methyl 2-((2-chlorobenzyl)oxy)benzoate | 52803-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-((2-chlorobenzyl)oxy)benzoate
• 英文别名: Methyl-2-(2-chlor-benzyloxy)benzoat；2-(2-chloro-benzyloxy)benzoic acid methyl ester；Methyl 2-[(2-chlorobenzyl)oxy]benzoate；methyl 2-[(2-chlorophenyl)methoxy]benzoate
• CAS: 52803-83-5
• 化学式: C₁₅H₁₃ClO₃
• 分子量: 276.719
• InChiKey: ZXVAPDOKLJAVNW-UHFFFAOYSA-N

物化性质

• 沸点：
  392.2±22.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-((2-chlorobenzyl)oxy)benzoate 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以90%的产率得到2-(2-chloro-benzyloxy)benzoic acid hydrazide
  参考文献：
  名称：

  Design and Synthesis of New 2-Substituted-5-[2-(2-halobenzyloxy)phenyl]-1,3,4-oxadiazoles as Anticonvulsant Agents

  摘要：

  设计并合成了一系列新的 2-取代-5-[2-(2-卤苄氧基)苯基]-1,3,4-恶二唑，作为抗惊厥剂。电击和戊四唑诱导的致死性惊厥试验表明，在 1,3,4-oxadiazole 环的第 2 位引入一个氨基和在苄氧基的正交位置引入一个氟取代基具有最佳的抗惊厥活性。我们的研究结果表明，这种作用是通过苯并二氮杂卓受体机制介导的。

  DOI：

  10.1248/cpb.56.509
• 作为产物：
  描述：

  2-氯甲苯 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 6.0h， 生成 methyl 2-((2-chlorobenzyl)oxy)benzoate
  参考文献：
  名称：

  钯催化芳烃羧酸/酯与芳基溴化物的分子内脱羧偶联

  摘要：

  给我一个戒指？已经开发出一种有效的方法用于芳烃羧酸/酯与钯催化的芳基溴化物的分子内脱羧偶联（参见方案）。从合成的观点来看，该方法极具吸引力，因为催化剂的负载量低，优化的反应条件温和且底物范围广。

  DOI：

  10.1002/chem.201103438

文献信息

• Discovery, synthesis and anti-atherosclerotic activities of a novel selective sphingomyelin synthase 2 inhibitor
  作者：Yali Li、Taomin Huang、Bin Lou、Deyong Ye、Xiangyu Qi、Xiaoxia Li、Shuang Hu、Tingbo Ding、Yan Chen、Yang Cao、Mingguang Mo、Jibin Dong、Min Wei、Yong Chu、Huiti Li、Xian-Cheng Jiang、Nengneng Cheng、Lu Zhou

  DOI：10.1016/j.ejmech.2018.12.028

  日期：2019.2

  The sphingomyelin synthase 2 (SMS2) is a potential target for pharmacological intervention in atherosclerosis. However, so far, few selective SMS2 inhibitors and their pharmacological activities were reported. In this study, a class of 2-benzyloxybenzamides were discovered as novel SMS2 inhibitors through scaffold hopping and structural optimization. Among them, Ly93 as one of the most potent inhibitors exhibited IC50 values of 91 nM and 133.9 mu M against purified SMS2 and SMS1 respectively. The selectivity ratio of Ly93 was more than 1400-fold for purified SMS2 over SMS1. The in vitro studies indicated that Ly93 not only dose-dependently diminished apoB secretion from Huh7 cells, but also significantly reduced the SMS activity and increased cholesterol efflux from macrophages. Meanwhile, Ly93 inhibited the secretion of LPS-mediated pro-inflammatory cytokine and chemokine in macrophages. The pharmacokinetic profiles of Ly93 performed on C57BL/6J mice demonstrated that Ly93 was orally efficacious. As a potent selective SMS2 inhibitor, Ly93 significantly decreased the plasma SM levels of C57BL/6J mice. Furthermore, Ly93 was capable of dose-dependently attenuating the atherosclerotic lesions in the root and the entire aorta as well as macrophage content in lesions, in apolipoprotein E gene knockout mice treated with Ly93. In conclusion, we discovered a novel selective SMS2 inhibitor Ly93 and demonstrated its anti-atherosclerotic activities in vivo. The preliminary molecular mechanism-of-action studies revealed its function in lipid homeostasis and inflammation process, which indicated that the selective inhibition of SMS2 would be a promising treatment for atherosclerosis. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Design, synthesis and molecular docking of salicylic acid derivatives containing metronidazole as a new class of antimicrobial agents
  作者：Zhi-Hua Guo、Yong Yin、Cong Wang、Peng-Fei Wang、Xing-Tao Zhang、Zhong-Chang Wang、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2015.07.075

  日期：2015.9

  A series of novel salicylic acid derivatives containing metronidazole as Staphylococcus aureus Tyrosyl-tRNA synthetase (TyrRS) inhibitors have been synthesized and evaluated their biology activities as potential antibacterial agents. Among these compounds, compound 5r exhibited the most potent antibacterial activity against Gram-positive (S. aureus ATCC 6538 and Bacillus subtilis ATCC 6633) and Gram-negative (Escherichia coli ATCC 35218 and Pseudomonas aeruginosa ATCC 13525) with MICs of 0.39-1.57 mu g/mL and showed the most potent S. aureus Tyrosyl-tRNA synthetase inhibitory with 2.3 mu M. Docking simulation was performed to insert compound 5r into the crystal structure of S. aureus Tyrosyl-tRNA synthetase active site to determine the probable binding model. These results suggested that compound 5r may be a promising antibacterial agent. (c) 2015 Elsevier Ltd. All rights reserved.
• DE2252818
  申请人：——

  公开号：——

  公开（公告）日：——
• Ginger and Its Bioactive Component Inhibit Enterotoxigenic <i>Escherichia coli</i> Heat-Labile Enterotoxin-Induced Diarrhea in Mice
  作者：Jaw-Chyun Chen、Li-Jiau Huang、Shih-Lu Wu、Sheng-Chu Kuo、Tin-Yun Ho、Chien-Yun Hsiang

  DOI：10.1021/jf071460f

  日期：2007.10.1

  Ginger is one of the most commonly used fresh herbs and spices. Enterotoxigenic Escherichia coli heat-labile enterotoxin (LT)-induced diarrhea is the leading cause of infant death in developing countries. In this study, we demonstrated that ginger significantly blocked the binding of LT to cell-surface receptor G(M1), resulting in the inhibition of fluid accumulation in the closed ileal loops of mice. Biological-activity-guided searching for active components showed that zingerone (vanillylacetone) was the likely active constituent responsible for the antidiarrheal efficacy of ginger. Further analysis of chemically synthesized zingerone derivatives revealed that compound 31 (2-[(4-methoxybenzyl)oxy]benzoic acid) significantly suppressed LT-induced diarrhea in mice via an excellent surface complementarity with the B subunits of LT. In conclusion, our findings provide evidence that ginger and its derivatives may be effective herbal supplements for the clinical treatment of enterotoxigenic Escherichia coli diarrhea.
• FR2204351
  申请人：——

  公开号：——

  公开（公告）日：——