2-(4-(3,4-dichlorobenzyloxy)phenyl)acetaldehyde | 1334930-93-6

• 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: 2-(4-(3,4-dichlorobenzyloxy)phenyl)acetaldehyde
• 英文别名: 2-[4-[(3,4-Dichlorophenyl)methoxy]phenyl]acetaldehyde；2-[4-[(3,4-dichlorophenyl)methoxy]phenyl]acetaldehyde
• CAS: 1334930-93-6
• 化学式: C₁₅H₁₂Cl₂O₂
• 分子量: 295.165
• InChiKey: SEBZSSHAIHSJPF-UHFFFAOYSA-N

物化性质

• 沸点：
  427.9±40.0 °C(predicted)
• 密度：
  1.293±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-(3,4-dichlorobenzyloxy)phenyl)acetaldehyde 在 sulfur 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 ethyl 2-(4-chlorobenzamido)-5-(4-(3,4-dichlorobenzyloxy)phenyl)thiophene-3-carboxylate
  参考文献：
  名称：

  Design, synthesis and anti-tubercular evaluation of new 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives. Part 1

  摘要：

  A series of 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives were synthesized and evaluated for anti-tubercular activity. Among these compounds, 10d, 15, 12h and 12k inhibited Mycobacterium tuberculosis (Mtb) growth with MIC values between 1.9 and 7.7 mu M and low toxicity against VERO cells. The four compounds were also tested against multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) clinical strains, which were found to show moderate activity. In addition, molecular docking simulation was performed to position compounds 10d, 15, 12h and 12k into mtFabH active site to predict the probable binding mode. These studies thus suggest that the designed 2-amino-5-phenylthiophene-3-carboxylic acid scaffold may serve as new promising template for further elaboration as anti-TB drugs. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.018
• 作为产物：
  描述：

  3,4-二氯氯苄 在 2,2,6,6-四甲基哌啶氧化物 、 sodium bromite trihydrate 、 碳酸氢钠 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 24.5h， 生成 2-(4-(3,4-dichlorobenzyloxy)phenyl)acetaldehyde
  参考文献：
  名称：

  Design, synthesis and anti-tubercular evaluation of new 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives. Part 1

  摘要：

  A series of 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives were synthesized and evaluated for anti-tubercular activity. Among these compounds, 10d, 15, 12h and 12k inhibited Mycobacterium tuberculosis (Mtb) growth with MIC values between 1.9 and 7.7 mu M and low toxicity against VERO cells. The four compounds were also tested against multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) clinical strains, which were found to show moderate activity. In addition, molecular docking simulation was performed to position compounds 10d, 15, 12h and 12k into mtFabH active site to predict the probable binding mode. These studies thus suggest that the designed 2-amino-5-phenylthiophene-3-carboxylic acid scaffold may serve as new promising template for further elaboration as anti-TB drugs. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.018

文献信息

• RETINOIDS AND SMALL MOLECULES AS NRF2 ANTAGONISTS FOR USE IN THE TREATMENT OF DISEASES ASSOCIATED WITH ABNORMAL CELL PROLIFERATION
  申请人：The University Court of the University of Dundee

  公开号：EP2046308A2

  公开（公告）日：2009-04-15
• [EN] IMPROVEMENTS IN RELATION TO CANCER THERAPY<br/>[FR] AMÉLIORATIONS RELATIVES À LA THÉRAPIE ANTICANCÉREUSE
  申请人：UNIV DUNDEE

  公开号：WO2008012534A2

  公开（公告）日：2008-01-31

  [EN] The present invention relates to an improved assay for identifying compounds that may be of use in conjunction with cancer chemotherapeutic agents and anti-proliferative agents, to improve efficacy of such agents and/or render effective compounds with relatively little therapeutic activity. There is also provided a class of compounds identified by said assay which may be used in a combination therapy, with current and novel agents, to treat cancers and other diseases associated with abnormal host cell proliferation, such as psoriasis.
  [FR] Cette invention concerne une analyse améliorée permettant d'identifier des composés pouvant être utilisés conjointement à des agents chimiothérapeutiques contre le cancer et à des agents antiprolifératifs afin d'améliorer l'efficacité de ces agents et/ou de rendre efficaces des composés dont l'activité thérapeutique est relativement faible. Cette invention concerne également une classe de composés identifiés par ladite analyse pouvant être utilisés dans une polythérapie, conjointement à des agents connus et nouveaux, pour traiter des cancers et autres maladies associées à une prolifération anormale de cellules hôtes, telles que le psoriasis.
• Design, synthesis and anti-tubercular evaluation of new 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives. Part 1
  作者：Xiaoyun Lu、Baojie Wan、Scott G. Franzblau、Qidong You

  DOI：10.1016/j.ejmech.2011.05.018

  日期：2011.9

  A series of 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives were synthesized and evaluated for anti-tubercular activity. Among these compounds, 10d, 15, 12h and 12k inhibited Mycobacterium tuberculosis (Mtb) growth with MIC values between 1.9 and 7.7 mu M and low toxicity against VERO cells. The four compounds were also tested against multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) clinical strains, which were found to show moderate activity. In addition, molecular docking simulation was performed to position compounds 10d, 15, 12h and 12k into mtFabH active site to predict the probable binding mode. These studies thus suggest that the designed 2-amino-5-phenylthiophene-3-carboxylic acid scaffold may serve as new promising template for further elaboration as anti-TB drugs. (C) 2011 Elsevier Masson SAS. All rights reserved.