rotenonic acid | 129569-80-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: rotenonic acid
• 英文别名: 9-hydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6a,12a-dihydro-6H-chromeno[3,4-b]chromen-12-one
• CAS: 129569-80-8
• 化学式: C₂₃H₂₄O₆
• 分子量: 396.44
• InChiKey: GBVCHRDRVDOMQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  rotenone 在 palladium on activated charcoal 氢气 作用下， 以 氯仿 为溶剂， 反应 22.0h， 以20%的产率得到rotenonic acid
  参考文献：
  名称：

  Banerjee; Bhattacharyya; Halder, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1990, vol. 29, # 5, p. 419 - 421

  摘要：

  DOI：

文献信息

• Compounds that act to modulate insect growth and methods and systems for identifying such compounds
  申请人：Henrich C. Vincent

  公开号：US20050049230A1

  公开（公告）日：2005-03-03

  Disclosed are methods and systems for screening for compounds that act to modulate insect growth. Bioassays including cell culture and/or transgenic insects engineered with various components of the ecdysoid receptor (EcR) and/or the farsenoid-X receptor (RXR) systems to identify compounds that act as insecticides and/or hormone receptor activators are described. Also described are compounds, and compositions, identified as being putative insecticides based upon their ability to activate EcR and/or FXR mediated transcription.

  本发明涉及筛选调节昆虫生长的化合物的方法和系统。描述了生物测定法，包括细胞培养和/或转基因昆虫，这些昆虫经过工程改造，具有ecdysoid受体（EcR）和/或farsenoid-X受体（RXR）系统的各种组分，以识别作为杀虫剂和/或激素受体激活剂的化合物。还描述了被鉴定为潜在杀虫剂的化合物和组合物，这些化合物和组合物的鉴定基于它们激活EcR和/或FXR介导的转录的能力。
• CONTRAST AGENTS FOR MYOCARDIAL PERFUSION IMAGING
  申请人：CASEBIER S. DAVID

  公开号：US20080112884A1

  公开（公告）日：2008-05-15

  The present disclosure is directed, in part, to compounds and methods for imaging myocardial perfusion, comprising administering to a patient a contrast agent which comprises a compound that binds MC-1, and an imaging moiety, and scanning the patient using diagnostic imaging.

  本公开涉及部分化合物和成像心肌灌注方法，包括向患者注射一种对MC-1具有结合能力的化合物和成像部分，并使用诊断成像扫描患者的对比剂。
• Compounds That Act To Modulate Insect Growth And Methods And Systems For Identifying Such Compounds
  申请人：Henrich Vincent C.

  公开号：US20110207707A1

  公开（公告）日：2011-08-25

  Disclosed are methods and systems for screening for compounds that act to modulate insect growth. Bioassays including cell culture and/or transgenic insects engineered with various components of the ecdysoid receptor (EcR) and/or the farsenoid-X receptor (RXR) systems to identify compounds that act as insecticides and/or hormone receptor activators are described. Also described are compounds, and compositions, identified as being putative insecticides based upon their ability to activate EcR and/or FXR mediated transcription.

  本发明涉及筛选调节昆虫生长的化合物的方法和系统。本发明描述了生物测定方法，包括细胞培养和/或转基因昆虫，这些昆虫经过工程设计，具有各种成分的ecdysoid受体（EcR）和/或farsenoid-X受体（RXR）系统，以识别作为杀虫剂和/或激素受体激活剂的化合物。本发明还描述了通过其激活EcR和/或FXR介导的转录而被认为是杀虫剂的化合物和组合物。
• METHODS AND COMPOSITIONS FOR TREATING DEGENERATIVE AND ISCHEMIC DISORDERS
  申请人：Mootha Vamsi K.

  公开号：US20120136007A1

  公开（公告）日：2012-05-31

  Model systems have shown that shifting a cell's reliance from oxidative phosphorylation (OXPHOS) to glycolysis can protect against cell death. Exploiting the therapeutic potential of this strategy, however, has been limited by the lack of clinically safe agents that remodel energy metabolism. The present invention identifies non-toxic small molecules (e.g., drug-like compounds) that are capable of modulating oxidative metabolism. One identified compound comprises meclizine. As described herein, meclizine, and its enantiomer S-meclizine, redirects OXPHOS to glycolysis. Such compounds could be protective or therapeutic in degenerative disorders such as diabetes, Huntington's, Parkinson's, and Alzheimer's disease and/or ischemic disorders including, but not limited to, stroke, heart attack, or reperfusion injuries.

  模型系统表明，将细胞从氧化磷酸化（OXPHOS）转向糖酵解可以保护细胞免受死亡的影响。然而，利用这种策略的治疗潜力受到了缺乏临床安全制剂来重塑能量代谢的限制。本发明确定了能够调节氧化代谢的非毒性小分子（例如药物类化合物）。其中一种已确定的化合物包括美克林。如本文所述，美克林及其对映体S-美克林将OXPHOS重定向到糖酵解。这样的化合物可以在退行性疾病（如糖尿病、亨廷顿病、帕金森病和阿尔茨海默病）以及缺血性疾病（包括但不限于中风、心脏病发作或再灌注损伤）中具有保护或治疗作用。
• Methods and compositions for treating degenerative and ischemic disorders
  申请人：The General Hospital Corporation

  公开号：US10322122B2

  公开（公告）日：2019-06-18

  Model systems have shown that shifting a cell's reliance from oxidative phosphorylation (OXPHOS) to glycolysis can protect against cell death. Exploiting the therapeutic potential of this strategy, however, has been limited by the lack of clinically safe agents that remodel energy metabolism. The present invention identifies non-toxic small molecules (e.g., drug-like compounds) that are capable of modulating oxidative metabolism. One identified compound comprises meclizine. As described herein, meclizine, and its enantiomer S-meclizine, redirects OXPHOS to glycolysis. Such compounds could be protective or therapeutic in degenerative disorders such as diabetes, Huntington's, Parkinson's, and Alzheimer's disease and/or ischemic disorders including, but not limited to, stroke, heart attack, or reperfusion injuries.

  模型系统显示，将细胞对氧化磷酸化（OXPHOS）的依赖转移到糖酵解，可以防止细胞死亡。然而，由于缺乏重塑能量代谢的临床安全药物，这一策略的治疗潜力一直受到限制。本发明确定了能够调节氧化代谢的无毒小分子（如药物样化合物）。其中一种已确定的化合物包括麦考嗪。如本文所述，麦考嗪及其对映体 S-麦考嗪可将 OXPHOS 重定向至糖酵解。这类化合物对退化性疾病，如糖尿病、亨廷顿氏病、帕金森氏病和阿尔茨海默氏症和/或缺血性疾病，包括但不限于中风、心脏病发作或再灌注损伤具有保护或治疗作用。