5,6,7-trihydroxy-8-isobutyl-2-methyl-chromen-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5,6,7-trihydroxy-8-isobutyl-2-methyl-chromen-4-one
• 英文别名: 5,6,7-trihydroxy-8-isobutyl-2-methyl-4H-chromen-4-one；5,6,7-trihydroxy-2-methyl-8-(2-methylpropyl)chromen-4-one
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: ADNKLAAIRXDEOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 在 吡啶 、 三乙基硅烷 、 三氟化硼乙醚 、 三溴化硼 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 5,6,7-trihydroxy-8-isobutyl-2-methyl-chromen-4-one
  参考文献：
  名称：

  Structure-Based Design of Flavonoid Compounds As a New Class of Small-Molecule Inhibitors of the Anti-apoptotic Bcl-2 Proteins

  摘要：

  Structure-based strategy was employed to design flavonoid compounds to mimic the Bim BH3 peptide as a new class of inhibitors of the anti-apoptotic Bcl-2 proteins. The most potent compound, 4 (BI-33), binds to Bcl-2 and Mcl-1 with K-i values of 17 and 18 nM, respectively. Compound 4 inhibits cell growth in the MDA-MB-231 breast cancer cell line with an IC50 value of 110 nM and effectively induces apoptosis.

  DOI：

  10.1021/jm070383c

文献信息

• Chromen-4-one inhibitors of anti-apoptotic Bcl-2 family members and the uses thereof
  申请人：Wang Shaomeng

  公开号：US20060247305A1

  公开（公告）日：2006-11-02

  The invention relates to small molecules which function as inhibitors of anti-apoptotic Bcl-2 family member proteins (e.g., Bcl-2 and Bcl-xL). The invention also relates to the use of these compounds for inducing apoptotic cell death and sensitizing cells to the induction of apoptotic cell death.

  本发明涉及小分子化合物，其作为抗凋亡Bcl-2家族成员蛋白（例如Bcl-2和Bcl-xL）的抑制剂。本发明还涉及使用这些化合物诱导细胞凋亡和使细胞对诱导细胞凋亡敏感的方法。
• CHROMEN-4-ONE INHIBITORS OF ANTI-APOPTOTIC BCL-2 FAMILY MEMBERS AND THE USES THEREOF
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：EP1856083A2

  公开（公告）日：2007-11-21
• EP1856083A4
  申请人：——

  公开号：EP1856083A4

  公开（公告）日：2009-05-27
• [EN] CHROMEN-4-ONE INHIBITORS OF ANTI-APOPTOTIC BCL-2 FAMILY MEMBERS AND THE USES THEREOF<br/>[FR] INHIBITEURS DE CHROMEN-4-ONE DES ELEMENTS ANTI-APOPTOTIQUES DE LA FAMILLE BCL-2 ET UTILISATIONS
  申请人：UNIV MICHIGAN

  公开号：WO2006099193A2

  公开（公告）日：2006-09-21

  [EN] The invention relates to small molecules which function as inhibitors of anti-apoptotic Bcl-2 family member proteins (e.g., Bcl-2 and Bcl-xL). The invention also relates to the use of these compounds for inducing apoptotic cell death and sensitizing cells to the induction of apoptotic cell death.
  [FR] L'invention concerne de petites molécules servant d'inhibiteurs des protéines anti-apoptotiques de la famille Bcl-2 (par exemple Bcl-2 et Bcl-xL). L'invention concerne également l'utilisation de ces composés dans l'induction de la mort cellulaire apoptotique et la sensibilisation des cellules à l'induction de la mort cellulaire apoptotique.
• Structure-Based Design of Flavonoid Compounds As a New Class of Small-Molecule Inhibitors of the Anti-apoptotic Bcl-2 Proteins
  作者：Guozhi Tang、Ke Ding、Zaneta Nikolovska-Coleska、Chao-Yie Yang、Su Qiu、Sanjeev Shangary、Renxiao Wang、Jie Guo、Wei Gao、Jennifer Meagher、Jeanne Stuckey、Krzysztof Krajewski、Sheng Jiang、Peter P. Roller、Shaomeng Wang

  DOI：10.1021/jm070383c

  日期：2007.7.1

  Structure-based strategy was employed to design flavonoid compounds to mimic the Bim BH3 peptide as a new class of inhibitors of the anti-apoptotic Bcl-2 proteins. The most potent compound, 4 (BI-33), binds to Bcl-2 and Mcl-1 with K-i values of 17 and 18 nM, respectively. Compound 4 inhibits cell growth in the MDA-MB-231 breast cancer cell line with an IC50 value of 110 nM and effectively induces apoptosis.