N-[(3-chlorophenyl)methyl]-N-[2-[(17-methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-yl)oxy]ethyl]-2-(1,2,4-triazol-1-yl)ethanamine;chloride | 1383981-90-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: N-[(3-chlorophenyl)methyl]-N-[2-[(17-methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-yl)oxy]ethyl]-2-(1,2,4-triazol-1-yl)ethanamine;chloride
• CAS: 1383981-90-5
• 化学式: C₃₂H₃₁ClN₅O₄*Cl
• 分子量: 620.535
• InChiKey: WPWMFLMMSHKBBW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-Chlor-α--toluol 在 三溴化磷 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 N-[(3-chlorophenyl)methyl]-N-[2-[(17-methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-yl)oxy]ethyl]-2-(1,2,4-triazol-1-yl)ethanamine;chloride
  参考文献：
  名称：

  Berberine azoles as antimicrobial agents: synthesis, biological evaluation and their interactions with human serum albumin

  摘要：

  合成并表征了一系列小檗碱噁唑化合物，采用了核磁共振（NMR）、红外光谱（IR）、质谱（MS）和高分辨率质谱（HRMS）等技术。对所有新制备的化合物进行了抗菌活性筛选。生物活性实验表明，大多数小檗碱噁唑化合物表现出良好的抗菌活性。特别是化合物7a在抑制变形杆菌和抗念珠菌微球菌方面显示出显著效果，其活性与参考药物相当甚至更好。化合物7a与人血清白蛋白（HSA）的结合行为表明，疏水作用和氢键在化合物7a与HSA的结合中起着重要作用。分子对接实验表明，化合物7a对HSA具有适度亲和力，而且理论计算结果与实验结果一致。

  DOI：

  10.1039/c3md00032j

文献信息

• Berberine azoles as antimicrobial agents: synthesis, biological evaluation and their interactions with human serum albumin
  作者：Shao-Lin Zhang、Juan-Juan Chang、Guri L. V. Damu、Rong-Xia Geng、Cheng-He Zhou

  DOI：10.1039/c3md00032j

  日期：——

  A series of berberine azoles was synthesized and characterized by NMR, IR, MS and HRMS spectroscopy. All the newly prepared compounds were screened for their antimicrobial activities. Bioactivity assays manifested that most of the berberine azoles exhibited good antimicrobial activities. Especially compound 7a displayed remarkable anti-Proteus vulgaris and anti-Candida mycoderma efficacies, which were comparable to or even better than for the reference drugs. The binding behavior of compound 7a to human serum albumin (HSA) revealed that hydrophobic interactions and hydrogen bonds play important roles in the association of compound 7a with HSA. Molecular docking experiments showed that compound 7a has moderate affinity to HSA, and the theoretical calculations were in accordance with the experimental results.

  合成并表征了一系列小檗碱噁唑化合物，采用了核磁共振（NMR）、红外光谱（IR）、质谱（MS）和高分辨率质谱（HRMS）等技术。对所有新制备的化合物进行了抗菌活性筛选。生物活性实验表明，大多数小檗碱噁唑化合物表现出良好的抗菌活性。特别是化合物7a在抑制变形杆菌和抗念珠菌微球菌方面显示出显著效果，其活性与参考药物相当甚至更好。化合物7a与人血清白蛋白（HSA）的结合行为表明，疏水作用和氢键在化合物7a与HSA的结合中起着重要作用。分子对接实验表明，化合物7a对HSA具有适度亲和力，而且理论计算结果与实验结果一致。
• Novel berberine triazoles: Synthesis, antimicrobial evaluation and competitive interactions with metal ions to Human Serum Albumin
  作者：Shao-Lin Zhang、Juan-Juan Chang、Guri L.V. Damu、Bo Fang、Xiang-Dong Zhou、Rong-Xia Geng、Cheng-He Zhou

  DOI：10.1016/j.bmcl.2012.12.036

  日期：2013.2

  A series of novel berberine triazoles were synthesized and characterized by IR, NMR, MS and HRMS spectra. All target compounds and their precursors were screened for antimicrobial activities in vitro against four Gram-positive bacteria, four Gram-negative bacteria and two fungal strains. Bioactive assay indicated that most of the prepared compounds exhibited good antibacterial and antifungal activities with low MIC values ranging from 2 to 64 mu g/mL, which were comparable to or even better than the reference drugs Berberine, Chloromycin, Norfloxacin and Fluconazole. The competitive interactions between compound 5a and metal ions to Human Serum Albumin (HSA) revealed that the participation of Mg2+ Fe3+ ions in compound 5a-HSA association could result in the concentration increase of free compound 5a, shorten the storage time and half-life of compound 5a in the blood, thus improving its antimicrobial efficacy. (C) 2012 Elsevier Ltd. All rights reserved.