4-(3-aminophenyl)-3-butyn-1-ol | 851859-74-0

• 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-(3-aminophenyl)-3-butyn-1-ol
• 英文别名: 4-(3-aminophenyl)but-3-yl-1-ol；4-(3-Aminophenyl)but-3-yn-1-ol
• CAS: 851859-74-0
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: VDELNSIDFKSGNA-UHFFFAOYSA-N

物化性质

• 沸点：
  361.2±27.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3-aminophenyl)-3-butyn-1-ol 、 氯乙基异氰酸酯 以 二氯甲烷 为溶剂， 反应 20.0h， 以51%的产率得到1-(2-chloro-ethyl)-3-[3-(4-hydroxy-but-1-ynyl)-phenyl]-urea
  参考文献：
  名称：

  Optimized N-phenyl-N′-(2-chloroethyl)ureas as potential antineoplastic agents: Synthesis and growth inhibition activity

  摘要：

  In our ongoing research program aimed at the optimization of microtubule-self-assembly disrupting agents, we have prepared three series of phenylurea analogues (CEU), derived from N-(3-omega-hydroxyalkyl or 4-omega-hydroxyalkyl or 3-omega-hydroxyalkynyl)phenyl-N'-(2-chloroethyl)ureas. Most compounds exhibit potent growth inhibitory activity on human colon carcinoma HT-29, human skin melanoma M21, and human breast carcinoma MCF-7 tumor cell lines, with a GI(50) ranging from 250 nM to 8 mu M. Among these new molecules, three CEUs exhibit GI(50) in the nanomolar range. They are more potent by approximately an order of magnitude than previously described CEU analogues. As such, they are attractive hit compounds for the development of potent new alkylating antitubulin drugs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.048
• 作为产物：
  描述：

  4-(3-硝基苯基)丁-3-炔-1-醇 在 盐酸 、 铁粉 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以49%的产率得到4-(3-aminophenyl)-3-butyn-1-ol
  参考文献：
  名称：

  Optimized N-phenyl-N′-(2-chloroethyl)ureas as potential antineoplastic agents: Synthesis and growth inhibition activity

  摘要：

  In our ongoing research program aimed at the optimization of microtubule-self-assembly disrupting agents, we have prepared three series of phenylurea analogues (CEU), derived from N-(3-omega-hydroxyalkyl or 4-omega-hydroxyalkyl or 3-omega-hydroxyalkynyl)phenyl-N'-(2-chloroethyl)ureas. Most compounds exhibit potent growth inhibitory activity on human colon carcinoma HT-29, human skin melanoma M21, and human breast carcinoma MCF-7 tumor cell lines, with a GI(50) ranging from 250 nM to 8 mu M. Among these new molecules, three CEUs exhibit GI(50) in the nanomolar range. They are more potent by approximately an order of magnitude than previously described CEU analogues. As such, they are attractive hit compounds for the development of potent new alkylating antitubulin drugs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.048

文献信息

• [EN] PHENETANOLAMINE DERIVATIVES<br/>[FR] DERIVES DE PHENETANOLAMINE
  申请人：GLAXO GROUP LTD

  公开号：WO2005044787A1

  公开（公告）日：2005-05-19

  Compounds of formula (I) and salts, solvates, and physiologically functional derivatives thereof, useful for the prophylaxis or treatment of a clinical condition for which a selective β2-adrenoreceptor agonist is indicated, for example asthma or chronic obstructive pulmonary disease (COPD).

  化合物的化学式(I)及其盐、溶剂合物和生理功能衍生物，可用于预防或治疗需要选择性β2-肾上腺素受体激动剂的临床病症，例如哮喘或慢性阻塞性肺疾病（COPD）。
• Phenetanolamine derivatives
  申请人：Biggadike Keith

  公开号：US20070135490A1

  公开（公告）日：2007-06-14

  Compounds of formula (I): and salts, solvates, and physiologically functional derivatives thereof, useful for the prophylaxis or treatment of a clinical condition for which a selective β 2 -adrenoreceptor agonist is indicated, for example asthma or chronic obstructive pulmonary disease (COPD).

  公式（I）的化合物及其盐，溶剂合物和生理学上的功能衍生物，可用于预防或治疗选择性β2-肾上腺素受体激动剂适用的临床疾病，例如哮喘或慢性阻塞性肺疾病（COPD）。
• PHENETANOLAMINE DERIVATIVES
  申请人：GLAXO GROUP LIMITED

  公开号：EP1675821A1

  公开（公告）日：2006-07-05
• Optimized N-phenyl-N′-(2-chloroethyl)ureas as potential antineoplastic agents: Synthesis and growth inhibition activity
  作者：Emmanuel Moreau、Sébastien Fortin、Michel Desjardins、Jean L.C. Rousseau、Éric Petitclerc、René C.-Gaudreault

  DOI：10.1016/j.bmc.2005.07.048

  日期：2005.12

  In our ongoing research program aimed at the optimization of microtubule-self-assembly disrupting agents, we have prepared three series of phenylurea analogues (CEU), derived from N-(3-omega-hydroxyalkyl or 4-omega-hydroxyalkyl or 3-omega-hydroxyalkynyl)phenyl-N'-(2-chloroethyl)ureas. Most compounds exhibit potent growth inhibitory activity on human colon carcinoma HT-29, human skin melanoma M21, and human breast carcinoma MCF-7 tumor cell lines, with a GI(50) ranging from 250 nM to 8 mu M. Among these new molecules, three CEUs exhibit GI(50) in the nanomolar range. They are more potent by approximately an order of magnitude than previously described CEU analogues. As such, they are attractive hit compounds for the development of potent new alkylating antitubulin drugs. (c) 2005 Elsevier Ltd. All rights reserved.