1-O-hexadecyl-2-O-methyl-rac-glycerol | 84337-41-7

• 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-hexadecyl-2-O-methyl-rac-glycerol
• 英文别名: (+/-)-1-O-hexadecyl-2-O-methylglycerol；3-(hexadecyloxy)-2-methoxy-1-propanol；3-hexadecoxy-2-methoxypropan-1-ol
• CAS: 84337-41-7
• 化学式: C₂₀H₄₂O₃
• mdl: MFCD00079344
• 分子量: 330.552
• InChiKey: XAWCMDFDFNRKGK-UHFFFAOYSA-N

物化性质

• 沸点：
  430.6±25.0 °C(Predicted)
• 密度：
  0.895±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  23
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-O-hexadecyl-2-O-methyl-rac-glycerol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以92%的产率得到1-O-hexadecyl-2-O-methyl-3-iodide-sn-glycerol
  参考文献：
  名称：

  [EN] GLYCOSYLATED ANTITUMOR ETHER LIPIDS AS NOVEL CANCER STEM CELL CYTOTOXIC AGENTS
  [FR] ÉTHER-LIPIDES ANTICANCÉREUX GLYCOSYLÉS EN TANT QUE NOUVEAUX AGENTS CYTOTOXIQUES DE CELLULES SOUCHES CANCÉREUSES

  摘要：

  糖基化抗肿瘤醚脂质（GAELs）是有效的细胞毒性剂，可针对癌干细胞。此外，将通过一种与半胱氨酸蛋白酶无关的途径杀死细胞的GAELs与通过凋亡杀死细胞的药物结合，将导致消除分化的肿瘤细胞和未分化的癌干细胞，从而消除肿瘤并预防复发。

  公开号：

  WO2013116949A1
• 作为产物：
  描述：

  对甲苯磺酸十六烷基酯 在 吡啶 、 amberlyst-15 、 硫酸 、 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 57.0h， 生成 1-O-hexadecyl-2-O-methyl-rac-glycerol
  参考文献：
  名称：

  Analogs of platelet activating factor. 6. Mono- and bis-aryl phosphate antagonists of platelet activating factor

  摘要：

  A series of aryl phosphoglyceride (3, 19-6 1) and bis-aryl phosphate (67-135) antagonists of platelet activating factor (PAF) were prepared. A group of four bifunctional phosphorus reagents (5a-c and 7) were developed that allowed the preparation of these aryl phosphates in which the position of aromatic substitution can be varied. These compounds were examined for their ability to inhibit PAF-induced platelet aggregation of rabbit platelets. Selected compounds were also evaluated for their ability to displace [H-3]PAF from its receptor on rabbit platelets. These in vitro data were compared to similar data obtained for a number of known PAF antagonists. The compounds were evaluated in vivo, in both the mouse and rabbit, for their ability to prevent death induced by a lethal challenge of PAF. The relationships between the biological activity and the nature, lipophilicity, and position of substituents of the aromatic rings were studied. Compound 105 (CL 184005) has been selected to undergo further development as a potential therapeutic agent for the treatment of septic shock in man.

  DOI：

  10.1021/jm00087a023

文献信息

• Syntheses and antimicrobial activities of alkyl lysophospholipids.
  作者：SUSUMU TSUSHIMA、YOSHIO YOSHIOKA、SEIICHI TANIDA、HIROAKI NOMURA、SHOSHICHI NOJIMA、MOTOO HOZUMI

  DOI：10.1248/cpb.30.3260

  日期：——

  Twenty-seven alkyl analogs of lysophospholipid were synthesized and their structureantimicrobial activity relationships were examined. These analogs differed in the structures of the long-chain alkyl moiety at position 1 and the β-N-substituted aminoethylphosphoryl moiety at position 3, and in the presence or absence of the 2-methoxy group of the glycerol moiety. Many of the alkyl lysophospholipids were found to possess antimicrobial activities much more potent than those of naturally occuring lysolecithin and lecithin against Tetrahymena pyriformis W and a variety of fungi, including human pathogens. The maximal activity was observed with 2-methyl-1-tetradecylglycero-3-phosphocholines. 1-Alkyl-2-methylglycero-3-phosphocholines with longer as well as shorter alkyl chains tended to have lower antimicrobial activity. Alkyl lysophospholipids with pyridinioethyl instead of the choline group showed potent antifungal activity comparable to alkyl glycerophosphocholines with the corresponding alkyl group but lower antiprotozoal activity. The tetradecyl congeners in these two classes of compounds showed potent inhibitory activity against Trichophyton species, comparable to that of clotrimazole. In contrast, alkyl lysophospholipids with an ethanolamine moiety in the polar head group showed decreased activity. Changing the molecular backbone from glycerol to 1, 3-propanediol had little effect upon the activity, and the resulting 1-alkyl-2-deoxyglycero-3-phosphocholines displayed antimicrobial properties similar to those of 1-alkyl-2-methylglycero-3-phosphocholines.

  合成了二十七种脂肪基类溶血磷脂，并研究了它们的结构与抗微生物活性之间的关系。这些类似物在位置1的长链脂肪基和位置3的β-N取代氨乙基磷酸基的结构上有所不同，同时存在或缺失甘油基团的2-甲氧基。许多脂肪基溶血磷脂的抗微生物活性被发现远强于自然存在的溶血卵磷脂和卵磷脂，对四核变形虫W和多种真菌（包括人类病原体）具有显著的杀灭作用。最大活性出现在2-甲基-1-十四烷基甘油-3-phosphocholines中。带有更长或更短的烷基链的1-烷基-2-甲基甘油-3-phosphocholines的抗微生物活性则相对较低。用吡啶乙基取代胆碱基团的脂肪基溶血磷脂显示出强效的抗真菌活性，其效果与相应烷基的脂肪基磷酸甘油胆碱相当，但抗原虫活性较低。这两类化合物中的十四烷基同类物对皮肤癣菌表现出显著的抑制活性，与克霉唑的效果相当。相反，具有乙醇胺基团的脂肪基溶血磷脂显示出活性下降。将分子骨架从甘油改为1,3-丙二醇对活性影响较小，得到的1-烷基-2-脱氧甘油-3-phosphocholines展现出与1-烷基-2-甲基甘油-3-phosphocholines相似的抗微生物特性。
• Antidiabetic phosphates
  申请人：American Cyanamid Company

  公开号：US04968790A1

  公开（公告）日：1990-11-06

  Phosphates are disclosed which stimulate the enzyme fructose-1,6-bisphosphatase and inhibit the enzyme 6-phosphofructo-1-kinase, thereby lowering glucose levels in mammals. These phosphates may thus be used to treat hyperglycemia and/or diabetes. Processes for the synthesis of the phosphates are also disclosed.

  揭示了一种能够刺激酶果糖-1,6-二磷酸酶并抑制酶6-磷酸果糖-1-激酶的磷酸盐，从而降低哺乳动物体内的葡萄糖水平。这些磷酸盐可以用于治疗高血糖和/或糖尿病。同时还揭示了合成这些磷酸盐的方法。
• A Novel Class of Platelet Activating Factor(PAF) Antagonists. I. Synthesis and Structure-Activity Studies on PAF-Sulfonamide Isosteres.
  作者：Tatsuo TSURI、Nobuhiro HAGA、Takeaki MATSUI、Susumu KAMATA、Hisato KAKUSHI、Kiyohisa UCHIDA

  DOI：10.1248/cpb.40.75

  日期：——

  New platelet activating factor (PAF) antagonists, 3 were synthesized by replacing the charged phosphate and trimethylammonium moieties with sulfonamide and heterocyclic quarternary ammonium functionalities, respectively(PAF-sulfonamide isosteres). Darmstoff phosphatidic acid analogues of this class (Darmstoff-sulfonamide isosteres), 6 were also synthesized.The activity of these compounds as PAF antagonists was evaluated from their in vitro inhibitory effect on PAF-induced platelet aggregation in rabbit platelet-rich plasma. Among the compounds tested, some of the 2-methoxypropane derivatives with an octadecylcarbamoyloxy or octadecylcarbamoylthio side chain at the 1-position and a propylsulfonamide function bearing a terminal polar substituent such as a quarternary quinolinium or substituted quinolinium group at the 3-position were found to be the most potent (IC50=0.3-0.6μM).

  通过分别用磺酰胺和杂环季铵官能团取代带电的磷酸盐和三甲基铵，合成了新的血小板活化因子（PAF）拮抗剂 3（PAF-磺酰胺异构体）。这些化合物作为 PAF 拮抗剂的活性是通过它们对 PAF 诱导的兔血小板富集血浆中血小板聚集的体外抑制作用来评估的。在测试的化合物中，一些 2-甲氧基丙烷衍生物的 1 位具有十八烷基氨基甲酰氧基或十八烷基氨基甲酰硫代侧链，3 位具有丙磺酰胺功能并带有末端极性取代基（如四元喹啉基或取代的喹啉基），这些化合物的效力最强（IC50=0.3-0.6μM）。
• Synthesis and biological activity of novel quaternary ammonium derivatives of alkylglycerols as potent inhibitors of protein kinase C
  作者：Canio J. Marasco、Claude Piantadosi、Karen L. Meyer、Susan Morris-Natschke、Khalid S. Ishaq、George W. Small、Larry W. Daniel

  DOI：10.1021/jm00165a016

  日期：1990.3

  effect on the metastasis and growth of various cancer cell lines. Alkyl phospholipids have been shown to accumulate at the surface in several cell lines, the selectivity of which is still not clearly understood. A consequence of this action may lead to the inhibition of cell membrane related protein kinase C (PKC). The goal of this research was to develop ether lipid inhibitors of PKC to augment antineoplastic

  烷基甘油，例如rac-1-O-十八烷基-2-O-甲基甘油磷酸胆碱（Et-18-OMe）对多种癌细胞系的转移和生长均显示出抑制作用。已显示烷基磷脂积聚在几种细胞系的表面，其选择性仍不清楚。该作用的结果可能导致抑制细胞膜相关蛋白激酶C（PKC）。这项研究的目的是开发PKC的醚脂质抑制剂以增强抗肿瘤活性。这导致了一系列烷基甘油的新型季铵衍生物的合成和体外测试。这些类似物在用rac-1-O-油酰基-2-O-乙酰甘油刺激的PKC上的生物学测试表明，其抑制作用与Et-18-OMe相当。
• DiGalactosyl-Glycero-Ether Lipid: synthetic approaches and evaluation as SK3 channel inhibitor
  作者：Charlotte M. Sevrain、Jean-Pierre Haelters、Aurélie Chantôme、Hélène Couthon-Gourvès、Maxime Gueguinou、Marie Potier-Cartereau、Christophe Vandier、Paul-Alain Jaffrès

  DOI：10.1039/c3ob40634b

  日期：——

  discoveries of the involvement of SK3 channel in some cell motility mechanisms occurring in cancer disease have opened up the way to the synthesis of inhibitors that could reduce metastasis formation. On the basis of our recent previous works showing that both lactose-glycero-ether lipid (Ohmline) and some phosphate analogues (GPGEL) were efficient compounds to modulate SK3 channel activity, the present study

  SK3通道参与癌症疾病中某些细胞运动机制的最新发现为合成可以减少转移形成的抑制剂开辟了道路。根据我们最近的先前研究表明，乳糖-甘油-醚脂质（Ohmline）和一些磷酸盐类似物（GPGEL）是调节SK3通道活性的有效化合物，本研究在天然糖脂DiG​​alactosylDiacylGlycerol（DGDG）的结构中获得了启发，并报道了二半乳糖基部分（α-半乳糖吡喃糖基-（1→6）-β- galactopyranosyl-）作为甘油醚脂质的极性头。对于二半乳糖基片段的构建，比较了两种合成方法。将基于使用苄基保护基产生1→6二糖单元的标准策略与使用三甲基甲硅烷基部分作为保护基的第二种方法进行了比较。该第二种策略首次应用于（1→6）-二糖单元的合成，在功效（更好的全球产量）和成本方面表现出了净优势。最后，化合物16以（1→6）DiGalactosyl unit（DG）作为两亲结构的极性头为特征，已