4-(2-diethylaminoethoxy)benzoic acid hydrochloride | 59931-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-diethylaminoethoxy)benzoic acid hydrochloride
• 英文别名: 4-(2-Diaethylamino-aethoxy)-benzoesaeure; Hydrochlorid；4-[2-(Diethylamino)ethoxy]benzoic acid hydrochloride；4-[2-(diethylamino)ethoxy]benzoic acid;hydrochloride
• CAS: 59931-28-1
• 化学式: C₁₃H₁₉NO₃*ClH
• mdl: MFCD12197102
• 分子量: 273.76
• InChiKey: SOEBUSCNBNZIRA-UHFFFAOYSA-N

物化性质

• 熔点：
  160-161 °C(Solv: methanol (67-56-1); ethyl ether (60-29-7))

计算性质

• 辛醇/水分配系数(LogP)：
  -0.53
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-diethylaminoethoxy)benzoic acid hydrochloride 在 氯化亚砜 、 三乙胺 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3,5-bis(4-chlorophenylmethylene)-1-[4-(2-diethylaminoethoxy)phenylcarbonyl]-4-piperidone
  参考文献：
  名称：

  Design, synthesis and cytotoxic properties of novel 1-[4-(2-alkylaminoethoxy)phenylcarbonyl]-3,5-bis(arylidene)-4-piperidones and related compounds

  摘要：

  The 3,5-bis(arylidene)-4-piperidones I contain the 1,5-diaryl-3-oxo-1,4-pentadienyl pharmacophore which is considered to interact at a complementary binding site in susceptible neoplasms. The hypothesis was formulated that the presence of an acyl group attached to the piperidyl nitrogen atom in series 1 may interact with an additional binding site thereby enhancing cytotoxic potencies. This concept led to the synthesis of various N-acyl-3,5-bis(arylidene)-4-pipetidones 3-7 many of which displayed significant cytotoxicity towards a variety of cancer cell lines. A comparison of the potencies between the compounds in series I and the related nonquaternary analogues 3-6 revealed that in approximately half of the comparisons made, the N-acyl analogues had increased potencies. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.08.002
• 作为产物：
  描述：

  2-二乙氨基氯乙烷盐酸盐 在 potassium carbonate 、 sodium hydroxide 作用下， 生成 4-(2-diethylaminoethoxy)benzoic acid hydrochloride
  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

文献信息

• Substituted benzofurans and benzothiophenes
  申请人：SmithKline Corporation

  公开号：US03947470A1

  公开（公告）日：1976-03-30

  The compounds of this invention are substituted benzofurans and benzothiophenes having pharmacological activity. In particular, these compounds have coronary vasodilator activity and are useful in the treatment angina pectoris.

  本发明的化合物是具有药理活性的取代苯并呋喃和苯并噻吩。具体来说，这些化合物具有冠状血管扩张剂活性，并且在治疗心绞痛中很有用。
• Process for preparing 3-(4-aminoethoxybenzoyl)benzo[b]thiophenes
  申请人：Eli Lilly and Company

  公开号：US04358593A1

  公开（公告）日：1982-11-09

  The use of particularly advantageous protecting groups for the hydroxy groups of 6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophenes provides a high-yielding process for the preparation of such compounds having a 4-(2-aminoethoxy)benzoyl 3-group.

  特别有利的保护基团用于对6-羟基-2-(4-羟基苯基)苯并[b]噻吩的羟基，提供了一种高产率的制备具有4-(2-氨基乙氧基)苯甲酰基3基团的化合物的方法。
• [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。
• Coronary vasodilator and anti-anginal compositions comprising
  申请人：SmithKline Corporation

  公开号：US04024273A1

  公开（公告）日：1977-05-17

  The compounds of this invention are substituted benzofurans and benzothiophenes having pharmacological activity. In particular, these compounds have coronary vasodilator activity and are useful in the treatment of angina pectoris.

  该发明的化合物是具有药理活性的取代苯并呋喃和苯并噻吩。具体而言，这些化合物具有冠状动脉扩张剂活性，可用于治疗心绞痛。
• 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。