1-(4-((3-chlorobenzyl)oxy)phenyl)ethanone | 79615-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-((3-chlorobenzyl)oxy)phenyl)ethanone
• 英文别名: 1-(4-(3-chlorobenzyloxy)phenyl)ethanone；1-{4-[(3-Chlorobenzyl)oxy]phenyl}ethanone；1-[4-[(3-chlorophenyl)methoxy]phenyl]ethanone
• CAS: 79615-76-2
• 化学式: C₁₅H₁₃ClO₂
• mdl: MFCD11522608
• 分子量: 260.72
• InChiKey: ZOVUQNNOBWTRAT-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93 °C
• 沸点：
  405.9±25.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-((3-chlorobenzyl)oxy)phenyl)ethanone 在 三氯化铝 、 氯 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 4.0h， 以97.1%的产率得到2-Chloro-1-[4-(3-chloro-benzyloxy)-phenyl]-ethanone
  参考文献：
  名称：

  Kawamatsu; Sohda; Iami, European Journal of Medicinal Chemistry, 1981, vol. 16, # 4, p. 355 - 362

  摘要：

  DOI：
• 作为产物：
  描述：

  间氯氯苄 、 对羟基苯乙酮 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.67h， 以73%的产率得到1-(4-((3-chlorobenzyl)oxy)phenyl)ethanone
  参考文献：
  名称：

  Novel aryloxy azolyl chalcones with potent activity against Mycobacterium tuberculosis H37Rv

  摘要：

  A series of twenty seven novel aryloxy azolyl chalcones were synthesized and evaluated in vitro for the growth inhibition of Mycobacterium tuberculosis H37Rv. Ten compounds from this series exhibited good activity with MIC in the range of 3.12-0.78 mu g/mL and six of them were found non-toxic against VERO cells and MBMDMos (mouse bone-marrow derived macrophages), were further evaluated ex-vivo for their potential to kill intracellular bacilli. Two compounds 4 and 19 showed 99% and 71% killing respectively, of intracellular bacilli in MBMDMos infection model. Further, compound 19, an imidazolyl chalcone with a 2,4-difluorobenzyloxy moiety also exhibited moderate in vivo activity in mice against virulent M. tuberculosis, thus providing a new structural lead towards TB drug development. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.037

文献信息

• Neuroprotective effects of benzyloxy substituted small molecule monoamine oxidase B inhibitors in Parkinson’s disease
  作者：Zhimin Wang、Jiajia Wu、Xuelian Yang、Pei Cai、Qiaohong Liu、Kelvin D.G. Wang、Lingyi Kong、Xiaobing Wang

  DOI：10.1016/j.bmc.2016.09.050

  日期：2016.11

  The benzyloxy substituted small molecules are well-known highly potent monoamine oxidase B inhibitors, but their therapeutic potential against Parkinson’s disease have not been investigated in detail. In this paper, a series of representative benzyloxy substituted derivatives were synthesized and evaluated for MAO-A/B inhibition. In addition, their neuroprotective effects were investigated in 6-OHDA-

  苄氧基取代的小分子是众所周知的高效单胺氧化酶B抑制剂，但尚未详细研究其对帕金森氏病的治疗潜力。在本文中，合成了一系列代表性的苄氧基取代的衍生物，并评估了对MAO-A / B的抑制作用。此外，在6-OHDA和鱼藤酮处理的PC12细胞中研究了它们的神经保护作用。观察到，大多数化合物在用神经毒素处理的PC12细胞的存活率中显示出明显的增加。其中，有13种表现出显着且平衡的神经保护效能。流式细胞术和染色方法证实了13对神经毒素诱导的细胞凋亡的保护作用。此外，根据体外BBB预测和体内急性毒性试验，13还显示出良好的BBB通透性和低毒性。结果表明13是有效和有希望的候选者，可以进一步开发作为帕金森氏病治疗的疾病缓解药物。
• Acetophenone derivatives: novel and potent small molecule inhibitors of monoamine oxidase B
  作者：Zhi-Min Wang、Xue-Mei Li、Wei Xu、Fan Li、Jin Wang、Ling-Yi Kong、Xiao-Bing Wang

  DOI：10.1039/c5md00357a

  日期：——

  series of acetophenone derivatives have been designed, synthesized and evaluated for human monoamine oxidase A and B inhibitory activity in vitro. Most of the tested compounds acted preferentially on MAO-B with IC50 values in the nanomolar range and weak or no inhibition of MAO-A. In particular, compounds 1j (IC50 = 12.9 nM) and 2e (IC50 = 11.7 nM) were the most potent MAO-B inhibitors being 2.76- and 2

  已经设计，合成和评估了两个系列的苯乙酮衍生物在体外对人单胺氧化酶A和B的抑制活性。大多数测试的化合物优先以30纳摩尔范围的IC 50值对MAO-B起作用，对MAO-A的抑制作用弱或无抑制作用。特别是化合物1j（IC 50 = 12.9 nM）和2e（IC 50= 11.7 nM）是最有效的MAO-B抑制剂，其活性比司来吉兰高2.76倍和2.99倍。此外，MAO-B抑制的结构-活性关系表明，苯乙酮部分C3和C4处的取代基，特别是被卤素取代的苄氧基取代，对MAO-B抑制更有利。已经进行了分子对接和动力学研究以解释MAO-B与苯乙酮衍生物的结合模式。此外，代表性化合物1j和2e在SH-SY5Y细胞中显示出低神经毒性。可以得出结论，苯乙酮衍生物可用于开发有望用于治疗神经退行性疾病的先导化合物。
• Design, synthesis, and biological evaluation of 4-(5-nitrofuran-2-yl)prop-2-en-1-one derivatives as potent antitubercular agents
  作者：Nilesh R. Tawari、Ranjeet Bairwa、M.K. Ray、M.G.R. Rajan、Mariam S. Degani

  DOI：10.1016/j.bmcl.2010.08.127

  日期：2010.11

  Based on stereoelectronic feature analysis using density functional theory (DFT) at B3LYP/3-21*G level, a series of 4-(5-nitrofuran-2-yl)prop-2-en-1-one derivatives with low LUMO energies (<-0.10 eV); concentrated over the nitro group, furan moiety and alpha,beta-unsaturated carbonyl bridge were envisaged as potential antitubercular agents. The target compounds were prepared by condensation of 5-nitro-2-furaldehyde with various ketones under acidic condition. The compounds were evaluated for antitubercular activity against Mycobacterium tuberculosis H37Rv and their cytotoxicity in VERO cell line. Several synthesized compounds showed good antitubercular activity of <5 mu M along with low cytotoxicity. In particular, compound ((E)-3-(5-nitrofuran-2-yl)-1-(4-(piperidin-1-yl) phenyl) prop-2-en-1-one) (3v) was found to be very potent (MIC: 0.19 mu M) with good selectivity index (MIC90/CC50: > 1800). Thus, this study shows the potential of stereoelectronic property analysis in developing improved nitroaromatics as antitubercular agents. (C) 2010 Elsevier Ltd. All rights reserved.
• Kawamatsu; Sohda; Iami, European Journal of Medicinal Chemistry, 1981, vol. 16, # 4, p. 355 - 362
  作者：Kawamatsu、Sohda、Iami

  DOI：——

  日期：——
• Novel aryloxy azolyl chalcones with potent activity against Mycobacterium tuberculosis H37Rv
  作者：Vijay K. Marrapu、Vinita Chaturvedi、Shubhra Singh、Shyam Singh、Sudhir Sinha、Kalpana Bhandari

  DOI：10.1016/j.ejmech.2011.06.037

  日期：2011.9

  A series of twenty seven novel aryloxy azolyl chalcones were synthesized and evaluated in vitro for the growth inhibition of Mycobacterium tuberculosis H37Rv. Ten compounds from this series exhibited good activity with MIC in the range of 3.12-0.78 mu g/mL and six of them were found non-toxic against VERO cells and MBMDMos (mouse bone-marrow derived macrophages), were further evaluated ex-vivo for their potential to kill intracellular bacilli. Two compounds 4 and 19 showed 99% and 71% killing respectively, of intracellular bacilli in MBMDMos infection model. Further, compound 19, an imidazolyl chalcone with a 2,4-difluorobenzyloxy moiety also exhibited moderate in vivo activity in mice against virulent M. tuberculosis, thus providing a new structural lead towards TB drug development. (C) 2011 Elsevier Masson SAS. All rights reserved.