{2-[5-(3-chloro-4-methyl-phenylamino)-[1,2,4]thiadiazol-3-yl]-1-methylethyl}-(2,2,6,6-tetramethylpiperidine-4-yl)-amine | 1371630-57-7

• 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: {2-[5-(3-chloro-4-methyl-phenylamino)-[1,2,4]thiadiazol-3-yl]-1-methylethyl}-(2,2,6,6-tetramethylpiperidine-4-yl)-amine
• 英文别名: {2-[5-(3-Chloro-4-methyl-phenylamino)-1,2,4-thiadiazole-3-yl]-1-methyl-ethyl}-(2,2,6,6-tetramethyl-piperidine-4-yl)-amine；N-(3-chloro-4-methylphenyl)-3-[2-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]propyl]-1,2,4-thiadiazol-5-amine
• CAS: 1371630-57-7
• 化学式: C₂₁H₃₂ClN₅S
• 分子量: 422.038
• InChiKey: NTMZDLWXKAFGBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  90.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二十二碳六烯酸 、 {2-[5-(3-chloro-4-methyl-phenylamino)-[1,2,4]thiadiazol-3-yl]-1-methylethyl}-(2,2,6,6-tetramethylpiperidine-4-yl)-amine 在 三乙胺 、 氯甲酸异丁酯 作用下， 以 乙腈 、 甲醇 为溶剂， 反应 1.33h， 以30%的产率得到N-{2'-[5-(3-chloro-4-methylphenylamino)-1,2,4-thiadiazol-3-yl]-1'-methylethyl}-(2'',2'',6'',6''-tetramethylpiperidin-4''-yl)aminodocosa-4Z,7Z,10Z,13Z,16Z,19Z-hexaenoic acid amide
  参考文献：
  名称：

  Novel hybrid compounds based on amino derivatives of 1,2,4-thiadiazole and docosahexaenoic acid

  摘要：

  DOI：

  10.1134/s0012500812110031
• 作为产物：
  描述：

  2,2,6,6-四甲基哌啶胺 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 {2-[5-(3-chloro-4-methyl-phenylamino)-[1,2,4]thiadiazol-3-yl]-1-methylethyl}-(2,2,6,6-tetramethylpiperidine-4-yl)-amine
  参考文献：
  名称：

  Novel hybrid compounds based on amino derivatives of 1,2,4-thiadiazole and docosahexaenoic acid

  摘要：

  DOI：

  10.1134/s0012500812110031

文献信息

• 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。
• Complex formation of cyclodextrins with some pharmacologically active 1,2,4-thiadiazole derivatives
  作者：Mikhail Chislov、Oleg Silyukov、Roman Kumeev、Alexey Proshin、German Perlovich、Irina Terekhova

  DOI：10.1007/s10973-016-5929-1

  日期：2017.2

  Previously synthesized 1,2,4-thiadiazole derivatives displayed an activity in the treatment of Alzheimer’s disease; however, these compounds are poorly soluble in aqueous solutions. Inclusion complex formation with cyclodextrins is proposed for the development of water-soluble dosage forms of 1,2,4-thiadiazoles under study. To this end, binding of 1,2,4-thiadiazole derivatives with α-, β- and γ-cyclodextrins

  先前合成的1,2,4-噻二唑衍生物在阿尔茨海默氏病的治疗中具有活性。但是，这些化合物难溶于水溶液。有人提议与环糊精形成包合物，以开发正在研究的1,2,4-噻二唑的水溶性剂型。为此，通过等温滴定量热法，1 H NMR和UV-Vis光谱在缓冲水溶液中研究了1,2,4-噻二唑衍生物与α-，β-和γ-环糊精的结合以及改性的β-环糊精的结合。溶液（pH = 7.4）在298.15 K下进行。给出了对复合物形成的热力学参数的详细分析。1,2,4-噻二唑/环糊精复合物的结构基于2D 1进行了评估NMR（ROESY）实验。讨论了结构因素（大环腔的尺寸，主体外表面的修饰，客体分子的结构）对热力学和结合方式的影响。
• 5-AMINO-1,2,4-THIADIAZOLE DERIVATIVES
  申请人：Federalnoe Gosudarstvennoe Bydzhetnoe Uchrezhdenie Nauki Institut Fiziologicheski Aktivnikh Veschestv Rossiiskoi Akademii Nauk (IFAV RAN)

  公开号：EP2628734A2

  公开（公告）日：2013-08-21

  The present invention relates in general to the field of organic chemistry and, in particular, to novel biologically active compounds of 5-amino[1,2,4]thiadiazole derivatives of the general formula: wherein X is ONO2 or NHR3; R1, R2, and R3 may be the same or different and independently represent hydrogen, alkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, cycloalkyl, as well as R1 together with R2 may represent heterocyclyl (for example, optionally substituted pyrrolidine, piperidine, azepane, piperazine, morpholine, etc.) provided that, when R1 is H, then R2 is other than hydrogen or methyl. 5-Amino-[1,2,4]thiadiazole derivatives are of special interest as drug candidates for prevention and treatment of neurodegenerative diseases, for example, Alzheimer's disease.

  本发明总体上涉及有机化学领域，特别是通式为 5-氨基[1,2,4]噻二唑衍生物的新型生物活性化合物： 其中 X 是 ONO2 或 NHR3； R1、R2和R3可以相同或不同，并独立地代表氢、烷基、芳基、芳烷基、杂芳基、杂烷基、环烷基，以及R1与R2一起代表杂环烷基（例如，任选取代的吡咯烷、哌啶、氮杂环烷、哌嗪、吗啉等），条件是当R1为H时，R2不是氢或甲基。 5-氨基-[1,2,4]噻二唑衍生物作为预防和治疗神经退行性疾病（例如阿尔茨海默病）的候选药物具有特殊的意义。
• EP2628734
  申请人：——

  公开号：——

  公开（公告）日：——
• Novel hybrid compounds based on amino derivatives of 1,2,4-thiadiazole and docosahexaenoic acid
  作者：I. V. Serkov、A. N. Proshin、L. N. Petrova、N. M. Gretskaya、V. V. Bezuglov、S. O. Bachurin

  DOI：10.1134/s0012500812110031

  日期：2012.11