(2-{3-[(12-aminododecyl)amino]-3-oxopropyl}-4-{[(4-{[(2,6-dimethylphenyl)carbamoyl] amino}phenyl)acetyl]amino}phenoxy)acetic acid trifluoroacetate | 1355027-64-3

• 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: (2-{3-[(12-aminododecyl)amino]-3-oxopropyl}-4-{[(4-{[(2,6-dimethylphenyl)carbamoyl] amino}phenyl)acetyl]amino}phenoxy)acetic acid trifluoroacetate
• 英文别名: 2-[2-[3-(12-Aminododecylamino)-3-oxopropyl]-4-[[2-[4-[(2,6-dimethylphenyl)carbamoylamino]phenyl]acetyl]amino]phenoxy]acetic acid;2,2,2-trifluoroacetic acid
• CAS: 1355027-64-3
• 化学式: C₂HF₃O₂*C₄₀H₅₅N₅O₆
• 分子量: 815.931
• InChiKey: BVHBNCKEAUCKJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  58
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  209
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2-{3-[(12-aminododecyl)amino]-3-oxopropyl}-4-{[(4-{[(2,6-dimethylphenyl)carbamoyl] amino}phenyl)acetyl]amino}phenoxy)acetic acid trifluoroacetate 、 (+)生物素-N-琥珀酰亚胺基酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以58%的产率得到[4-{[(4-{[(2,6-dimethylphenyl)carbamoyl]amino}phenyl)acetyl]amino}-2-(3-oxo-3-{[12-({5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl}amino)dodecyl]amino}propyl)phenoxy]acetic acid
  参考文献：
  名称：

  LDV peptidomimetics equipped with biotinylated spacer-arms: Synthesis and biological evaluation on CCRF-CEM cell line

  摘要：

  The tripeptide Leu-Asp-Val (LDV) is known to bind alpha(4)beta(1) integrin in leukemia cells. Here we have synthesized a LDV peptidomimetic equipped with a biotin-conjugated spacer-arm. Compound 9 acts as an inhibitor of the alpha(4)beta(1) integrin in an adhesion assay using fluorescently labeled, alpha(4)beta(1) integrin-expressing leukemia CCRF-CEM cells. Furthermore, when bound to neutravidin-coated plates, compound 9 could capture CCRF-CEM cells. Such biotin-conjugated LDV peptidomimetic may thus represent a novel tool for biotechnological applications using avidin interaction for leukapheresis or leukemia cell targeting. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.078
• 作为产物：
  描述：

  Methyl 3-(5-amino-2-hydroxyphenyl)propanoate 在 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 硫酸 、 palladium 10% on activated carbon 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 caesium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 (2-{3-[(12-aminododecyl)amino]-3-oxopropyl}-4-{[(4-{[(2,6-dimethylphenyl)carbamoyl] amino}phenyl)acetyl]amino}phenoxy)acetic acid trifluoroacetate
  参考文献：
  名称：

  LDV peptidomimetics equipped with biotinylated spacer-arms: Synthesis and biological evaluation on CCRF-CEM cell line

  摘要：

  The tripeptide Leu-Asp-Val (LDV) is known to bind alpha(4)beta(1) integrin in leukemia cells. Here we have synthesized a LDV peptidomimetic equipped with a biotin-conjugated spacer-arm. Compound 9 acts as an inhibitor of the alpha(4)beta(1) integrin in an adhesion assay using fluorescently labeled, alpha(4)beta(1) integrin-expressing leukemia CCRF-CEM cells. Furthermore, when bound to neutravidin-coated plates, compound 9 could capture CCRF-CEM cells. Such biotin-conjugated LDV peptidomimetic may thus represent a novel tool for biotechnological applications using avidin interaction for leukapheresis or leukemia cell targeting. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.078