Synthesis of Procyanidin B3 and Its Anti-inflammatory Activity. The Effect of 4-Alkoxy Group of Catechin Electrophile in the Yb(OTf)3-Catalyzed Condensation with Catechin Nucleophile
Yb(OTf)3-catalyzed equimolar condensation of the benzylated catechin with various 4-alkoxy catechin derivatives was studied. In particular, the reaction using 4-(2′′-ethoxyethoxy)flavan derivative gave good yield with excellent stereoselectivity. The condensed product was successfully converted to p...
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| Veröffentlicht in: | Journal of organic chemistry 2010-07, Vol.75 (14), p.4884-4886 |
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| container_end_page | 4886 |
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| container_issue | 14 |
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| container_title | Journal of organic chemistry |
| container_volume | 75 |
| creator | Oizumi, Yukiko Mohri, Yoshihiro Hirota, Mitsuru Makabe, Hidefumi |
| description | Yb(OTf)3-catalyzed equimolar condensation of the benzylated catechin with various 4-alkoxy catechin derivatives was studied. In particular, the reaction using 4-(2′′-ethoxyethoxy)flavan derivative gave good yield with excellent stereoselectivity. The condensed product was successfully converted to procyanidin B3 (1). The anti-inflammatory effect of procyanidin B3 (1) on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation of mouse ears was examined. The anti-inflammatory activity of 1 was stronger than that of indomethacin and glycyrrhetinic acid, the normally used anti-inflammatory agents. |
| doi_str_mv | 10.1021/jo1009382 |
| format | Article |
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The anti-inflammatory activity of 1 was stronger than that of indomethacin and glycyrrhetinic acid, the normally used anti-inflammatory agents.</description><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Terpenoids</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNptkMFuGyEURVHVSHWTLvoHbCrVi3EfMIwzS9dyHEtREinuoivrDQMa0jFYgJNMP6zfFyxXziZsEOjc8_QuIV8ZTBhw9uPRM4BaXPIPZMQkh6KqofxIRgCcF4JX4hP5HOMj5COlHJF_D4NLnY42Um_offBqQGdb6-hPQdG1dJUinblkC-tMj9stJh8GOlPJPtk0TOi603RhjFbpICiLWf_Hvwx0Gfx-d_iZY9Kqy75Fn5ngd53tNc3vPJX-br7frc1YFJnCfvirWzr3rtUuYrLe0WebujfD7V71-ii4IGcG-6i__L_Pya-rxXp-XdzcLVfz2U2BHMpUXFaiErLSrShrJnUjG4ZC5p5a1RhdlbI2MC1ZBVNWtdMaUHBsZC0MB8WgNOKcjI9eFXyMQZvNLtgthmHDYHMofHMqPLPfjuwOo8LeBHTKxlOAC-CS8_qNQxVzfB9c3uAd3yvbY4x1</recordid><startdate>20100716</startdate><enddate>20100716</enddate><creator>Oizumi, Yukiko</creator><creator>Mohri, Yoshihiro</creator><creator>Hirota, Mitsuru</creator><creator>Makabe, Hidefumi</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20100716</creationdate><title>Synthesis of Procyanidin B3 and Its Anti-inflammatory Activity. 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| source | ACS Publications |
| subjects | Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties Terpenoids |
| title | Synthesis of Procyanidin B3 and Its Anti-inflammatory Activity. The Effect of 4-Alkoxy Group of Catechin Electrophile in the Yb(OTf)3-Catalyzed Condensation with Catechin Nucleophile |
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