Tert-butyl 4-[5-(4-chloro-2-hydroxy-phenoxy)thiophene-2-carbonyl]piperazine-1-carboxylate | 1428627-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Tert-butyl 4-[5-(4-chloro-2-hydroxy-phenoxy)thiophene-2-carbonyl]piperazine-1-carboxylate
• 英文别名: tert-butyl 4-[5-(4-chloro-2-hydroxyphenoxy)thiophene-2-carbonyl]piperazine-1-carboxylate
• CAS: 1428627-06-8
• 化学式: C₂₀H₂₃ClN₂O₅S
• 分子量: 438.932
• InChiKey: SCLMNRGNCLBCLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Tert-butyl 4-[5-(4-chloro-2-hydroxy-phenoxy)thiophene-2-carbonyl]piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到[5-(4-Chloro-2-hydroxy-phenoxy)-2-thienyl]-piperazin-1-yl-methanone
  参考文献：
  名称：

  Design, synthesis, and biological activity of diaryl ether inhibitors of Toxoplasma gondii enoyl reductase

  摘要：

  Triclosan is a potent inhibitor of Toxoplasma gondii enoyl reductase (TgENR), which is an essential enzyme for parasite survival. In view of triclosan's poor druggability, which limits its therapeutic use, a new set of B-ring modified analogs were designed to optimize its physico-chemical properties. These derivatives were synthesized and evaluated by in vitro assay and TgENR enzyme assay. Some analogs display improved solubility, permeability and a comparable MIC50 value to that of triclosan. Modeling of these inhibitors revealed the same overall binding mode with the enzyme as triclosan, but the B-ring modifications have additional interactions with the strongly conserved Asn130. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.019
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 在 sodium chlorite 、 potassium dihydrogenphosphate 、 三溴化硼 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 68.0h， 生成 Tert-butyl 4-[5-(4-chloro-2-hydroxy-phenoxy)thiophene-2-carbonyl]piperazine-1-carboxylate
  参考文献：
  名称：

  Design, synthesis, and biological activity of diaryl ether inhibitors of Toxoplasma gondii enoyl reductase

  摘要：

  Triclosan is a potent inhibitor of Toxoplasma gondii enoyl reductase (TgENR), which is an essential enzyme for parasite survival. In view of triclosan's poor druggability, which limits its therapeutic use, a new set of B-ring modified analogs were designed to optimize its physico-chemical properties. These derivatives were synthesized and evaluated by in vitro assay and TgENR enzyme assay. Some analogs display improved solubility, permeability and a comparable MIC50 value to that of triclosan. Modeling of these inhibitors revealed the same overall binding mode with the enzyme as triclosan, but the B-ring modifications have additional interactions with the strongly conserved Asn130. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.019