1-O-(6-cyanohexyl)glycerol | 138594-19-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1-O-(6-cyanohexyl)glycerol
• 英文别名: Heptanenitrile, 7-(2,3-dihydroxypropoxy)-；7-(2,3-dihydroxypropoxy)heptanenitrile
• CAS: 138594-19-1
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: QYLFLUQAGDDLCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  73.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三苯基氯甲烷 、 1-O-(6-cyanohexyl)glycerol 在 吡啶 作用下， 反应 22.0h， 以69%的产率得到1-O-(6-cyanohexyl)-3-O-tritylglycerol
  参考文献：
  名称：

  Synthesis of Alkyl Chain-Modified Ether Lipids and Evaluation of Their in Vitro Cytotoxicity

  摘要：

  A series of alkyl lysophospholipid (ALP) analogs of ET-18-OCH3 (1-O-octadecyl-2-O-methylrac-glycero-3-phosphocholine) containing modifications in the long C-1 chain has been synthesized and evaluated in human tumor cell line cytotoxicity assays. The compounds have also been evaluated in platelet activating factor (PAF) receptor agonism and hemolysis tests. Two modifications have been studied, introduction of a carbonyl group at different positions of the C-1 chain and branching of this chain, in some compounds with incorporation of a phenyl group. Several compounds showed a cytotoxic potency comparable to that of the reference compound ET-18-OCH3, associated with reduced proaggregating and hemolytic effects. The two enantiomers of 1-0-(7-oxooctadecyl)-2-O-methyl-rac-glycero-3-phospho choline (2) showed the same level of cytotoxicity or antiproliferative activity, with the PAF-agonistic effect confined to R-2. The very low stereoselectivity found in the in vitro cytotoxicity confirms earlier results and indicates a lack of stereospecific interactions with a macromolecular target.

  DOI：

  10.1021/jm00007a018
• 作为产物：
  描述：

  1-O-(6-cyanohexyl)-2,3-O-isopropylideneglycerol 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以83%的产率得到1-O-(6-cyanohexyl)glycerol
  参考文献：
  名称：

  Synthesis of Alkyl Chain-Modified Ether Lipids and Evaluation of Their in Vitro Cytotoxicity

  摘要：

  A series of alkyl lysophospholipid (ALP) analogs of ET-18-OCH3 (1-O-octadecyl-2-O-methylrac-glycero-3-phosphocholine) containing modifications in the long C-1 chain has been synthesized and evaluated in human tumor cell line cytotoxicity assays. The compounds have also been evaluated in platelet activating factor (PAF) receptor agonism and hemolysis tests. Two modifications have been studied, introduction of a carbonyl group at different positions of the C-1 chain and branching of this chain, in some compounds with incorporation of a phenyl group. Several compounds showed a cytotoxic potency comparable to that of the reference compound ET-18-OCH3, associated with reduced proaggregating and hemolytic effects. The two enantiomers of 1-0-(7-oxooctadecyl)-2-O-methyl-rac-glycero-3-phospho choline (2) showed the same level of cytotoxicity or antiproliferative activity, with the PAF-agonistic effect confined to R-2. The very low stereoselectivity found in the in vitro cytotoxicity confirms earlier results and indicates a lack of stereospecific interactions with a macromolecular target.

  DOI：

  10.1021/jm00007a018

文献信息

• [EN] KETOALKYLGLYCEROPHOSPHOLIPIDS HAVING ANTITUMOR AND ANTI-PLATELET AGGREGATION ACTIVITIES, PROCESSES FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS THEREFROM
  申请人：LABORATORIOS MENARINI S.A.

  公开号：WO1993001196A1

  公开（公告）日：1993-01-21

  (EN) Compounds of general formula (I) wherein R1 is a C1-C16 straight or branched alkyl group, a phenyl group or a phenyl-C6-C16alkyl group; n is an integer from 3 to 18, inclusive; R2 is a C1-C12 straight or branched alkyl group; R3 is hydrogen, a carboxy, alkoxycarbonyl, arylalkoxycarbonyl or aryloxycarbonyl group of less than 12 carbon atoms in the last three cases; R4, R5 and R6, which can be the same or different, are hydrogen, a C1-C6 alkyl group or N+R4R5R6 is a cyclic ammonium group, which can be aromatic or non-aromatic, wherein two of the R4, R5 or R6 groups form a ring together with the nitrogen atom, and the other group is hydrogen or C1-C6 alkyl, have antitumor and anti-platelet aggregating activities.(FR) L'invention se rapporte à des composés représentés par la formule générale (I), où R1 représente un groupe alkyle droit ou ramifié C1-C16, un groupe phényle ou un groupe phényle-alkyle C6-C16; n représente un nombre entier compris entre 3 et 18, inclus; R2 représente un groupe alkyle droit ou ramifié C1-C12; R3 représente de l'hydrogène, un groupe carboxy, alcoxycarbonyle, arylalcoxycarbonyle ou aryloxycarbonyle ayant moins de 12 atomes de carbone dans les trois derniers cas; R4, R5 et R6 qui peuvent être identiques ou différents, représentent de l'hydrogène, un groupe alkyle C1-C6, ou N+R4R5R6 représente un groupe d'ammonium cyclique, qui peut être aromatique ou non aromatique, dans lequel deux des groupes R4, R5 ou R6 forment une chaîne fermée avec l'atome d'azote, et l'autre groupe représente hydrogène ou alkyle C1-C6. Ces composés ont des propriétés telles qu'ils peuvent être utilisés comme agents antitumoraux et comme antiagrégants plaquettaires.
• Synthesis of Alkyl Chain-Modified Ether Lipids and Evaluation of Their in Vitro Cytotoxicity
  作者：Empar Fos、Nuria Suesa、Liset Borras、Cinta Lobato、Patrizia Banfi、Romolo A. Gambetta、Franco Zunino、David Mauleon、Germano Carganico

  DOI：10.1021/jm00007a018

  日期：1995.3

  A series of alkyl lysophospholipid (ALP) analogs of ET-18-OCH3 (1-O-octadecyl-2-O-methylrac-glycero-3-phosphocholine) containing modifications in the long C-1 chain has been synthesized and evaluated in human tumor cell line cytotoxicity assays. The compounds have also been evaluated in platelet activating factor (PAF) receptor agonism and hemolysis tests. Two modifications have been studied, introduction of a carbonyl group at different positions of the C-1 chain and branching of this chain, in some compounds with incorporation of a phenyl group. Several compounds showed a cytotoxic potency comparable to that of the reference compound ET-18-OCH3, associated with reduced proaggregating and hemolytic effects. The two enantiomers of 1-0-(7-oxooctadecyl)-2-O-methyl-rac-glycero-3-phospho choline (2) showed the same level of cytotoxicity or antiproliferative activity, with the PAF-agonistic effect confined to R-2. The very low stereoselectivity found in the in vitro cytotoxicity confirms earlier results and indicates a lack of stereospecific interactions with a macromolecular target.