1- bromo-2-octadecyloxyethane | 343248-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1- bromo-2-octadecyloxyethane
• 英文别名: 1-(2-bromoethoxy)Octadecane
• CAS: 343248-28-2
• 化学式: C₂₀H₄₁BrO
• 分子量: 377.449
• InChiKey: VZLNJSZZNMSQGA-UHFFFAOYSA-N

物化性质

• 沸点：
  419.5±18.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  22
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1- bromo-2-octadecyloxyethane 在 N-甲基咪唑 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 17.08h， 生成 3-[[(2R,5R)-5-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-(2-octadecoxyethoxy)tetrahydrofuran-3-yl]oxy(diisopropylamino)phosphanyl]oxypropanenitrile
  参考文献：
  名称：

  WO2024006953A2

  摘要：

  公开号：
• 作为产物：
  描述：

  硬脂基溴 在 四溴化碳 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 3.5h， 生成 1- bromo-2-octadecyloxyethane
  参考文献：
  名称：

  脂质修饰精胺衍生物及利用该衍生物制备的 脂质体

  摘要：

  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；

  公开号：

  CN104876831B

文献信息

• Enhanced Inhibition of Orthopoxvirus Replication In Vitro by Alkoxyalkyl Esters of Cidofovir and Cyclic Cidofovir
  作者：Earl R. Kern、Caroll Hartline、Emma Harden、Kathy Keith、Natalie Rodriguez、James R. Beadle、Karl Y. Hostetler

  DOI：10.1128/aac.46.4.991-995.2002

  日期：2002.4

  reported to have activity against orthopoxvirus replication in vitro and in animal models when administered parenterally or by aerosol. To obtain better oral activity, we synthesized a novel series of analogs of CDV and cCDV by esterification with two long-chain alkoxyalkanols, 3-hexadecyloxy-1-propanol (HDP-CDV; HDP-cCDV) or 3-octadecyloxy-1-ethanol (ODE-CDV; ODE-cCDV). Their activities were evaluated

  肠胃外给药时，核苷酸膦酸酯西多福韦（CDV）和环状西多福韦（cCDV）是有效的抗病毒化合物，但口服吸收不好。据报道，这些化合物在肠胃外或通过气雾剂给药时在体外和动物模型中均具有抗正痘病毒复制的活性。为了获得更好的口服活性，我们通过与两种长链烷氧基烷醇，3-十六烷氧基-1-丙醇（HDP-CDV; HDP-cCDV）或3-十八烷氧基-1-乙醇酯化合成了一系列新的CDV和cCDV类似物。 （ODE-CDV; ODE-cCDV）。使用斑块减少测定法评估了它们的活性，并与被牛痘病毒（VV）或牛痘病毒（CV）感染的人包皮成纤维细胞（HFF）细胞中的CDV和cCDV进行了比较。HFF细胞中针对CDV和cCDV的VV的50％有效浓度（EC（50）s）为46。2和50.6 microM，而HDP-CDV和HDP-cCDV分别为0.84和3.8 microM。ODE-CDV和ODE-cCDV的EC（50）分别为0
• Alkoxyalkyl Esters of Cidofovir and Cyclic Cidofovir Exhibit Multiple-Log Enhancement of Antiviral Activity against Cytomegalovirus and Herpesvirus Replication In Vitro
  作者：James R. Beadle、Caroll Hartline、Kathy A. Aldern、Natalie Rodriguez、Emma Harden、Earl R. Kern、Karl Y. Hostetler

  DOI：10.1128/aac.46.8.2381-2386.2002

  日期：2002.8

  The incidence of cytomegalovirus (CMV) retinitis is declining in AIDS patients but remains a significant clinical problem in patients with organ transplants and bone marrow transplants. Prophylaxis with ganciclovir (GCV) or valganciclovir reduces the incidence of CMV disease but may lead to the emergence of drug-resistant virus with mutations in the UL97 or UL54 gene. It would be useful to have other types of oral therapy for CMV disease. We synthesized hexadecyloxypropyl and octadecyloxyethyl derivatives of cyclic cidofovir (cCDV) and cidofovir (CDV) and found that these novel analogs had 2.5- to 4-log increases in antiviral activity against CMV compared to the activities of unmodified CDV and cCDV. Multiple-log increases in activity were noted against laboratory CMV strains and various CMV clinical isolates including GCV-resistant strains with mutations in the UL97 and UL54 genes. Preliminary cell studies suggest that the increase in antiviral activity may be partially explained by a much greater cell penetration of the novel analogs. 1- O -Hexadecyloxypropyl-CDV, 1- O -octadecyloxyethyl-CDV, and their corresponding cCDV analogs are worthy of further preclinical evaluation for treatment and prevention of CMV and herpes simplex virus infections in humans.

  摘要 巨细胞病毒（CMV）视网膜炎在艾滋病患者中的发病率正在下降，但在器官移植和骨髓移植患者中仍是一个严重的临床问题。使用更昔洛韦（GCV）或缬更昔洛韦进行预防可降低 CMV 的发病率，但可能会导致 UL97 或 UL54 基因突变的耐药病毒的出现。如果能有其他类型的口服疗法来治疗 CMV 病，将会非常有用。我们合成了环状西多福韦（cCDV）和西多福韦（CDV）的十六烷氧基丙基和十八烷氧基乙基衍生物，发现与未修饰的 CDV 和 cCDV 相比，这些新型类似物对 CMV 的抗病毒活性提高了 2.5 到 4 个对数值。针对实验室 CMV 株系和各种 CMV 临床分离株（包括 UL97 和 UL54 基因突变的 GCV 耐药株）的活性提高了多个对数值。初步细胞研究表明，新型类似物的细胞穿透力更强，这可能是抗病毒活性提高的部分原因。1- O -十六烷氧基丙基-CDV、1- O O -十八烷氧基乙基-CDV 及其相应的 cCDV 类似物值得进一步进行临床前评估，以治疗和预防人类 CMV 和单纯疱疹病毒感染。
• Anchor Dependency for Non-Glycerol Based Cationic Lipofectins: Mixed Bag of Regular and Anomalous Transfection Profiles
  作者：Rajkumar Sunil Singh、Koushik Mukherjee、Rajkumar Banerjee、Arabinda Chaudhuri、Samik Kumar Hait、Satya Priya Moulik、Yerramsetti Ramadas、Amash Vijayalakshmi、Nalam Madhusudhana Rao

  DOI：10.1002/1521-3765(20020215)8:4<900::aid-chem900>3.0.co;2-x

  日期：2002.2.15

  Although detailed structure activity, physicochemical and biophysical investigations in probing the anchor influence in liposomal gene delivery have been reported for glycerol-based transfection lipids, the corresponding investigation for non-glycerol based simple monocationic transfection lipids have not yet been undertaken. Towards this end, herein, we delineate our structure - activity and physicochemical approach in deciphering the anchor dependency in liposomal gene delivery using fifteen new structural analogues (lipids 1 - 15) of recently reported nonglycerol based monocationic transfection lipids. The C-14 analogues in both series 1 (lipids 1 - 6) and series 2 (lipids 7-15) showed maximum efficiency in transfecting COS-1 and CHO cells. However, the C-12 analogue of the ether series (lipid 3) exhibited a seemingly anomalous behavior compared with its transfection efficient C-10 and C-14 analogues (lipids 2 and 4) in being completely inefficient to transfect both COS-1 and CHO cells. The present structure - activity investigation also convincingly demonstrates that enhancement of transfection efficiencies through incorporation of membrane reorganizing unsaturation elements in the hydrophobic anchor of cationic lipids is not universal but cell dependent. The strength of the interaction of lipids 1 - 15 with DNA was assessed by their ability to exclude ethidium bromide bound to the DNA. Cationic lipids with long hydrophobic tails were found, in general, to be efficient in excluding EtBr from DNA. Gel to liquid crystalline transition temperatures of the lipids was measured by fluorescence anisotropy measurement technique. In general (lipid 2 being an exception), transfection efficient lipids were found to have their mid transition temperatures at or below physiological temperatures (37degreesC).
• WO2006/110655
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR THE TREATMENT OF VIRAL INFECTIONS AND OTHER MEDICAL DISORDERS<br/>[FR] COMPOSES, COMPOSITIONS ET METHODES DE TRAITEMENT D'INFECTIONS VIRALES ET AUTRES TROUBLES MEDICAUX
  申请人：CHIMERIX INC

  公开号：WO2006110656A3

  公开（公告）日：2009-04-16