1-benzyl-1H-indol-5-ol | 142769-36-6

• 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-benzyl-1H-indol-5-ol
• 英文别名: 5-hydroxy-1-(phenylmethyl)-1H-indole；1-benzyl-5-hydroxy-1H-indole；1H-Indol-5-ol, 1-(phenylmethyl)-；1-benzylindol-5-ol
• CAS: 142769-36-6
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: LTNFQIYLCBXXCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-1H-indol-5-ol 在 盐酸 、 氨 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 4-[[3-(2-amino-1,2-dioxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid
  参考文献：
  名称：

  Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 3. Indole-3-glyoxamides

  摘要：

  The preceding papers of this series detail the development of functionalized indole-3-acetamides as inhibitors of hnps-PLA(2). We describe here the extension of the structure-activity relationship to include a series of indole-3-glyoxamide derivatives. Functionalized indole-3-glyoxamides with an acidic substituent appended to the 4- or 5-position of the indole ring were prepared and tested as inhibitors of hnps-PLA(2). It was found that the indole-3-glyoxamides with a 4-oxyacetic acid substituent had optimal inhibitory activity. These inhibitors exhibited an improvement in potency over the best of the indole-3-acetamides, and LY315920 (6m) was selected for evaluation clinically as an hnps-PLA(2) inhibitor.

  DOI：

  10.1021/jm960487f
• 作为产物：
  描述：

  5-苄氧基吲哚 在 palladium on activated charcoal 氢氧化钾 、 ammonium formate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 6.83h， 生成 1-benzyl-1H-indol-5-ol
  参考文献：
  名称：

  A Novel Class of Inhibitors for Human Steroid 5.ALPHA.-Reductase: Synthesis and Biological Evaluation of Indole Derivatives. II.

  摘要：

  在寻找新型非类固醇人前列腺5α-还原酶抑制剂的过程中，我们发现了一系列新型的吲哚衍生物，这些衍生物对人酶表现出强效抑制活性。其中，4-[(1-苯基-1H-吲哚-5-基)氧]-3-氯苯甲酸（2d, YM-32906）的抑制活性比非那雄胺更强，IC50值为0.44 nM。3-氯-4-{[1-(4-苯氧苄基)-1H-吲哚-5-基]氧}苯甲酸（2m）对人和大鼠前列腺5α-还原酶均表现出抑制活性，IC50值分别为2.1 nM和73 nM。本文展示了这些吲哚衍生物的合成及结构-活性关系。

  DOI：

  10.1248/cpb.48.382

文献信息

• Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions
  作者：Shanghua Xia、Lu Gan、Kailiang Wang、Zheng Li、Dawei Ma

  DOI：10.1021/jacs.6b08114

  日期：2016.10.19

  powerful catalytic system for hydroxylation of (hetero)aryl halides. A wide range of (hetero)aryl chlorides bearing either electron-donating or -withdrawing groups proceeded well at 130 °C, delivering the corresponding phenols and hydroxylated heteroarenes in good to excellent yields. When more reactive (hetero)aryl bromides and iodides were employed, the hydroxylation reactions completed at relatively

  Cu(acac)2 和 N,N'-双(4-羟基-2,6-二甲基苯基)草酰胺 (BHMPO) 的组合为（杂）芳基卤化物的羟基化提供了强大的催化系统。各种带有给电子或吸电子基团的（杂）芳基氯化物在 130 °C 下均能很好地进行，以良好到极好的产率提供相应的酚类和羟基化杂芳烃。当使用反应性更强的（杂）芳基溴化物和碘化物时，羟基化反应在相对较低的温度（分别为 80 和 60 °C）下在低催化负载（0.5 mol% Cu）下完成。
• Benzofuran derivatives as anticancer inhibitors of mTOR signaling
  作者：Christophe Salomé、Nigel Ribeiro、Thierry Chavagnan、Frédéric Thuaud、Maria Serova、Armand de Gramont、Sandrine Faivre、Eric Raymond、Laurent Désaubry

  DOI：10.1016/j.ejmech.2014.05.014

  日期：2014.6

  A series of 32 derivatives and isosteres of the mTOR inhibitor 2 were synthesized and compared for their cytotoxicity in radioresistant SQ20B cancer cell line. Several of these compounds, in particular 30b, were significantly more cytotoxic than 2. Importantly, 30b was shown to block both mTORC1 and Akt signaling, suggesting insensitivity to the resistance associated to Akt overactivation observed

  合成了一系列32种mTOR抑制剂2的衍生物和等排物，并比较了它们在抗放射SQ20B癌细胞系中的细胞毒性。这些化合物中的几种，特别是30b，比2具有明显更高的细胞毒性。重要的是，显示30b可以同时阻断mTORC1和Akt信号传导，表明对目前在临床上使用的雷帕霉素衍生物观察到的与Akt过度活化相关的抗药性不敏感。
• [EN] HISTONE DEMETHYLASE INHIBITORS<br/>[FR] INHIBITEURS DE L'HISTONE DÉMÉTHYLASE
  申请人：QUANTICEL PHARMACEUTICALS INC

  公开号：WO2016044429A1

  公开（公告）日：2016-03-24

  The present invention relates generally to compositions and methods for treating cancer and neoplastic disease. Provided herein are substituted pyrido[3,4-d]pyrimidin-4-one derivative compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for inhibition of histone demethylase. Furthermore, the subject compounds and compositions are useful for the treatment of cancer, such as prostate cancer, breast cancer, bladder cancer, lung cancer and/or melanoma and the like.

  本发明通常涉及治疗癌症和肿瘤性疾病的组合物和方法。本文提供了替代的吡啶并[3,4-d]嘧啶-4-酮衍生物化合物和包含该化合物的药物组合物。所述化合物和组合物对组蛋白去甲基化酶的抑制有用。此外，所述化合物和组合物对于治疗癌症，如前列腺癌、乳腺癌、膀胱癌、肺癌和/或黑色素瘤等方面是有用的。
• 1H-indole-3-glyoxylamide SPLA.sub.2 inhibitors
  申请人：Eli Lilly and Company

  公开号：US05654326A1

  公开（公告）日：1997-08-05

  A class of novel 1H-indole-3-glyoxylamides is disclosed together with the use of such indole compounds for inhibiting sPLA.sub.2 mediated release of fatty acids for treatment of conditions such as septic shock.

  一类新型的1H-吲哚-3-甘氧酰胺被披露，以及使用这种吲哚化合物来抑制sPLA.sub.2介导的脂肪酸释放，用于治疗诸如感染性休克等疾病的方法。
• Aryl, aryloxy, and alkyloxy substituted 1H-indol-3-yl glyoxylic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
  申请人：Wyeth

  公开号：US20040138283A1

  公开（公告）日：2004-07-15

  Compounds of formula I are provided: 1 wherein: R1, R2, and R3, are as defined herein, as well as pharmaceutical composition and methods using the compounds as inhibitors of plasminogen activator inhibitor (PAI-1) and as therapeutic composition for treating conditions resulting from fibrinolytic disorders, such as deep vein thrombosis, coronary heart disease and pulmonary fibrosis.

  提供了化学式I的化合物：1其中：R1、R2和R3如此定义，在此定义中，以及使用这些化合物作为纤溶酶原激活抑制剂（PAI-1）的抑制剂和作为治疗成分治疗由纤溶障碍引起的病症的药物组合物和方法，例如深静脉血栓、冠心病和肺纤维化。