(E)-3-(4,9-dioxobenzo[f][1]benzofuran-2-yl)prop-2-enoic acid | 1393549-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (E)-3-(4,9-dioxobenzo[f][1]benzofuran-2-yl)prop-2-enoic acid
• CAS: 1393549-85-3
• 化学式: C₁₅H₈O₅
• 分子量: 268.226
• InChiKey: HJGPUHBGONUOGN-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙醇 、 (E)-3-(4,9-dioxobenzo[f][1]benzofuran-2-yl)prop-2-enoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 3.0h， 以14%的产率得到ethyl (E)-3-(4,9-dioxobenzo[f][1]benzofuran-2-yl)prop-2-enoate
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of Lapacho Analogues. 1. Suppression of Human Keratinocyte Hyperproliferation by 2-Substituted Naphtho[2,3-b]furan-4,9-diones, Activation by Enzymatic One- and Two-Electron Reduction, and Intracellular Generation of Superoxide

  摘要：

  A series of linearly anellated lapacho quinone analogues substituted at the 2-position of the tricyclic naphtho-[2,3-b]furan-4,9-dione system were synthesized and evaluated for their ability to suppress keratinocyte hyperproliferation using HaCaT cells as the primary test system. While very good in vitro potency with IC50 values in the submicromolar range was attained with electron-withdrawing substituents, some compounds were found to induce plasma membrane damage, as evidenced by the release of LDH activity from cytoplasm of the keratinocytes. The most potent analogue against keratinocyte hyperproliferation was the 1,2,4-oxadiazole 18, the potency of which was combined with comparably low cytotoxic membrane damaging effects. Structure-activity relationship studies with either metabolically stable or labile analogues revealed that the quinone moiety was required for activity. Selected compounds were studied in detail for their capability to generate superoxide radicals both in isolated enzymatic one- and two-electron reduction assays as well as in a HaCaT cell-based assay.

  DOI：

  10.1021/jm3009597
• 作为产物：
  描述：

  2-methylnaphtho[2,3-b]furan-4,9-dione 在 吡啶 、 selenium(IV) oxide 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-(4,9-dioxobenzo[f][1]benzofuran-2-yl)prop-2-enoic acid
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of Lapacho Analogues. 1. Suppression of Human Keratinocyte Hyperproliferation by 2-Substituted Naphtho[2,3-b]furan-4,9-diones, Activation by Enzymatic One- and Two-Electron Reduction, and Intracellular Generation of Superoxide

  摘要：

  A series of linearly anellated lapacho quinone analogues substituted at the 2-position of the tricyclic naphtho-[2,3-b]furan-4,9-dione system were synthesized and evaluated for their ability to suppress keratinocyte hyperproliferation using HaCaT cells as the primary test system. While very good in vitro potency with IC50 values in the submicromolar range was attained with electron-withdrawing substituents, some compounds were found to induce plasma membrane damage, as evidenced by the release of LDH activity from cytoplasm of the keratinocytes. The most potent analogue against keratinocyte hyperproliferation was the 1,2,4-oxadiazole 18, the potency of which was combined with comparably low cytotoxic membrane damaging effects. Structure-activity relationship studies with either metabolically stable or labile analogues revealed that the quinone moiety was required for activity. Selected compounds were studied in detail for their capability to generate superoxide radicals both in isolated enzymatic one- and two-electron reduction assays as well as in a HaCaT cell-based assay.

  DOI：

  10.1021/jm3009597