4-[(5R,6R,9S,13S)-7-formyl-1,7-diazatricyclo[7.3.1.05,13]tridecan-6-yl]butanoic acid | 1331769-79-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-[(5R,6R,9S,13S)-7-formyl-1,7-diazatricyclo[7.3.1.05,13]tridecan-6-yl]butanoic acid
• CAS: 1331769-79-9
• 化学式: C₁₆H₂₆N₂O₃
• 分子量: 294.394
• InChiKey: GIEONNRZWXNNAF-NHIYQJMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苦参碱 在 水 、 potassium carbonate 、 间甲酚 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 Petroleum ether 为溶剂， 反应 9.0h， 生成 4-[(5R,6R,9S,13S)-7-formyl-1,7-diazatricyclo[7.3.1.05,13]tridecan-6-yl]butanoic acid
  参考文献：
  名称：

  Synthesis, structure−activity relationship and biological evaluation of novel N-substituted matrinic acid derivatives as host heat-stress cognate 70 (Hsc70) down-regulators

  摘要：

  Oxymatrine (1) is a natural anti-hepatitis B virus (HBV) drug that down-regulates host heat-stress cognate 70 (Hsc70) expression through a mechanism different from that of nucleosides. Taking Hsc70 as a target against HBV, 26 novel N-substituted matrinic acid analogs were designed, synthesized and evaluated for their regulation of Hsc70 mRNA expression with 1 as the lead. The SAR analysis revealed that (i) the carboxyl group at the 11-position was required for activity; (ii) introducing of a substituent on the nitrogen atom at the 12-position of 3, especially substituted benzyl, might significantly improve the activity. Among these analogs, compound 9p possessing N-p-methoxylbenzyl afforded an increased anti-HBV effect in comparison with 1. We consider 9p a promising anti-HBV candidate. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.071

文献信息

• Synthesis, structure−activity relationship and biological evaluation of novel N-substituted matrinic acid derivatives as host heat-stress cognate 70 (Hsc70) down-regulators
  作者：Na-Na Du、Xin Li、Yu-Ping Wang、Fei Liu、Yan-Xin Liu、Chun-Xin Li、Zong-Gen Peng、Li-Mei Gao、Jian-Dong Jiang、Dan-Qing Song

  DOI：10.1016/j.bmcl.2011.06.071

  日期：2011.8

  Oxymatrine (1) is a natural anti-hepatitis B virus (HBV) drug that down-regulates host heat-stress cognate 70 (Hsc70) expression through a mechanism different from that of nucleosides. Taking Hsc70 as a target against HBV, 26 novel N-substituted matrinic acid analogs were designed, synthesized and evaluated for their regulation of Hsc70 mRNA expression with 1 as the lead. The SAR analysis revealed that (i) the carboxyl group at the 11-position was required for activity; (ii) introducing of a substituent on the nitrogen atom at the 12-position of 3, especially substituted benzyl, might significantly improve the activity. Among these analogs, compound 9p possessing N-p-methoxylbenzyl afforded an increased anti-HBV effect in comparison with 1. We consider 9p a promising anti-HBV candidate. (C) 2011 Elsevier Ltd. All rights reserved.