4-(2-diethylamino-ethoxy)-benzoyl chloride ; hydrochloride | 59931-29-2

• 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-diethylamino-ethoxy)-benzoyl chloride ; hydrochloride
• 英文别名: 4-(2-Diaethylamino-aethoxy)-benzoylchlorid; Hydrochlorid；4-(2-Diethylaminoethoxy)benzoyl chloride hydrochloride；4-[2-(diethylamino)ethoxy]benzoyl chloride;hydrochloride
• CAS: 59931-29-2
• 化学式: C₁₃H₁₈ClNO₂*ClH
• 分子量: 292.205
• InChiKey: UNPSTKNBFGFSEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-diethylamino-ethoxy)-benzoyl chloride ; hydrochloride 在 三乙胺 作用下， 以 1,2-二氯乙烷 、 丙酮 为溶剂， 生成 1-[4-(2-diethylaminoethoxy)phenylcarbonyl]-3,5-bis((E)-4-methylphenylmethylene)-4-piperidone methoiodide
  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：

  甲基4-(2-二乙基氨基乙氧基)苯甲酸酯 在 盐酸 、 sodium hydroxide 、 氯化亚砜 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 4-(2-diethylamino-ethoxy)-benzoyl chloride ; hydrochloride
  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

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。
• 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。
• 1-[4-(2-Aminoethoxy)phenylcarbonyl]-3,5-bis-(benzylidene)-4-oxopiperidines: A novel series of highly potent revertants of P-glycoprotein associated multidrug resistance
  作者：Umashankar Das、Joseph Molnár、Zoltán Baráth、Zsuzsanna Bata、Jonathan R. Dimmock

  DOI：10.1016/j.bmcl.2008.05.034

  日期：2008.6

  The 1-[4-(2-aminoethoxy) phenylcarbonyl]-3,5-bis-(benzylidene)-4-oxopiperidines 5-8 are a novel cluster of highly potent P-glycoprotein dependent multidrug resistance (MDR) revertants. Using a concentration of 4 mu g/mL, these compounds possess 11-43 times the potency of verapamil in reversing MDR in murine L-5178 lymphoma cells transfected with the human MDR1 gene. Structure-activity relationships reveal that the attachment of the N-aroyl group to various 3,5-bis(benzylidene)-4-piperidones is essential for MDR reversal to occur. In terms of potencies, the 1-piperidinyl group is the preferred terminal amine while the 4-methyl and 4-chloro substituents are the optimal groups for placement in the benzylidene aryl rings. (C) 2008 Elsevier Ltd. All rights reserved.
• WO2007/59613
  申请人：——

  公开号：——

  公开（公告）日：——
• US3947470A
  申请人：——

  公开号：US3947470A

  公开（公告）日：1976-03-30