[2-(2-adamantylamino)ethyl-[(2E)-3,7-dimethylocta-2,6-dienyl]carbamoyl]oxymethyl 2,2-dimethylpropanoate;(Z)-but-2-enedioic acid | 1173502-12-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [2-(2-adamantylamino)ethyl-[(2E)-3,7-dimethylocta-2,6-dienyl]carbamoyl]oxymethyl 2,2-dimethylpropanoate;(Z)-but-2-enedioic acid
• CAS: 1173502-12-9
• 化学式: C₄H₄O₄*C₂₉H₄₈N₂O₄
• 分子量: 604.784
• InChiKey: WYGSNTUHANQRNG-CAJYZTMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  [2-(2-adamantylamino)ethyl-[(2E)-3,7-dimethylocta-2,6-dienyl]carbamoyl]oxymethyl 2,2-dimethylpropanoate 、 顺丁烯二酸 以 乙醇 为溶剂， 反应 0.5h， 生成 [2-(2-adamantylamino)ethyl-[(2E)-3,7-dimethylocta-2,6-dienyl]carbamoyl]oxymethyl 2,2-dimethylpropanoate;(Z)-but-2-enedioic acid
  参考文献：
  名称：

  Synthesis and evaluation of carbamate prodrugs of SQ109 as antituberculosis agents

  摘要：

  The low bioavailability of SQ109 in rats, resulting from first-pass effect in the liver, may be remedied by prodrug strategy. Based on esterase-sensitive carbamate prodrug strategy, a novel series of prodrugs of SQ109 has been reported. Bioavailability of SQ109 after administration of prodrug 7a was 91.4% compared with 21.4% after oral administration of SQ109. After oral administration of compound 7a, the parent drug SQ109 exhibited preferential tissue distribution into lung and spleen, the target organs of tubercular infection and replication. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.091

文献信息

• Synthesis and evaluation of carbamate prodrugs of SQ109 as antituberculosis agents
  作者：Qingyi Meng、Huibing Luo、Yibin Liu、Wei Li、Wen Zhang、Qizheng Yao

  DOI：10.1016/j.bmcl.2009.03.091

  日期：2009.5

  The low bioavailability of SQ109 in rats, resulting from first-pass effect in the liver, may be remedied by prodrug strategy. Based on esterase-sensitive carbamate prodrug strategy, a novel series of prodrugs of SQ109 has been reported. Bioavailability of SQ109 after administration of prodrug 7a was 91.4% compared with 21.4% after oral administration of SQ109. After oral administration of compound 7a, the parent drug SQ109 exhibited preferential tissue distribution into lung and spleen, the target organs of tubercular infection and replication. (C) 2009 Elsevier Ltd. All rights reserved.