oxymatrinic acid

• 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: oxymatrinic acid
• 英文别名: DM-1001；4-[(5R,6R,9S,13S)-1-oxido-7-aza-1-azoniatricyclo[7.3.1.05,13]tridecan-6-yl]butanoic acid
• 化学式: C₁₅H₂₆N₂O₃
• 分子量: 282.383
• InChiKey: RZGCANOYFFSIHN-LHDUFFHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  20
• 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：
  67.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  oxymatrinic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 oxymatrinol
  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
• 作为产物：
  描述：

  氧化苦参碱 在 potassium hydroxide 作用下， 生成 oxymatrinic acid
  参考文献：
  名称：

  苦参碱类生物碱衍生物及其在制备多靶点多器官组织细胞损伤抑制剂中的应用

  摘要：

  本发明涉及苦参碱类生物碱衍生物及其在制备多靶点多器官组织细胞损伤抑制剂中的应用，涉及药物技术领域。本发明利用半合成的方法得到了一系列结构新颖的苦参碱类生物碱衍生物，该类衍生物能够用于制备多靶点多器官、组织和细胞损伤和死亡抑制剂，其中，多靶点为抑制PP2B、BNP的同时激活ADCY5、CREB3L4、VEGFA、ESR1、eNOS，可用于预防治疗或缓解由PP2B、BNP和ADCY5、CREB3L4、VEGFA、ESR1、eNOS介导的相关疾病。本发明的苦参碱类生物碱衍生物可进一步开发应用于预防、治疗或缓解由上述靶点通路介导的多器官、组织和细胞损伤和死亡导致疾病的治疗药物。

  公开号：

  CN117486882A

文献信息

• 苦参碱类生物碱衍生物及其在制备多靶点多器官组织细胞损伤抑制剂中的应用
  申请人：吉林农业大学

  公开号：CN117486882A

  公开（公告）日：2024-02-02

  本发明涉及苦参碱类生物碱衍生物及其在制备多靶点多器官组织细胞损伤抑制剂中的应用，涉及药物技术领域。本发明利用半合成的方法得到了一系列结构新颖的苦参碱类生物碱衍生物，该类衍生物能够用于制备多靶点多器官、组织和细胞损伤和死亡抑制剂，其中，多靶点为抑制PP2B、BNP的同时激活ADCY5、CREB3L4、VEGFA、ESR1、eNOS，可用于预防治疗或缓解由PP2B、BNP和ADCY5、CREB3L4、VEGFA、ESR1、eNOS介导的相关疾病。本发明的苦参碱类生物碱衍生物可进一步开发应用于预防、治疗或缓解由上述靶点通路介导的多器官、组织和细胞损伤和死亡导致疾病的治疗药物。
• EP2581376
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• Synthesis and evolution of neuroprotective effects of oxymatrine derivatives as anti‐Alzheimer’s disease agents
  作者：Pei‐Liang Dong、ZhengQing Li、Cui‐li Teng、Xin Yin、Xian‐Kai Cao、Hua Han

  DOI：10.1111/cbdd.13862

  日期：2021.7

  AbstractWhile screening for natural product scaffolds as potential anti‐Alzheimer's disease (AD), oxymatrine (OMT) was found to relieve symptoms of AD through diminishing death of neuronal cells caused by microglia‐induced inflammation. In this study, 13 derivatives of OMT were synthesized and their neuroprotective effects were evaluated on Aβ1‐42‐induced PC12 cells using MTT method. In addition, the best neuroprotective potencies were obtained with compounds 4, 6e, and 6f, which were selected for evaluation of decrease in IL‐1β and TNF‐α in Aβ1‐42‐treated PC12 cells. Collectively, these data reveal that derivatives 6e and 6f possess the best ability of diminish IL‐1β production and reverse cell damage in all compounds, which are possible to develop as therapeutic agents for AD.