(E)-2-methyl-5-thiophen-3-ylpent-2-enoic acid ethyl ester | 1331771-32-4

• 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)-2-methyl-5-thiophen-3-ylpent-2-enoic acid ethyl ester
• 英文别名: ethyl (E)-2-methyl-5-thiophen-3-ylpent-2-enoate
• CAS: 1331771-32-4
• 化学式: C₁₂H₁₆O₂S
• 分子量: 224.324
• InChiKey: NPCBMVWXBDZVCO-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-5-thiophen-3-ylpent-2-enoic acid ethyl ester 在 四溴化碳 、 potassium tert-butylate 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.83h， 生成 3-((3E,7E,11E)-4,8,12,16-tetramethyl-6-(phenylsulfonyl)heptadeca-3,7,11,15-tetraen-1-yl)thiophene
  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：

  (E)-3-(thiophen-3-yl)prop-2-en-1-ol 在 palladium on activated charcoal 、 氢气 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 15.0h， 生成 (E)-2-methyl-5-thiophen-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：Kobayashi Motomasa

  公开号：US20130065937A1

  公开（公告）日：2013-03-14

  A compound represented by the general formula (C): (wherein R 101 represents a substituted or unsubstituted aromatic heterocyclic group, R 102 , R 103 , R 104 and R 105 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 R 106 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 R 101 is a 3-furyl group, R 102 , R 103 , R 104 and R 105 are all methyl groups, and R 106 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.
• 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.