(E)-5-furan-3-ylpent-2-enoic acid ethyl ester | 1331771-26-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-5-furan-3-ylpent-2-enoic acid ethyl ester
• 英文别名: ethyl (E)-5-(furan-3-yl)pent-2-enoate
• CAS: 1331771-26-6
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: JBILASCAKAGTRZ-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-furan-3-ylpent-2-enoic acid ethyl ester 在 [1,3-双(二苯基膦基)丙烷]二氯化钯(II) 、 四溴化碳 、 potassium tert-butylate 、 二异丁基氢化铝 、 三乙基硼氢化锂 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 3-[(3E,7E,11E)-8,12,16-trimethylheptadeca-3,7,11,15-tetraenyl]furan
  参考文献：
  名称：

  Concise synthesis and structure–activity relationship of furospinosulin-1, a hypoxia-selective growth inhibitor from marine sponge

  摘要：

  Structure activity relationship of furospinosulin-1 (1), a hypoxia-selective growth inhibitor isolated from marine sponge, was investigated. Concise synthetic method of 1 was developed, and some structurally modified analogues were prepared. Biological evaluation of them revealed that the whole chemical structure was important for the hypoxia-selective growth inhibitory activity of 1. Among prepared, the desmethyl analogue 30 showed excellent hypoxia-selective inhibitory activity similar to that of 1 and also exhibited in vivo anti-tumor activity with oral administration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.009
• 作为产物：
  描述：

  3-(3-furanyl)propan-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (E)-5-furan-3-ylpent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Concise synthesis and structure–activity relationship of furospinosulin-1, a hypoxia-selective growth inhibitor from marine sponge

  摘要：

  Structure activity relationship of furospinosulin-1 (1), a hypoxia-selective growth inhibitor isolated from marine sponge, was investigated. Concise synthetic method of 1 was developed, and some structurally modified analogues were prepared. Biological evaluation of them revealed that the whole chemical structure was important for the hypoxia-selective growth inhibitory activity of 1. Among prepared, the desmethyl analogue 30 showed excellent hypoxia-selective inhibitory activity similar to that of 1 and also exhibited in vivo anti-tumor activity with oral administration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.009

文献信息

• NOVEL PRENYLARENE COMPOUND AND USE THEREOF
  申请人：Osaka University

  公开号：EP2567956A1

  公开（公告）日：2013-03-13

  A compound represented by the general formula (C): (wherein R101 represents a substituted or unsubstituted aromatic heterocyclic group, R102, R103, R104 and R105 may be the same or different, and each represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms, or a haloalkyl group having 1 to 3 carbon atoms, and R106 represents a hydrogen atom, or a saturated or unsaturated hydrocarbon group which is a straight or branched chain having 1 to 12 carbon atoms, but excluded is the case where R101 is a 3-furyl group, R102, R103, R104 and R105 are all methyl groups, and R106 is a methyl group, a 4-methyl-3-pentenyl group or a 4,8-dimethyl-3,7-nonadienyl group); or a pharmaceutically acceptable salt thereof has selective inhibitory activity on hypoxic cell growth in a broad range of the concentration and therefore is useful as an active ingredient of a medicament for cancer prevention or treatment.

  通式(C)代表的化合物： (其中 R101 代表取代或未取代的芳香杂环基团、 R102、R103、R104 和 R105 可以相同或不同，各自代表氢原子、卤素原子、具有 1 至 3 个碳原子的烷基或具有 1 至 3 个碳原子的卤代烷基，以及 R106 代表氢原子，或具有 1 至 12 个碳原子的直链或支链的饱和或不饱和烃基，但 R101为3-呋喃基，R102、R103、R104和R105均为甲基，R106为甲基、4-甲基-3-戊烯基或4,8-二甲基-3,7-壬二烯基）的情况除外；或 其药学上可接受的盐在较宽的浓度范围内对缺氧细胞生长具有选择性抑制活性，因此可用作预防或治疗癌症药物的活性成分。
• US9371301B2
  申请人：——

  公开号：US9371301B2

  公开（公告）日：2016-06-21
• Concise synthesis and structure–activity relationship of furospinosulin-1, a hypoxia-selective growth inhibitor from marine sponge
  作者：Naoyuki Kotoku、Shinichi Fujioka、Chiaki Nakata、Masaki Yamada、Yuji Sumii、Takashi Kawachi、Masayoshi Arai、Motomasa Kobayashi

  DOI：10.1016/j.tet.2011.05.009

  日期：2011.9

  Structure activity relationship of furospinosulin-1 (1), a hypoxia-selective growth inhibitor isolated from marine sponge, was investigated. Concise synthetic method of 1 was developed, and some structurally modified analogues were prepared. Biological evaluation of them revealed that the whole chemical structure was important for the hypoxia-selective growth inhibitory activity of 1. Among prepared, the desmethyl analogue 30 showed excellent hypoxia-selective inhibitory activity similar to that of 1 and also exhibited in vivo anti-tumor activity with oral administration. (C) 2011 Elsevier Ltd. All rights reserved.