[4-(2-Bromoethyl)piperazin-1-yl]-(4-bromophenyl)methanone | 1448021-86-0

• 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: [4-(2-Bromoethyl)piperazin-1-yl]-(4-bromophenyl)methanone
• 英文别名: [4-(2-bromoethyl)piperazin-1-yl]-(4-bromophenyl)methanone
• CAS: 1448021-86-0
• 化学式: C₁₃H₁₆Br₂N₂O
• mdl: MFCD25007167
• 分子量: 376.091
• InChiKey: BSRYNWPMQNPJBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [4-(2-Bromoethyl)piperazin-1-yl]-(4-bromophenyl)methanone 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Small-Molecule-Induced Clustering of Heparan Sulfate Promotes Cell Adhesion

  摘要：

  Adhesamine is an organic small molecule that promotes adhesion and growth of cultured human cells by binding selectively to heparan sulfate on the cell surface. The present study combined chemical, physicochemical, and cell biological experiments, using adhesamine and its analogues, to examine the mechanism by which this dumbbell-shaped, non-peptidic molecule induces physiologically relevant cell adhesion. The results suggest that multiple adhesamine molecules cooperatively bind to heparan sulfate and induce its assembly, promoting clustering of heparan sulfate-bound syndecan-4 on the cell surface. A pilot study showed that adhesamine improved the viability and attachment of transplanted cells in mice. Further studies of adhesamine and other small molecules could lead to the design of assembly-inducing molecules for use in cell biology and cell therapy.

  DOI：

  10.1021/ja4018682
• 作为产物：
  描述：

  1,2-二溴乙烷 、 (4-溴苯基)(1-哌嗪基)甲酮 在 N,N-二异丙基乙胺 作用下， 以40%的产率得到[4-(2-Bromoethyl)piperazin-1-yl]-(4-bromophenyl)methanone
  参考文献：
  名称：

  Small-Molecule-Induced Clustering of Heparan Sulfate Promotes Cell Adhesion

  摘要：

  Adhesamine is an organic small molecule that promotes adhesion and growth of cultured human cells by binding selectively to heparan sulfate on the cell surface. The present study combined chemical, physicochemical, and cell biological experiments, using adhesamine and its analogues, to examine the mechanism by which this dumbbell-shaped, non-peptidic molecule induces physiologically relevant cell adhesion. The results suggest that multiple adhesamine molecules cooperatively bind to heparan sulfate and induce its assembly, promoting clustering of heparan sulfate-bound syndecan-4 on the cell surface. A pilot study showed that adhesamine improved the viability and attachment of transplanted cells in mice. Further studies of adhesamine and other small molecules could lead to the design of assembly-inducing molecules for use in cell biology and cell therapy.

  DOI：

  10.1021/ja4018682

文献信息

• Small-Molecule-Induced Clustering of Heparan Sulfate Promotes Cell Adhesion
  作者：Naohiro Takemoto、Tetsuya Suehara、Heidie L. Frisco、Shin-ichi Sato、Takuhito Sezaki、Kosuke Kusamori、Yoshinori Kawazoe、Sun Min Park、Sayumi Yamazoe、Yoshiyuki Mizuhata、Rintaro Inoue、Gavin J. Miller、Steen U. Hansen、Gordon C. Jayson、John M. Gardiner、Toshiji Kanaya、Norihiro Tokitoh、Kazumitsu Ueda、Yoshinobu Takakura、Noriyuki Kioka、Makiya Nishikawa、Motonari Uesugi

  DOI：10.1021/ja4018682

  日期：2013.7.31

  Adhesamine is an organic small molecule that promotes adhesion and growth of cultured human cells by binding selectively to heparan sulfate on the cell surface. The present study combined chemical, physicochemical, and cell biological experiments, using adhesamine and its analogues, to examine the mechanism by which this dumbbell-shaped, non-peptidic molecule induces physiologically relevant cell adhesion. The results suggest that multiple adhesamine molecules cooperatively bind to heparan sulfate and induce its assembly, promoting clustering of heparan sulfate-bound syndecan-4 on the cell surface. A pilot study showed that adhesamine improved the viability and attachment of transplanted cells in mice. Further studies of adhesamine and other small molecules could lead to the design of assembly-inducing molecules for use in cell biology and cell therapy.