2-(4-bromophenyl)-5-chloroindole | 891846-25-6

• 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: 2-(4-bromophenyl)-5-chloroindole
• 英文别名: 2-(4-bromophenyl)-5-chloro-1H-indole
• CAS: 891846-25-6
• 化学式: C₁₄H₉BrClN
• 分子量: 306.589
• InChiKey: NUQHRAPOTZEKIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)-5-chloroindole 在 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  Synthesis and in vitro binding of N,N-dialkyl-2-phenylindol-3-yl-glyoxylamides for the peripheral benzodiazepine binding sites

  摘要：

  A series of NN-dialkyl-2-phenylindol-3-glyoxylamides bearing the halogens iodine and bromine were synthesised and their binding affinity for the peripheral benzodiazepine binding sites (PBBS) in rat kidney mitochondrial membranes was evaluated Using [H-3]PK11195. Central benzodiazepine receptor (CBR) affinities were also evaluated in rat cortices using [H-3]flumazenil to determine their selectivity for PBBS over CBR. The tested compounds had PBBS binding affinities (IC50) ranging from 7.86 to 618 nM, with all compounds showing high selectivity over the CBR (CBR IC50 > 5000 nM). Among the 12 compounds tested, those with a diethylamide group were the most potent. The highest affinity iodinated PBBS ligand, N,N-diethyl-[5-chloro-2-(4-iodophenyl)indol-3-yl]glyoxylamide (4c), was radiolabelled with iodine-123. This high affinity and selective radioligand may be useful for imaging neurodegencration, inflammation and tumours using single photon emission computed tomography. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.039
• 作为产物：
  描述：

  4-溴苯乙酮 在 PPA 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 2-(4-bromophenyl)-5-chloroindole
  参考文献：
  名称：

  Synthesis and in vitro binding of N,N-dialkyl-2-phenylindol-3-yl-glyoxylamides for the peripheral benzodiazepine binding sites

  摘要：

  A series of NN-dialkyl-2-phenylindol-3-glyoxylamides bearing the halogens iodine and bromine were synthesised and their binding affinity for the peripheral benzodiazepine binding sites (PBBS) in rat kidney mitochondrial membranes was evaluated Using [H-3]PK11195. Central benzodiazepine receptor (CBR) affinities were also evaluated in rat cortices using [H-3]flumazenil to determine their selectivity for PBBS over CBR. The tested compounds had PBBS binding affinities (IC50) ranging from 7.86 to 618 nM, with all compounds showing high selectivity over the CBR (CBR IC50 > 5000 nM). Among the 12 compounds tested, those with a diethylamide group were the most potent. The highest affinity iodinated PBBS ligand, N,N-diethyl-[5-chloro-2-(4-iodophenyl)indol-3-yl]glyoxylamide (4c), was radiolabelled with iodine-123. This high affinity and selective radioligand may be useful for imaging neurodegencration, inflammation and tumours using single photon emission computed tomography. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.039

文献信息

• Efficient synthesis of 2-arylindoles, 2-arylimidazo[1,2-a]pyridines and 2-arylquinoxalines, and their bis-derivatives using [Hmim]OTf ionic liquid supported on nano-silica as a reusable catalyst
  作者：Mohammad Soltani、Iraj Mohammadpoor-Baltork、Ahmad R. Khosropour、Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani

  DOI：10.1007/s13738-015-0603-2

  日期：2015.8

  AbstractAn efficient and facile method for the synthesis of 2-arylindoles, 2-arylimidazo[1,2-a]pyridines and 2-arylquinoxalines by the reaction of various α-bromo ketones with anilines, 2-aminopyridine and 1,2-phenylenediamine, respectively, in the presence of N-methylimidazolium trifluoromethanesulfonate ionic liquid supported on nano-silica ([Hmim]OTf@nano-SiO2) as a reusable catalyst under solvent-free

  摘要通过各种α-溴代酮与苯胺，2-氨基吡啶和1,2-苯二胺的反应，合成2-芳基吲哚，2-芳基咪唑并[1,2- a ]吡啶和2-芳基喹喔啉的一种高效简便的方法，分别在无溶剂条件下，在可重复使用的催化剂上，负载在纳米二氧化硅上的N-甲基咪唑三氟甲磺酸盐离子液体（[Hmim] OTf @ nano-SiO 2）存在。这些化合物的双衍生物也首次使用该催化体系得到了有效的制备。所有产物均以高收率和短反应时间获得。 图形概要
• Synthesis and in vitro binding of N,N-dialkyl-2-phenylindol-3-yl-glyoxylamides for the peripheral benzodiazepine binding sites
  作者：Taryn P. Homes、Filomena Mattner、Paul A. Keller、Andrew Katsifis

  DOI：10.1016/j.bmc.2006.01.039

  日期：2006.6

  A series of NN-dialkyl-2-phenylindol-3-glyoxylamides bearing the halogens iodine and bromine were synthesised and their binding affinity for the peripheral benzodiazepine binding sites (PBBS) in rat kidney mitochondrial membranes was evaluated Using [H-3]PK11195. Central benzodiazepine receptor (CBR) affinities were also evaluated in rat cortices using [H-3]flumazenil to determine their selectivity for PBBS over CBR. The tested compounds had PBBS binding affinities (IC50) ranging from 7.86 to 618 nM, with all compounds showing high selectivity over the CBR (CBR IC50 > 5000 nM). Among the 12 compounds tested, those with a diethylamide group were the most potent. The highest affinity iodinated PBBS ligand, N,N-diethyl-[5-chloro-2-(4-iodophenyl)indol-3-yl]glyoxylamide (4c), was radiolabelled with iodine-123. This high affinity and selective radioligand may be useful for imaging neurodegencration, inflammation and tumours using single photon emission computed tomography. (c) 2006 Elsevier Ltd. All rights reserved.