β--3-bromopropiophenone hydrochloride | 2192-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β--3-bromopropiophenone hydrochloride
• 英文别名: 3-Brom-ω-dimethylamino-propiophenon；[3-(3-Bromophenyl)-3-oxopropyl]-dimethylazanium;chloride
• CAS: 2192-15-6
• 化学式: C₁₁H₁₄BrNO*ClH
• 分子量: 292.603
• InChiKey: VFZWWIDLBQXROK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  β--3-bromopropiophenone hydrochloride 反应 2.0h， 生成 3-环丙基苯甲酸
  参考文献：
  名称：

  Smejkal,J. et al., Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 2950 - 2955

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二甲基氯烯亚胺 、 3'-溴苯乙酮 以 乙腈 为溶剂， 以89%的产率得到β--3-bromopropiophenone hydrochloride
  参考文献：
  名称：

  Synthesis and anti-tubercular activity of conformationally-constrained and bisquinoline analogs of TMC207

  摘要：

  TMC207的构象限制和双喹啉类似物作为抗结核药物。

  DOI：

  10.1039/c5md00131e

文献信息

• Synthesis of dicationic diarylpyridines as nucleic-acid binding agents
  作者：A Kumar、RA Rhodes、J Spychala、WD Wilson、DW Boykin、RR Tidwell、CC Dykstra、JE Hall、SK Jones、RF Schinazi

  DOI：10.1016/0223-5234(96)88214-6

  日期：1995.1

  4-bromoacetophenone in six steps is presented. The dications bind to poly dA.dT in the order 7 > 13 > 18 > 8 > 9; the order of binding to poly A.U is 7 > 13 > 8 > 9; 18 essentially does not bind to the RNA model. Only 7 inhibits topoisomerase II at millimolar concentrations. The dicationic compounds that were tested against Pneumonocystis carinii in the immuno-suppressed rat model show only modest activity

  2,6-双[4-(4,5-二氢-1H-咪唑-2-基)苯基]吡啶7, 2-[4-(4,5-二氢-1H-咪唑-2-基)的合成)-苯基]-6-[3-(4,5-二氢-1H-咪唑-2-基)苯基]吡啶8和2,6-双[3-(4,5-二氢-1H-咪唑-描述了来自适当取代的溴苯乙酮的五个步骤中的 2-基)苯基]吡啶 9。还报道了 3,5-双[4-(4,5-二氢-1H-咪唑-2-基)苯基]吡啶 13，由 4-溴苯基乙腈分四步制备。2,5-双[4-(4,5-二氢-1H-咪唑-2-基)-苯基]吡啶 18 由 4-溴苯乙酮分六步制备。指示以 7 > 13 > 18 > 8 > 9 的顺序与聚 dA.dT 结合；与poly AU的结合顺序为7>13>8>9；18 基本上不与 RNA 模型结合。只有 7 在毫摩尔浓度下抑制拓扑异构酶 II。在免疫抑制大鼠模型中针对卡氏肺囊虫测试的双阳离子化合物仅显示出中等活性并且具有中
• Synthesis, spectral studies and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3-phenyl-2-pyrazolines
  作者：Mohammad Abid、Abdul Roouf Bhat、Fareeda Athar、Amir Azam

  DOI：10.1016/j.ejmech.2007.10.032

  日期：2009.1

  Thirty new pyrazoline derivatives were synthesized by cyclization of Mannich bases with thiosemicarbazides being substituted by different cyclic and aromatic amines. The structures of the compounds were elucidated by elemental analyses, UV, IR, H-1 and C-13 NMR and ESI-MS spectral data. The in vitro antiamoebic activity was evaluated against Entamoeba histolytica in comparison with metronidazole used as reference substance. Out of the 30 compounds screened for antiamoebic activity, 10 (5, 6, 15, 18, 25-30) were found to be better inhibitors of E. histolytica since they showed lesser IC50 values than metronidazole. The preliminary results indicated that the presence of 3-chloro or 3-bromo substituent on the phenyl ring at position 3 of the pyrazoline ring enhanced the antiamoebic activity as compared to unsubstituted phenyl ring. The study suggests that the preliminary activity of these compounds may further be explored for the development of new targets for amoebiasis. (C) 2007 Elsevier Masson SAS. All rights reserved.
• Synthesis and Structure−Activity Relationship Study of Potent Trypanocidal Thio Semicarbazone Inhibitors of the Trypanosomal Cysteine Protease Cruzain
  作者：Xiaohui Du、Chun Guo、Elizabeth Hansell、Patricia S. Doyle、Conor R. Caffrey、Tod P. Holler、James H. McKerrow、Fred E. Cohen

  DOI：10.1021/jm010459j

  日期：2002.6.1

  American trypanosomiasis, or Chagas' disease, is the leading cause of heart disease in Latin America. Currently there is an urgent need to develop antitrypanosomal therapy due to the toxicity of existing agents and emerging drug resistance. A novel series of potent thio semicarbazone small-molecule inhibitors of the Trypanosoma cruzi cysteine protease cruzain have been identified. Some of these inhibitors have been shown to be trypanocidal. We initially discovered that X-bromopropiophenone thio semicarbazone (1i) inhibited cruzain and could cure mammalian cell cultures infected with T cruzi. 3'-Bromopropiophenone thio semicarbazone showed no toxicity for mammalian cells at concentrations that were trypanocidal. Following this lead, more than 100 compounds were designed and synthesized. A specific structure-activity relationship (SAR) was established, and many potent analogues with IC50 values in the low nanomolar range were identified. Eight additional analogues were trypanocidal in a cell culture assay, and this indicates that aryl thio semicarbazone is a productive scaffold for killing the parasites. Kinetic studies show that these are time-dependent inhibitors. Molecular modeling studies of the enzyme-inhibitor complex have led to a proposed mechanism of interaction as well as insight into the SAR of the thio semicarbazone series. The nonpeptide nature of this series, small size, and extremely low cost of production suggest this is a promising direction for the development of new antitrypanosome chemotherapy.
• Substituent effects in the homolytic brominolysis of substituted phenylcyclopropanes
  作者：Douglas E. Applequist、Lee F. McKenzie

  DOI：10.1021/jo00875a009

  日期：1976.6
• Synthesis, characterization and antiamoebic activity of 1-(thiazolo[4,5-b]quinoxaline-2-yl)-3-phenyl-2-pyrazoline derivatives
  作者：Mohammad Abid、Amir Azam

  DOI：10.1016/j.bmcl.2006.01.116

  日期：2006.5

  A new series of 1-N-thiocarboxamide-3-phenyl-2-pyrazolines 1-6 was synthesized by cyclization of different Mannich bases with unsubstituted thiosemicarbazide. The reaction of cyclized pyrazoline derivatives 1-6 with 2,3-dichloroquinoxaline afforded the title compounds 7-12. The structures of the new compounds were confirmed by elemental analyses as well as H-1, C-13 NMR, IR and electronic spectral data. The HM1:IMSS strain of Entamoeba histolytica parasite was cultured in vitro and the sensitivity of the parasite to the synthesized compounds was evaluated using the microdilution method. Among all the pyrazoline derivatives 1-6, none was found to be a better inhibitor as compared to the reference drug, metronidazole. The quinoxaline derivatives, 9, 11 and 12 were found to be potent inhibitors of E. histolytica. (C) 2006 Elsevier Ltd. All rights reserved.