N-hydroxy-2-phenyl-2-(2-phenyl-1H-indol-3-yl)acetamide | 1459775-52-0

• 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: N-hydroxy-2-phenyl-2-(2-phenyl-1H-indol-3-yl)acetamide
• CAS: 1459775-52-0
• 化学式: C₂₂H₁₈N₂O₂
• 分子量: 342.397
• InChiKey: GWACTDALALJKLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-hydroxy-2-phenyl-2-(2-phenyl-1H-indol-3-yl)acetamide 在 三氯化磷 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 2-(2-(naphthalen-2-yl)-1H-indol-3-yl)-2-phenylacetamide
  参考文献：
  名称：

  Activity of 2-Aryl-2-(3-indolyl)acetohydroxamates against Drug-Resistant Cancer Cells

  摘要：

  Many types of tumor, including glioma, melanoma, non-small cell lung, esophageal, and head and neck cancer, among others, are intrinsically resistant to apoptosis induction and poorly responsive to current therapies with proapoptotic agents. In addition, tumors often develop multidrug resistance based on the cellular efflux of chemotherapeutic agents. Thus, novel anticancer agents capable of overcoming these intrinsic or developed tumor resistance mechanisms are urgently needed. We describe a series of 2-aryl-2-(3-indolyl)acetohydroxamic acids that are active against apoptosis- and multidrug-resistant cancer cells as well as glioblastoma neurosphere stemlike cell cultures derived from patients. Thus, the described compounds serve as a novel chemical scaffold for the development of potentially highly effective clinical cancer drugs.

  DOI：

  10.1021/jm501518y
• 作为产物：
  描述：

  1-苯基-2-硝基乙醇 在 polyphosphoric acid 作用下， 反应 0.5h， 生成 N-hydroxy-2-phenyl-2-(2-phenyl-1H-indol-3-yl)acetamide
  参考文献：
  名称：

  硝基烯烃与吲哚的无金属环扩环：3-取代的2-喹诺酮类的简单模块化方法†

  摘要：

  3-取代的2-喹诺酮是通过2-硝基烯烃与2-取代的吲哚在多磷酸中的新型无金属环转移反应获得的。这种酸介导的级联转化通过ANRORC（亲核试剂的添加，开环和闭环）机理进行操作，可以与Fisher吲哚合成结合使用，以提供一种实用的三组分杂环化方法从芳基肼，2-硝基烯烃和苯乙酮。还证明了该化学方法的另一种选择，该方法采用了富电子芳烃和戊烯与1-（2-吲哚基）-2-硝基烯烃的烷基化反应。

  DOI：

  10.1039/c4ra14406f

文献信息

• [EN] CANNABINOID TYPE 1 RECEPTOR MODULATORS<br/>[FR] MODULATEURS DU RÉCEPTEUR CANNABINOÏDE DE TYPE 1
  申请人：UNIV TORONTO

  公开号：WO2016029310A1

  公开（公告）日：2016-03-03

  The present disclosure relates to indole derivatives of the formula (I) which are cannabinoid type 1 receptor modulators and which are useful in the treatment of diseases in which modulation of the receptor is beneficial; to processes for their preparation; to pharmaceutical compositions comprising them; and to methods of using them.

  本公开涉及公式（I）的吲哚衍生物，这些衍生物是大麻素类型1受体调节剂，对于治疗需要调节受体的疾病是有益的；涉及它们的制备方法；包含它们的药物组合物；以及使用它们的方法。
• TREATMENT OF DRUG-RESISTANT CANCER WITH 2-ARYL-2-(3-INDOLYL) ACETOHYDROXAMATES
  申请人：New Mexico Technical Research Foundation

  公开号：US20150105439A1

  公开（公告）日：2015-04-16

  A pharmaceutical composition, a method of producing same, and a method of providing cancer therapy therein comprising a pharmaceutically acceptable excipient or carrier and a compound Formula 3 as follows: or a pharmaceutically acceptable salt or prodrug thereof, wherein: R 1 , R 2 , R 3 and R 4 are optionally substituted and are hydrogen, haloalkyl, aryl, fused aryl, carbocyclic, a heterocyclic group, a heteroaryl group, C 1-10 alkyl, alkenyl, alkynyl, arylalkyl, arylalkenyl, arylalkynyl, heteroarylalkyl, heteroarylalkenyl, carbocycloalkyl, heterocycloalkyl, hydroxyalkyl, aminoalkyl, carboxyalkyl, nitroalkyl, cyanoalkyl, acetamidoalkyl, acyloxyalkyl, hydroxyl, alkoxy, acetoxy, amino, alkylamino, acetamido.

  一种药物组合物，其制备方法以及其中提供癌症治疗的方法，包括一个药用可接受的赋形剂或载体和一个化合物Formula 3，如下所示：或其药用可接受的盐或前药，其中：R1、R2、R3和R4可选择地被取代，可以是氢、卤代烷基、芳基、融合芳基、碳环、杂环基、杂芳基、C1-10烷基、烯基、炔基、芳基烷基、芳基烯基、芳基炔基、杂芳基烷基、杂芳基烯基、碳环烷基、杂环烷基、羟基烷基、氨基烷基、羧基烷基、硝基烷基、氰基烷基、乙酰氨基烷基、酰氧基烷基、羟基、烷氧基、乙酰氧基、氨基、烷基氨基、乙酰氨基。
• Metal-free transannulation reaction of indoles with nitrostyrenes: a simple practical synthesis of 3-substituted 2-quinolones
  作者：Alexander V. Aksenov、Alexander N. Smirnov、Nicolai A. Aksenov、Inna V. Aksenova、Liliya V. Frolova、Alexander Kornienko、Igor V. Magedov、Michael Rubin

  DOI：10.1039/c3cc45696j

  日期：——

  3-Substituted 2-quinolones are obtained via a novel, metal-free transannulation reaction of 2-substituted indoles with 2-nitroalkenes in polyphosphoric acid. The reaction can be used in conjunction with the Fisher indole synthesis offering a practical three-component heteroannulation methodology to produce 2-quinolones from arylhydrazines, 2-nitroalkenes and acetophenone.

  3-取代的2-喹啉是通过2-取代吲哚与2-硝基烯烃在聚磷酸中进行的新型无金属跨环反应获得的。该反应可以与费舍尔吲哚合成联用，提供了一种实用的三组分杂环闭环方法，将芳基肼、2-硝基烯烃和乙酰苯one转化为2-喹啉。
• An efficient synthesis of (3-indolyl)acetonitriles by reduction of hydroxamic acids
  作者：Alexander V. Aksenov、Nicolai A. Aksenov、Zarema V. Dzhandigova、Inna V. Aksenova、Leonid G. Voskressensky、Alexander N. Smirnov、Michael A. Rubin

  DOI：10.1007/s10593-016-1881-z

  日期：2016.5

  A new, highly efficient method was developed for the synthesis of (3-indolyl)acetonitriles by reduction of readily available (3-indolyl)hydroxamic acids with phosphorus trichloride. The nitriles obtained according to this method are of significant interest for structure-activity studies of potential anticancer agents.

  通过用三氯化磷还原易得的（3-吲哚基）异羟肟酸，开发了一种新的高效方法来合成（3-吲哚基）乙腈。根据该方法获得的腈对于潜在抗癌剂的结构活性研究具有重大意义。
• Direct reductive coupling of indoles to nitrostyrenes en route to (indol-3-yl)acetamides
  作者：Alexander V. Aksenov、Nicolai A. Aksenov、Zarema V. Dzhandigova、Dmitrii A. Aksenov、Leonid G. Voskressensky、Valentine G. Nenajdenko、Michael Rubin

  DOI：10.1039/c6ra21399e

  日期：——

  A highly efficient one-pot method for the reductive coupling of indoles to nitrostyrenes in polyphosphoric acid doped with PCl3 was developed. This method allows direct and expeditious access to primary (indol-3-yl)acetamides, interesting as anti-cancer drug candidates.

  开发了一种高效的一锅法，用于在PCl 3掺杂的多磷酸中将吲哚还原为硝基苯乙烯。这种方法可以直接和迅速地获得作为抗癌候选药物感兴趣的伯（吲哚-3-基）乙酰胺。