(((2E,6E,10E,14E)-17-(furan-3-yl)-2,6,10,14-tetramethyl-12-(phenylsulfonyl)heptadeca-2,6,10,14-tetraen-1-yl)oxy)triisopropylsilane | 1594985-74-6

• 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: (((2E,6E,10E,14E)-17-(furan-3-yl)-2,6,10,14-tetramethyl-12-(phenylsulfonyl)heptadeca-2,6,10,14-tetraen-1-yl)oxy)triisopropylsilane
• 英文别名: [(2E,6E,10E,14E)-12-(benzenesulfonyl)-17-(furan-3-yl)-2,6,10,14-tetramethylheptadeca-2,6,10,14-tetraenoxy]-tri(propan-2-yl)silane
• CAS: 1594985-74-6
• 化学式: C₄₀H₆₂O₄SSi
• 分子量: 667.081
• InChiKey: QYILBFCGWZXFBX-BVSQICBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.98
• 重原子数：
  46
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (((2E,6E,10E,14E)-17-(furan-3-yl)-2,6,10,14-tetramethyl-12-(phenylsulfonyl)heptadeca-2,6,10,14-tetraen-1-yl)oxy)triisopropylsilane 在 正丁基锂 、 1,4-双(二苯基膦丁烷)二氯化钯 、 四丁基氟化铵 、 三乙基硼氢化锂 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 22.83h， 生成 ((5E,9E,13E,17E)-20-(furan-3-yl)-5,9,13,17-tetramethylicosa-5,9,13,17-tetraen-1-yn-1-yl)trimethylsilane
  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 、 potassium tert-butylate 、 水 、 水杨酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.67h， 生成 (((2E,6E,10E,14E)-17-(furan-3-yl)-2,6,10,14-tetramethyl-12-(phenylsulfonyl)heptadeca-2,6,10,14-tetraen-1-yl)oxy)triisopropylsilane
  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

• 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.