1-[5-(4-Chloroanilino)-1,2,4-thiadiazol-3-YL]acetone | 443110-91-6

• 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-(4-Chloroanilino)-1,2,4-thiadiazol-3-YL]acetone
• 英文别名: 1-[5-(4-chloroanilino)-1,2,4-thiadiazol-3-yl]propan-2-one
• CAS: 443110-91-6
• 化学式: C₁₁H₁₀ClN₃OS
• 分子量: 267.739
• InChiKey: VRAZYDKVCRLSEA-UHFFFAOYSA-N

物化性质

• 沸点：
  420.4±55.0 °C(Predicted)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 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：
  5

反应信息

• 作为反应物：
  描述：

  1-[5-(4-Chloroanilino)-1,2,4-thiadiazol-3-YL]acetone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-[5-(4-chlorophenylamino)-1,2,4-thiadiazol-3-yl]-propan-2-ol
  参考文献：
  名称：

  Novel 1,2,4-Thiadiazole Derivatives as Potent Neuroprotectors: Approach to Creation of Bioavailable Drugs

  摘要：

  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.

  DOI：

  10.1021/mp300011r
• 作为产物：
  描述：

  3-氨基-5-甲基异恶唑 、 4-氯异硫氰酸苯酯 以 乙腈 为溶剂， 生成 1-[5-(4-Chloroanilino)-1,2,4-thiadiazol-3-YL]acetone
  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

• Conjugates of tacrine and 1,2,4-thiadiazole derivatives as new potential multifunctional agents for Alzheimer’s disease treatment: Synthesis, quantum-chemical characterization, molecular docking, and biological evaluation
  作者：Galina F. Makhaeva、Nadezhda V. Kovaleva、Natalia P. Boltneva、Sofya V. Lushchekina、Elena V. Rudakova、Tatyana S. Stupina、Alexey A. Terentiev、Igor V. Serkov、Alexey N. Proshin、Eugene V. Radchenko、Vladimir A. Palyulin、Sergey O. Bachurin、Rudy J. Richardson

  DOI：10.1016/j.bioorg.2019.103387

  日期：2020.1

  radical-scavenging capacity. Conjugates 5 had higher anti-BChE activity and greater anti-aggregant potential as well relatively lower potency against carboxylesterase than compounds 4. Quantum-mechanical (QM) characterization agreed with NMR data to identify the most stable forms of conjugates for docking studies, which showed that the compounds bind to both CAS and PAS of AChE consistent with mixed reversible

  我们合成了他克林与1,2,4-噻二唑衍生物的共轭物，它们通过两个不同的间隔基戊基氨基丙烯（化合物4）和戊基氨基丙烷（化合物5）连接，作为治疗阿尔茨海默氏病（AD）的潜在药物。结合物有效抑制胆碱酯酶，对丁酰胆碱酯酶（BChE）起主要作用。它们还可以有效地从乙酰胆碱酯酶（AChE）的外围阴离子位点（PAS）置换丙啶，表明它们可以阻断AChE诱导的β-淀粉样蛋白聚集。另外，这些化合物表现出高的自由基清除能力。与化合物4相比，缀合物5具有更高的抗BChE活性和更高的抗聚集潜力，并且相对于羧酸酯酶的效力相对较低。量子力学（QM）表征与NMR数据相符，以鉴定最稳定形式的偶联物，用于对接研究，这表明化合物与AChE的CAS和PAS结合均具有可逆的混合抑制作用。结合物4是更有效的自由基清除剂，与HOMO在烯胺-噻二唑系统中的定位一致。计算研究表明，所有结合物均预期具有良好的肠道吸收能力，而结合物4和5则分
• 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，
• Novel binary compounds derived from 1,2,4-thiadiazole
  作者：A. N. Proshin、I. V. Serkov、S. O. Bachurin

  DOI：10.1134/s0012500812090017

  日期：2012.9
• 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.
• Towards the rational design of novel drugs based on solubility, partitioning/distribution, biomimetic permeability and biological activity exemplified by 1,2,4-thiadiazole derivatives
  作者：T. V. Volkova、I. V. Terekhova、O. I. Silyukov、A. N. Proshin、A. Bauer-Brandl、G. L. Perlovich

  DOI：10.1039/c6md00545d

  日期：——

  Novel 1,2,4-thiadiazole derivatives as potent neuroprotectors were synthesized and their solubility, distribution coefficients, permeability and biological properties were studied.

  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。