1-cyclohexylmethyl-6-methoxyisatin | 1103774-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-cyclohexylmethyl-6-methoxyisatin
• 英文别名: 1-Cyclohexylmethyl-6-methoxy-isatin；1-(cyclohexylmethyl)-6-methoxyindole-2,3-dione
• CAS: 1103774-08-8
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: BIMVHYRDXMPDGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-cyclohexylmethyl-6-methoxyisatin 、 苯甲酰肼 生成 N'-[(3Z)-1-(cyclohexylmethyl)-6-methoxy-2-oxo-1,2-dihydro-3H-indol-3-ylidene]benzohydrazide
  参考文献：
  名称：

  Hydrazone modulators of cannabinoid receptors

  摘要：

  本文介绍了调节大麻素受体的腙类化合物。还描述了含有这些化合物的药物组合物，将这些化合物用作大麻素受体调节剂的方法以及合成这些化合物的过程。

  公开号：

  US09079854B2
• 作为产物：
  描述：

  6-甲氧基靛红 、 溴甲基环己烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以64%的产率得到1-cyclohexylmethyl-6-methoxyisatin
  参考文献：
  名称：

  6-Methoxy-N-alkyl Isatin Acylhydrazone Derivatives as a Novel Series of Potent Selective Cannabinoid Receptor 2 Inverse Agonists: Design, Synthesis, and Binding Mode Prediction

  摘要：

  Recently, we discovered and reported a series of N-alkyl isatin acylhydrazone derivatives that are potent CB2 agonists. Here, we describe a novel series of selective CB2 inverse agonists resulting from introduction of a methoxy moiety in position 6 of the isatin scaffold. These novel 6-methoxy-N-alkyl isatin acylhydrazone derivatives exhibited high CB2 functional activity and selectivity at human CB2. Compound 16 (MDA77) had high activity (EC50 = 5.82 nM) at CB2 and no activity at CB1. Compound 15 (MDA55) (K-i = 89.9 nM, EC50 = 88.2 nM at CB2) inhibited the effect of compound 1 (MDA7), a selective CB2 agonist, in an animal model of neuropathic pain. The molecular modeling study presented here represents a first study of CB2 based on the structure of beta(2)-adrenergic receptor. A ligand-based homology model of the CB2 binding site was developed, and on the basis of our results, we propose a general binding mode for this class of inverse agonists with CB2.

  DOI：

  10.1021/jm801353p

文献信息

• [EN] HYDRAZONE MODULATORS OF CANNABINOID RECEPTORS<br/>[FR] HYDRAZONES MODULATEURS DE RÉCEPTEURS CANNABINOÏDES
  申请人：UNIV TEXAS

  公开号：WO2009012227A1

  公开（公告）日：2009-01-22

  Hydrazone compounds which modulate cannabinoid receptors are presented. Pharmaceutical compositions containing these compounds, methods of using these compounds as modulators of cannabinoid receptors and processes for synthesizing these compounds are also described herein.

  呈现了调节大麻素受体的腙类化合物。本文还描述了含有这些化合物的药物组合物、使用这些化合物作为大麻素受体调节剂的方法以及合成这些化合物的过程。
• HYDRAZONE MODULATORS OF CANNABINOID RECEPTORS
  申请人：Attala Mohamed Naguib

  公开号：US20100197755A1

  公开（公告）日：2010-08-05

  Hydrazone compounds which modulate cannabinoid receptors are presented. Pharmaceutical compositions containing these compounds, methods of using these compounds as modulators of cannabinoid receptors and processes for synthesizing these compounds are also described herein.

  本文介绍了调节大麻素受体的腙类化合物。还描述了含有这些化合物的制药组合物，使用这些化合物作为大麻素受体调节剂的方法以及合成这些化合物的过程。
• Hydrazone modulators of cannabinoid receptors
  申请人：Board of Regents, The University of Texas System

  公开号：US08309595B2

  公开（公告）日：2012-11-13

  Hydrazone compounds which modulate cannabinoid receptors are presented. Pharmaceutical compositions containing these compounds, methods of using these compounds as modulators of cannabinoid receptors and processes for synthesizing these compounds are also described herein.

  本文介绍了调节大麻素受体的腙化合物。本文还描述了含有这些化合物的药物组合物，使用这些化合物作为大麻素受体调节剂的方法以及合成这些化合物的过程。
• US8309595B2
  申请人：——

  公开号：US8309595B2

  公开（公告）日：2012-11-13
• US9079854B2
  申请人：——

  公开号：US9079854B2

  公开（公告）日：2015-07-14