[3-(2-溴-乙酰基氨基)-苯并呋喃-2-基]-苯基-甲酮 | 70344-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [3-(2-溴-乙酰基氨基)-苯并呋喃-2-基]-苯基-甲酮
• 英文名称: N-(2-benzoylbenzofuran-3-yl)-2-bromoacetamide
• 英文别名: 2-Benzoyl-3-(2-bromacetamido)benzofuran；[3-(2-bromo-acetylamino)-benzofuran-2-yl]-phenyl-methanone；N-(2-benzoyl-1-benzofuran-3-yl)-2-bromoacetamide
• CAS: 70344-80-8
• 化学式: C₁₇H₁₂BrNO₃
• 分子量: 358.191
• InChiKey: PEQCXNPXRQTVMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3-(2-溴-乙酰基氨基)-苯并呋喃-2-基]-苯基-甲酮 在 sodium iodide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 18.0h， 以76%的产率得到N-(2-benzoylbenzofuran-3-yl)-2-iodoacetamide
  参考文献：
  名称：

  Novel iodoacetamido benzoheterocyclic derivatives with potent antileukemic activity are inhibitors of STAT5 phosphorylation

  摘要：

  Signal Transducer and Activator of Transcription 5 (STAT5) protein, a component of the STAT family of signaling proteins, is considered to be an attractive therapeutic target because of its involvement in the progression of acute myeloid leukemia. In an effort to discover potent molecules able to inhibit the phosphorylation-activation of STAT5, twenty-two compounds were synthesized and evaluated on the basis of our knowledge of the activity of 2-(3',4',5'-trimethoxybenzoyl)-3-iodoacetamido-6-methoxy benzo[b]furan derivative I as a potent STAT5 inhibitor. Most of these molecules, structurally related to compound 1, were characterized by the presence of a common 3',4',5'-trimethoxybenzoyl moiety at the 2-position of different benzoheterocycles such as benzo[b]furan, benzo[b]thiophene, indole and N-methylindole. Effects on biological activity of the iodoacetamido group and of different moieties (methyl and methoxy) at the C-3 to C-7 positions were examined. In the series of benzo[b]furan derivatives, moving the iodoacetylamino group from the C-4 to the C-5 or C-6 positions did not significantly affect antiproliferative activity. Compounds 4, 15, 20 and 23 blocked STAT5 signals and induced apoptosis of K562 BCR-ABL positive cells. For compound 23, the trimethoxybenzoyl moiety at the 2-position of the benzo[b]furan core was not essential for potent inhibition of STAT5 activation. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.022
• 作为产物：
  描述：

  (3-氨基-1-苯并呋喃-2-基)(苯基)甲酮 、 溴乙酰溴 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以76%的产率得到[3-(2-溴-乙酰基氨基)-苯并呋喃-2-基]-苯基-甲酮
  参考文献：
  名称：

  Novel iodoacetamido benzoheterocyclic derivatives with potent antileukemic activity are inhibitors of STAT5 phosphorylation

  摘要：

  Signal Transducer and Activator of Transcription 5 (STAT5) protein, a component of the STAT family of signaling proteins, is considered to be an attractive therapeutic target because of its involvement in the progression of acute myeloid leukemia. In an effort to discover potent molecules able to inhibit the phosphorylation-activation of STAT5, twenty-two compounds were synthesized and evaluated on the basis of our knowledge of the activity of 2-(3',4',5'-trimethoxybenzoyl)-3-iodoacetamido-6-methoxy benzo[b]furan derivative I as a potent STAT5 inhibitor. Most of these molecules, structurally related to compound 1, were characterized by the presence of a common 3',4',5'-trimethoxybenzoyl moiety at the 2-position of different benzoheterocycles such as benzo[b]furan, benzo[b]thiophene, indole and N-methylindole. Effects on biological activity of the iodoacetamido group and of different moieties (methyl and methoxy) at the C-3 to C-7 positions were examined. In the series of benzo[b]furan derivatives, moving the iodoacetylamino group from the C-4 to the C-5 or C-6 positions did not significantly affect antiproliferative activity. Compounds 4, 15, 20 and 23 blocked STAT5 signals and induced apoptosis of K562 BCR-ABL positive cells. For compound 23, the trimethoxybenzoyl moiety at the 2-position of the benzo[b]furan core was not essential for potent inhibition of STAT5 activation. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.022

文献信息

• The synthesis of some benzo[<i>d</i>¹]furo[3,2-e] [1,4] diazepin-2-ones
  作者：John Ashby、E. M. Ramage

  DOI：10.1002/jhet.5570160136

  日期：1979.1

  bromoacetyl bromide followed by cyclization in methanolic ammonia gave 5-phenyl-1,3-dihydrobenzo[d′] furo[3,2-e] [1,4]diazepin-2-one, a representative of a new ring-system. The corresponding chloro substituted diazepin-2-one was similarly prepared from 3-amino-2-(4-chlorobenzoyl) benzo[b] furan. Some alkylation and thionation reactions of these diazepines have been investigated.

  3-氨基-2-苯甲酰基苯并[ b ]呋喃与溴代乙酰溴反应，然后在甲醇氨中环化，得到5-苯基-1,3-二氢苯并[ d ']呋喃[3,2- e ] [1,4]二氮杂pin -2-one，代表新的环形系统。由3-氨基-2-（4-氯苯甲酰基）苯并[ b ]呋喃类似地制备相应的氯取代的二氮杂-2-酮。已经研究了这些二氮杂的一些烷基化和硫磺化反应。
• ASHBY J.; RAMAGE E. M., J. HETEROCYCL. CHEM., 1979, 16, NO 1, 189-190
  作者：ASHBY J.、 RAMAGE E. M.

  DOI：——

  日期：——
• Novel iodoacetamido benzoheterocyclic derivatives with potent antileukemic activity are inhibitors of STAT5 phosphorylation
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Filippo Prencipe、Carlota Lopez-Cara、Riccardo Rondanin、Daniele Simoni、Ernest Hamel、Stefania Grimaudo、Rosaria Maria Pipitone、Maria Meli、Manlio Tolomeo

  DOI：10.1016/j.ejmech.2015.11.022

  日期：2016.1

  Signal Transducer and Activator of Transcription 5 (STAT5) protein, a component of the STAT family of signaling proteins, is considered to be an attractive therapeutic target because of its involvement in the progression of acute myeloid leukemia. In an effort to discover potent molecules able to inhibit the phosphorylation-activation of STAT5, twenty-two compounds were synthesized and evaluated on the basis of our knowledge of the activity of 2-(3',4',5'-trimethoxybenzoyl)-3-iodoacetamido-6-methoxy benzo[b]furan derivative I as a potent STAT5 inhibitor. Most of these molecules, structurally related to compound 1, were characterized by the presence of a common 3',4',5'-trimethoxybenzoyl moiety at the 2-position of different benzoheterocycles such as benzo[b]furan, benzo[b]thiophene, indole and N-methylindole. Effects on biological activity of the iodoacetamido group and of different moieties (methyl and methoxy) at the C-3 to C-7 positions were examined. In the series of benzo[b]furan derivatives, moving the iodoacetylamino group from the C-4 to the C-5 or C-6 positions did not significantly affect antiproliferative activity. Compounds 4, 15, 20 and 23 blocked STAT5 signals and induced apoptosis of K562 BCR-ABL positive cells. For compound 23, the trimethoxybenzoyl moiety at the 2-position of the benzo[b]furan core was not essential for potent inhibition of STAT5 activation. (C) 2015 Elsevier Masson SAS. All rights reserved.