N-{2-[5-(azepan-1-yl)[1,2,4]thiadiazol-3-yl]-1-methylvinyl}-(2,2,6,6-tetramethylpiperidin-4-yl)amine | 1371630-71-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-{2-[5-(azepan-1-yl)[1,2,4]thiadiazol-3-yl]-1-methylvinyl}-(2,2,6,6-tetramethylpiperidin-4-yl)amine
• 英文别名: N-[1-[5-(azepan-1-yl)-1,2,4-thiadiazol-3-yl]prop-1-en-2-yl]-2,2,6,6-tetramethylpiperidin-4-amine
• CAS: 1371630-71-5
• 化学式: C₂₀H₃₅N₅S
• 分子量: 377.597
• InChiKey: HYWQLELYVUQIJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-{2-[5-(azepan-1-yl)[1,2,4]thiadiazol-3-yl]-1-methylvinyl}-(2,2,6,6-tetramethylpiperidin-4-yl)amine 在 甲醇 、 sodium tetrahydroborate 作用下， 以85%的产率得到N-[2-(5-(azepan-1-yl)-[1,2,4]thiadiazol-3-yl)-1-methylethyl](2,2,6,6-tetramethyl-piperidin-4-yl)amine
  参考文献：
  名称：

  EP2628734

  摘要：

  公开号：
• 作为产物：
  描述：

  环己亚胺 在 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 生成 N-{2-[5-(azepan-1-yl)[1,2,4]thiadiazol-3-yl]-1-methylvinyl}-(2,2,6,6-tetramethylpiperidin-4-yl)amine
  参考文献：
  名称：

  EP2628734

  摘要：

  公开号：

文献信息

• Screening of a series of 3,5-disubstituted 1,2,4-thiadiazoles for selectivity of cytotoxic action to cancer cells
  作者：A. N. Proshin、T. P. Trofimova、O. N. Zefirova、I. V. Zhirkina、D. A. Skvortsov、S. O. Bachurin

  DOI：10.1007/s11172-021-3116-4

  日期：2021.3

  New 3,5-disubstituted-1,2,4-thiadiazoles were synthesized and together with a series of their analogs obtained earlier were tested for cytotoxic activity to breast adenocarcinoma MCF-7 and lung carcinoma A 549 cells. The selectivity of cytotoxic action was determined in comparison to etiologically noncancerous breast epithelial cells MCF-10A and lung fibroblasts VA13. From five- to six-fold selectivity of cytotoxic action was revealed for 3,4-dichlorophenyl-3-[2-(2-morpholin-4-ylethylamino)propyl]-[1,2,4]thiadiazol-5-yl}amine and (2-5-[(4-diethylami-nobenzyl)pyridin-3-ylmethylamino]-[1,2,4]thiadiazol-3-yl}-1-methylvinyl)-(2,2,6,6-tetra-methylpiperidin-4-yl)amine in the pairs A 549/VA13 and MCF-7/MCF-10A, respectively. Some structure—property relationships for the compounds under study were discussed.

  合成了新的 3,5-二取代-1,2,4-噻二唑，并与之前获得的一系列类似物一起测试了对乳腺癌 MCF-7 和肺癌 A 549 细胞的细胞毒活性。与病因学上的非癌性乳腺上皮细胞 MCF-10A 和肺成纤维细胞 VA13 相比，确定了细胞毒作用的选择性。 3,4-二氯苯基-3-[2-(2-吗啉-4-基乙基氨基)丙基]-[1,2,4]噻二唑-5-基的细胞毒性作用选择性提高了五到六倍}胺和(2-5-[(4-二乙基氨基苄基)吡啶-3-基甲基氨基]-[1,2,4]噻二唑-3-基}-1-甲基乙烯基)-(2,2,6, 6-四甲基哌啶-4-基)胺分别为 A 549/VA13 和 MCF-7/MCF-10A 对。讨论了所研究化合物的一些结构-性质关系。
• 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。