4-(2-哌啶-1-乙氧基)苯甲醛 | 26815-04-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-(2-哌啶-1-乙氧基)苯甲醛
• 中文别名: 2-哌啶-1-乙氧基)苯甲醛
• 英文名称: 4-(2-(piperidin-1-yl)ethoxy)benzaldehyde
• 英文别名: 4-[2-(1-piperidinyl)ethoxy]benzaldehyde；4-[2-(1-piperidino)ethoxy]benzaldehyde；[4-[2-(1-piperidinyl)ethoxy]-phenyl] methanone；4-(2-piperidin-1-ylethoxy)benzaldehyde
• CAS: 26815-04-3
• 化学式: C₁₄H₁₉NO₂
• mdl: MFCD00800249
• 分子量: 233.31
• InChiKey: WCLJTEXCGGSJJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 储存条件：
  存储条件：2-8°C，避光，惰性气体保护。

反应信息

• 作为反应物：
  描述：

  4-(2-哌啶-1-乙氧基)苯甲醛 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成 [4-(2-Piperidin-1-yl-ethoxy)-phenyl]-methanethiol
  参考文献：
  名称：

  Spironolactone-related inhibitors of type II 17β-hydroxysteroid dehydrogenase: chemical synthesis, receptor binding affinities, and proliferative/antiproliferative activities

  摘要：

  The family of 17 beta-hydroxysteroid dehydrogenases (17 beta-HSDs) catalyzes the formation and inactivation of testosterone (T), dihydrotestosterone (DHT), and estradiol (E-2), thus playing a crucial role in the regulation of active steroid hormones in target tissues. Among the five known 17 beta-HSD enzymes, type II catalyzes the oxidation of E-2 into estrone (El), T into androstenedione, DHT into androstanedione, and 20 alpha-dihydroprogesterone into progesterone. Specific inhibitors are thus an interesting means to study the regulation and to probe the structure of type II 17 beta-HSD. In this context, we have efficiently synthesized a series of 7 alpha-thioalkyl and 7 alpha-thioaryl derivatives of spironolactone that inhibit type II 17 beta-HSD. These new C19-steroidal inhibitors possess two important pharmacophores, namely 17-spiro-gamma-lactone and a bulky side-chain at the 7 alpha-position. It was found that a para-substituted benzylthio group at the 7 alpha-position enhances the inhibitory potency of spironolactone derivatives on type II 17 beta-HSD. In fact, the compound with a para-hydroxy-benzylthio group showed an IC50 value of 0.5 mu M against type II 17 beta-HSD, whereas the compound with a para-[2-(1-piperidinyl)-ethoxy]-benzylthio group inhibited this enzyme with an IC50 value of 0.7 mu M. The latter inhibitor is more selective than the former because it did not show any inhibitory potency against P450 aromatase as well as any affinity towards four steroid receptors (AR, PR, GR, ER). As a result, this inhibitor did not show any proliferative effect on androgen-sensitive Shionogi cells and estrogen-sensitive ZR-75-1 cells. These findings contribute to a better knowledge of the structure of type II 17 beta-HSD and offer an interesting tool to study the regulation of this enzyme in several biological systems. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00260-0
• 作为产物：
  描述：

  对羟基苯甲醛 在 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 4-(2-哌啶-1-乙氧基)苯甲醛
  参考文献：
  名称：

  查尔酮-O-烷基胺衍生物作为对抗阿尔茨海默氏病的多功能药物的开发。

  摘要：

  设计，合成和评估了一系列新颖的查耳酮-O-烷基胺衍生物，作为多功能抗阿尔茨海默氏病药物。根据实验结果，化合物23c对乙酰胆碱酯酶（IC50 = 1.3±0.01μM）和丁酰胆碱酯酶（IC50 = 1.2±0.09μM）均表现出良好的抑制作用。此外，23c表现出选择性的MAO-B抑制活性，IC50值为0.57±0.01μM。化合物23c也是潜在的抗氧化剂和神经保护剂。另外，化合物23c可以抑制自诱导的Aβ1-42聚集。此外，化合物23c是一种选择性金属螯合剂，可以抑制和分解Cu2 +诱导的Aβ1-42聚集，这在进一步的透射电子显微镜图像的支持下得以实现。此外，23c可能在体外穿过血脑屏障，并改进了东pol碱诱导的体内记忆障碍。分子模型研究表明23c可以结合AChE，BuChE，Aβ1-42和MAO-B的活性位点。综上所述，这些结果表明化合物23c可能是用于治疗AD的潜在多功能剂。

  DOI：

  10.1016/j.ejmech.2019.111737
• 作为试剂：
  描述：

  1,2-(2’-羟基-4’,4’’-二-alpha-吡喃醇)二苯基乙酮 、 4-(2-哌啶-1-乙氧基)苯甲醛 在 4-(2-哌啶-1-乙氧基)苯甲醛 作用下， 以86.1的产率得到
  参考文献：
  名称：

  [EN] ENANTIOSELECTIVE SYNTHESIS
  [FR] SYNTHESE ENANTIOSELECTIVE

  摘要：

  一种简短实用的商业化进程，用于高效对映选择性合成公式（I）或（XIV）的非甾体抗雌激素或其药用可接受盐。

  公开号：

  WO2000009493A1

文献信息

• Blood–brain barrier permeable anticholinesterase aurones: Synthesis, structure–activity relationship, and drug-like properties
  作者：Kok-Fui Liew、Kit-Lam Chan、Chong-Yew Lee

  DOI：10.1016/j.ejmech.2015.02.055

  日期：2015.4

  A series of novel aurones bearing amine and carbamate functionalities at various positions (rings A and/or B) of the scaffold was synthesized and evaluated for their acetylcholinesterase and butyrylcholinesterase inhibitory activities. Structure–activity relationship study disclosed several potent submicromolar acetylcholinesterase inhibitors (AChEIs) particularly aurones bearing piperidine and pyrrolidine

  合成了一系列在支架的各个位置（环A和/或B）具有胺和氨基甲酸酯官能团的新型金氧烷，并对其乙酰胆碱酯酶和丁酰胆碱酯酶的抑制活性进行了评估。结构-活性关系研究揭示了几种有效的亚微摩尔乙酰胆碱酯酶抑制剂（AChEI），特别是在环A或环B上带有哌啶和吡咯烷部分的金黄色素。以三甲氧基金4 – 3为代表的金黄色。活性金黄色素表现出较低的丁酰胆碱酯酶抑制作用。3'-氯金龙6 – 3最初旨在提高支架的代谢稳定性的药物是该系列中最有效的药物。分子对接模拟显示，这些AChEI的光环在加利福尼亚鱼雷AChE（Tc AChE）的活性位点范围内采用有利的结合模式，包括6 – 3的氯与氯的非正常相互作用，从而建立了与Tc AChE疏水残基的附加键。使用PAMPA-BBB测定法和体外大鼠肝微粒体（RLM）评估强力金黄色素对血脑屏障（BBB）的通透性和代谢稳定性的影响，鉴定为4 – 3作为一种具有良好的被动BBB通透性和
• Novel heteroatom containing tetracyclic derivatives as selective estrogen receptor modulators
  申请人：——

  公开号：US20040259915A1

  公开（公告）日：2004-12-23

  The present invention is directed to novel heteroatom containing tetracyclic derivatives, pharmaceutical compositions containing them, their use in the treatment and/or prevention of disorders mediated by one or more estrogen receptors and processes for their preparation. The compounds of the invention are useful in the treatment and/or prevention of disorders associated with the depletion of estrogen such as hot flashes, vaginal dryness, osteopenia and osteoporosis; hormone sensitive cancers and hyperplasia of the breast, endometrium, cervix and prostate; endometriosis, uterine fibroids, osteoarthritis and as contraceptive agents, alone or in combination with a progestogen or progestogen antagonist.

  本发明涉及新颖的含杂原子四环衍生物、含有它们的药物组合物、它们在治疗和/或预防由一个或多个雌激素受体介导的疾病中的应用，以及它们的制备方法。本发明的化合物在治疗和/或预防与雌激素耗竭相关的疾病中具有用途，例如热潮红、阴道干燥、骨量减少和骨质疏松症；激素敏感性癌症以及乳腺、子宫内膜、宫颈和前列腺的增生；子宫内膜异位症、子宫肌瘤、骨关节炎，以及作为避孕剂，单独使用或与孕激素或孕激素拮抗剂联合使用。
• Synthesis, antimalarial activity and cytotoxic potential of new monocarbonyl analogues of curcumin
  作者：Sunny Manohar、Shabana I. Khan、Shamseer Kulangara Kandi、Kranthi Raj、Guojing Sun、Xiaochuan Yang、Angie D. Calderon Molina、Nanting Ni、Binghe Wang、Diwan S. Rawat

  DOI：10.1016/j.bmcl.2012.11.004

  日期：2013.1

  A series of novel monocarbonyl analogues of curcumin have been designed, synthesized and tested for their activity against Molt4, HeLa, PC3, DU145 and KB cancer cell lines. Six of the analogues showed potent cytotoxicity towards these cell lines with IC50 values below 1 μM, which is better than doxorubicin, a US FDA approved drug. Several analogues were also found to be active against both CQ-resistant

  已经设计，合成并测试了一系列姜黄素的新型单羰基类似物，它们针对Molt4，HeLa，PC3，DU145和KB癌细胞系的活性。其中六个类似物显示出对这些细胞系的有效细胞毒性，IC 50值低于1μM，优于美国FDA批准的阿霉素。在体外抗疟疾筛选中，还发现几种类似物对恶性疟原虫的CQ耐药（W2克隆）和CQ敏感（D6）菌株均具有活性。这种活性水平需要进一步研究这些化合物作为抗癌药和抗疟药的发展。
• [EN] BENZIMIDAZOLES AND BENZOTHIAZOLES AS INHIBITORS OF MAP KINASE<br/>[FR] BENZIMIDAZOLES ET BENZOTHIAZOLES UTILISES COMME INHIBITEURS DE LA MAP KINASE
  申请人：LILLY CO ELI

  公开号：WO2004014900A1

  公开（公告）日：2004-02-19

  The present invention provides kinase inhibitors of Formula I: wherein W represents inter alia imidazol, oxazol, pyrazol, thiazol as triazol, which are substituted by phenyl or thienyl. The disclosed compounds inhibit p-38 kinase and are useful in the treatment of metastasis or rheumatoid arthritis.

  本发明提供了一种化合物I的激酶抑制剂：其中W代表咪唑、噁唑、吡唑、噻唑或三唑等，这些化合物被苯基或噻吩基取代。所公开的化合物抑制p-38激酶，在转移或类风湿性关节炎的治疗中很有用。
• [EN] USE OF AND SOME NOVEL IMIDAZOPYRIDINES<br/>[FR] NOUVELLES IMIDAZOPYRIDINES ET LEUR UTILISATION
  申请人：ASTRAZENECA AB

  公开号：WO2004016611A1

  公开（公告）日：2004-02-26

  The use of compounds of formula (I) wherein R1, R3, R10, m and Ar are as defined in the Specification and pharmaceutically acceptable salts thereof in the manufacture of a medicament for the treatment or prophylaxis of diseases or conditions in which inhibition of kinase Itk activity is beneficial is disclosed. Certain novel compounds of formula (I), together with processes for their preparation, compositions containing them and their use in therapy are also disclosed.

  公开了在制备药物用于治疗或预防抑制激酶Itk活性有益的疾病或症状中，使用式(I)中R1、R3、R10、m和Ar所定义的化合物及其药学上可接受的盐。还公开了式(I)的某些新化合物，以及它们的制备方法、含有它们的组合物和它们在治疗中的用途。