-triazepinone nucleoside and its photochemical generation via a 6-azidopurine modified oligonucleotide. Tetrahedron Lett., 2013, 54(29), 3781-3784.
[http://dx.doi.org/10.1016/j.tetlet.2013.05.051]
[90]
de Castro, S.; Familiar, O.; Andrei, G.; Snoeck, R.; Balzarini, J.; Camarasa, M.J.; Velázquez, S. From β-amino-γ-sultone to unusual bicyclic pyridine and pyrazine heterocyclic systems: Synthesis and cytostatic and antiviral activities. ChemMedChem, 2011, 6(4), 686-697.
[http://dx.doi.org/10.1002/cmdc.201000546] [PMID: 21370477]
[91]
Liu, X.W.; Chen, Z.Y.; Wang, G.L.; Ma, X.T.; Gong, Y.; Liu, X.L.; Feng, T.T.; Zhou, Y. Diversity-oriented TsOH catalysis-enabled construction of tanshinone-substituted bis(indolyl/pyrrolyl)methanes and their biological evaluation for anticancer activities. Synth. Commun., 2017, 47(24), 2378-2386.
[http://dx.doi.org/10.1080/00397911.2017.1378359]
[92]
Bi, Y.F.; Xu, H.W.; Liu, X.Q.; Zhang, X.J.; Wang, Z.J.; Liu, H.M. Synthesis and vasodilative activity of tanshinone IIA derivatives. Bioorg. Med. Chem. Lett., 2010, 20(16), 4892-4894.
[http://dx.doi.org/10.1016/j.bmcl.2010.06.076] [PMID: 20637608]
[93]
Cheng, X.; Zhang, D.L.; Li, X.B.; Ye, J.T.; Shi, L.; Huang, Z.S.; Gu, L.Q.; An, L.K. Syntheses of diacyltanshinol derivatives and their suppressive effects on macrophage foam cell formation by reducing oxidized LDL uptake. Bioorg. Chem., 2014, 52, 24-30.
[http://dx.doi.org/10.1016/j.bioorg.2013.11.001] [PMID: 24300390]
[94]
Qin, Y.L.; Chen, L.; He, W.; Su, M.; Jin, Q.; Fang, Z.; Ouyang, P.K.; Guo, K. Continuous synthesis and anti-myocardial injury of tanshinone IIA derivatives. J. Asian Nat. Prod. Res., 2018, 20(2), 139-147.
[http://dx.doi.org/10.1080/10286020.2017.1337751] [PMID: 28595458]
[95]
Wang, M.; Niu, A.; Gong, Z.; Xu, Z.; Li, L.; Li, B.; Wang, J. PEG-amino acid-przewaquinone a conjugations: Synthesis, physicochemical properties and protective effect in a rat model of brain ischemia-reperfusion. Bioorg. Med. Chem. Lett., 2020, 30(1), 126780.
[http://dx.doi.org/10.1016/j.bmcl.2019.126780] [PMID: 31784321]
[96]
Greenwald, R.B.; Pendri, A.; Conover, C.D.; Lee, C.; Choe, Y.H.; Gilbert, C.; Martinez, A.; Xia, J.; Wu, D.; Hsue, M. Camptothecin-20-PEG ester transport forms: The effect of spacer groups on antitumor activity. Bioorg. Med. Chem., 1998, 6(5), 551-562.
[http://dx.doi.org/10.1016/S0968-0896(98)00005-4] [PMID: 9629468]
[97]
Ding, C.; Chen, H.; Liang, B.; Jiao, M.; Liang, G.; Zhang, A. Biomimetic synthesis of the natural product salviadione and its hybrids: discovery of tissue-specific anti-inflammatory agents for acute lung injury. Chem. Sci. (Camb.), 2019, 10(17), 4667-4672.
[http://dx.doi.org/10.1039/C9SC00086K] [PMID: 31123577]
[98]
Yang, R.; Lu, Y.; Liu, J. Identification of tanshinone IIA as a natural monoacylglycerol lipase inhibitor by combined in silico and in vitro approach. MedChemComm, 2014, 5(10), 1528-1532.
[http://dx.doi.org/10.1039/C4MD00186A]
[99]
Li, Q.N.; Huang, Z.P.; Gu, Q.L.; Zhi, Z.E.; Yang, Y.H.; He, L.; Chen, K.L.; Wang, J.X. Synthesis and biological evaluation of novel tanshinone IIA derivatives for treating pain. Chin. J. Nat. Med., 2018, 16(2), 113-124.
[http://dx.doi.org/10.1016/S1875-5364(18)30037-2] [PMID: 29455726]
[100]
Bi, X.; Zhang, K.; He, L.; Gao, B.; Gu, Q.; Li, X.; Chen, J.; Wang, J. Synthesis and biological evaluation of tanshinone IIA derivatives as novel endothelial protective agents. Future Med. Chem., 2017, 9(10), 1073-1085.
[http://dx.doi.org/10.4155/fmc-2016-0241] [PMID: 28632415]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy