6a-Hydroxy-3,10-bis(3-methylbut-2-enoxy)-6,7-dihydroindeno[2,1-c]chromen-9-one | 1215097-64-5

• 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: 6a-Hydroxy-3,10-bis(3-methylbut-2-enoxy)-6,7-dihydroindeno[2,1-c]chromen-9-one
• CAS: 1215097-64-5
• 化学式: C₂₆H₂₈O₅
• 分子量: 420.505
• InChiKey: VUESCTWSUAFRRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-溴-3-甲基-2-丁烯 、 巴西红 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 6a-Hydroxy-3,10-bis(3-methylbut-2-enoxy)-6,7-dihydroindeno[2,1-c]chromen-9-one
  参考文献：
  名称：

  Antitumor agents. 271: Total synthesis and evaluation of brazilein and analogs as anti-inflammatory and cytotoxic agents

  摘要：

  The first total synthesis of the naturally occurring tetracyclic homoisoflavonoid brazilein (1) and 14 new analogs (1a-n) is reported. Target compounds and intermediates were assayed for anti-inflammatory effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB, and for cytotoxic activity against nasopharyngeal (KB), vincristine-resistant nasopharyngeal (KBvin), lung (A549) and prostate (DU-145) human cancer cell lines. The most active compound 1b showed potent effects on superoxide anion generation and elastase release with IC50 values of 1.2 and 1.9 mu M, respectively, and was 65 times more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in the latter assay. Additionally, 1b exhibited broad spectrum in vitro anticancer activity with IC50 values of 6-11 mu M against the four tested cancer cell lines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.041

文献信息

• Antitumor agents. 271: Total synthesis and evaluation of brazilein and analogs as anti-inflammatory and cytotoxic agents
  作者：Chiao-Ting Yen、Kyoko Nakagawa-Goto、Tsong-Long Hwang、Pei-Chi Wu、Susan L. Morris-Natschke、Wan-Chun Lai、Kenneth F. Bastow、Fang-Rong Chang、Yang-Chang Wu、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2009.12.041

  日期：2010.2

  The first total synthesis of the naturally occurring tetracyclic homoisoflavonoid brazilein (1) and 14 new analogs (1a-n) is reported. Target compounds and intermediates were assayed for anti-inflammatory effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB, and for cytotoxic activity against nasopharyngeal (KB), vincristine-resistant nasopharyngeal (KBvin), lung (A549) and prostate (DU-145) human cancer cell lines. The most active compound 1b showed potent effects on superoxide anion generation and elastase release with IC50 values of 1.2 and 1.9 mu M, respectively, and was 65 times more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in the latter assay. Additionally, 1b exhibited broad spectrum in vitro anticancer activity with IC50 values of 6-11 mu M against the four tested cancer cell lines. (C) 2009 Elsevier Ltd. All rights reserved.