2-(2-氯苄氧基)-苯甲酸 | 52803-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2-氯苄氧基)-苯甲酸
• 中文别名: 2-[(2-氯苯基)甲氧基]苯甲酸；2-(2-氯苄基)氧基苯甲酸
• 英文名称: 2-((2-chlorobenzyl)oxy)benzoic acid
• 英文别名: 2-(2-chlorobenzyloxy)benzoic acid；2-(2-Chlorbenzyloxy)-benzoesaeure；2-[(2-Chlorobenzyl)oxy]benzoic acid；2-[(2-chlorophenyl)methoxy]benzoic acid
• CAS: 52803-70-0
• 化学式: C₁₄H₁₁ClO₃
• mdl: MFCD02724735
• 分子量: 262.693
• InChiKey: WIMYONIKOLZLBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  2-(2-氯苄氧基)-苯甲酸 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 72.0h， 以25%的产率得到6H-苯并[c]苯并吡喃
  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
• 作为产物：
  描述：

  2-氯甲苯 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 potassium hydroxide 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 水 、 丙酮 为溶剂， 反应 8.0h， 生成 2-(2-氯苄氧基)-苯甲酸
  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：——
• FR2204351
  申请人：——

  公开号：——

  公开（公告）日：——
• PIPERAZINE DERIVATIVES AS ALPHA 1A-ADRENERGIC RECEPTOR ANTAGONISTS
  申请人：RECORDATI INDUSTRIA CHIMICA E FARMACEUTICA S.p.a.

  公开号：EP0711288A1

  公开（公告）日：1996-05-15