(5S,6R,E)-methyl 5,6-bis(tert-butyldimethylsilyloxy)-8-(2-(1-(tert-butyldimethylsilyloxy)hexyl)phenyl)oct-7-enoate | 864516-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5S,6R,E)-methyl 5,6-bis(tert-butyldimethylsilyloxy)-8-(2-(1-(tert-butyldimethylsilyloxy)hexyl)phenyl)oct-7-enoate
• 英文别名: methyl (E,5S,6R)-5,6-bis[[tert-butyl(dimethyl)silyl]oxy]-8-[2-[1-[tert-butyl(dimethyl)silyl]oxyhexyl]phenyl]oct-7-enoate
• CAS: 864516-85-8
• 化学式: C₃₉H₇₄O₅Si₃
• 分子量: 707.27
• InChiKey: ZCKLPFZIUSVBQV-SQPWCOSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.47
• 重原子数：
  47
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S,6R,E)-methyl 5,6-bis(tert-butyldimethylsilyloxy)-8-(2-(1-(tert-butyldimethylsilyloxy)hexyl)phenyl)oct-7-enoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到(5S,6R,E)-methyl 5,6-dihydroxy-8-(2-(1-hydroxyhexyl)phenyl)oct-7-enoate
  参考文献：
  名称：

  Design and synthesis of benzo-lipoxin A4 analogs with enhanced stability and potent anti-inflammatory properties

  摘要：

  A new class of chemically and metabolically stable lipoxin analogs featuring a replacement of the tetraene unit of native LXA(4) with a substituted benzo-fused ring system have been designed and studied. These molecules were readily synthesized via a convergent synthetic route involving iterative palladium-mediated cross-coupling, and exhibit enhanced chemical stability, as well as resistance to metabolic inactivation via eicosanoid oxido-reductase. These new LX analogs were evaluated in a model of acute inflammation and were shown to exhibit potent anti-inflammatory properties, significantly decreasing neutrophil infiltration in vivo. The most potent among these was compound 9 (o-[9,12]-benzo-15-epi-LXA(4) methyl ester. Taken together, these findings help identify a new class of stable and easily prepared LX analogs that may serve as novel tools and as promising leads for new anti-inflammatory agents with improved therapeutic pro. le. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.013
• 作为产物：
  描述：

  、 (5S,6R,E)-methyl 5,6-bis(tert-butyldimethylsilyloxy)-8-iodooct-7-enoate 在 1,1'-双(二苯基膦)二茂铁 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium phosphate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 16.0h， 以45%的产率得到(5S,6R,E)-methyl 5,6-bis(tert-butyldimethylsilyloxy)-8-(2-(1-(tert-butyldimethylsilyloxy)hexyl)phenyl)oct-7-enoate
  参考文献：
  名称：

  Benzo lipoxin analogues

  摘要：

  提供苯唑啉类似物、其制备方法以及含有这些化合物的药物组合物。这些化合物和组合物在治疗各种疾病的方法中非常有用，包括炎症、自身免疫疾病和异常细胞增殖。

  公开号：

  US20050203184A1

文献信息

• Benzo lipoxin analogues
  申请人：Petasis A. Nicos

  公开号：US20050203184A1

  公开（公告）日：2005-09-15

  Benzolipoxin analogs, methods of their preparation and pharmaceutical compositions containing the compounds are provided. The compounds and compositions are useful in methods for treatment of various diseases, including, inflammation, autoimmune disease and abnormal cell proliferation.

  提供苯唑啉类似物、其制备方法以及含有这些化合物的药物组合物。这些化合物和组合物在治疗各种疾病的方法中非常有用，包括炎症、自身免疫疾病和异常细胞增殖。
• Design and synthesis of benzo-lipoxin A4 analogs with enhanced stability and potent anti-inflammatory properties
  作者：Nicos A. Petasis、Raquel Keledjian、Yee-Ping Sun、Kalyan C. Nagulapalli、Eric Tjonahen、Rong Yang、Charles N. Serhan

  DOI：10.1016/j.bmcl.2008.01.013

  日期：2008.2

  A new class of chemically and metabolically stable lipoxin analogs featuring a replacement of the tetraene unit of native LXA(4) with a substituted benzo-fused ring system have been designed and studied. These molecules were readily synthesized via a convergent synthetic route involving iterative palladium-mediated cross-coupling, and exhibit enhanced chemical stability, as well as resistance to metabolic inactivation via eicosanoid oxido-reductase. These new LX analogs were evaluated in a model of acute inflammation and were shown to exhibit potent anti-inflammatory properties, significantly decreasing neutrophil infiltration in vivo. The most potent among these was compound 9 (o-[9,12]-benzo-15-epi-LXA(4) methyl ester. Taken together, these findings help identify a new class of stable and easily prepared LX analogs that may serve as novel tools and as promising leads for new anti-inflammatory agents with improved therapeutic pro. le. (c) 2008 Elsevier Ltd. All rights reserved.