- A facile three-step total synthesis of tanshinone I
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A facile synthetic approach for total synthesis of tanshinone I has been accomplished. The key precursor is a novel compound, epoxy phenanthraquinone. And this synthesis of tanshinone I is achieved in only three simple stages, which include Diels–Alder reaction, Δ2-Weitz–Scheffer-type epoxidation, and Feist–Bénary reaction from commercially available styrene.
- Yang, Han-Rui,Wang, Jie-Jie,Shao, Peng-Peng,Yuan, Si-Yi,Li, Xu-Qin
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- Evaluation of the anti-inflammatory effects of synthesised tanshinone I and isotanshinone I analogues in zebrafish
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During inflammation, dysregulated neutrophil behaviour can play a major role in a range of chronic inflammatory diseases, for many of which current treatments are generally ineffective. Recently, specific naturally occurring tanshinones have shown promising anti-inflammatory effects by targeting neutrophils in vivo, yet such tanshinones, and moreover, their isomeric isotanshinone counterparts, are still a largely underexplored class of compounds, both in terms of synthesis and biological effects. To explore the anti-inflammatory effects of isotanshinones, and the tanshinones more generally, a series of substituted tanshinone and isotanshinone analogues was synthesised, alongside other structurally similar molecules. Evaluation of these using a transgenic zebrafish model of neutrophilic inflammation revealed differential anti-inflammatory profiles in vivo, with a number of compounds exhibiting promising effects. Several compounds reduce initial neutrophil recruitment and/or promote resolution of neutrophilic inflammation, of which two also result in increased apoptosis of human neutrophils. In particular, the methoxy-substituted tanshinone 39 specifically accelerates resolution of inflammation without affecting the recruitment of neutrophils to inflammatory sites, making this a particularly attractive candidate for potential pro-resolution therapeutics, as well as a possible lead for future development of functionalised tanshinones as molecular tools and/or chemical probes. The structurally related β-lapachones promote neutrophil recruitment but do not affect resolution. We also observed notable differences in toxicity profiles between compound classes. Overall, we provide new insights into the in vivo anti-inflammatory activities of several novel tanshinones, isotanshinones, and structurally related compounds.
- Foulkes, Matthew J.,Tolliday, Faith H.,Henry, Katherine M.,Renshaw, Stephen A.,Jones, Simon
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- Total synthesis of (±)-tanshinol B, tanshinone I, and (±)-tanshindiol B and C
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A concise and efficient approach was established for the divergent total synthesis of (±)-tanshindiol B and C and tanshinone I from a ubiquitous ene intermediate in 1-2 steps. This critical intermediate was derived from (±)-tanshinol B, which was synthesized in 50% overall yield over 3 steps using an ultrasound-promoted cycloaddition as a key step. Compared to a previously reported strategy, our approach is more step-economic, thus greatly improving the synthetic efficiency. The bioactivity evaluation indicates that the diol stereochemistry of the tanshidiols has an impact on the EZH2 inhibitory activity.
- Wang, Fan,Yang, Hong,Yu, Shujuan,Xue, Yu,Fan, Zhoulong,Liang, Gaolin,Geng, Meiyu,Zhang, Ao,Ding, Chunyong
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p. 3376 - 3381
(2018/05/23)
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- Total Synthesis of Tanshinone i
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A novel total synthesis of tanshinone I (1) via the intermediate 3-hydroxy-8-methyl-1,4-phenanthrenedione (8) is described. The low overall yields and the use of expensive reagents in the synthesis process were minimized by the use of the Diels-Alder reaction to directly construct the 1,4-phenanthrenedione scaffold, providing tanshinone I (1) in only three steps.
- Wu, Nan,Ma, Wei-Cong,Mao, Sheng-Jun,Wu, Yong,Jin, Hui
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p. 1697 - 1700
(2017/05/31)
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- Facile construction of 3-hydroxyphenanthrene-1,4-diones: Key intermediates to tanshinone i and its A-ring-modified analogue
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A mild synthetic approach was established allowing for a convenient construction of tricyclic hydroxyphenanthraquinones, the key precursor for total synthesis of tanshinone I. This tandem process includes decarboxylative radical alkylation, intramolecular C-H arylation and one-pot O-demethylation and aromatization. Variously substituted phenylpropanoic acids were well tolerated in this approach, and synthesis of tanshinone I (1) was finally successful in six straight steps in 19% overall yields from commercially available 5-bromovanillin.
- Jiao, Mingkun,Ding, Chunyong,Zhang, Ao
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p. 2976 - 2981
(2014/04/17)
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- TOTAL SYNTHESIS OF DAN SHEN DITERPENOID QUINONES
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A photochemical aromatic annulation strategy provides efficient synthetic routes to the diterpenoid quinones (+)-danshexinkun A, danshexinkun B, danshexinkun C, (-)-dihydrotanshinone I, and tanshinone I.
- Danheiser, Rick L.,Casebier, David S.,Loebach, Jennifer L.
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p. 1149 - 1152
(2007/10/02)
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