Benzyl 3-[5-[[2-[4-[(2,6-dimethylphenyl)carbamoylamino]phenyl]acetyl]amino]-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]propanoate | 1355027-77-8

• 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: Benzyl 3-[5-[[2-[4-[(2,6-dimethylphenyl)carbamoylamino]phenyl]acetyl]amino]-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]propanoate
• 英文别名: benzyl 3-[5-[[2-[4-[(2,6-dimethylphenyl)carbamoylamino]phenyl]acetyl]amino]-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]propanoate
• CAS: 1355027-77-8
• 化学式: C₃₉H₄₃N₃O₇
• 分子量: 665.786
• InChiKey: OZQHAXKEKUVHKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzyl 3-[5-[[2-[4-[(2,6-dimethylphenyl)carbamoylamino]phenyl]acetyl]amino]-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]propanoate 在 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 palladium 10% on activated carbon 、 氢气 、 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 为溶剂， 反应 4.0h， 生成 [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 硫酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 caesium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 Benzyl 3-[5-[[2-[4-[(2,6-dimethylphenyl)carbamoylamino]phenyl]acetyl]amino]-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]propanoate
  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

文献信息

• LDV peptidomimetics equipped with biotinylated spacer-arms: Synthesis and biological evaluation on CCRF-CEM cell line
  作者：Estelle Gérard、Aline Meulle、Olivier Feron、Jacqueline Marchand-Brynaert

  DOI：10.1016/j.bmcl.2011.10.078

  日期：2012.1

  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.