9,9-bis(2-cyanoethyl)-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatetradecan-14-oic acid | 1338965-00-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 9,9-bis(2-cyanoethyl)-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatetradecan-14-oic acid
• 英文别名: 3-[[4-Cyano-2-(2-cyanoethyl)-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]butanoyl]amino]propanoic acid
• CAS: 1338965-00-6
• 化学式: C₁₈H₂₇N₅O₆
• 分子量: 409.442
• InChiKey: RECHXOHGCPESGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  181
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9,9-bis(2-cyanoethyl)-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatetradecan-14-oic acid 在 platinum(IV) oxide 、 氯仿 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 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 9,9-bis(2-cyanoethyl)-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatetradecan-14-oate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以90%的产率得到9,9-bis(2-cyanoethyl)-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