1-(3,4-二甲氧基-苄基)-哌嗪 | 32231-07-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(3,4-二甲氧基-苄基)-哌嗪
• 英文名称: 1-(3,4-dimethoxy-benzyl)-piperazine
• 英文别名: 1-(3,4-dimethoxybenzyl)piperazine；N-3,4-dimethoxybenzylpiperazine；1-[(3,4-dimethoxyphenyl)methyl]piperazine
• CAS: 32231-07-5
• 化学式: C₁₃H₂₀N₂O₂
• mdl: MFCD00128074
• 分子量: 236.314
• InChiKey: ONIFCGFFEZDWSC-UHFFFAOYSA-N

物化性质

• 沸点：
  343.6±37.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  33.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  1-(3,4-二甲氧基-苄基)-哌嗪 在 potassium hydrogencarbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.8h， 生成
  参考文献：
  名称：

  Flavonoid-Related Modulators of Multidrug Resistance:  Synthesis, Pharmacological Activity, and Structure−Activity Relationships

  摘要：

  A series of 28 flavonoid derivatives containing a N-benzylpiperazine chain have been synthesized and tested for their ability to modulate multidrug resistance (MDR) in vitro. At 5 mu M, most compounds potentiated doxorubicin cytotoxicity on resistant K562/DOX cells. They were also able to increase the intracellular accumulation of JC-1, a fluorescent molecule recently described as a probe of P-glycoprotein-mediated MDR. This suggests that these compounds act, at least in part, by inhibiting P-glycoprotein activity. As in other studies, lipophilicity was shown to influence MDR-modulating activity but was not the only determinant. Diverse di- and trimethoxy substitutions on N-benzyl were examined and found to affect the activity differently. The most active compounds had a 2,3,4-trimethoxybenzylpiperazine chain attached to either a flavone or a flavanone moiety (13, 19, 33, and 37) and were found to be more potent; than verapamil.

  DOI：

  10.1021/jm981064b
• 作为产物：
  描述：

  3,4-二甲氧基苄醇 在 polymer supported cyanoborohydride 、 polymer supported perruthenate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 74.0h， 生成 1-(3,4-二甲氧基-苄基)-哌嗪
  参考文献：
  名称：

  Ley, Steven V.; Bolli, Martin H.; Hinzen, Berthold, Journal of the Chemical Society. Perkin transactions I, 1998, # 15, p. 2239 - 2241

  摘要：

  DOI：

文献信息

• Synthesis and biological evaluation as AChE inhibitors of new indanones and thiaindanones related to donepezil
  作者：Ziad Omran、Thomas Cailly、Elodie Lescot、Jana Sopkova-de Oliveira Santos、Jean-Hugues Agondanou、Vincent Lisowski、Frédéric Fabis、Anne-Marie Godard、Silvia Stiebing、Guillaume Le Flem、Michel Boulouard、François Dauphin、Patrick Dallemagne、Sylvain Rault

  DOI：10.1016/j.ejmech.2005.07.009

  日期：2005.12

  Sixty-four new indanones and thiaindanones related to donepezil were synthesized and evaluated in vitro as potential AChE inhibitors. Among them, 11 derivatives were found to inhibit the enzyme in the submicromolar range; the best compound revealed its inhibitory activity with an IC50 in the same range (0.06 microM) than the reference compound, donepezil (IC50=0.02 microM).

  合成了与多奈哌齐有关的六十四种新的茚满酮和硫丹酮，并在体外评估了其作为潜在的AChE抑制剂。其中，发现了11种衍生物在亚微摩尔范围内抑制该酶。最好的化合物显示出其抑制活性，其IC50与参考化合物多奈哌齐（IC50 = 0.02 microM）处于相同范围（0.06 microM）。
• Design, synthesis and SAR of antitubercular benzylpiperazine ureas
  作者：Sohal Satish、Rohan Chitral、Amitkumar Kori、Basantkumar Sharma、Jayashree Puttur、Afreen A. Khan、Deepali Desle、Kavita Raikuvar、Aaron Korkegian、Elvis A. F. Martis、Krishna R. Iyer、Evans C. Coutinho、Tanya Parish、Santosh Nandan

  DOI：10.1007/s11030-020-10158-3

  日期：2022.2

  With the aim of delineating the SAR associated with (I), fifty-five analogs were synthesized and screened against Mtb. The SAR suggests that the piperazine ring, benzyl urea and piperonyl moieties are essential signatures of this series. Active compounds in this series are metabolically stable, have low cellular toxicity and are valuable leads for optimization. Molecular docking suggests these molecules

  摘要 GSK Tres Cantos 的科学家披露的N-糠基哌嗪脲被选为来自表型全细胞筛选的抗分枝杆菌。用苯环取代 GSK Tres Cantos 分子中的呋喃环产生的分子 ( I ) 对Mtb H37Rv 的 MIC 为 1 μM，细胞毒性低（HepG2 IC 50  ~ 80 μM），良好的 DMPK 特性和特异性山地车_ 为了描绘与 ( I ) 相关的 SAR，合成了 55 种类似物并针对Mtb进行了筛选. SAR 表明哌嗪环、苄基脲和胡椒基部分是该系列的基本特征。该系列中的活性化合物代谢稳定，细胞毒性低，是优化的宝贵线索。分子对接表明这些分子像 Q203 一样占据 QcrB 的 Q0 位点。 图形摘要 N-糠基哌嗪-1-羧酰胺的生物等排替代产生了分子 (I) 一种具有令人满意的 PD、代谢和毒性特征的新型先导。
• IMIDAZO PYRIDINE DERIVATIVES
  申请人：Taracido Ivan Cornella

  公开号：US20090291942A1

  公开（公告）日：2009-11-26

  The invention relates to novel imidazopyridine derivatives and to their use in the treatment of diseases and disorders which may e.g. involve angiogenesis and/or pain, including autoimmune and inflammatory diseases.

  这项发明涉及新型咪唑吡啶衍生物及其在治疗可能涉及血管生成和/或疼痛的疾病和紊乱中的应用，包括自身免疫和炎症性疾病。
• ACTIVATOR OF ADIPONECTIN RECEPTOR
  申请人：THE UNIVERSITY OF TOKYO

  公开号：US20160214967A1

  公开（公告）日：2016-07-28

  An AdipoR activator for activating both AdipoR1 and AdipoR2 is provided. A compound represented by the following formula (1), wherein A is a substituted or unsubstituted aryl group or the like, Y 1 is (CHR 2 ) a — or the like, X is CH or N, R 1 is a C 1-7 alkyl group, m is an integer of 0-4, Y 2 is *—O—CH 2 —CONH—, *—CONH—(CH 2 ) b —CO— or the like, Z is a cyclic group, B may be a substituent of the cyclic group represented by Z, and n is an integer of 0-3.

  提供了一种用于激活AdipoR1和AdipoR2的AdipoR激活剂。以下式（1）表示的化合物，其中A是取代或未取代的芳基或类似物，Y1是（CHR2）a—或类似物，X是CH或N，R1是C1-7烷基基团，m是0-4的整数，Y2是*—O—CH2—CONH—，*—CONH—（CH2）b—CO—或类似物，Z是环基团，B可以是Z代表的环基团的取代基，n是0-3的整数。
• Benzylpiperazine derivatives. X. Syntheses and structure-antiulcer activity relationship of 1-benzyl-4-piperazineacetic acid esters.
  作者：HIROSHI OHTAKA、KENJI YOSHIDA、KENJI SUZUKI、KOICHI SHIMOHARA、SHIGERU TAJIMA、KEIZO ITO

  DOI：10.1248/cpb.36.4825

  日期：——

  A series of ester derivatives of1-benzy1-4-piperazineacetic acid was synthesized and evaluated as antiulcer agents. Quantitative structure-activity relationships (QSAR) analyses by using the ALS (adaptive least-squares) method were performed in each step to decrease the synthetic efforts. The QSAR for the esters is much the same as that for the previously examined amide derivatives. The antiulcer activity of these compounds was considered to be based on the cytoprotective activity. The most active and the least toxic compounds, 5n and 5y, were selected for further study.

  合成了一系列1-苄基-4-哌嗪乙酸的酯衍生物，并评估其作为抗溃疡剂的效果。使用自适应最小二乘法（ALS）进行的定量结构-活性关系（QSAR）分析在每一步中都进行了，以减少合成工作。酯的QSAR与之前研究的酰胺衍生物的QSAR非常相似。这些化合物的抗溃疡活性被认为是基于其细胞保护活性。最活跃且毒性最低的化合物5n和5y被选中进行进一步研究。