6-(4-chlorobenzyloxy)-2-naphthaldehyde | 1417915-75-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(4-chlorobenzyloxy)-2-naphthaldehyde
• CAS: 1417915-75-3
• 化学式: C₁₈H₁₃ClO₂
• 分子量: 296.753
• InChiKey: ZMUMHDLTEFFJHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-(4-chlorobenzyloxy)-2-naphthaldehyde 、 盐酸二甲双胍 在 溶剂黄146 作用下， 以70%的产率得到6-(6-((4-chlorobenzyl)oxy)naphthalen-2-yl)-N²,N²-dimethyl-3,6-dihydro-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  芳基取代的二氢三嗪衍生物的合成和抗菌活性的评价

  摘要：

  设计并合成了包含查尔酮（13a–i），苯氧基苯乙酮（14a–b），苄苯（15a–c），萘氧基苯乙酮（16a–b）和苄基萘（17a–h）部分的五个系列的二氢三嗪衍生物。评估了这些化合物对几种革兰氏阳性和革兰氏阴性细菌菌株以及单一真菌的抗菌和抗真菌活性。发现化合物17h是所有测试化合物中最有效的，对几种革兰氏阳性菌（金黄色葡萄球菌4220和QRSA CCARM 3505）和革兰氏阴性菌（大肠杆菌）的MIC值为0.5μg/ mL1924）菌株。但是，该化合物对铜绿假单胞菌2742和鼠伤寒沙门氏菌2421无活性，表明其抗菌谱与阳性对照加替沙星和莫西沙星相似。在人正常肝细胞中评估了化合物13i，16b和17h的细胞毒活性。

  DOI：

  10.1016/j.bmcl.2018.03.037
• 作为产物：
  描述：

  4-氯氯苄 、 6-羟基-2-萘甲醛 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以90%的产率得到6-(4-chlorobenzyloxy)-2-naphthaldehyde
  参考文献：
  名称：

  Synthesis and Antimicrobial Activities of Some Novel 2,3-Substituted-1,3-Thiazolidin-4-ones Derived from 2-Amino-1,3-thiazole

  摘要：

  新型2,3取代的1,3-噻唑烷-4-酮（6a-f）是通过将2-[6-(4-氯苄氧)-2-萘烯]-4-(4-取代苯基)-5-甲基-1,3-噻唑（5a-f）与巯基乙酸在苯中缩合制备的。合成的化合物通过元素分析、1H NMR、13C NMR和FT-IR进行表征。所制备的化合物在体外针对两种革兰阳性菌金黄色葡萄球菌、表皮葡萄球菌和两种革兰阴性菌大肠杆菌、铜绿假单胞菌进行抗菌活性筛选，以及针对两种真菌菌株白色念珠菌、克鲁斯氏念珠菌进行抗真菌活性评估，使用环丙沙星、氨苄青霉素和酮康唑，最低抑菌浓度（MIC）值为10 mcg/L在DMSO中。化合物6a和6d相较于本研究中使用的参考药物显示出良好的抗菌和抗真菌活性。

  DOI：

  10.14233/ajchem.2017.20925

文献信息

• Synthesis and biological evaluation of dihydrotriazine derivatives as potential antibacterial agents
  作者：Tian-Yi Zhang、Chao Li、Yu-Shun Tian、Jia-Jun Li、Liang-Peng Sun、Chang-Ji Zheng、Hu-Ri Piao

  DOI：10.1016/j.cclet.2017.05.022

  日期：2017.8

  Abstract A series of 1,4-dihydro-1,3,5-triazine derivatives were designed and synthesized and their antibacterial and antifungal activities were evaluated. Most of the synthesized compounds showed potent inhibition of several Gram-positive bacterial strains (including multidrug-resistant clinical isolates) and Gram-negative bacterial strains, with minimum inhibitory concentrations (MICs) in the range

  摘要设计合成了一系列的1,4-二氢-1,3,5-三嗪衍生物，并对其抗菌和抗真菌活性进行了评价。大多数合成的化合物对几种革兰氏阳性细菌菌株（包括耐多药临床分离株）和革兰氏阴性细菌菌株均具有有效的抑制作用，其最低抑菌浓度（MIC）在2.1-181.2μmol/ L范围内。化合物7a和7c对革兰氏阳性菌（例如金黄色葡萄球菌4220），革兰氏阴性菌（例如大肠杆菌1924）和白色念珠菌7535表现出最强的抑制活性，MIC值为2.1或4.1μmol/ L. 尤其是，化合物7a最有效，对四种具有多重耐药性的革兰氏阳性细菌菌株的MIC为2.1μmol/ L。
• Synthesis and biological evaluation of tryptophan-derived rhodanine derivatives as PTP1B inhibitors and anti-bacterial agents
  作者：Hongyan Liu、Danwen Sun、Hang Du、Changji Zheng、Jingya Li、Huri Piao、Jia Li、Liangpeng Sun

  DOI：10.1016/j.ejmech.2019.03.059

  日期：2019.6

  Several series of novel tryptophan-derived rhodanine derivatives were synthesized and identified as potential competitive PTP1B inhibitors and antibacterial agents. Among the compounds studied, 10b was found to have the best in vitro inhibition activity against PTP1B (IC50= 0.36 +/- 0.02 mu M). In addition, the compounds also showed potent inhibition against other PTPs, especially CDC25B. Molecular docking analysis demonstrated that compounds 7c and 10b could occupy both the catalytic site and the adjacent pTyr binding site simultaneously. The compounds also showed higher levels of activity against gram-positive strains, the gram-negative strain Escherichia coli 1924, and multidrug-resistant gram-positive bacterial strains. Compounds 7c, 8c, 9e, 10a, and 10c had comparable or more potent antibacterial activity than the positive controls. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Synthesis and potential antibacterial activity of new rhodanine-3-acetic acid derivatives
  作者：Jing Miao、Chang-Ji Zheng、Liang-Peng Sun、Ming-Xia Song、Li-Li Xu、Hu-Ri Piao

  DOI：10.1007/s00044-012-0417-z

  日期：2013.9

  A series of rhodanine-3-acetic acid derivatives were synthesized and investigated for their antibacterial activity against gram-positive bacteria including multidrug-resistant clinical isolates. Among these compounds, 6k with a MIC of 2 mu g/mL was as active as the standard drug (norfloxacin) but less active than oxacillin against S. aureus. The compounds 6b, 6e, 6h, 6k, 6n, and 6u presented better activities against multidrug-resistant Staphylococcus aureus than the standard drugs (norfloxacin and oxacillin), especially 6k with a MIC of 1 mu g/mL. However, none of the compounds were active against gram-negative bacteria at 64 mu g/mL.