(2-phenyl-1H-indol-3-yl)methanol | 76869-07-3

• 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: (2-phenyl-1H-indol-3-yl)methanol
• 英文别名: 2-(phenyl-1H-indol-3-yl)methanol；3-hydroxymethyl-2-phenylindole；HMPI；(2-phenyl-indol-3-yl)-methanol
• CAS: 76869-07-3
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: WWOMARKUBVSTBK-UHFFFAOYSA-N

物化性质

• 熔点：
  129-130 °C(Solv: benzene (71-43-2); pentane (109-66-0))
• 沸点：
  482.2±33.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-phenyl-1H-indol-3-yl)methanol 在 benzoyl t-butyl nitroxide 作用下， 以 苯 为溶剂， 反应 24.0h， 以70%的产率得到2-苯基吲哚-3-酮
  参考文献：
  名称：

  3-取代的吲哚与苯甲酰基叔丁基硝基氧化物的Ipso取代反应

  摘要：

  苯甲酰基叔丁基氮氧化物与在C-3处带有取代基的烯基2-苯基吲哚之间的反应得到2-苯基-3 H-吲哚-3-酮；2-苯基吲哚本身产生化合物（7）。

  DOI：

  10.1039/c39810000694
• 作为产物：
  描述：

  2-苯基吲哚-3-甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (2-phenyl-1H-indol-3-yl)methanol
  参考文献：
  名称：

  2-苯基吲哚和咔唑的衍生物作为磷光有机发光二极管的主体材料

  摘要：

  报道了咔唑和2-苯基吲哚的衍生物的合成及其热，电化学，光物理和电荷传输性质。强调具有反应性官能团的化合物。两种化合物形成分子玻璃，其玻璃化转变温度为57°C和134°C。合成的化合物吸收200-375 nm范围内的电磁辐射，并发射350-550 nm范围内的辐射。他们的解决方案显示斯托克斯位移高达81 nm。发现它们的三重态能级范围为2.88–3.04 eV。发现合成化合物的电离电势为5.45eV至5.88eV。通过ATR-FTIR光谱法证明了合成单体在固态中的光聚合能力。通过空间电荷限制电流（SCLC）方法研究了电荷传输性质。零场空穴迁移率达到1.97×10-5 厘米2个 V -1小号-1观察到。根据表征结果，选择了两种化合物作为蓝色和绿色磷光有机发光二极管的主体进行研究。由铟锡氧化物阳极，空穴传输层，带有3-（（1-（4-乙烯基苄基）-2-苯基-1 H-吲哚-3-基）甲基）-9-乙基的发光层组成的最佳制造器件-9

  DOI：

  10.1016/j.dyepig.2016.09.038

文献信息

• [EN] INDOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'INDOLE
  申请人：UNIV CENTRAL LANCASHIRE

  公开号：WO2014049364A1

  公开（公告）日：2014-04-03

  The present invention relates to compounds for use as therapeutic agents, particularly in the treatment and/or prevention of proliferative disorders, such as cancer, especially brain cancers/tumours, wherein the compounds are generally defined by the formula I: wherein A is an aryl or heteroaryl ring system; and R1 to R 4 are various possible substituent groups, provided that at least one of an R2 group, the R3 group, or an R4 group is or comprises a hydroxy, amino, NH(R x ), or mercapto group.

  本发明涉及化合物作为治疗剂的用途，特别是在治疗和/或预防增生性疾病，如癌症，特别是脑癌/肿瘤方面的应用，其中该化合物通常由公式I定义：其中A是芳基或杂环芳基环系统；R1至R4是各种可能的取代基，但至少一个R2基团、R3基团或R4基团是或包含一个羟基、氨基、NH(Rx)或巯基。
• INDOLE DERIVATIVES
  申请人：UNIVERSITY OF CENTRAL LANCASHIRE

  公开号：US20150272928A1

  公开（公告）日：2015-10-01

  The present invention relates to compounds for use as therapeutic agents, particularly in the treatment and/or prevention of proliferative disorders, such as cancer, especially brain cancers/tumours, wherein the compounds are generally defined by the formula I: wherein A is an aryl or heteroaryl ring system; and R 1 to R 4 are various possible substituent groups, provided that at least one of an R 2 group, the R 3 group, or an R 4 group is or comprises a hydroxy, amino, NH(R x ), or mercapto group.

  本发明涉及用作治疗剂的化合物，特别是用于治疗和/或预防增殖性疾病，如癌症，尤其是脑癌/肿瘤，其中这些化合物通常由式I定义：其中A是芳基或杂环芳基环系；R1至R4是各种可能的取代基，只要其中至少一个R2基团、R3基团或R4基团是或包含一个羟基、氨基、NH(Rx)或巯基。
• 3-Hydroxymethylindoles
  作者：Edward Leete

  DOI：10.1021/ja01531a042

  日期：1959.11
• Preliminary SAR on indole-3-carbinol and related fragments reveals a novel anticancer lead compound against resistant glioblastoma cells
  作者：Christopher Sherer、Ibrahim Tolaymat、Farzana Rowther、Tracy Warr、Timothy J. Snape

  DOI：10.1016/j.bmcl.2017.02.033

  日期：2017.4

  The prognosis for glioblastoma patients is, at best, poor, with the median time of survival after diagnosis measured in months. As such, there is much need for the rapid development of potent and novel treatments. Herein, we report our preliminary findings on the SAR of a series of indole-3-carbinol and related fragments and reveal a potent lead with low micromolar activity against a particularly resistant glioblastoma cell culture, providing a new platform for future development of a new therapy in this area. (C) 2017 Elsevier Ltd. All rights reserved.
• Preliminary biological evaluation and mechanism of action studies of selected 2-arylindoles against glioblastoma
  作者：Saurabh Prabhu、Zaheer Akbar、Frederick Harris、Katherine Karakoula、Robert Lea、Farzana Rowther、Tracy Warr、Timothy Snape

  DOI：10.1016/j.bmc.2013.01.032

  日期：2013.4

  A series of related 2-arylindoles have been evaluated for their anticancer activity against a range of glioblastoma cell lines using a number of different cell-based assays to determine cell viability after treatment with the compounds. The best indoles, which showed comparable activity to cisplatin against a U87MG cell line in the MTS assay, were taken forward and initial studies suggest that their mechanism of action is consistent with the generation of reactive oxygen species followed by autophagic cell death. Furthermore, activity was also observed in glioblastoma short-term cell cultures for the best lead compound and in some cases gave low micromolar IC(50)s. (C) 2013 Elsevier Ltd. All rights reserved.