1-(4-[(2,4-二氯苄基)氧基]苯基)-1-乙酮 | 61292-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-[(2,4-二氯苄基)氧基]苯基)-1-乙酮
• 英文名称: 4-(2,4-Dichlorbenzyloxy)acetophenon
• 英文别名: 1-(4-(2,4-dichlorobenzyloxy)phenyl)ethanone；1-{4-[(2,4-Dichlorobenzyl)oxy]phenyl}-1-ethanone；1-[4-[(2,4-dichlorophenyl)methoxy]phenyl]ethanone
• CAS: 61292-27-1
• 化学式: C₁₅H₁₂Cl₂O₂
• mdl: MFCD03001252
• 分子量: 295.165
• InChiKey: SJGSBISIYWRANO-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93°C

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 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

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2914700090
• 储存条件：
  室温、密封、干燥

反应信息

• 作为反应物：
  描述：

  1-(4-[(2,4-二氯苄基)氧基]苯基)-1-乙酮 在 三氯化铝 、 氯 作用下， 以 四氯化碳 、 乙醚 、 乙醇 为溶剂， 反应 5.0h， 生成
  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：

  2,4-二氯氯苄 、 对羟基苯乙酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(4-[(2,4-二氯苄基)氧基]苯基)-1-乙酮
  参考文献：
  名称：

  新型嘧啶衍生物作为潜在抗菌剂的合成与分子对接研究。

  摘要：

  摘要 本工作描述了一些新型嘧啶衍生物的体外抗菌评价。设计，合成并初步探索了22种目标化合物的抗菌活性。抗菌测定表明，某些目标化合物对细菌和真菌（包括耐药病原体）表现出明显的抑制作用。化合物7c对革兰氏阳性细菌（例如金黄色葡萄球菌4220），革兰氏阴性细菌（例如大肠杆菌1924）和真菌白色念珠菌7535表现出最强的抑制活性，MIC为2.4μmol/ L。化合物7c也是最有效的，对四种具有多重耐药性的革兰氏阳性细菌菌株的MIC为2.4或4.8μmol/ L。在人正常肝细胞（L02细胞）中评估了化合物7c，10a，19d和26b的毒性评估。分子对接模拟和分析表明，化合物7c与二氢叶酸还原酶（DHFR）的活性腔具有良好的相互作用。体外酶研究暗示化合物7c也显示出DHFR抑制作用。 图形摘要

  DOI：

  10.1007/s11030-019-10019-8

文献信息

• Design and synthesis of novel chloropyridazine hybrids as promising anticancer agents acting by apoptosis induction and PARP-1 inhibition through a molecular hybridization strategy
  作者：Norhan A. Abdelrahman、Ahmed A. Al-Karmalawy、Maiy Y. Jaballah、Galal Yahya、Marwa Sharaky、Khaled A. M. Abouzid

  DOI：10.1039/d3md00751k

  日期：——

  and 5) was designed and synthesized as proposed apoptotic inducers and PARP-1 inhibitors. The growth inhibition % of the designed hybrids was investigated in eleven cancer cell lines, where the anticancer activities were found to be in the following order: 4-chloropyridazinoxyphenyl-aromatic ketones hybrids (3a–h) > 4-chloropyridazinoxyphenyl-benzyloxyphenylethan-1-one hybrids (4a–e) > 4-chloropy

  在分子杂交原理的指导下，设计并合成了一系列新型4-氯哒嗪氧基苯基缀合物（ 3a-h 、 4a-e和5 ）作为细胞凋亡诱导剂和PARP-1抑制剂。在 11 种癌细胞系中研究了设计的杂合体的生长抑制百分比，发现其抗癌活性按以下顺序排列： 4-氯哒嗪氧基苯基-芳香酮杂合体 ( 3a–h ) > 4-氯哒嗪氧基苯基-苄氧基苯基乙烷-1-一种杂化物 ( 4a–e ) > 4-氯哒嗪氧基苯基-噻唑烷-2,4-二酮杂化物 ( 5 )。此外，选择最敏感的三种癌细胞系（HNO97、FaDu和MDA-MB-468）来测量新杂交体的IC 50值。此外，选择前沿三个成员（ 3c 、 3e和4b ）来测量凋亡蛋白标记物（p53、BAX、caspase 3、caspase 6、BCL-2和CK 18）。此外，还研究了化合物3a-e和4b对 PARP-1 活性的影响，其中3c 、 3d和3e表现出与奥拉帕尼相当的效率。此外，还检查了
• 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.
• Strehlke; Kessler, European Journal of Medicinal Chemistry, 1979, vol. 14, # 3, p. 231 - 237
  作者：Strehlke、Kessler

  DOI：——

  日期：——
• 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.
• US4006243A
  申请人：——

  公开号：US4006243A

  公开（公告）日：1977-02-01