3-(dodecyloxy)propan-1-ol | 84337-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(dodecyloxy)propan-1-ol
• 英文别名: 3-dodecoxypropan-1-ol；2-(dodecyloxy)methyl-1-ethanol；3-dodecyloxy-1-propanol
• CAS: 84337-56-4
• 化学式: C₁₅H₃₂O₂
• 分子量: 244.418
• InChiKey: GOOXAZXQGWKGKT-UHFFFAOYSA-N

物化性质

• 沸点：
  330.9±10.0 °C(Predicted)
• 密度：
  0.872±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(dodecyloxy)propan-1-ol 在 叠氮磷酸二苯酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.17h， 生成 3-十二烷氧基丙胺
  参考文献：
  名称：

  Lipophilic amines as potent inhibitors of N-acylethanolamine-hydrolyzing acid amidase

  摘要：

  N-Acylethanolamines (NAEs) including N-arachidonoylethanolamine (anandamide) and N-palmitoylethanolamine are endogenous lipid mediators. These molecules are degraded to the corresponding fatty acids and ethanolamine by fatty acid amide hydrolase (FAAH) or NAE-hydrolyzing acid amidase (NAAA). Lipophilic amines, especially pentadecylamine (2c) and tridecyl 2-aminoacetate (11b), were found to exhibit potent NAAA inhibitory activities (IC50 = 5.7 and 11.8 mu M), with much weaker effects on FAAH. These simple structures would provide a scaffold for further improvement in NAAA inhibitory activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.065
• 作为产物：
  描述：

  十二烷醇 在 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 3-(dodecyloxy)propan-1-ol
  参考文献：
  名称：

  Structure-activity relationship of lipopeptide from outer membrane of Escherichia coli and synthesis of highly immunopotenting lipopeptide derivatives with an achiral lipo-part.

  摘要：

  为了突出脂肽衍生物的结构-活性关系，新近合成了具有非手性脂部分的生物活性高的脂肽衍生物。

  DOI：

  10.1248/cpb.41.627

文献信息

• Acyloxybenzyl and Alkoxyalkyl Prodrugs of a Fosmidomycin Surrogate as Antimalarial and Antitubercular Agents
  作者：Charlotte Courtens、Martijn Risseeuw、Guy Caljon、Paul Cos、Serge Van Calenbergh

  DOI：10.1021/acsmedchemlett.8b00223

  日期：2018.10.11

  Two classes of prodrugs of a fosmidomycin surrogate were synthesized and investigated for their ability to inhibit in vitro growth of P. falciparum and M. tuberculosis. To this end, a novel efficient synthesis route was developed involving a cross metathesis reaction as a key step. Alkoxyalkyl prodrugs show decent antimalarial activities, but acyloxybenzyl prodrugs proved to be the most interesting

  合成了两类磷霉素的前药，并研究了它们抑制恶性疟原虫和结核分枝杆菌体外生长的能力。为此，开发了涉及交叉复分解反应作为关键步骤的新颖的有效合成途径。烷氧基烷基前药显示出良好的抗疟活性，但事实证明，酰氧基苄基前药是最令人感兴趣的，并显示出增强的抗疟和抗结核活性。最具活性的抗疟疾类似物显示出较低的纳摩尔IC 50值。
• [EN] PROPOFOL PHOSPHONYL DERIVATIVES, SYNTHESIS, AND USE IN LONG ACTING FORMULATIONS<br/>[FR] DÉRIVÉS DE PROPOFOL PHOSPHONYLE, SYNTHÈSE, ET UTILISATION DANS DES PRÉPARATIONS À LONGUE DURÉE D'ACTION
  申请人：SEPS PHARMA N V

  公开号：WO2010115869A1

  公开（公告）日：2010-10-14

  This invention relates to compounds represented by the structural formula (I), and the salts and stereoisomers thereof, wherein: - L is a linker selected from the group consisting of -(CH2)P-O-, a single bond, formula (IA), -(CH2)1-8-O-X(O)-, and - p is an integer from 1 to 8, - each R3 and each R4 is independently selected from the group consisting of C1-20alkyl, C3-12alkyl, C3-12cycloalkyl-C1-4alkyl, saturated heterocyclyl and saturated heterocyclyl-C1-4alkyl, and - X and Y are each independently C or S(O), - Z is selected from the group consisting of O, S(O) and NR5, - W is selected from the group consisting of halogen, OH, S(O)H and O-M+ wherein M+ is a monovalent cation; and - R5 is selected from the group consisting of hydrogen and C1-10 alkyl. These compounds are useful pharmaceutical agents with improved oral bioavailability.

  这项发明涉及由结构式（I）表示的化合物，以及其盐和立体异构体，其中：- L是从羟基-(CH2)P-O-、单键、式（IA）、-(CH2)1-8-O-X(O)-和中选择的连接剂，- p是1到8之间的整数，- 每个R3和每个R4分别从C1-20烷基、C3-12烷基、C3-12环烷基-C1-4烷基、饱和杂环烷基和饱和杂环烷基-C1-4烷基组中选择，- X和Y各自独立地为C或S(O)，- Z从O、S(O)和NR5组中选择，- W从卤素、羟基、S(O)H和O-M+中选择，其中M+是一价阳离子；- R5从氢和C1-10烷基组中选择。这些化合物是具有改善口服生物利用度的有用药物。
• 脂质修饰精胺衍生物及利用该衍生物制备的 脂质体
  申请人：苏州圣诺生物医药技术有限公司

  公开号：CN104876831B

  公开（公告）日：2017-05-17

  本发明提供了一种具有通式(1)的脂质修饰精胺衍生物以及利用该衍生物制备的脂质体。精胺衍生物通过直接使用，或与胆固醇、中性脂质和聚乙二醇修饰脂质中的一种或几种混合使用，可作为载体用于包载或吸附生物活性分子药物，并将其送入细胞达到调节、干预或治疗的用途。通式(1)中，X1为‑(CH2)n‑或羰基，其中n为1，2或3；X2选自‑(CH2)‑、酯基、酰胺基、氧或硫；R1和R2独立地选自C6‑C18烷基、含有烯键的C6‑C18烷基或亲脂性胆固醇类分子；
• Long-chain triazolyl acids as inhibitors of osteoclastogenesis
  作者：Andrew J. Marshall、Jian-Ming Lin、Andrew Grey、Ian R. Reid、Jillian Cornish、William A. Denny

  DOI：10.1016/j.bmc.2013.05.013

  日期：2013.7

  osteoclasts in primary mouse bone marrow cultures. The oxyacids were generally prepared by condensation of the appropriate alkyl halides and diols, followed by Jones oxidation. The triazolyl acids were prepared by copper-catalysed click chemistry between alkyl azides and acetylenic acids, or with the appropriately-protected azides and alkynes, followed by deprotection and oxidation. The oxyacids were little

  已知饱和脂肪酸（例如棕榈酸）在体外可适度抑制破骨细胞的发育。为了寻求更有效的破骨细胞抑制剂，我们探索了两类新的棕榈酸类似物，它们在链的各个位置上都含有醚或三唑基。评价化合物在原代小鼠骨髓培养物中抑制破骨细胞形成的能力。含氧酸通常通过适当的烷基卤化物和二醇的缩合，然后进行琼斯氧化来制备。三唑基酸是通过烷基叠氮化物和炔酸之间的铜催化点击化学反应，或用适当保护的叠氮化物和炔烃，然后脱保护和氧化制备的。含氧酸的功效比棕榈酸稍强，
• 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。