5-Hydroxy-2,6-dimethyl-indol | 6239-53-8

• 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: 5-Hydroxy-2,6-dimethyl-indol
• 英文别名: 2,6-dimethyl-1H-indol-5-ol
• CAS: 6239-53-8
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: KJOSXCHQZCVLIV-UHFFFAOYSA-N

物化性质

• 熔点：
  183-184 °C
• 沸点：
  130 °C(Press: 0.1 Torr)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  甲基苯醌 在 sodium hydroxide 、 水 、 丙酮 作用下， 生成 5-Hydroxy-2,6-dimethyl-indol
  参考文献：
  名称：

  Beer et al., Journal of the Chemical Society, 1951, p. 2029,2031

  摘要：

  DOI：

文献信息

• Cyclic N-Acyl O-Amino Phenol CBI Derivative
  申请人：BOGER Dale L.

  公开号：US20160016972A1

  公开（公告）日：2016-01-21

  A group of cyclic N-acyl O-amino phenol CBI derivatives were synthesized and shown to be pro-drugs, subject to reductive activation by cleavage of a N—O bond, effectively releasing the free drug in functional in vitro cellular assays for cytotoxic activity approaching the activity of the free drug, yet remain essentially stable to ex vivo DNA alkylation conditions. Assessment of the in vivo antitumor activity of a representative pro-drug indicates that a contemplated pro-drug approaches the potency and exceeds the efficacy of the free drug itself (CBI-indole 2 ), indicating that the inactive pro-drugs not only effectively release the free drug in vivo, but that they offer additional advantages related to a controlled or targeted release in vivo.

  一组环状N-酰基O-氨基苯酚CBI衍生物被合成并表明是前药，受还原活化的影响，通过断裂N-O键有效地释放自由药物，在体外细胞活性测定中，细胞毒性活性接近自由药物，但基本稳定于体外DNA烷基化条件。对代表性前药的体内抗肿瘤活性评估表明，考虑的前药接近于自由药物的效力，并超过了自由药物本身（CBI-indole2），表明不活性前药不仅在体内有效地释放自由药物，而且它们提供了与体内控制或靶向释放相关的额外优势。
• CBI DERIVATIVES SUBJECT TO REDUCTIVE ACTIVATION
  申请人：Boger Dale

  公开号：US20110112163A1

  公开（公告）日：2011-05-12

  A unique class of N-acyl O-amino phenol prodrugs of CBI-TMI and CBI-indole 2 were synthesized and shown to be prodrugs, subject to reductive activation by nucleophilic cleavage of a weak N—O bond, effectively releasing the free drug in functional cellular assays for cytotoxic activity approaching or matching the activity of the free drug, yet remain essentially stable to ex vivo DNA alkylation conditions. Most impressively, assessment of the in vivo antitumor activity of a representative O-(acylamino) prodrug, 8, indicate that they approach the potency and exceed the efficacy of the free drug itself (CBI-indole 2 ), indicating that the inactive prodrugs not only effectively release the free drug in vivo, but that they offer additional advantages related to a controlled or targeted release in vivo.
• US4013404A
  申请人：——

  公开号：US4013404A

  公开（公告）日：1977-03-22
• US8377981B2
  申请人：——

  公开号：US8377981B2

  公开（公告）日：2013-02-19
• US9586974B2
  申请人：——

  公开号：US9586974B2

  公开（公告）日：2017-03-07