2-(2-{[(tert-butoxy)carbonyl]amino}acetamido)-4-cyano-2-(2-cyanoethyl)butanoic acid | 1338964-97-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2-{[(tert-butoxy)carbonyl]amino}acetamido)-4-cyano-2-(2-cyanoethyl)butanoic acid
• 英文别名: 4-Cyano-2-(2-cyanoethyl)-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]butanoic acid
• CAS: 1338964-97-8
• 化学式: C₁₅H₂₂N₄O₅
• 分子量: 338.363
• InChiKey: RMBZAHITTBIOAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  152
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-{[(tert-butoxy)carbonyl]amino}acetamido)-4-cyano-2-(2-cyanoethyl)butanoic acid 在 platinum(IV) oxide 、 氯仿 、 氢气 、 碳酸氢钠 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 2.0h， 生成 9,9-bis(3-(9-fluorenylmethoxy)carbonylaminopropyl)-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatetradecan-14-oic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Studies of Efficient Multivalent Melanotropin Ligands: Tools toward Melanoma Diagnosis and Treatment

  摘要：

  To achieve early detection and specific cancer treatment, we propose the use of multivalent interactions in which a series of binding events leads to increased affinity and consequently to selectivity. Using melanotropin (MSH) ligands, our aim is to target melanoma cells which overexpress melanocortin receptors. In this study, we report the design and efficient synthesis of new trivalent ligands bearing MSH ligands. Evaluation of these multimers on a cell model engineered to overexpress melanocortin 4 receptors (MC4R) showed up to a 350-fold increase in binding compared to the monomer, resulting in a trivalent construct with nanomolar affinity starting from a micromolar affinity ligand. Cyclic adenosine monophosphate (cAMP) production was also investigated, leading to more insights into the effects of multivalent compounds on transduction mechanisms.

  DOI：

  10.1021/jm2009937
• 作为产物：
  描述：

  methyl bis-(cyanoethyl)glycinate 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2-{[(tert-butoxy)carbonyl]amino}acetamido)-4-cyano-2-(2-cyanoethyl)butanoic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Studies of Efficient Multivalent Melanotropin Ligands: Tools toward Melanoma Diagnosis and Treatment

  摘要：

  To achieve early detection and specific cancer treatment, we propose the use of multivalent interactions in which a series of binding events leads to increased affinity and consequently to selectivity. Using melanotropin (MSH) ligands, our aim is to target melanoma cells which overexpress melanocortin receptors. In this study, we report the design and efficient synthesis of new trivalent ligands bearing MSH ligands. Evaluation of these multimers on a cell model engineered to overexpress melanocortin 4 receptors (MC4R) showed up to a 350-fold increase in binding compared to the monomer, resulting in a trivalent construct with nanomolar affinity starting from a micromolar affinity ligand. Cyclic adenosine monophosphate (cAMP) production was also investigated, leading to more insights into the effects of multivalent compounds on transduction mechanisms.

  DOI：

  10.1021/jm2009937

文献信息

• Design, Synthesis, and Biological Studies of Efficient Multivalent Melanotropin Ligands: Tools toward Melanoma Diagnosis and Treatment
  作者：Nabila Brabez、Ronald M. Lynch、Liping Xu、Robert J. Gillies、Gerard Chassaing、Solange Lavielle、Victor J. Hruby

  DOI：10.1021/jm2009937

  日期：2011.10.27

  To achieve early detection and specific cancer treatment, we propose the use of multivalent interactions in which a series of binding events leads to increased affinity and consequently to selectivity. Using melanotropin (MSH) ligands, our aim is to target melanoma cells which overexpress melanocortin receptors. In this study, we report the design and efficient synthesis of new trivalent ligands bearing MSH ligands. Evaluation of these multimers on a cell model engineered to overexpress melanocortin 4 receptors (MC4R) showed up to a 350-fold increase in binding compared to the monomer, resulting in a trivalent construct with nanomolar affinity starting from a micromolar affinity ligand. Cyclic adenosine monophosphate (cAMP) production was also investigated, leading to more insights into the effects of multivalent compounds on transduction mechanisms.