4-[(3-氯苄基)氧基]苯甲枉醛 | 59067-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-[(3-氯苄基)氧基]苯甲枉醛
• 英文名称: 4-((3-chlorobenzyl)oxy)benzaldehyde
• 英文别名: 4-(3-chloro benzyloxy) benzaldehyde；4-(3-chlorobenzyloxy)benzaldehyde；4-(3-chloro-benzyloxy)-benzaldehyde；4-(3-chlorobenzyloxy)-benzaldehyde；4-(3-Chlorbenzyloxy)benzaldehyd；4-[(3-Chlorophenyl)methoxy]benzaldehyde
• CAS: 59067-43-5
• 化学式: C₁₄H₁₁ClO₂
• mdl: MFCD02091000
• 分子量: 246.693
• InChiKey: QLYLREZHERJGAH-UHFFFAOYSA-N

物化性质

• 熔点：
  53-55°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi

反应信息

• 作为反应物：
  描述：

  4-[(3-氯苄基)氧基]苯甲枉醛 在 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 反应 10.25h， 生成 2-[[4-[(3-chlorophenyl)methoxy]phenyl]methylamino]-N,N-dimethylacetamide
  参考文献：
  名称：

  Synthesis and Anticonvulsant Activity of a New Class of 2-[(Arylalkyl)amino]alkanamide Derivatives

  摘要：

  Although most epilepsies are adequately treated by conventional antiepileptic therapy, there remains an unfulfilled need for safer and more effective anticonvulsant agents. Starting from milacemide, a weak anticonvulsant, and trying to elucidate its mechanism of action, we discovered a structurally novel class of potent and preclinically safe anticonvulsants. Here we report the structure-activity relationship (SAR) study within this series of compounds. Different parts of the structural lead 2-[[4-(3-chlorobenzoxy)benzyl]amino] acetamide (6) were thus varied (Figure 1), and many potent anticonvulsants were found. As an outcome of this study, 57 ((S)-2-[[4-(3-fluorobenzoxy)benzyl]amino]propanamide methanesulfonate, PNU-151774E) emerged as a promising candidate for further development for its potent anticonvulsant activity and outstanding therapeutic indexes (TIs) in different animal tests.

  DOI：

  10.1021/jm970599m
• 作为产物：
  描述：

  对羟基苯甲醛 、 间氯氯苄 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以98 %的产率得到4-[(3-氯苄基)氧基]苯甲枉醛
  参考文献：
  名称：

  Synthesis and Spectroscopy Characterizations of Some New Bis 1,3-thiazolidin-4-ones Derived from 4-hydroxybenzaldehyde Substrate

  摘要：

  通过三个主要的简便步骤，我们合成了一系列新型双-希夫碱和双-1,3-噻唑烷-4-酮衍生物：首先，在温和的条件下，4-羟基苯甲醛底物与邻氯、间氯和对氯苄基氯发生醚化反应。其次，4-((氯苄基)氧基)苯甲醛化合物与一些芳香族二胺在酸性环境中发生缩合反应，生成所需的双-希夫中间体。最后，通过在苯中与巯基乙酸进行回流反应，合成出所需的双 1,3-噻唑烷-4-酮产品，从而完成了实际的环化步骤，收率为 79-97%。

  DOI：

  10.13005/ojc/390508

文献信息

• Synthesis and structure–activity relationship study of novel quinazolinone-based inhibitors of MurA
  作者：Martina Hrast、Kaja Rožman、Marko Jukič、Delphine Patin、Stanislav Gobec、Matej Sova

  DOI：10.1016/j.bmcl.2017.05.064

  日期：2017.8

  is essential for peptidoglycan biosynthesis, and is therefore an important target for antibacterial drug discovery. We report the synthesis, in silico studies and extensive structure–activity relationships of a series of quinazolinone-based inhibitors of MurA from Escherichia coli. 3-Benzyloxyphenylquinazolinones showed promising inhibitory potencies against MurA, in the low micromolar range, with an

  MurA是肽聚糖生物合成必不可少的细胞内细菌酶，因此是抗菌药物发现的重要靶标。我们报告了一系列来自大肠杆菌的MurA的基于喹唑啉酮的抑制剂的合成，计算机模拟研究和广泛的结构-活性关系。3-苯甲氧基苯基喹唑啉酮类化合物在低微摩尔范围内显示出对MurA的抑制作用，最有效的衍生物的IC 50为8 µM（58）。此外，呋喃基取代的喹唑啉酮（38，46）的抗菌活性令人振奋，MIC浓度从1 µg / mL到8 µg / mL，并具有其MurA抑制能力。这些数据代表了开发新型抗菌剂以对抗不断增加的细菌耐药性的重要一步。
• 1-(Aralkoxyphenyl)-2-(bis-arylalkylamino)-alkanes
  申请人：Ciba-Geigy Corporation

  公开号：US04329367A1

  公开（公告）日：1982-05-11

  1-(Aralkoxyphenyl)-2 or 3-(bis-arylalkylamino)-alkanes, e.g. those of the formula: ##STR1## or therapeutically acceptable salts thereof are hypotensive and cardioactive agents.

  1-(芳氧基苯基)-2或3-(双芳基烷基氨基)-烷烃，例如以下结构的化合物：##STR1##或其治疗上可接受的盐是降压和心脏活性药物。
• [EN] AGONISTS AND ANTAGONISTS OF THE S1P5 RECEPTOR, AND METHODS OF USES THEREOF<br/>[FR] AGONISTES ET ANTAGONISTES DU RÉCEPTEUR S1P5, ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ABBOTT LAB

  公开号：WO2010093704A1

  公开（公告）日：2010-08-19

  Disclosed are compounds that are agonists or antagonists of the S1P5 receptor, compositions comprising said compounds, and methods of using said compounds and compositions. In certain embodiments, said compounds are 1-benzylazetidine-3-carboxylic acid derivatives. In certain embodiments, said methods relate to the treatment of neuropatic pain and/or a neurodegenerative disorder. In certain embodiments, said compounds may be used in combination with a second therapeutic agent.

  本文披露了作为S1P5受体激动剂或拮抗剂的化合物，包括含有这些化合物的组合物，以及使用这些化合物和组合物的方法。在某些实施例中，这些化合物是1-苄基氮杂环丙氨酸衍生物。在某些实施例中，这些方法涉及治疗神经痛和/或神经退行性疾病。在某些实施例中，这些化合物可以与第二治疗剂结合使用。
• [EN] SUBSTITUTED ISOXAZOLE AMIDE COMPOUNDS AS INHIBITORS OF STEAROYL-COA DESATURASE 1 (SCD1)<br/>[FR] COMPOSÉS D'AMIDE D'ISOXAZOLE SUBSTITUÉS EN TANT QU'INHIBITEURS DE STÉAROYL-COA DÉSATURASE 1 (SCD1)
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014086704A1

  公开（公告）日：2014-06-12

  The invention is concerned with a compound of formula (I) and pharmaceutically acceptable salts thereof. In addition, the present invention relates to methods of manufacturing and using the compound of formula (I) as well as pharmaceutical compositions containing such compounds. The compound of formula (I) are SCD1 inhibitors and may be useful in treating cancer.

  该发明涉及一种具有化学式(I)及其药学上可接受的盐的化合物。此外，本发明涉及制造和使用化学式(I)化合物的方法，以及含有这种化合物的药物组合物。化学式(I)的化合物是SCD1抑制剂，可能在治疗癌症方面有用。
• Synthesis and Analysis of Anticonvulsant Activities of New 4-[2-(4- alkoxybenzylamino)ethyl]-2H-1,2,4-triazol-3(4H)-one Derivatives
  作者：Qing-Kun Shen、Shi-Ben Wang、Guo-Hua Gong、Xiu-Mei Yin、Zhe-Shan Quan

  DOI：10.2174/1570180812666141111235746

  日期：2015.3.24

  The present study involved the design and synthesis of new substituted 4-[2-(4- alkoxybenzylamino) ethyl]-2H-1,2,4-triazol-3(4H)-one derivatives (8a-w) starting from 1,2- ethanediamine. The final compounds were screened for their in vivo anticonvulsant activities and neurotoxicities by maximal electroshock (MES) and rotarod tests, respectively. Among the compounds studied, 4-[2-(4-butoxybenzylamino)ethyl]-2H-1,2,4-triazol-3(4H)-one hydrochloride (8b) was found by intraperitoneal administration in mice to be the most potent compound with a median effective dose (ED50) value of 33.2 mg/kg and a high protective index (PI) value of 11.4. Compound 8b showed significant oral activity against MES-induced seizures in mice with an ED50 value of 83.1 mg/kg and a PI of 18.1. The results demonstrated that compound 8b possessed better anticonvulsant activity and higher safety than the marketed drug carbamazepine.

  本研究涉及从1,2-乙二胺出发设计合成新型取代的4-[2-(4-烷氧基苯基氨基)乙基]-2H-1,2,4-三唑-3(4H)-酮衍生物（8a-w）。最终化合物通过最大电击（MES）和转杆测试分别筛选其在体抗癫痫活性和神经毒性。在研究的化合物中，4-[2-(4-丁氧基苯基氨基)乙基]-2H-1,2,4-三唑-3(4H)-酮盐酸盐（8b）通过腹腔给药在小鼠中被发现是最有效的化合物，其中位有效剂量（ED50）为33.2 mg/kg，保护指数（PI）值为11.4。化合物8b对MES诱导的小鼠癫痫发作表现出显著的口服活性，ED50值为83.1 mg/kg，PI为18.1。结果表明，化合物8b具有比市场药物卡马西平更好的抗癫痫活性和更高的安全性。