tert-butyl (3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)carbamate | 1085928-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: tert-butyl (3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)carbamate
• 英文别名: tert-Butyl 3-(4-(2-methoxyphenyl)piperazin-1-yl)propylcarbamate；tert-butyl N-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]carbamate
• CAS: 1085928-20-6
• 化学式: C₁₉H₃₁N₃O₃
• 分子量: 349.473
• InChiKey: LJPFHXAKXNKRIV-UHFFFAOYSA-N

物化性质

• 沸点：
  496.2±45.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)carbamate 在 三氟乙酸 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 以86%的产率得到1-(3-氨基)-4-(2-甲氧基苯基)哌嗪
  参考文献：
  名称：

  Novel naftopidil-related derivatives and their biological effects as alpha1-adrenoceptors antagonists and antiproliferative agents

  摘要：

  Eleven novel naftopidil-related compounds that contain amide and indole groups were designed and synthesized. The biological effects of these compounds on three alpha(1)-adrenoceptor subtypes and cancerous human prostate cell lines (PC-3, DU-145, and LNCaP) were determined. Compounds 2, 3, 5, 11, and 12 exhibited an alpha(1)-adrenoceptor antagonistic activity, whereas compounds 9, 10, and 12 displayed moderate antiproliferative activities. Compound 3 exhibited a significant alpha(1D/1A) blocking activity in isolated rat tissues (97.7- and 64.6-fold selective for alpha(1D) and alpha(1A) compared with alpha(1B)) but not a relevant cytotoxic activity. Compound 12 demonstrated a potent and selective alpha(1D/1A) antagonistic activity (47.9- and 19.1-fold for alpha(1D) and alpha(1A), compared with alpha(1B)) and a potent antiproliferative activity in PC-3 cells (IC50 = 15.70 mu M). Further testing confirmed that compound 12 inhibited the growth of PC-3 cells by inducing apoptosis and GO/G1 cell cycle arrest, which was mediated by alpha(1)-adrenoceptor. Therefore, compound 12 is a potential multipotent agent that can act as an effective alpha(1)-adrenoceptor subtype antagonist for treating benign prostatic hyperplasia and a preventive medication against human prostate cancer. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.005
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 tert-butyl (3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)carbamate
  参考文献：
  名称：

  Novel naftopidil-related derivatives and their biological effects as alpha1-adrenoceptors antagonists and antiproliferative agents

  摘要：

  Eleven novel naftopidil-related compounds that contain amide and indole groups were designed and synthesized. The biological effects of these compounds on three alpha(1)-adrenoceptor subtypes and cancerous human prostate cell lines (PC-3, DU-145, and LNCaP) were determined. Compounds 2, 3, 5, 11, and 12 exhibited an alpha(1)-adrenoceptor antagonistic activity, whereas compounds 9, 10, and 12 displayed moderate antiproliferative activities. Compound 3 exhibited a significant alpha(1D/1A) blocking activity in isolated rat tissues (97.7- and 64.6-fold selective for alpha(1D) and alpha(1A) compared with alpha(1B)) but not a relevant cytotoxic activity. Compound 12 demonstrated a potent and selective alpha(1D/1A) antagonistic activity (47.9- and 19.1-fold for alpha(1D) and alpha(1A), compared with alpha(1B)) and a potent antiproliferative activity in PC-3 cells (IC50 = 15.70 mu M). Further testing confirmed that compound 12 inhibited the growth of PC-3 cells by inducing apoptosis and GO/G1 cell cycle arrest, which was mediated by alpha(1)-adrenoceptor. Therefore, compound 12 is a potential multipotent agent that can act as an effective alpha(1)-adrenoceptor subtype antagonist for treating benign prostatic hyperplasia and a preventive medication against human prostate cancer. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.005

文献信息

• Compositions, Synthesis, and Methods of Using Quinolinone Based Atypical Antipsychotic Agents
  申请人：Bhat Laxminarayan

  公开号：US20080293736A1

  公开（公告）日：2008-11-27

  The present invention provides novel quinolinone derivatives which can be advantageously used for treating schizophrenia and related psychoses such as acute manic, bipolar disorder, autistic disorder, and depression.

  本发明提供了新型喹诺酮衍生物，可以有效用于治疗精神分裂症及相关精神病，如急性躁狂症、双相情感障碍、自闭症和抑郁症。
• Structure–Activity Relationships of Privileged Structures Lead to the Discovery of Novel Biased Ligands at the Dopamine D₂ Receptor
  作者：Monika Szabo、Carmen Klein Herenbrink、Arthur Christopoulos、J. Robert Lane、Ben Capuano

  DOI：10.1021/jm500457x

  日期：2014.6.12

  Biased agonism at GPCRs highlights the potential for the discovery and design of pathway-selective ligands and may confer therapeutic advantages to ligands targeting the dopamine D-2 receptor (D2R). We investigated the determinants of efficacy, affinity, and bias for three privileged structures for the D2R, exploring changes to linker length and incorporation of a heterocyclic unit. Profiling the compounds in two signaling assays (cAMP and pERK1/2) allowed us to identify and quantify determinants of biased agonism at the D2R. Substitution on the phenylpiperazine privileged structures (2-methoxy vs 2,3-dichloro) influenced bias when the thienopyridine heterocycle was absent. Upon inclusion of the thienopyridine unit, the substitution pattern (4,6-dimethyl vs 5-chloro-6-methoxy-4-methyl) had a significant effect on bias that overruled the effect of the phenylpiperazine substitution pattern. This latter observation could be reconciled with an extended binding mode for these compounds, whereby the interaction of the heterocycle with a secondary binding pocket may engender bias.
• US8247420B2
  申请人：——

  公开号：US8247420B2

  公开（公告）日：2012-08-21
• [EN] COMPOSITIONS, SYNTHESIS, AND METHODS OF USING QUINOLINONE BASED ATYPICAL ANTIPSYCHOTIC AGENTS<br/>[FR] COMPOSITIONS, SYNTHÈSES ET PROCÉDÉS D'UTILISATION D'AGENTS ANTIPSYCHOTIQUES ATYPIQUES À BASE DE QUINOLINONE
  申请人：REVIVA PHARMACEUTICALS INC

  公开号：WO2008144764A1

  公开（公告）日：2008-11-27

  [EN] The present invention provides novel quinolinone derivatives which can be advantageously used for treating schizophrenia and related psychoses such as acute manic, bipolar disorder, autistic disorder, and depression.
  [FR] La présente invention concerne de nouveaux dérivés de quinolinone qui peuvent être avantageusement utilisés pour traiter la schizophrénie et des psychoses apparentées telles que la manie aiguë, le trouble bipolaire, le trouble autistique et la dépression.
• CN116496234
  申请人：——

  公开号：——

  公开（公告）日：——