3-oleyloxy-1-propanol | 17367-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-oleyloxy-1-propanol
• 英文别名: 3-[(Z)-octadec-9-enoxy]propan-1-ol
• CAS: 17367-37-2
• 化学式: C₂₁H₄₂O₂
• 分子量: 326.563
• InChiKey: RHEFZZHALQVVFD-KTKRTIGZSA-N

物化性质

• 沸点：
  436.5±28.0 °C(Predicted)
• 密度：
  0.876±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  23
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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-oleyloxy-1-propanol 在 N-甲基咪唑 、 N,O-双三甲硅基乙酰胺 、 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 16.25h， 生成 3-O-oleyloxypropyl-1-phosphate
  参考文献：
  名称：

  Compositions containing lysophosphatidic acids which inhibit apoptosis and uses thereof

  摘要：

  该发明提供了抗凋亡组合物溶磷脂酸及其制备和使用方法。这种组合物还可以包含增强LPA作用的剂，包括蛋白质、脂质膜结构和聚合物，如聚乙二醇。该组合物还可以额外含有其他药用有效剂，如药物、抗生素、伤口愈合剂和抗氧化剂。

  公开号：

  US06949528B1
• 作为产物：
  描述：

  油醇 在 sodium hydride 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 88.0h， 生成 3-oleyloxy-1-propanol
  参考文献：
  名称：

  Compositions containing lysophosphatidic acids which inhibit apoptosis and uses thereof

  摘要：

  该发明提供了抗凋亡组合物溶磷脂酸及其制备和使用方法。这种组合物还可以包含增强LPA作用的剂，包括蛋白质、脂质膜结构和聚合物，如聚乙二醇。该组合物还可以额外含有其他药用有效剂，如药物、抗生素、伤口愈合剂和抗氧化剂。

  公开号：

  US06949528B1

文献信息

• Alkoxyalkyl Esters of ( <i>S</i> )-9-[3-Hydroxy-2-(Phosphonomethoxy)Propyl]Adenine Are Potent Inhibitors of the Replication of Wild-Type and Drug-Resistant Human Immunodeficiency Virus Type 1 In Vitro
  作者：Karl Y. Hostetler、Kathy A. Aldern、William B. Wan、Stephanie L. Ciesla、James R. Beadle

  DOI：10.1128/aac.01223-05

  日期：2006.8

  ( S )-9-[3-Hydroxy-2-(phosphonomethoxy)propyl]adenine [( S )-HPMPA], is an effective broad-spectrum antiviral against many DNA viruses but has been reported to be inactive against human immunodeficiency virus (HIV). We synthesized several alkoxyalkyl esters of ( S )-HPMPA and now report that hexadecyloxypropyl-( S )-HPMPA [HDP-( S )-HPMPA] and octadecyloxyethyl-( S )-HPMPA [ODE-( S )-HPMPA]had 50% effective concentrations of 0.4 to 7.0 nanomolar and were nearly fully active against HIV variants having reverse transcriptase mutations M184V and K103N and against a zidovudine-resistant variant with mutations D67N, K70R, T215Y, and K219Q. Resistance to HDP-( S )-HPMPA and ODE-( S )-HPMPA was noted for a mutant with mutation K65R. HDP-( S )-HPMPA is also active against herpes simplex virus type 1, human cytomegalovirus, hepatitis B virus, adenoviruses, and orthopoxviruses and is worthy of further evaluation as a possibly therapy for HIV infection.

  摘要 ( S )-9-[3-羟基-2-(磷酰甲氧基)丙基]腺嘌呤[( S )-HPMPA]是一种对多种 DNA 病毒有效的广谱抗病毒药物，但据报道对人类免疫缺陷病毒（HIV）无效。我们合成了几种(S)-HPMPA 的烷氧基烷基酯。 S )-HPMPA的几种烷氧基烷基酯，现在报告说，十六烷氧基丙基-( S )-HPMPA[HDP-( S )-HPMPA]和十八烷氧基乙基-( S )-HPMPA[ODE-( S )-HPMPA]的50%有效浓度为0.4至7.0纳摩尔，对具有逆转录酶突变M184V和K103N的HIV变体以及具有突变D67N、K70R、T215Y和K219Q的齐多夫定耐药变体几乎完全有效。对 HDP-( S )-HPMPA和ODE-( S )-HPMPA的耐药性。HDP-( S )-HPMPA对 1 型单纯疱疹病毒、人类巨细胞病毒、乙型肝炎病毒、腺病毒和正疱疹病毒也有活性，值得作为一种可能的艾滋病病毒感染疗法进行进一步评估。
• Lysophosphatidylethanolamine and 2-desoxylysophosphatidylethanolamine derivatives. 1. Potential renin inhibitors
  作者：Francis R. Pfeiffer、Suzanne C. Hoke、Clara K. Miao、Ralph E. Tedeschi、Josephine Pasternak、Richard Hahn、Robert W. Erickson、Herman W. Levin、Charlotte A. Burton、Jerry A. Weisbach

  DOI：10.1021/jm00288a008

  日期：1971.6
• Structure–Activity Relationships of Lysophosphatidylserine Analogs as Agonists of G-Protein-Coupled Receptors GPR34, P2Y10, and GPR174
  作者：Masaya Ikubo、Asuka Inoue、Sho Nakamura、Sejin Jung、Misa Sayama、Yuko Otani、Akiharu Uwamizu、Keisuke Suzuki、Takayuki Kishi、Akira Shuto、Jun Ishiguro、Michiyo Okudaira、Kuniyuki Kano、Kumiko Makide、Junken Aoki、Tomohiko Ohwada

  DOI：10.1021/jm5020082

  日期：2015.5.28

  Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator generated by hydrolysis of membrane phospholipid phosphatidylserine. Recent ligand screening of orphan G-protein-coupled receptors (GPCRs) identified two LysoPS specific human GPCRs, namely, P2Y10 (LPS2) and GPR174 (LPS3), which, together with previously reported GPR34 (LPS1), comprise a LysoPS receptor family. Herein, we examined the structure-attivity relationships of a series of synthetic LysoPS analogues toward these recently deorphanized LysoPS,receptors, based on the idea that LysoPS can be regarded as consisting of distinct modules (fatty acid, glycerol, and L-Serine) connected by phosphodiester and ester linkages. Starting from the endogenous ligand (1-oleoyl-LysolPS, 1), we optimized the structure of each module and the ester linkage. Accordingly, we identified some structural requirements of each module for potency and for receptor subtype selectivity. Further assembly of individually structure-optimized modules yielded a series of potent and LysoPS receptor subtype-selective agonists, particularly for P2Y10 and GPR174.
• Synthesis and Antiviral Evaluation of Alkoxyalkyl Derivatives of 9-(<i>S</i>)-(3-Hydroxy-2-phosphonomethoxypropyl)adenine against Cytomegalovirus and Orthopoxviruses
  作者：James R. Beadle、William B. Wan、Stephanie L. Ciesla、Kathy A. Keith、Caroll Hartline、Earl R. Kern、Karl Y. Hostetler

  DOI：10.1021/jm050473m

  日期：2006.3.1

  9-(S)-(3-Hydroxy-2-phosphonomethoxypropyl)adenine [(S)-HPMPA] was one of the first acyclic nucleoside phosphonates described and has been reported to have good antiviral activity against most double-stranded DNA viruses, including the herpes group viruses and the orthopoxviruses. However, (S)-HPMPA is not orally bioavailable and has not been developed for clinical use. We have prepared orally bioavailable lipid esters of (S)-HPMPA and report their synthesis and antiviral evaluation against cytomegalovirus and orthopoxviruses. These esters were evaluated in vitro in cells infected with human cytomegalovirus (HCMV), murine cytomegalovirus (MCMV), vaccinia (VV), and cowpox viruses (CV). The most active compound, oleyloxyethyl-(S)-HPMPA, was found to have EC50 value of 0.003 mu M against HCMV vs 1.4 mu M for unmodified HPMPA. In cells infected with VV and CV, octadecyloxyethyl-(S)-HPMPA had EC50 values of 0.01-0.02 mu M versus 2.7 -4.0 mu M for unmodified HPMPA. When compared with the alkoxyalkyl esters of cidofovir, the corresponding alkoxyalkyl esters of (S)-HPMPA were equally active against HCMV and MCMV but were 15-20-fold more active against VV and CV in vitro. The alkoxyalkyl esters of (S)-HPMPA are promising new compounds worthy of further investigation for treatment of infections caused by herpes viruses and orthopoxviruses.
• [EN] METHODS FOR PREPARATION OF NUCLEOSIDE PHOSPHONATE ESTERS<br/>[FR] ELABORATION DE PHORPHONATES-ESTERS NUCLEOSIDIQUES
  申请人：UNIV CALIFORNIA

  公开号：WO2005087788A2

  公开（公告）日：2005-09-22

  A process is provided for the preparation of lipophilic monoesters of formula (3) and their stereoisomers. The process includes the steps of esterification of a phosphonate with a lipophilic alcohol, then allowing the resultant product to react with a suitably protected nucleoside in the presence of a strong base. In certain embodiments, the process is used for the preparation of alkyl or alkoxyalkyl lipid ether monoesters of nucleoside phosphonates which are useful as antiviral, anticancer or antiparasitic agents.