N-Dodecyl-difluoracetamid | 71113-61-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-Dodecyl-difluoracetamid
• 英文别名: N-Dodecyl difluoroacetamide；N-dodecyl-2,2-difluoroacetamide
• CAS: 71113-61-6
• 化学式: C₁₄H₂₇F₂NO
• 分子量: 263.371
• InChiKey: LBCGCCYASAXCAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Dodecyl-difluoracetamid 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 生成 N-(2,2-difluoroethyl)dodecylamine
  参考文献：
  名称：

  Lysosomotropic agents. 1. Synthesis and cytotoxic action of lysosomotropic detergents

  摘要：

  Amines whose pK values lie between about 5 and 9 are lysosomotropic because lysosomes are acidic intracellular compartments. If such amines bear long hydrophobic chains, they become detergents upon protonation inside the lysosomes, rupturing the lysosomal membrane and killing the cell. Six types of lysosomotropic amines have been prepared that all behave in the expected manner. They are cytotoxic to all lysosome-bearing cells but not red blood cells, which lack lysosomes. Their mode of action, the effect of alkyl chain length on activity, and the fact that their cytotoxic action appears only above a threshhold intracellular concentration support the belief that they behave as lysosomotropic detergents. Among the potential applications is cancer chemotherapy.

  DOI：

  10.1021/jm00195a026
• 作为产物：
  描述：

  十二烷基伯胺 、 二氟乙酸乙酯 以 乙腈 为溶剂， 生成 N-Dodecyl-difluoracetamid
  参考文献：
  名称：

  Lysosomotropic agents. 1. Synthesis and cytotoxic action of lysosomotropic detergents

  摘要：

  Amines whose pK values lie between about 5 and 9 are lysosomotropic because lysosomes are acidic intracellular compartments. If such amines bear long hydrophobic chains, they become detergents upon protonation inside the lysosomes, rupturing the lysosomal membrane and killing the cell. Six types of lysosomotropic amines have been prepared that all behave in the expected manner. They are cytotoxic to all lysosome-bearing cells but not red blood cells, which lack lysosomes. Their mode of action, the effect of alkyl chain length on activity, and the fact that their cytotoxic action appears only above a threshhold intracellular concentration support the belief that they behave as lysosomotropic detergents. Among the potential applications is cancer chemotherapy.

  DOI：

  10.1021/jm00195a026

文献信息

• Lysosometropic detergent therapeutic agents
  申请人：Merck & Co., Inc.

  公开号：US04719312A1

  公开（公告）日：1988-01-12

  The present invention is concerned with the preparation of lysosomotropic detergent agents and pharmaceutical composition useful in the treatment of cancer. These compounds are amine derivatives having a pK of 3.5 of the general structure ##STR1## in which R.sub.1 is C.sub.8-30 alkyl, C.sub.8-30 -alkenyl, substituted C.sub.4-30 alkyl or substituted C.sub.4-30 -alkenyl; R.sub.2 is hydrogen or C.sub.1-4 alkyl and Y is an electron withdrawing group, to control the pK, selected from trifluoroethyl, and difluoroethyl.

  本发明涉及制备溶酶体靶向性清洁剂剂和用于癌症治疗的药物组合物。这些化合物是具有pK值为3.5的胺衍生物，其一般结构为##STR1##其中R.sub.1为C.sub.8-30烷基，C.sub.8-30烯基，取代的C.sub.4-30烷基或取代的C.sub.4-30烯基；R.sub.2为氢或C.sub.1-4烷基，Y为电子吸引基，以控制pK值，所选自三氟乙基和二氟乙基。
• Lysosomotropic agents. 1. Synthesis and cytotoxic action of lysosomotropic detergents
  作者：Raymond A. Firestone、Judith M. Pisano、Robert J. Bonney

  DOI：10.1021/jm00195a026

  日期：1979.9

  Amines whose pK values lie between about 5 and 9 are lysosomotropic because lysosomes are acidic intracellular compartments. If such amines bear long hydrophobic chains, they become detergents upon protonation inside the lysosomes, rupturing the lysosomal membrane and killing the cell. Six types of lysosomotropic amines have been prepared that all behave in the expected manner. They are cytotoxic to all lysosome-bearing cells but not red blood cells, which lack lysosomes. Their mode of action, the effect of alkyl chain length on activity, and the fact that their cytotoxic action appears only above a threshhold intracellular concentration support the belief that they behave as lysosomotropic detergents. Among the potential applications is cancer chemotherapy.