5,6-dimethoxy-benzo[1,3]dioxole-4-carbaldehyde | 36938-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5,6-dimethoxy-benzo[1,3]dioxole-4-carbaldehyde
• 英文别名: 2,3-Dimethoxy-5,6-methylendioxy-benzaldehyd；5,6-Dimethoxy-1,3-benzodioxole-4-carbaldehyde
• CAS: 36938-28-0
• 化学式: C₁₀H₁₀O₅
• 分子量: 210.186
• InChiKey: ZIIRHJHYKIBNJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-dimethoxy-benzo[1,3]dioxole-4-carbaldehyde 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 高氯酸 、 ammonium cerium(IV) nitrate 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 49.17h， 生成 2,5-dihydroxy-3-octylcyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Design, synthesis, and characterization of new embelin derivatives as potent inhibitors of X-linked inhibitor of apoptosis protein

  摘要：

  X-Linked inhibitor of apoptosis protein (XIAP) is a promising molecular target for the design of new anticancer drugs aiming at promoting apoptosis in cancer cells. We have previously identified embelin as an inhibitor of XIAP through computational structure-based database screening. Herein, we report the design, synthesis, and evaluation of new embelin analogues as inhibitors of XIAP. Our efforts led to the identification of new and more potent inhibitors. For example, compound 6g has a K-i value of 180 nM binding to XIAP BIR3, in a competitive binding assay and represents a promising lead compound for further optimization. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.072
• 作为产物：
  描述：

  5,6-二甲氧基-1,3-苯并二氧戊环 、 N,N-二甲基甲酰胺 、 正丁基锂 、 四氢呋喃 、 正己烷 以81%的产率得到
  参考文献：
  名称：

  DALLACKER F.; SANDERS G., CHEM.-ZTG, 110,(1986) N 10, 369-371

  摘要：

  DOI：

文献信息

• DALLACKER F.; SANDERS G., CHEM.-ZTG, 110,(1986) N 10, 369-371
  作者：DALLACKER F.、 SANDERS G.

  DOI：——

  日期：——
• DALLACKER F.; SANDERS G., CHEM.-ZTG., 110,(1986) N 10, 372-373
  作者：DALLACKER F.、 SANDERS G.

  DOI：——

  日期：——
• Fluoreszenzfarbstoff und seine Verwendung
  申请人：Universität Potsdam

  公开号：EP2399913B1

  公开（公告）日：2013-09-18
• Design, synthesis, and characterization of new embelin derivatives as potent inhibitors of X-linked inhibitor of apoptosis protein
  作者：Jianyong Chen、Zaneta Nikolovska-Coleska、Guoping Wang、Su Qiu、Shaomeng Wang

  DOI：10.1016/j.bmcl.2006.08.072

  日期：2006.11

  X-Linked inhibitor of apoptosis protein (XIAP) is a promising molecular target for the design of new anticancer drugs aiming at promoting apoptosis in cancer cells. We have previously identified embelin as an inhibitor of XIAP through computational structure-based database screening. Herein, we report the design, synthesis, and evaluation of new embelin analogues as inhibitors of XIAP. Our efforts led to the identification of new and more potent inhibitors. For example, compound 6g has a K-i value of 180 nM binding to XIAP BIR3, in a competitive binding assay and represents a promising lead compound for further optimization. (c) 2006 Elsevier Ltd. All rights reserved.