3-(2-溴乙酰基)苯甲酰胺 | 92132-77-9

• 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)苯甲酰胺
• 英文名称: 3-(bromoacetyl)benzenecarboxamide
• 英文别名: 3-(bromoacetyl)benzamide；3-(2-bromoacetyl)benzamide
• CAS: 92132-77-9
• 化学式: C₉H₈BrNO₂
• 分子量: 242.072
• InChiKey: GKELVJRETHDKCL-UHFFFAOYSA-N

物化性质

• 沸点：
  367.2±22.0 °C(Predicted)
• 密度：
  1.583±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-溴乙酰基)苯甲酰胺 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 生成 3-(2-环氧乙烷基)苯甲酰胺
  参考文献：
  名称：

  Synthesis of 3-Substituted Benzamides and 5-Substituted Isoquinolin-1(2H)-ones and Preliminary Evaluation as Inhibitors of Poly(ADP-ribose)polymerase (PARP)

  摘要：

  Inhibitors of poly(ADP-ribose)polymerase (PARP) inhibit repair of damaged DNA and thus potentiate radiotherapy and chemotherapy of cancer. 3-Substituted benzamides and 5-substituted isoquinolin-1-ones have been synthesised and evaluated for inhibition of PARP. Reduction of 3-(bromoacetyl)benzamide, followed by treatment with base, gave RS-3-oxiranylbenzamide. Reduction of 3-(hydroxyacetyl)benzonitrile with bakers' yeast gave 'the R-diol which was converted to R-3-(1,2-dihydroxyethyl)benzamide. Similar reduction of 3-(acetoxyacetyl)benzonitrile led towards the S-diol which was converted to its cyclic acetonide. E-2-(2,6-Dicyanophenyl)-N,N-dimethylethenamine was formed by condensation of 2,6-dicyanotoluene with dimethylformamide dimethyl acetal (DMFDMA); cyclisation under acidic conditions afforded 5-cyanoisoquinolin-1-one. Heck coupling of 5-iodoisoquinolin-1-one with propenoic acid formed E-3-(1-oxoisoquinolin-5-yl)propenoic acid. 3-Oxiranylbenzamide, 5-bromoisoquinolin-1-one and 5-iodoisoquinolin-1-one were among the most potent inhibitors of PARP activity in a preliminary screen in vitro. (C) 1998 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00029-7
• 作为产物：
  描述：

  3-(2-溴乙酰基)苯甲腈 在 sodium hydroxide 、 双氧水 、 溴 、 potassium acetate 、 sodium iodide 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 9.5h， 生成 3-(2-溴乙酰基)苯甲酰胺
  参考文献：
  名称：

  Synthesis of 3-Substituted Benzamides and 5-Substituted Isoquinolin-1(2H)-ones and Preliminary Evaluation as Inhibitors of Poly(ADP-ribose)polymerase (PARP)

  摘要：

  Inhibitors of poly(ADP-ribose)polymerase (PARP) inhibit repair of damaged DNA and thus potentiate radiotherapy and chemotherapy of cancer. 3-Substituted benzamides and 5-substituted isoquinolin-1-ones have been synthesised and evaluated for inhibition of PARP. Reduction of 3-(bromoacetyl)benzamide, followed by treatment with base, gave RS-3-oxiranylbenzamide. Reduction of 3-(hydroxyacetyl)benzonitrile with bakers' yeast gave 'the R-diol which was converted to R-3-(1,2-dihydroxyethyl)benzamide. Similar reduction of 3-(acetoxyacetyl)benzonitrile led towards the S-diol which was converted to its cyclic acetonide. E-2-(2,6-Dicyanophenyl)-N,N-dimethylethenamine was formed by condensation of 2,6-dicyanotoluene with dimethylformamide dimethyl acetal (DMFDMA); cyclisation under acidic conditions afforded 5-cyanoisoquinolin-1-one. Heck coupling of 5-iodoisoquinolin-1-one with propenoic acid formed E-3-(1-oxoisoquinolin-5-yl)propenoic acid. 3-Oxiranylbenzamide, 5-bromoisoquinolin-1-one and 5-iodoisoquinolin-1-one were among the most potent inhibitors of PARP activity in a preliminary screen in vitro. (C) 1998 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00029-7

文献信息

• 2-Guanyl-4-(substituted phenyl) thiazole derivatives
  申请人：American Home Products Corporation

  公开号：US04452985A1

  公开（公告）日：1984-06-05

  Compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, cyano or cyano(lower)alkyl; R.sup.2 is hydrogen, cyano, carboxy, carbamoyl, guanyl, (lower)alkoxyimino, hydrazinocarbonyl, (lower)alkylaminoimino, ##STR2## with the proviso that one but never both of R.sup.1 and R.sup.2 is hydrogen; and the pharmacologically acceptable salts thereof exhibit H.sub.2 -receptor antagonist and gastric secretion inhibition activity.

  式为：##STR1## 其中 R.sup.1 为氢、氰基或氰基(较低)烷基；R.sup.2 为氢、氰基、羧基、氨基甲酰基、鸟氨酸基、(较低)烷氧基亚胺基、叠氮基甲酰基、(较低)烷基氨基亚胺基，##STR2## 其中 R.sup.1 和 R.sup.2 中的一个但从不同时为氢；其药理学上可接受的盐具有 H.sub.2 -受体拮抗剂和抑制胃分泌活性。
• Thiazole compounds and pharmaceutical compositions for inhibiting protein kinases and methods for their use
  申请人：Agouron Pharmaceuticals, Inc.

  公开号：US20020025976A1

  公开（公告）日：2002-02-28

  Diaminothiazole compounds that modulate and/or inhibit the activity of certain protein kinases are described. These compounds and pharmaceutical compositions containing them are capable of mediating tyrosine kinase signal transduction in order to modulate and/or inhibit unwanted cell proliferation. The invention is also directed to the therapeutic or prophylactic use of pharmaceutical compositions containing such compounds, and to methods of treating cancer as well as other disease states associated with unwanted angiogenesis and/or cellular proliferation, such as diabetic retinopathy, neovascular glaucoma, rheumatoid arthritis, and psoriasis, by administering effective amounts of such compounds.

  二氨基噻唑化合物可调节和/或抑制特定蛋白激酶的活性。这些化合物及含有它们的药物组合物能够介导酪氨酸激酶信号传导，以调节和/或抑制不需要的细胞增殖。本发明还涉及含有这些化合物的药物组合物的治疗或预防用途，以及通过给予这些化合物的有效量来治疗癌症以及与不需要的血管生成和/或细胞增殖相关的其他疾病状态，如糖尿病视网膜病变、新生血管性青光眼、类风湿性关节炎和牛皮癣的方法。
• Synthesis, biological evaluation and molecular modeling studies of imidazo[1,2- a ]pyridines derivatives as protein kinase inhibitors
  作者：Marie Lawson、Jordi Rodrigo、Blandine Baratte、Thomas Robert、Claire Delehouzé、Olivier Lozach、Sandrine Ruchaud、Stéphane Bach、Jean-Daniel Brion、Mouad Alami、Abdallah Hamze

  DOI：10.1016/j.ejmech.2016.07.040

  日期：2016.11

  We report here the synthesis, the biological evaluation and the molecular modeling studies of new imidazo[1,2-a]pyridines derivatives designed as potent kinase inhibitors. This collection was obtained from 2-aminopyridines and 2-bromoacetophenone which afforded final compound in only one step. The bioactivity of this family of new compounds was tested using protein kinase and ATP competition assays

  我们在这里报告了设计为有效激酶抑制剂的新型咪唑并[1,2-a]吡啶衍生物的合成，生物学评估和分子模型研究。该收集物是从2-氨基吡啶和2-溴苯乙酮中获得的，它们仅一步即可得到最终化合物。使用蛋白激酶和ATP竞争测定法测试了这一新化合物家族的生物活性。构效关系（SAR）表明，六种化合物在微摩尔范围内抑制DYRK1A和CLK1。对接研究提供了与SAR数据相关的可能解释。活性最高的化合物4c抑制CLK1（IC50为0.7μM）和DYRK1A（IC50为2.6μM）。
• Synthesis of 2-guanyl-4-(3-substituted-phenyl)thiazoles with potent histamine H₂-antagonism activity
  作者：Arthur A. Santilli、Anthony C. Scotese、Robert L. Morris、Stanley C. Bell

  DOI：10.1002/jhet.5570280839

  日期：1991.12

  The syntheses of novel 2-guanyl-4-(3-substituted-phenyl)thiazoles showing potent histamine H2-antagonism activity is reported. The most potent compound is 17 where the substitution at the 3-position of the phenyl ring is an N-methylamidino function.

  报道了显示出有效的组胺H 2拮抗活性的新型2-胍基-4-（3-取代的苯基）噻唑的合成。最有效的化合物是17，其中在苯环的3位上的取代是N-甲基ami基官能团。
• New anti-viral drugs for the treatment of the common cold
  作者：Caterina Maugeri、Maria A. Alisi、Claudia Apicella、Luciano Cellai、Patrizia Dragone、Elena Fioravanzo、Saverio Florio、Guido Furlotti、Giorgina Mangano、Rosella Ombrato

  DOI：10.1016/j.bmc.2007.12.030

  日期：2008.3.15

  (HRV) is the most important aetiologic agent of common cold in adults and children. HRV is a single-stranded, positive sense RNA virus and, despite the high level of conservation among different serotypes, sequence alignment of viral protease 3C with mammalian protease reveals no homology. Thus, protease 3C is an optimal target for the development of anti-HRV agents. In the present work we investigated

  人鼻病毒（HRV）是成人和儿童感冒的最重要病原学剂。HRV是一种单链正向RNA病毒，尽管不同血清型之间的保守程度很高，但病毒蛋白酶3C与哺乳动物蛋白酶的序列比对并未显示出同源性。因此，蛋白酶3C是开发抗HRV试剂的最佳靶标。在本工作中，我们研究了针对HRV蛋白酶3C的新型潜在可逆抑制剂的设计，合成和开发。对HRV2蛋白酶3C结晶结构的对接研究使我们得以设计和合成了一系列能够作为底物类似物的3,5双取代的苯甲酰胺。我们还开发了1,3 5个三取代的苯甲酰胺，其中芳基环上的芳香取代基导致我们研究pi-pi相互作用对稳定蛋白酶3C-抑制剂复合物的重要性。测试了所有结构对HRV14蛋白酶3C的酶促抑制作用。结果强调了化合物13、14和20的抑制活性（在10 microM时分别为91％，81％和85％），后者具有ID（50）（抑制50％病毒细胞病变作用的剂量） ）于HRV-14 = 25 microg