1-{5-[(3-Chloro-4-fluorophenyl)amino]-1,2,4-thiadiazol-3-yl}propan-2-one | 443110-73-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-{5-[(3-Chloro-4-fluorophenyl)amino]-1,2,4-thiadiazol-3-yl}propan-2-one
• 英文别名: 1-[5-(3-chloro-4-fluoroanilino)-1,2,4-thiadiazol-3-yl]propan-2-one
• CAS: 443110-73-4
• 化学式: C₁₁H₉ClFN₃OS
• mdl: MFCD03176012
• 分子量: 285.729
• InChiKey: PVTOEOLJKUYXHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-{5-[(3-Chloro-4-fluorophenyl)amino]-1,2,4-thiadiazol-3-yl}propan-2-one 在 甲醇 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N-[3-(2-benzylaminopropyl)-[1,2,4]thiadiazol-5-yl]-3-chloro-4-fluorophenylamine
  参考文献：
  名称：

  5-Amino-3-(2-aminopropyl)-1,2,4-thiadiazoles as the basis of hybrid multifunctional compounds

  摘要：

  从侧链中含有氨基的 1,2,4-噻二唑开始，我们开发了一种合成混合多功能化合物的方法。

  DOI：

  10.1007/s11172-014-0563-1
• 作为产物：
  描述：

  3-氨基-5-甲基异恶唑 、 3-氯-4-氟苯基异硫氰酸酯 以 乙腈 为溶剂， 生成 1-{5-[(3-Chloro-4-fluorophenyl)amino]-1,2,4-thiadiazol-3-yl}propan-2-one
  参考文献：
  名称：

  Towards the rational design of novel drugs based on solubility, partitioning/distribution, biomimetic permeability and biological activity exemplified by 1,2,4-thiadiazole derivatives

  摘要：

  合成了新型1,2,4-噻二唑衍生物，作为有效的神经保护剂，并研究了它们的溶解度、分配系数、渗透性和生物学性质。

  DOI：

  10.1039/c6md00545d

文献信息

• 1,2,4-Thiadiazoles as promising multifunctional agents for treatment of neurodegenerative diseases
  作者：G. F. Makhaeva、A. N. Proshin、N. P. Boltneva、E. V. Rudakova、N. V. Kovaleva、O. G. Serebryakova、I. V. Serkov、S. O. Bachurin

  DOI：10.1007/s11172-016-1486-9

  日期：2016.6

  substituents at position 3 of the thiadiazole ring were carried out, in particular, their esterase profile and antioxidant properties. It was found that the presence in the molecule of 2-aminopropyl fragment determines an efficient and selective inhibition of butyrylcholinesterase as compared to acetylcholinesterase and carboxylesterase, with radical-scavenging activity being weak. The compounds containing

  对在噻二唑环的第 3 位含有不同取代基的新型 3-取代 5-苯胺基-1,2,4-噻二唑的性质进行了详细研究，特别是它们的酯酶谱和抗氧化性质。发现与乙酰胆碱酯酶和羧酸酯酶相比，2-氨基丙基片段分子中的存在决定了对丁酰胆碱酯酶的有效和选择性抑制，自由基清除活性较弱。含有2-氨基丙烯基片段的化合物具有高自由基清除活性，弱抑制胆碱酯酶，并表现出抗羧酸酯酶活性。3-取代 5-anilino-1,2 的广泛活性，
• 1,2,4-Thiadiazole derivatives as effective NMDA receptor blockers with anticholinesterase activity and antioxidant properties
  作者：V. V. Grigoriev、G. F. Makhaeva、A. N. Proshin、N. V. Kovaleva、E. V. Rudakova、N. P. Boltneva、A. V. Gabrel´yan、B. V. Lednev、S. O. Bachurin

  DOI：10.1007/s11172-017-1890-9

  日期：2017.7

  with different substituents at position 3 were synthesized and their influence on the key binding sites of NMDA receptors, inhibitory activity against acetylcholinesterase, butyrylcholinesterase, and carboxylesterase, as well as antioxidant properties were studied. The compounds with a 2-aminopropyl fragment were found to be efficient blockers of allosteric modulator [3H]ifenprodil binding site of the

  合成了新的3位不同取代基的5-苯胺基-1,2,4-噻二唑衍生物，并研究了它们对NMDA受体关键结合位点、乙酰胆碱酯酶、丁酰胆碱酯酶和羧酸酯酶的抑制活性以及抗氧化性能的影响. 发现具有 2-氨基丙基片段的化合物是含有 NR2B 的 NMDA 受体和中度丁酰胆碱酯酶抑制剂的变构调节剂 [3H] 芬普地尔结合位点的有效阻断剂。发现一些化合物能够同时阻断 NMDA 受体的 [3H] 芬普地尔和通道内 [3H]MК-801 结合位点。含有 2-氨基丙烯基片段的化合物不表现出对 NMDA 受体和丁酰胆碱酯酶的活性，但表现出高自由基清除活性。
• Novel 1,2,4-Thiadiazole Derivatives as Potent Neuroprotectors: Approach to Creation of Bioavailable Drugs
  作者：German L. Perlovich、Alexey N. Proshin、Tatyana V. Volkova、Ludmila N. Petrova、Sergey O. Bachurin

  DOI：10.1021/mp300011r

  日期：2012.8.6

  Novel 1,2,4-thiadiazole derivatives as potent neuroprotectors were synthesized and identified. Their ability to inhibit the glutamate stimulated Ca uptake was measured. Permeation experiments on the phospholipid membranes were conducted, and the apparent permeability coefficients were obtained. The partition coefficients in n-octanol/buffer (pH 7.4) and n-hexane/buffer (pH 7.4) immiscible phases (as model systems for characterizing gastrointestinal tract membranes and BBB) were determined. A classification of the studied compounds from the standpoint of "permeability-activity" properties was proposed.