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Current Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 0929-8673
ISSN (Online): 1875-533X

Review Article

Tanshinone IIA: Pharmacology, Total Synthesis, and Progress in Structure-modifications

Author(s): Xing Huang, Hao Deng, Qing-kun Shen* and Zhe-Shan Quan*

Volume 29, Issue 11, 2022

Published on: 14 January, 2022

Page: [1959 - 1989] Pages: 31

DOI: 10.2174/0929867328666211108110025

Price: $65

Abstract

Tanshinone IIA, a major bioactive constituent of Danshen, a Chinese herbal medicine, has gained extensive exploration owing to its unique structural features and multiple promising biological activities. This review focuses on the pharmacology, total synthesis, and structural modifications of tanshinone IIA. We hope this review will contribute to a better understanding of the progress in the field and provide constructive suggestions for further study of tanshinone IIA.

Keywords: Tanshinone IIA, pharmacology, synthesis, structure-modifications, Salvia miltiorrhiza, Chinese medicine.

[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]

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