3-(phenylethynyl)-1H-indazole | 1150101-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 3-(phenylethynyl)-1H-indazole
• 英文别名: 3-(phenylethynyl)indazole；3-(2-phenylethynyl)-2H-indazole
• CAS: 1150101-32-8
• 化学式: C₁₅H₁₀N₂
• 分子量: 218.258
• InChiKey: PBVODLIVAWFCPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  tert-butyl 3-(phenylethynyl)-1H-indazole-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到3-(phenylethynyl)-1H-indazole
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of 3-Ethynyl-1H-indazoles as Inhibitors of the Phosphatidylinositol 3-Kinase Signaling Pathway

  摘要：

  A new series of 3-ethynyl-1H-indazoles has been synthesized and evaluated in both biochemical and cell-based assays as potential kinase inhibitors. Interestingly, a selected group of compounds identified from this series exhibited low micromolar inhibition against critical components of the PI3K pathway, targeting PI3K, PDK1, and mTOR kinases. A combination of computational modeling and structure-activity relationship studies reveals a possible novel mode for PI3K inhibition, resulting in a PI3K alpha isoform-specific compound. Hence, by targeting the most oncogenic mutant isoform of PI3K, the compound displays antiproliferative activity both in monolayer human cancer cell cultures and in three-dimensional tumor models. Because of its favorable physicochemical, in vitro ADME and drug-like properties, we propose that this novel ATP mimetic scaffold could prove useful in deriving novel selecting and multikinase inhibitors for clinical use.

  DOI：

  10.1021/jm100825h

文献信息

• C₁₅H₁₀ and C₁₅H₁₂ Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles
  作者：Curt Wentrup、Jürgen Becker、Manfred Diehl

  DOI：10.1021/acs.joc.5b01007

  日期：2015.7.17

  products. The products are explained in terms of the formation of N-phenyl-C-phenylethynylnitrile imine/(phenylazo)(phenylethynyl)carbene 45 and its cyclization to 3-(phenylethynyl)-3H-indazole 46b. Pyrolytic loss of N2 from 46b generates C15H10 intermediate 48. Cyclization of 48 to a dibenzocycloheptatetraene derivative and further rearrangements with analogies in the chemistry of phenylcarbene and

  2-苯基-5-（苯基乙炔基）四唑44为C 15 H 10能量表面提供了新的入口。使用降落固体闪蒸热解法（FS-FVP）的闪蒸真空热解法44提供了环戊五[ def ]菲31和环戊[ jk ]芴52作为主要产物。该产品在地层的来解释N-苯基Ç -phenylethynylnitrile亚胺/（苯偶氮基）（苯基乙炔基）卡宾45和它的环化3-（苯基乙炔基）-3- H-吲唑46B。N 2的热解损失从46b中产生C 15 H 10中间体48。将48环化成二苯并环庚二烯衍生物，并进一步类似于苯卡宾和萘基卡宾的化学反应进行重排，得到最终产物。2-苯基-5-苯乙烯基噻唑43的类似热解得到3-苯乙烯基吲唑58，其进一步热解消除了N 2以经由C 15 H 12中间体产生3-和2-苯基茚61和62。
• PYRAZOLE DERIVATIVES AS KINASE INHIBITORS
  申请人：Pellecchia Maurizio

  公开号：US20090124621A1

  公开（公告）日：2009-05-14

  The present invention provides compounds having the general structure I, or a pharmaceutically acceptable salt thereof: wherein X is a six-member ring selected from phenyl, pyridine, or pyrimidine; Y is H, an alkenyl, a substituted alkenyl, or alkynyl, and R is H or alkyl. Pharmaceutical compositions for treating various disorders such as cancers, the compositions including compound I are also provided.
• Pyrazole Derivatives as Kinase Inhibitors
  申请人：Pellecchia Maurizio

  公开号：US20110212961A1

  公开（公告）日：2011-09-01

  The present invention provides compounds having the general structure I, or a pharmaceutically acceptable salt thereof: wherein X is a six-member ring selected from phenyl, pyridine, or pyrimidine; Y is H, an alkenyl, a substituted alkenyl, or alkynyl, and R is H or alkyl. Pharmaceutical compositions for treating various disorders such as cancers, the compositions including compound I are also provided.
• US5760028A
  申请人：——

  公开号：US5760028A

  公开（公告）日：1998-06-02
• US6214834B1
  申请人：——

  公开号：US6214834B1

  公开（公告）日：2001-04-10