2-benzoyl-4H,9H-naphtho[2,3-b]furan-4,9-dione | 676158-78-4

• 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: 2-benzoyl-4H,9H-naphtho[2,3-b]furan-4,9-dione
• 英文别名: 2-Benzoylbenzo[f][1]benzofuran-4,9-dione
• CAS: 676158-78-4
• 化学式: C₁₉H₁₀O₄
• 分子量: 302.286
• InChiKey: RPYJCCQYRXZSAT-UHFFFAOYSA-N

物化性质

• 沸点：
  518.6±50.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzoyl-4H,9H-naphtho[2,3-b]furan-4,9-dione 、 乙酸酐 在 吡啶 、 锌 作用下， 以26%的产率得到(9-Acetyloxy-2-benzoylbenzo[f][1]benzofuran-4-yl) acetate
  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：

  4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-2-carbaldehyde 在 喹啉 、 正丁基锂 、 sodium dithionite 、 copper chromite 、 四丁基溴化铵 、 水 、 双氧水 、 溶剂黄146 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 3.66h， 生成 2-benzoyl-4H,9H-naphtho[2,3-b]furan-4,9-dione
  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

文献信息

• Novel lapacho compounds and methods of use thereof
  申请人：Muller Klaus

  公开号：US20060142271A1

  公开（公告）日：2006-06-29

  The invention provides new synthetic lapacho derivatives as well as methods of use thereof. These compounds can be used in pharmaceutical compositions for the treatment or prevention of cell proliferation disorders. These compounds can also be used in the treatment or prevention of psoriasis or cancer or precancerous conditions.

  本发明提供了新的合成拉帕昔衍生物及其使用方法。这些化合物可以用于制备药物组合物，用于治疗或预防细胞增殖障碍。这些化合物还可以用于治疗或预防牛皮癣、癌症或癌前病变。
• NOVEL STAT3 PATHWAY INHIBITORS AND CANCER STEM CELL INHIBITORS
  申请人：Jiang Zhiwei

  公开号：US20110112180A1

  公开（公告）日：2011-05-12

  The present invention relates to a novel naphtho class of compounds as Stat3 pathway inhibitors and as cancer stem cell inhibitors; to methods of using such compounds to treat cancer; to methods of using such compounds to treat disorders in a mammal related to aberrent Stat3 pathway activity; to pharmaceutical compositions containing such compounds.

  本发明涉及一种新型的萘类化合物，作为Stat3通路抑制剂和癌症干细胞抑制剂；以及使用这些化合物治疗癌症的方法；以及使用这些化合物治疗与哺乳动物中异常Stat3通路活性相关的疾病的方法；以及含有这些化合物的药物组合物。
• Stat3 pathway inhibitors and cancer stem cell inhibitors
  申请人：Sumitomo Dainippon Pharma Oncology, Inc.

  公开号：US10851075B2

  公开（公告）日：2020-12-01

  The present invention relates to a novel naphtho class of compounds as Stat3 pathway inhibitors and as cancer stem cell inhibitors; to methods of using such compounds to treat cancer; to methods of using such compounds to treat disorders in a mammal related to aberrent Stat3 pathway activity; to pharmaceutical compositions containing such compounds.

  本发明涉及作为Stat3通路抑制剂和癌症干细胞抑制剂的一类新型萘化合物；涉及使用此类化合物治疗癌症的方法；涉及使用此类化合物治疗哺乳动物体内与Stat3通路活性异常有关的疾病的方法；涉及含有此类化合物的药物组合物。
• JP2015/34179
  申请人：——

  公开号：——

  公开（公告）日：——
• NOVEL LAPACHO COMPOUNDS AND METHODS OF USE THEREOF
  申请人：ARQULE, INC.

  公开号：EP1551392A2

  公开（公告）日：2005-07-13