3-benzyl-4-methyl-5-(2-(prop-2-ynyloxy)ethyl)thiazol-3-ium Bromide | 1417745-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-benzyl-4-methyl-5-(2-(prop-2-ynyloxy)ethyl)thiazol-3-ium Bromide
• 英文别名: 3-Benzyl-4-methyl-5-(2-prop-2-ynoxyethyl)-1,3-thiazol-3-ium;bromide；3-benzyl-4-methyl-5-(2-prop-2-ynoxyethyl)-1,3-thiazol-3-ium;bromide
• CAS: 1417745-58-4
• 化学式: Br*C₁₆H₁₈NOS
• 分子量: 352.295
• InChiKey: KIQFEZDIFOJBNT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.41
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  41.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyl-4-methyl-5-(2-(prop-2-ynyloxy)ethyl)thiazol-3-ium Bromide 、 5-(2-azidoethyl)-3-benzyl-4-methylthiazol-3-ium bromide 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 1.0h， 以52%的产率得到3-benzyl-5-(2-(4-((2-(3-benzyl-4-methylthiazol-3-ium-5-yl)-ethoxy)methyl)-1H-1,2,3-triazol-1-yl)ethyl)-4-methylthiazol-3-ium dibromide
  参考文献：
  名称：

  New Bis-thiazolium Analogues as Potential Antimalarial Agents: Design, Synthesis, and Biological Evaluation

  摘要：

  Bis-thiazolium salts are able to inhibit phosphatidylcholine biosynthesis in Plasmodium and to block parasite proliferation in the low nanomolar range. However, due to their physicochemical properties (i.e., permanent cationic charges, the flexibility, and lipophilic character of the alkyl chain), the oral bioavailability of these compounds is low. New series of bis-thiazolium-based drugs have been designed to overcome this drawback. They feature linker rigidification via the introduction of aromatic rings and/or a decrease in the overall lipophilicity through the introduction of heteroatoms. On the basis of the structure-activity relationships, a few of the promising compounds (9, 10, and 11) were found to exhibit potent antimalarial in vitro and in vivo activities (EC50 < 10 nM and ED50 ip < 0.7 mg/kg).

  DOI：

  10.1021/jm3014585
• 作为产物：
  描述：

  4-甲基-5-(beta-羟乙基)噻唑 在 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.5h， 生成 3-benzyl-4-methyl-5-(2-(prop-2-ynyloxy)ethyl)thiazol-3-ium Bromide
  参考文献：
  名称：

  New Bis-thiazolium Analogues as Potential Antimalarial Agents: Design, Synthesis, and Biological Evaluation

  摘要：

  Bis-thiazolium salts are able to inhibit phosphatidylcholine biosynthesis in Plasmodium and to block parasite proliferation in the low nanomolar range. However, due to their physicochemical properties (i.e., permanent cationic charges, the flexibility, and lipophilic character of the alkyl chain), the oral bioavailability of these compounds is low. New series of bis-thiazolium-based drugs have been designed to overcome this drawback. They feature linker rigidification via the introduction of aromatic rings and/or a decrease in the overall lipophilicity through the introduction of heteroatoms. On the basis of the structure-activity relationships, a few of the promising compounds (9, 10, and 11) were found to exhibit potent antimalarial in vitro and in vivo activities (EC50 < 10 nM and ED50 ip < 0.7 mg/kg).

  DOI：

  10.1021/jm3014585