1-[5-(3-chloro-phenylamino)-1,2,4-thiadiazol-3-yl]-propan-2-ol | 1361124-49-3

• 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-phenylamino)-1,2,4-thiadiazol-3-yl]-propan-2-ol
• 英文别名: 1-[5-(3-Chloro-phenylamino)-1,2,4-thiadiazol-3-yl]-propan-2-ol；1-[5-(3-chloroanilino)-1,2,4-thiadiazol-3-yl]propan-2-ol
• CAS: 1361124-49-3
• 化学式: C₁₁H₁₂ClN₃OS
• 分子量: 269.755
• InChiKey: HISLNMGCIUVEIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[5-(3-chloro-phenylamino)-1,2,4-thiadiazol-3-yl]-propan-2-ol 、 β-环糊精 以 neat (no solvent) 为溶剂， 反应 1.0h， 生成 β-cyclodextrin complex 1:1 with 1-[5-(3-chloro-phenylamino)-1,2,4-thiadiazol-3-yl]propan-2-ol
  参考文献：
  名称：

  基于环糊精包合物的1,2,4-噻二唑衍生物的新水溶性剂型

  摘要：

  环糊精对合成的1- [5-（3-氯-苯基氨基）-1，2，4-噻二唑-3-基]-丙烷-2-醇（I）的水溶性的影响阿尔茨海默氏病的研究。首先，在水溶液中研究了具有不同环糊精的I包合物的形成。揭示了与β-和羟丙基-β-环糊精形成更稳定的复合物。接下来，通过机械研磨制备I与β-和羟丙基-β-环糊精的固体包合物，并通过粉末X射线衍射，FTIR光谱，显微镜和热化学方法证实它们以固态存在。在模拟生物环境的水溶液缓冲液中，对纯I及其与β-和羟丙基-β-环糊精的复合物进行了溶出度测试。观察到的复合物溶解程度和溶解速率的急剧增加归因于包合物的形成。

  DOI：

  10.1007/s10973-016-5955-z
• 作为产物：
  描述：

  5-甲基-3-异噁唑基异硫氰酸 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.5h， 生成 1-[5-(3-chloro-phenylamino)-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

文献信息

• Cocrystals of a 1,2,4-thiadiazole-based potent neuroprotector with gallic acid: solubility, thermodynamic stability relationships and formation pathways
  作者：Artem O. Surov、Andrei V. Churakov、Alexey N. Proshin、Xia-Lin Dai、Tongbu Lu、German L. Perlovich

  DOI：10.1039/c8cp02532k

  日期：——

  forms, namely anhydrous cocrystals with 2 : 1 and 1 : 1 drug/acid ratios ([TDZ : GA] (2 : 1), [TDZ : GA] (1 : 1)), and a hydrated one having 1 : 1 : 1 drug/acid/water stoichiometry ([TDZ : GA : H2O] (1 : 1 : 1)), have been formed by cocrystallization of the biologically active 1,2,4-thiadiazole derivative (TDZ) with gallic acid (GA). The thermodynamic stability relationships between the cocrystals

  三种不同的固体形式，即药物/酸比率为2：1和1：1的无水共晶体（[ TDZ  ：  GA ]（2：1），[ TDZ  ：  GA ]（1：1））和具有1的水合形式通过生物活性的1,2,4-噻二唑衍生物（TDZ）与生物活性的1,2,4-噻二唑衍生物（TDZ）共结晶形成了1：1：1的药物/酸/水化学计量比（[ TDZ  ：  GA  ：  H 2 O ]（1：1：1））。没食子酸（GA）。根据形成反应的吉布斯能量合理化了共晶之间的热力学稳定性关系，并通过进行一系列竞争性和交换性机械化学反应进一步验证了它们之间的热力学稳定性关系。有趣的是，在与结构相关的香草酸存在下的竞争性研磨导致[ TDZ  ： 香草酸]（1：1）共晶新多晶型的形成，其由没食子酸促进。机械化学方法也用于阐明[ TDZ  ：  GA  ：  H 2 O的替代途径。（1∶1∶1）共结晶形成。发现TDZ与一水合GA的直接共结晶比在乙
• 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.
• New water-soluble dosage forms of 1,2,4-thiadiazole derivative on the basis of inclusion complexes with cyclodextrins
  作者：Maria Brusnikina、Oleg Silyukov、Mikhail Chislov、Tatyana Volkova、Alexey Proshin、Irina Terekhova

  DOI：10.1007/s10973-016-5955-z

  日期：2017.2

  synthesized and proposed for the treatment of Alzheimer’s disease, was studied. First of all, inclusion complex formation of I with different cyclodextrins was studied in aqueous solutions. Formation of more stable complexes with β- and hydroxypropyl-β-cyclodextrins was revealed. Next, solid inclusion complexes of I with β- and hydroxypropyl-β-cyclodextrins were prepared by the mechanical grinding, and their

  环糊精对合成的1- [5-（3-氯-苯基氨基）-1，2，4-噻二唑-3-基]-丙烷-2-醇（I）的水溶性的影响阿尔茨海默氏病的研究。首先，在水溶液中研究了具有不同环糊精的I包合物的形成。揭示了与β-和羟丙基-β-环糊精形成更稳定的复合物。接下来，通过机械研磨制备I与β-和羟丙基-β-环糊精的固体包合物，并通过粉末X射线衍射，FTIR光谱，显微镜和热化学方法证实它们以固态存在。在模拟生物环境的水溶液缓冲液中，对纯I及其与β-和羟丙基-β-环糊精的复合物进行了溶出度测试。观察到的复合物溶解程度和溶解速率的急剧增加归因于包合物的形成。