1-(hexadecyloxy)-2-ethoxy-3-iodopropane | 126614-27-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(hexadecyloxy)-2-ethoxy-3-iodopropane
• 英文别名: 1-(2-Ethoxy-3-iodopropoxy)hexadecane
• CAS: 126614-27-5
• 化学式: C₂₁H₄₃IO₂
• 分子量: 454.476
• InChiKey: TYONZNHBYFKONQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  24
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲基-4-哌啶醇 、 1-(hexadecyloxy)-2-ethoxy-3-iodopropane 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以21%的产率得到CJM PIPER
  参考文献：
  名称：

  Synthesis of quaternary amine ether lipids and evaluation of neoplastic cell growth inhibitory properties

  摘要：

  Novel quaternary amine ether lipids have been synthesized and tested for inhibition of neoplastic cell proliferation with the HL-60 promyelocytic leukemia cell line. These compounds contain a positively charged quaternary amine functional group attached either directly to the glycerol backbone or at the end of an alkoxy chain. The biological testing has identified several analogues with activity equivalent to or greater than that exhibited by the reference compound in this assay, ET-18-OMe (1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine). Among the most active analogues are compounds 11, [N,N,N-triethyl-3-(hexadecyloxy)-2-ethoxy-1-propylammonium bromide] and 22 [N-[4-[3-(hexadecyloxy)-2-ethoxypropoxy]-1-butyl]pyridinium bromide], which are approximately 3 times as active as the reference standard.

  DOI：

  10.1021/jm00168a042
• 作为产物：
  描述：

  Methanesulfonic acid 3-hexadecyloxy-2-methoxy-propyl ester 在 sodium 作用下， 以 丙酮 为溶剂， 反应 36.0h， 生成 1-(hexadecyloxy)-2-ethoxy-3-iodopropane
  参考文献：
  名称：

  Synthesis of quaternary amine ether lipids and evaluation of neoplastic cell growth inhibitory properties

  摘要：

  Novel quaternary amine ether lipids have been synthesized and tested for inhibition of neoplastic cell proliferation with the HL-60 promyelocytic leukemia cell line. These compounds contain a positively charged quaternary amine functional group attached either directly to the glycerol backbone or at the end of an alkoxy chain. The biological testing has identified several analogues with activity equivalent to or greater than that exhibited by the reference compound in this assay, ET-18-OMe (1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine). Among the most active analogues are compounds 11, [N,N,N-triethyl-3-(hexadecyloxy)-2-ethoxy-1-propylammonium bromide] and 22 [N-[4-[3-(hexadecyloxy)-2-ethoxypropoxy]-1-butyl]pyridinium bromide], which are approximately 3 times as active as the reference standard.

  DOI：

  10.1021/jm00168a042

文献信息

• MORRIS-NATSCHKE, SUSAN L.;MEYER, KAREN L.;MARASCO, CANIO J. (JR);PIANTADO+, J. MED. CHEM., 33,(1990) N, C. 1812-1818
  作者：MORRIS-NATSCHKE, SUSAN L.、MEYER, KAREN L.、MARASCO, CANIO J. (JR)、PIANTADO+

  DOI：——

  日期：——
• US5614548A
  申请人：——

  公开号：US5614548A

  公开（公告）日：1997-03-25
• [EN] QUATERNARY AMINE CONTAINING ETHER OR ESTER LIPID DERIVATIVES AND THERAPEUTIC COMPOSITIONS
  申请人：WAKE FOREST UNIVERSITY

  公开号：WO1990004918A2

  公开（公告）日：1990-05-17

  (EN) Quaternary amine-containing ether lipid analogs of the formula R1-X-R2-N+(R3)(R4)(R5) Z- are disclosed. R1 represents a hydrophobic group and R2 represents the backbone of the molecule, with the quaternary amine being linked directly to the backbone. Pharmaceutical compositions including these compounds and methods of combating tumors with these compounds are disclosed. Also disclosed is a method of combating viral infections with both these compounds and ET-18-OMe and its analogs.(FR) L'invention concerne des analogues lipidiques d'éther contenant une amine quaternaire de la formule R1-X-R2-N+(R3)(R4)(R5) Z-. R1 représente un groupe hydrophobe et R2 représente le squelette de la molécule, l'amine quarternaire étant directement liée au squelette. L'invention concerne également des compositions pharmaceutiques comprenant ces composés ainsi que des procédés de lutte contre des tumeurs à l'aide desdits composés. Elle concerne en outre un procédé de lutte contre des infections virales à l'aide à la fois de ces composés et de ET-18-OMe ainsi que de ses analogues.