甲基4-(2-二乙基氨基乙氧基)苯甲酸酯 | 3483-96-3

• 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: 甲基4-(2-二乙基氨基乙氧基)苯甲酸酯
• 英文名称: methyl 4-(2-(diethylamino)ethoxy)benzoate
• 英文别名: methyl 4-[2-(diethylamino)ethoxy]benzoate
• CAS: 3483-96-3
• 化学式: C₁₄H₂₁NO₃
• mdl: MFCD01661126
• 分子量: 251.326
• InChiKey: OCHYTARYRUQPFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  甲基4-(2-二乙基氨基乙氧基)苯甲酸酯 在 氯化亚砜 、 sodium hydroxide 作用下， 生成 1-[4-(2-diethylaminoethoxy)phenylcarbonyl]-3,5-bis(benzylidene)-4-piperidone
  参考文献：
  名称：

  3,5-Bis(benzylidene)-4-piperidones and related N-acyl analogs: A novel cluster of antimalarials targeting the liver stage of Plasmodium falciparum

  摘要：

  Drug resistance is a major challenge in antimalarial chemotherapy. In addition, a complete cure of malaria requires intervention at various stages in the development of the parasite within the host. There are only a few antimalarials that target the liver stage of the Plasmodium species which is an essential part of the life cycle of the malarial parasite. We report a series of antimalarial 3,5-bis(benzylidene)-4-piperidones and related N-acyl analogs 1-5, a number of which exhibit potent in vitro growth-inhibiting properties towards drug-sensitive D6 and drug-resistant C235 strains of Plasmodium falciparum as well as inhibiting the liver stage development of the malarial life cycle. The compounds 2b (IC50: 165 ng/mL), 3b (IC50: 186 ng/mL), 5c (IC50: 159 ng/mL) and 5d (IC50: 93.5 ng/mL) emerged as lead molecules that inhibit liver stage Plasmodium berghei and are significantly more potent than chloroquine (IC50: >2000 ng/mL) and mefloquine (IC50: >2000 ng/mL) in this screen. All the compounds that showed potent inhibitory activity against the P. berghei liver stage were nontoxic to human HepG2 liver cells (IC50: >2000 ng/mL). The compounds 5a and 5b exhibit comparable metabolic stability as chloroquine and mefloquine in human plasma and the most potent compound 5d demonstrated suitable permeability characteristics using the MDCK monolayer. These results emphasize the value of 3,5-bis(benzylidene)-4-piperidones as novel antimalarials for further drug development. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.065
• 作为产物：
  描述：

  4-甲氧基羰基氯甲酸苯酯 在 苯 作用下， 生成 甲基4-(2-二乙基氨基乙氧基)苯甲酸酯
  参考文献：
  名称：

  Einhorn; Rothlauf, Justus Liebigs Annalen der Chemie, 1911, vol. 382, p. 263

  摘要：

  DOI：

文献信息

• Antiestrogens. 2. Structure-activity studies in a series of 3-aroyl-2-arylbenzo[b]thiophene derivatives leading to [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl]-[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride (LY 156758), a remarkably effective estrogen antagonist with only minimal intrinsic estrogenicity
  作者：Charles D. Jones、Mary G. Jevnikar、Andrew J. Pike、Mary K. Peters、Larry J. Black、Allen R. Thompson、Julie F. Falcone、James A. Clemens

  DOI：10.1021/jm00374a021

  日期：1984.8

  growth-stimulating action of estradiol on the immature rat uterus. Seemingly minor changes in the side-chain amine moiety were found to have profound effects on the ability of the compounds to antagonize estradiol. Analogues having basic side chains containing cyclic (pyrrolidine, piperidine, and hexamethyleneamine) moieties were found to have less intrinsic estrogenicity and to antagonize estradiol action more completely

  为了制备非甾体类抗雌激素，其显示出比目前可用的更高的拮抗作用和更低的内在雌激素性，合成了一系列3-芳基-2-芳基苯并[b]噻吩衍生物。这些化合物的制备方法是：将适当的O-保护的2-芳基苯并[b]噻吩核与带有碱性侧链的苯甲酰氯进行Friedel-Crafts芳基化反应，然后去除保护基，以提供既包含羟基又包含碱性侧基的所需化合物。链功能。发现一种特别有用的裂解芳基甲氧基醚而不除去分子中其他地方的（二烷基氨基）乙氧基侧链官能度的方法是AlCl 3 / EtSH。测试了苯并噻吩衍生物抑制雌二醇对未成熟大鼠子宫的生长刺激作用的能力。看来侧链胺部分的微小变化对化合物拮抗雌二醇的能力有深远的影响。发现具有包含环（吡咯烷，哌啶和六亚甲基胺）部分的碱性侧链的类似物具有比其非环状对应物更少的固有雌激素性并且更完全地拮抗雌二醇的作用。该系列中最有效的抗雌激素化合物，化合物44，[6-羟基-2-（4-羟基苯基）苯并[b]噻吩-3-基]-[4-
• [EN] INHIBITORS OF THE WNT/BETA-CATENIN PATHWAY<br/>[FR] INHIBITEURS DE LA VOIE WNT/BÊTA-CATÉNINE
  申请人：UNIV CALIFORNIA

  公开号：WO2019152536A1

  公开（公告）日：2019-08-08

  The present disclosure relates to compounds that are capable of modulating the WNT/Beta-Catenin pathway. The disclosure further relates to methods of treating colorectal cancer and other WNT/Beta-Catenin mediated cancers.

  本披露涉及能够调节WNT/Beta-Catenin通路的化合物。此外，该披露还涉及治疗结直肠癌和其他WNT/Beta-Catenin介导的癌症的方法。
• ANTINEOPLASTIC COMPOUNDS
  申请人：DIMMOCK R. Jonathan

  公开号：US20070155733A1

  公开（公告）日：2007-07-05

  The present invention relates to 4-piperidone derivatives represented by the following formula (I) and the acid addition salts thereof. The method of preparation and antineoplastic activity of the said compounds are disclosed. A number of the compounds possess submicromolar IC 50 and CC 50 values and have a selective toxicity for colon cancers and leukemic cells. In addition, many of the compounds are able to reverse multidrug resistance.

  本发明涉及以下公式（I）所表示的4-哌啶酮衍生物及其酸盐加成物。揭示了所述化合物的制备方法和抗肿瘤活性。其中一些化合物具有亚微摩尔级别的IC50和CC50值，并具有对结肠癌和白血病细胞的选择性毒性。此外，许多化合物能够逆转多药耐药性。
• Antineoplastic compounds
  申请人：University of Saskatchewan

  公开号：US07582655B2

  公开（公告）日：2009-09-01

  The present invention relates to 4-piperidone derivatives represented by the following formula (I) and the acid addition salts thereof. The method of preparation and antineoplastic activity of the said compounds are disclosed. A number of the compounds possess submicromolar IC50 and CC50 values and have a selective toxicity for colon cancers and leukemic cells. In addition, many of the compounds are able to reverse multidrug resistance.

  本发明涉及以下式(I)所表示的4-哌啶酮衍生物及其酸加成盐。本发明还公开了所述化合物的制备方法和抗肿瘤活性。其中许多化合物具有亚微摩尔IC50和CC50值，并具有对结肠癌和白血病细胞的选择性毒性。此外，许多化合物能够逆转多药耐药性。
• High‐Throughput Platform for Novel Reaction Discovery
  作者：Xiao Lu、Zhiji Luo、Ruili Huang、Donald C. Lo、Wenwei Huang

  DOI：10.1002/chem.202201421

  日期：2022.9.6

  simple technique that can rapidly isolate reaction products with excellent purity by solid-phase extraction. This unique technique enabled us to develop a high-throughput reaction discovery platform. The effectiveness of this strategy was demonstrated by one newly discovered transformation, which shed light on the laboratory-scale discovery of new reactions.

  提取、分离和发现：我们设计了一种简单的技术，可以通过固相萃取快速分离出纯度优异的反应产物。这种独特的技术使我们能够开发出高通量反应发现平台。一项新发现的转化证明了这一策略的有效性，该转化为实验室规模的新反应发现提供了线索。