16-{[(4-tert-butylphenyl)carbamoyl]amino}hexadecanoic acid | 1611446-59-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 16-{[(4-tert-butylphenyl)carbamoyl]amino}hexadecanoic acid
• 英文别名: 16-[(4-Tert-butylphenyl)carbamoylamino]hexadecanoic acid；16-[(4-tert-butylphenyl)carbamoylamino]hexadecanoic acid
• CAS: 1611446-59-3
• 化学式: C₂₇H₄₆N₂O₃
• 分子量: 446.674
• InChiKey: LOOXSHOHSMZXLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 16-{[(4-tert-butylphenyl)carbamoyl]amino}hexadecanoate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以94%的产率得到16-{[(4-tert-butylphenyl)carbamoyl]amino}hexadecanoic acid
  参考文献：
  名称：

  A Novel Arylurea Fatty Acid That Targets the Mitochondrion and Depletes Cardiolipin To Promote Killing of Breast Cancer Cells

  摘要：

  Cancer cell mitochondria are promising anticancer drug targets because they control cell death and are structurally and functionally different from normal cell mitochondria. We synthesized arylurea fatty acids and found that the analogue 16-({[4-chloro-3-(trifluoromethyl)-phenyl]carbamoyl}amino)hexadecanoic acid (13b) decreased proliferation and activated apoptosis in MDA-MB-231 breast cancer cells in vitro and in vivo. In mechanistic studies 13b emerged as the prototype of a novel class of mitochondrion-targeted agents that deplete cardiolipin and promote cancer cell death.

  DOI：

  10.1021/acs.jmedchem.7b00701

文献信息

• [EN] OMEGA-3 ANALOGUES<br/>[FR] ANALOGUES D'OMÉGA-3
  申请人：UNIV SYDNEY

  公开号：WO2014078895A1

  公开（公告）日：2014-05-30

  The present invention relates to new fatty acid analogues and to their use in cancer therapy, including antimetastatic therapy.

  本发明涉及新的脂肪酸类似物及其在癌症治疗中的使用，包括抗转移治疗。
• OMEGA-3 ANALOGUES
  申请人：The University of Sydney

  公开号：US20150322001A1

  公开（公告）日：2015-11-12

  The present invention relates to new fatty acid analogues and to their use in cancer therapy, including antimetastatic therapy.

  本发明涉及新的脂肪酸类似物及其在癌症治疗中的应用，包括抗转移治疗。
• A Novel Arylurea Fatty Acid That Targets the Mitochondrion and Depletes Cardiolipin To Promote Killing of Breast Cancer Cells
  作者：Tristan Rawling、Hassan Choucair、Nooshin Koolaji、Kirsi Bourget、Sarah E. Allison、Yong-Juan Chen、Colin R. Dunstan、Michael Murray

  DOI：10.1021/acs.jmedchem.7b00701

  日期：2017.10.26

  Cancer cell mitochondria are promising anticancer drug targets because they control cell death and are structurally and functionally different from normal cell mitochondria. We synthesized arylurea fatty acids and found that the analogue 16-([4-chloro-3-(trifluoromethyl)-phenyl]carbamoyl}amino)hexadecanoic acid (13b) decreased proliferation and activated apoptosis in MDA-MB-231 breast cancer cells in vitro and in vivo. In mechanistic studies 13b emerged as the prototype of a novel class of mitochondrion-targeted agents that deplete cardiolipin and promote cancer cell death.