4-(dodecahydropyrido[3,2,1-ij][1,6]naphthyridin-1-yl)butyric acid | 1233190-33-4

• 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: 4-(dodecahydropyrido[3,2,1-ij][1,6]naphthyridin-1-yl)butyric acid
• 英文别名: matrinic acid；Sophoridinsaeure；Matrinsaeure；4-(decahydro-pyrido[3,2,1-ij][1,6]naphthyridin-1-yl)-butyric acid；4-(decahydro-1H,4H-pyrido[3,2,1-ij][1,6]naphthyridin-1-yl)butanoic acid；4-(1,7-diazatricyclo[7.3.1.05,13]tridecan-6-yl)butanoic acid
• CAS: 1233190-33-4
• 化学式: C₁₅H₂₆N₂O₂
• 分子量: 266.384
• InChiKey: AZXHMEMRJYOODA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(dodecahydropyrido[3,2,1-ij][1,6]naphthyridin-1-yl)butyric acid 在 4-二甲氨基吡啶 、 乙醇 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.5h， 生成 N-[2-(4-benzenesulfonylfurazan-3-yloxy)-1-methylethyl]-4-(2-butyldodecahydropyrido[3,2,1-ij][1,6]naphthyridin-1-yl)butyramide
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Nitric Oxide-Releasing Derivatives of N-(n-Butyl)matrinic Acid And N-(n-Butyl)matrinol as Anti-Hepatocellular Carcinoma Agents

  摘要：

  A series of novel furoxan-based derivatives of N-n-butyl matrinic acid (9 a-m) and N-n-butyl matrinol (10a-m) were synthesized and their anti-human hepatocellular carcinoma (HCC) activities were evaluated. All derivatives displayed potential inhibition of HepG2 cell proliferation. Among these derivatives, compounds 9a-f, 9j and 10b, 10g-i (IC50: 0.69-4.66 mu M) were superior to 5-FU (IC50: 5.82 mu M). The further study showed that compounds 9a, 9c and 9f had higher antiproliferative activity on human hepatocellular carcinoma cells Bel-7402 (IC50: 2.55-3.26 mu M) and SMMC-7721 (IC50: 5.26-5.79 mu M).

  DOI：

  10.3987/com-14-13144
• 作为产物：
  描述：

  matrine 在 水 、 sodium hydroxide 、 硫酸 作用下， 以 水 为溶剂， 反应 4.0h， 以83.8%的产率得到4-(dodecahydropyrido[3,2,1-ij][1,6]naphthyridin-1-yl)butyric acid
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Nitric Oxide-Releasing Derivatives of N-(n-Butyl)matrinic Acid And N-(n-Butyl)matrinol as Anti-Hepatocellular Carcinoma Agents

  摘要：

  A series of novel furoxan-based derivatives of N-n-butyl matrinic acid (9 a-m) and N-n-butyl matrinol (10a-m) were synthesized and their anti-human hepatocellular carcinoma (HCC) activities were evaluated. All derivatives displayed potential inhibition of HepG2 cell proliferation. Among these derivatives, compounds 9a-f, 9j and 10b, 10g-i (IC50: 0.69-4.66 mu M) were superior to 5-FU (IC50: 5.82 mu M). The further study showed that compounds 9a, 9c and 9f had higher antiproliferative activity on human hepatocellular carcinoma cells Bel-7402 (IC50: 2.55-3.26 mu M) and SMMC-7721 (IC50: 5.26-5.79 mu M).

  DOI：

  10.3987/com-14-13144

文献信息

• MATRINIC ACID/MATRINE DERIVATIVES AND PREPARATION METHODS AND USES THEREOF
  申请人：Jiang Jiandong

  公开号：US20130190345A1

  公开（公告）日：2013-07-25

  The present invention relates to a N-substituted matrinic acid derivative or matrine derivative, and its preparation method and uses. Specifically, the present invention relates to a compound of Formula (I) or (II) (wherein all the definitions of substituted groups are those mentioned in the specification), or a pharmaceutically acceptable salt, geometric isomer, stereoisomer, solvate, ester or prodrug thereof. The present invention further relates to a method for preparing the compound of the present invention, a pharmaceutical composition containing the compound, and uses thereof in manufacture of a medicament. The compound of the present invention can be used for prophylaxis and/or treatment of a disease or disorder associated with viral infection such as hepatitis B and/orhepatitis C and/or AIDS.

  本发明涉及一种N-取代马陈酸衍生物或马陈衍生物，以及其制备方法和用途。具体地，本发明涉及一种化合物的化合物（其中所有取代基的定义均为规范中提到的那些），或其药学上可接受的盐、几何异构体、立体异构体、溶剂合物、酯或前药。本发明还涉及一种制备本发明化合物的方法，含有该化合物的药物组合物，以及在制造药物中使用的用途。本发明的化合物可用于预防和/或治疗与病毒感染相关的疾病或紊乱，如乙型肝炎和/或丙型肝炎和/或艾滋病。
• MATRINIC ACID/ MATRINE DERIVATIVES AND PREPARATION METHODS AND USES THEREOF
  申请人：Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences

  公开号：EP2581376A1

  公开（公告）日：2013-04-17

  The present invention relates to a N-substituted matrinic acid derivative or matrine derivative, and its preparation method and uses. Specifically, the present invention relates to a compound of Formula (I) or (II) (wherein all the definitions of substituted groups are those mentioned in the specification), or a pharmaceutically acceptable salt, geometric isomer, stereoisomer, solvate, ester or prodrug thereof. The present invention further relates to a method for preparing the compound of the present invention, a pharmaceutical composition containing the compound, and uses thereof in manufacture of a medicament. The compound of the present invention can be used for prophylaxis and/or treatment of a disease or disorder associated with viral infection such as hepatitis B and/orhepatitis C and/orAIDS.

  本发明涉及一种 N-取代的马钱子酸衍生物或马钱子碱衍生物及其制备方法和用途。具体地说，本发明涉及一种式（I）或（II）化合物（其中所有取代基团的定义均为说明书中提及的定义），或其药学上可接受的盐、几何异构体、立体异构体、溶液、酯或原药。本发明还涉及一种制备本发明化合物的方法、一种含有本发明化合物的药物组合物及其在制造药物中的用途。本发明化合物可用于预防和/或治疗与病毒感染有关的疾病或紊乱，如乙型肝炎和/或丙型肝炎和/或艾滋病。