4-[(4-氯苄基)氧基]-3-乙氧基苯甲醛 | 299441-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-[(4-氯苄基)氧基]-3-乙氧基苯甲醛
• 中文别名: 4-[(4-氯苯基)甲氧基]-3-乙氧基苯甲醛；4-(4-氯苄基)氧基-3-乙氧基-苯甲醛
• 英文名称: 4-(4-chlorobenzyloxy)-3-ethoxybenzaldehyde
• 英文别名: 4-[(4-Chlorobenzyl)oxy]-3-ethoxybenzaldehyde；4-[(4-chlorophenyl)methoxy]-3-ethoxybenzaldehyde
• CAS: 299441-96-6
• 化学式: C₁₆H₁₅ClO₃
• mdl: MFCD01191265
• 分子量: 290.746
• InChiKey: RKDKWRMABXGUPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2913000090

反应信息

• 作为反应物：
  描述：

  4-[(4-氯苄基)氧基]-3-乙氧基苯甲醛 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 29.0h， 生成 N-(4-(4-chlorobenzyloxy)-3-ethoxybenzyl)-1-(pyridin-4-yl)methanamine
  参考文献：
  名称：

  Vanillin-derived antiproliferative compounds influence Plk1 activity

  摘要：

  We synthesized a series of vanillin-derived compounds and analyzed them in HeLa cells for their effects on the proliferation of cancer cells. The molecules are derivatives of the lead compound SBE13, a potent inhibitor of the inactive conformation of human polo-like kinase 1 (Plk1). Some of the new designs were able to inhibit cancer cell proliferation to a similar extent as the lead structure. Two of the compounds ((({4-[(6-chloropyridin-3-yl)methoxy]-3-methoxyphenyl}methyl)(pyridin-4-ylmethyl)amine) and (({4-[(4-chlorophenyl)methoxy]-3-methoxyphenyl}methyl)(pyridin-4-ylmethyl)amine)) were much stronger in their capacity to reduce HeLa cell proliferation and turned out to potently induce apoptosis and reduce Plk1 kinase activity in vitro. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.09.015
• 作为产物：
  描述：

  乙基香兰素 、 4-氯氯苄 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以75%的产率得到4-[(4-氯苄基)氧基]-3-乙氧基苯甲醛
  参考文献：
  名称：

  Vanillin-derived antiproliferative compounds influence Plk1 activity

  摘要：

  We synthesized a series of vanillin-derived compounds and analyzed them in HeLa cells for their effects on the proliferation of cancer cells. The molecules are derivatives of the lead compound SBE13, a potent inhibitor of the inactive conformation of human polo-like kinase 1 (Plk1). Some of the new designs were able to inhibit cancer cell proliferation to a similar extent as the lead structure. Two of the compounds ((({4-[(6-chloropyridin-3-yl)methoxy]-3-methoxyphenyl}methyl)(pyridin-4-ylmethyl)amine) and (({4-[(4-chlorophenyl)methoxy]-3-methoxyphenyl}methyl)(pyridin-4-ylmethyl)amine)) were much stronger in their capacity to reduce HeLa cell proliferation and turned out to potently induce apoptosis and reduce Plk1 kinase activity in vitro. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.09.015

文献信息

• Studies on antidiabetic agents. III. 5-Arylthiazolidine-2,4-diones as potent aldose reductase inhibitors.
  作者：TAKASHI SOHDA、KATSUTOSHI MIZUNO、EIKO IMAMIYA、HIROYUKI TAWADA、KANJI MEGURO、YUTAKA KAWAMATSU、YUJIRO YAMAMOTO

  DOI：10.1248/cpb.30.3601

  日期：——

  Thiazolidine-2, 4-dione derivatives having one or two substituent (s) such as phenyl, heteryl and alkyl group (s) at the 5-position were synthesized and evaluated as aldose reductase inhibitors. Inhibition by the active compounds of the swelling of the lens in a rat-lens-culture assay was also measured. Among these compounds, a series of 5-(3, 4-dialkoxyphenyl) thiazolidine-2, 4-diones showed pronounced activities in both assays. Structure-activity relationships are discussed and a new approach to the synthesis of 5-arylthiazolidine-2, 4-diones is described.

  具有一个或两个取代基（如苯基、杂基和烷基）的噻唑烷-2,4-二酮衍生物在5位合成并评估为醛糖还原酶抑制剂。在鼠晶状体培养检测中，活性化合物的抑制作用也被测量。在这些化合物中，一系列5-(3,4-二烷氧基苯基)噻唑烷-2,4-二酮在两种检测中显示出显著的活性。结构-活性关系进行了讨论，并描述了一种合成5-芳基噻唑烷-2,4-二酮的新方法。
• [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。
• Agonists and Antagonists of the S1P5 Receptor, and Methods of Use Thereof
  申请人：Harris Christopher M.

  公开号：US20100216762A1

  公开（公告）日：2010-08-26

  Disclosed are compounds that are agonists or antagonists of the S1P 5 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.

  本发明涉及一种作为S1P5受体激动剂或拮抗剂的化合物，包括该化合物的组合物以及使用该化合物和组合物的方法。在某些实施例中，该化合物是1-苄基氮杂环丙氨酸衍生物。在某些实施例中，该方法涉及神经病性疼痛和/或神经退行性疾病的治疗。在某些实施例中，该化合物可以与第二种治疗药物联合使用。
• VOLTAGE-GATED SODIUM CHANNEL BLOCKERS
  申请人：Boehm Jeffrey Charles

  公开号：US20130023541A1

  公开（公告）日：2013-01-24

  The present invention relates to voltage-gated sodium channel blocker intermediates, compounds and dimers, corresponding pharmaceutical compositions, compound preparation and treatment methods for respiratory or respiratory tract diseases.

  本发明涉及电压门控钠通道阻滞剂中间体、化合物和二聚体，相应的药物组合物、化合物制备和治疗呼吸或呼吸道疾病的方法。
• Targeting the Grb2 cSH3 domain: Design, synthesis and biological evaluation of the first series of modulators
  作者：Marianna Bufano、Michela Puxeddu、Marianna Nalli、Giuseppe La Regina、Angelo Toto、Francesca Romana Liberati、Alessio Paone、Francesca Cutruzzolà、Domiziana Masci、Chiara Bigogno、Giulio Dondio、Romano Silvestri、Stefano Gianni、Antonio Coluccia

  DOI：10.1016/j.bioorg.2023.106607

  日期：2023.9

  Growth factor receptor bound protein 2 (Grb2) is an adaptor protein featured by a nSH3-SH2-cSH3 domains. Grb2 finely regulates important cellular pathways such as growth, proliferation and metabolism and a minor lapse of this tight control may totally change the entire pathway to the oncogenic. Indeed, Grb2 is found overexpressed in many tumours type. Consequently, Grb2 is an attractive therapeutic target

  生长因子受体结合蛋白 2 (Grb2) 是一种接头蛋白，具有 nSH3-SH2-cSH3 结构域。Grb2 精细调节重要的细胞途径，如生长、增殖和代谢，这种严格控制的轻微失误可能会完全改变整个致癌途径。事实上，Grb2 在许多肿瘤类型中都过度表达。因此，Grb2是开发新抗癌药物的一个有吸引力的治疗靶点。 在此，我们报道了一系列Grb2抑制剂的合成和生物学评价，这些抑制剂是从本研究单位已经报道的一种命中化合物开始开发的。通过动力学结合实验对新合成的化合物进行了评估，并在一小组癌细胞中对最有前途的衍生物进行了分析。五个新合成的衍生物被证明能够以一位数微摩尔浓度的有价值的抑制浓度结合目标蛋白。该系列中活性最强的化合物衍生物12，对胶质母细胞瘤和卵巢癌细胞的抑制浓度约为6 μM，对肺癌细胞的IC 50为1.67。对于衍生物12，还评估了代谢稳定性和 ROS 产生。生物学数据与对接研究一起使早期结构活性关系合理化。