4-tert-butoxycarbonylamino-1-(3,4-dichlorobenzyl)piperidine | 328083-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-tert-butoxycarbonylamino-1-(3,4-dichlorobenzyl)piperidine
• 英文别名: (i)-tert-Butyl 1-(3,4-dichlorobenzyl)-4-piperidinylcarbamate；tert-butyl 1-(3,4-dichlorobenzyl)-4-piperidinylcarbamate；tert-butyl N-[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]carbamate
• CAS: 328083-79-0
• 化学式: C₁₇H₂₄Cl₂N₂O₂
• mdl: MFCD09028521
• 分子量: 359.296
• InChiKey: TZURFUQMFTUBTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.588
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-tert-butoxycarbonylamino-1-(3,4-dichlorobenzyl)piperidine 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 38.17h， 生成 N-[1-(3,4-dichlorobenzyl)piperidin-4-yl]-(6-amino-2-benzothiazolylthio)acetamide
  参考文献：
  名称：

  Structure-Activity Relationships of 2-(Benzothiazolylthio)acetamide Class of CCR3 Selective Antagonist

  摘要：

  描述了新型选择性CCR3受体拮抗剂的结构-活性关系，2-(苯并噻唑基硫)乙酰胺衍生物。通过筛选基于我们的人类CCR1和CCR3受体双拮抗剂结构的专注文库，发现了一种领先结构（1a）。1a的衍生化，包括在苯并噻唑和哌啶侧链的每个苯环中引入取代基，结果识别出具有强效和选择性的化合物（1b、r、s），表现出纳摩尔结合亲和力（IC50：1.5—3.0 nM）并且对CCR3受体的选择性超过CCR1受体800倍以上。

  DOI：

  10.1248/cpb.51.697
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 60.0h， 生成 4-tert-butoxycarbonylamino-1-(3,4-dichlorobenzyl)piperidine
  参考文献：
  名称：

  通过抑制醛糖还原酶设计和开发新型噻唑磺酰胺衍生物作为 Wistar 大鼠糖尿病性白内障的保护剂

  摘要：

  摘要 近年来，ALR2（醛糖还原酶）抑制剂因其有效减缓糖尿病相关性白内障进展的能力而备受关注。因此，在本文中，我们打算开发新型噻唑-磺酰胺杂化物作为 ALR2 的有效抑制剂。这些分子显着抑制大鼠晶状体匀浆中的 ALR2 水平，其中最有效的化合物 7b 显示出与标准山梨醇相当的活性。在 Wistar 大鼠中，化合物 7b 改善了实验动物的胰岛素水平和体重，同时降低了葡萄糖输出。在蛋白质印迹分析中，化合物7b显示大鼠晶状体中ALR2的表达显着降低。

  DOI：

  10.1515/hc-2020-0124

文献信息

• Substituted piperidine compounds useful as modulators of chemokine receptor activity
  申请人：Thom Stephen

  公开号：US06903085B1

  公开（公告）日：2005-06-07

  The invention provides compounds of formula (I) wherein R 1 , R 2 , R 3 , R 6 , Z, Q, m, n, X 1 , X 2 , X 3 , X 4 and T are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them, and their use in therapy, especially for the treatment of chemokine receptor related diseases and conditions

  这项发明提供了式（I）中R1、R2、R3、R6、Z、Q、m、n、X1、X2、X3、X4和T的化合物，其制备方法，含有它们的药物组合物，以及它们在治疗中的应用，特别是用于治疗与趋化因子受体相关的疾病和症状。
• Substituted 2‐thioxothiazolidin‐4‐one derivatives showed protective effects against diabetic cataract via inhibition of aldose reductase
  作者：Wanrong Huang、Yue Zhang、Xu Liang、Lichun Yang

  DOI：10.1002/ardp.201900371

  日期：2020.6

  class of potent aldose reductase inhibitors against diabetic cataracts, a series of novel 2‐thioxothiazolidine‐4‐one derivatives was synthesized in excellent yields via a facile synthetic route. These compounds were tested against aldehyde (ALR1) and aldose reductase (ALR2) enzymes, where they showed considerable inhibitory activity. Among the tested derivatives, compound 6e showed selective and excellent

  为了开发一类新的针对糖尿病性白内障的强效醛糖还原酶抑制剂，通过简便的合成路线以优异的收率合成了一系列新型 2-thioxothiazolidine-4-one 衍生物。这些化合物针对醛 (ALR1) 和醛糖还原酶 (ALR2) 进行了测试，它们显示出相当大的抑制活性。在测试的衍生物中，化合物 6e 显示出对 ALR2 的选择性和优异的抑制作用，而不是 ALR1。实验性糖尿病是通过在雄性 Wistar 大鼠中腹腔注射链脲佐菌素诱导的。化合物 6e 在糖尿病大鼠中显示出对体重、血糖和血胰岛素水平的积极调节。正如在患有白内障的 Wistar 大鼠的晶状体匀浆中的蛋白质印迹分析所证明的那样，化合物 6e 也显示出 ALR2 抑制。
• WO2007/53082
  申请人：——

  公开号：——

  公开（公告）日：——
• Design and Development of a Novel Chalcone Derivative as an Anticholinesterase Inhibitor for Possible Treatment of Dementia
  作者：Fu-Chun Zhao、Yan Wu、Xiao-Jie Song

  DOI：10.12659/msm.901842

  日期：——

  Background: Cognitive decline (e.g., memory loss), which mainly occurs in the elderly, is termed dementia. In the present study, we intended to explore the cholinesterase inhibitory activity of some novel synthesized chalcones, together with their effect on beta-amyloid anti-aggregation.Material/Methods: A novel class of chalcone derivatives have been synthesized and characterized by FT-IR, H-1-NMR, C-13-NMR, and mass and elemental analysis. These derivatives were later used for the determination of acetylcholinesterase (AChE) inhibitory and beta-amyloid anti-aggregation activity.Results: The results of the study showed that among the developed compounds, 8g inhibits AChE more prominently than BuChE, as suggested by a selectivity index (SI) of 2.88. Furthermore, the most potent compound, 8g, showed considerable action in inhibition of beta-secretase and A beta aggregation, but not as prominent as that of curcumin as a standard.Conclusions: In conclusion, our study revealed a novel class of chalcone derivatives as a selective inhibitor of AChE with considerably action against beta-secretase and A beta aggregation. Our results may be useful in developing AD drug therapy and warrant further investigation to generate more advanced analogues.
• Structure-Activity Relationships of 2-(Benzothiazolylthio)acetamide Class of CCR3 Selective Antagonist
  作者：Akira Naya、Kensuke Kobayashi、Makoto Ishikawa、Kenji Ohwaki、Toshihiko Saeki、Kazuhito Noguchi、Norikazu Ohtake

  DOI：10.1248/cpb.51.697

  日期：——

  The structure activity relationships of novel selective CCR3 receptor antagonists, 2-(benzothiazolylthio)acetamimde derivatives were described. A lead structure (1a) was discovered from the screening of the focused library that was based on the structure of our dual antagonists for the human CCR1 and CCR3 receptors. Derivatization of 1a including incorporation of substituent(s) into each benzene ring of the benzothiazole and piperidine side chain resulted in the identification of potent and selective compounds (1b, r, s) exhibiting nano-molar binding affinity (IC50s: 1.5—3.0 nM) and greater than 800-fold selectivity for the CCR3 receptor over the CCR1 receptor.

  描述了新型选择性CCR3受体拮抗剂的结构-活性关系，2-(苯并噻唑基硫)乙酰胺衍生物。通过筛选基于我们的人类CCR1和CCR3受体双拮抗剂结构的专注文库，发现了一种领先结构（1a）。1a的衍生化，包括在苯并噻唑和哌啶侧链的每个苯环中引入取代基，结果识别出具有强效和选择性的化合物（1b、r、s），表现出纳摩尔结合亲和力（IC50：1.5—3.0 nM）并且对CCR3受体的选择性超过CCR1受体800倍以上。