3-((3E,7E,11E,15E)-4,8,12,16-tetramethylicosa-3,7,11,15-tetraen-19-yn-1-yl)furan | 1594985-90-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-((3E,7E,11E,15E)-4,8,12,16-tetramethylicosa-3,7,11,15-tetraen-19-yn-1-yl)furan
• 英文别名: 3-[(3E,7E,11E,15E)-4,8,12,16-tetramethylicosa-3,7,11,15-tetraen-19-ynyl]furan
• CAS: 1594985-90-6
• 化学式: C₂₈H₄₀O
• 分子量: 392.625
• InChiKey: AHTORTXNXYLTBA-DKWXWKAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-((3E,7E,11E,15E)-4,8,12,16-tetramethylicosa-3,7,11,15-tetraen-19-yn-1-yl)furan 、 N-((R)-22-azido-13,18-dioxo-1-(4-((5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)methyl)-1H-1,2,3-triazol-1-yl)-3,6,9-trioxa-16-thia-12,19-diazadocosan-14-yl)-4-benzoylbenzamide 在 copper(II) sulfate 、 叔丁醇 作用下， 以 水 为溶剂， 反应 24.0h， 以60%的产率得到4-benzoyl-N-((R)-22-(4-((3E,7E,11E,15E)-18-(furan-3-yl)-3,7,11,15-tetramethyloctadeca-3,7,11,15-tetraen-1-yl)-1H-1,2,3-triazol-1-yl)-13,18-dioxo-1-(4-((5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)methyl)-1H-1,2,3-triazol-1-yl)-3,6,9-trioxa-16-thia-12,19-diazadocosan-14-yl)benzamide
  参考文献：
  名称：

  Synthesis and evaluation of effective photoaffinity probe molecule of furospinosulin-1, a hypoxia-selective growth inhibitor

  摘要：

  The synthesis and evaluation of a photoaffinity probe molecule for furospinosulin-1, a hypoxia-selective growth inhibitor that we identified from marine sponge, was studied. An analogue carrying an alkyne tail showed potent hypoxia-selective inhibitory activity exceeding that of the parent molecule, and exhibited in vivo anti-tumor activity following oral administration. The alkyne moiety in the analogue was also found to be a good anchoring group for the preparation of probe molecules; a photoaffinity probe molecule having an optimized spacer length was selected through the systematic synthesis of several probes and the evaluation of their hypoxia-selective growth inhibitory activity and electrophoretic mobility shift properties. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.026
• 作为产物：
  描述：

  (E,E)-farnesyl phenylsulfone 在 咪唑 、 叔丁基过氧化氢 、 selenium(IV) oxide 、 正丁基锂 、 1,4-双(二苯基膦丁烷)二氯化钯 、 potassium tert-butylate 、 四丁基氟化铵 、 水 、 三乙基硼氢化锂 、 甲基磺酰氯 、 三乙胺 、 水杨酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.5h， 生成 3-((3E,7E,11E,15E)-4,8,12,16-tetramethylicosa-3,7,11,15-tetraen-19-yn-1-yl)furan
  参考文献：
  名称：

  Synthesis and evaluation of effective photoaffinity probe molecule of furospinosulin-1, a hypoxia-selective growth inhibitor

  摘要：

  The synthesis and evaluation of a photoaffinity probe molecule for furospinosulin-1, a hypoxia-selective growth inhibitor that we identified from marine sponge, was studied. An analogue carrying an alkyne tail showed potent hypoxia-selective inhibitory activity exceeding that of the parent molecule, and exhibited in vivo anti-tumor activity following oral administration. The alkyne moiety in the analogue was also found to be a good anchoring group for the preparation of probe molecules; a photoaffinity probe molecule having an optimized spacer length was selected through the systematic synthesis of several probes and the evaluation of their hypoxia-selective growth inhibitory activity and electrophoretic mobility shift properties. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.026

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
• Synthesis and evaluation of effective photoaffinity probe molecule of furospinosulin-1, a hypoxia-selective growth inhibitor
  作者：Naoyuki Kotoku、Chiaki Nakata、Takashi Kawachi、Takanori Sato、Xiu-Han Guo、Aoi Ito、Yuji Sumii、Masayoshi Arai、Motomasa Kobayashi

  DOI：10.1016/j.bmc.2014.02.026

  日期：2014.4

  The synthesis and evaluation of a photoaffinity probe molecule for furospinosulin-1, a hypoxia-selective growth inhibitor that we identified from marine sponge, was studied. An analogue carrying an alkyne tail showed potent hypoxia-selective inhibitory activity exceeding that of the parent molecule, and exhibited in vivo anti-tumor activity following oral administration. The alkyne moiety in the analogue was also found to be a good anchoring group for the preparation of probe molecules; a photoaffinity probe molecule having an optimized spacer length was selected through the systematic synthesis of several probes and the evaluation of their hypoxia-selective growth inhibitory activity and electrophoretic mobility shift properties. (C) 2014 Elsevier Ltd. All rights reserved.