[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[2-(2-aminoethylamino)ethyl]carbamate | 200337-42-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[2-(2-aminoethylamino)ethyl]carbamate
• CAS: 200337-42-4
• 化学式: C₃₂H₅₇N₃O₂
• 分子量: 515.823
• InChiKey: UWQYKEJSVDUBOR-PTHRTHQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  76.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[2-(2-aminoethylamino)ethyl]carbamate 、 1-[(2R,4S,5S)-4-azido-5-[[octadecoxy(oxido)phosphaniumyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 三乙胺 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Synthesis of Novel Steroidal Bioconjugates of Phospholipid with AZT

  摘要：

  Some novel asymmetry steroidal bioconjugates of phospholipid with AZT were synthesized by oxidation or conjugation with amines using Atherton-Todd reaction, and the structures were confirmed based on spectral methods. The result shown that some of bioconjugates possess activity against breast cancer MCF-7 in bioassay.

  DOI：

  10.1080/10426500701764874
• 作为产物：
  描述：

  N¹-cholesteryloxycarbonyl-1-amino-2-hydroxyethane 在 palladium on activated charcoal sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 环己烯 、 三甲基膦 作用下， 以 乙醇 为溶剂， 反应 21.33h， 生成 [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[2-(2-aminoethylamino)ethyl]carbamate
  参考文献：
  名称：

  Polyamine Analogues of 3β-[N-(N′,N′-Dimethylaminoethane)carbamoyl]cholesterol (DC-Chol) as Agents for Gene Delivery

  摘要：

  Cationic liposomes are rapidly proving very effective at mediating the delivery of genes to cells in vitro. Moreover, the use of cationic liposomes for gene delivery in vivo is now under consideration. In previous work, we were able to demonstrate that cationic liposomes, formulated from 3 beta-[N-(N',N'-dimethylaminoethane)carbamoyl]cholesterol (DC-Chol) and the neutral phospholipid, dioleoyl L-alpha-phosphatidylethanolamine (DOPE), were able to transfect the lungs of mice in vivo. However, it rapidly became apparent that substantial improvements in the gene delivery efficiency, by approximately two orders of magnitude, would be needed for human lung transfection to be possible. In the following paper we describe the synthesis of a range of polyamine analogues of DC-Chol, which were formulated into cationic liposomes with DOPE and evaluated for efficiency of gene delivery in vitro and in vivo in mice. We report that cationic liposomes formulated from DOPE and the novel pentamine N-15-cholesteryloxycarbonyl-3,7,12-triazapentadecane-1,15-diamine (CTAP) were 100 times more efficient than DC-Chol/DOPE liposomes at gene delivery in vivo (500 times more effective than DNA alone). Therefore, we believe that CTAP/DOPE cationic liposomes should have clinical applications in human gene therapy approaches to the treatment of lung disorders as well as to other clinical conditions.

  DOI：

  10.1002/(sici)1521-3765(199801)4:1<137::aid-chem137>3.0.co;2-2

文献信息

• DODAG; a versatile new cationic lipid that mediates efficient delivery of pDNA and siRNA
  作者：Mathieu Mével、Nazila Kamaly、Sergio Carmona、Morag H. Oliver、Michael R. Jorgensen、Carol Crowther、Felix H. Salazar、Patricia L. Marion、Masato Fujino、Yukikazu Natori、Maya Thanou、Patrick Arbuthnot、Jean-Jacques Yaouanc、Paul Alain Jaffrès、Andrew D. Miller

  DOI：10.1016/j.jconrel.2009.12.001

  日期：2010.4

  cholesteryl-moieties linked to guanidinium functional groups, and also cationic lipids comprising a dialkylglycylamide moiety conjugated with a polyamine or a guanidinium functional group. In plasmid DNA (pDNA) transfection studies, these cationic lipids were formulated into cationic liposomes with the neutral co-lipid dioleoyl-L-α-phosphatidylethanolamine (DOPE) or with a recently reported neutral lipophosphoramidate

  我们报道了由连接到胍基官能团的胆甾醇基部分组成的新型阳离子脂质的合成，还包括包含与多胺或胍基官能团缀合的二烷基甘氨酰胺部分的阳离子脂质。在质粒DNA（pDNA）转染研究中，将这些阳离子脂质与中性共脂质油酰-L-α-磷脂酰乙醇胺（DOPE）或最近报道的组胺中性脂磷酰胺酸酯衍生物配制成阳离子脂质体。我们观察到来自所述阳离子脂质制备的阳离子脂质体Ñ ' ，N '-dioctadecyl -N -4,8-二氮杂-10- aminodecanoylglycine酰胺（DODAG）和DOPE频繁介导的转染的最高水平在体外在存在或不存在血清的情况下，研究的所有三种不同细胞系（OVCAR-3，IGROV-1和HeLa）中的蛋白 另外，发现体外细胞毒性是最小的。或者，我们观察到DODAG单独与小的干扰RNA（siRNA）形成脂质复合物纳米颗粒，能够介导两种先前已验证的抗乙型肝炎病毒（HBV）的siRNA在体
• Synthesis of Some Novel 1,2,3-Triazole-Fused Oligonucleoside and Oligosaccharide Analogues
  作者：Yong Ju、Pei-Yuan Jin、Peng Jin、Yi-An Ruan、Yu-Fen Zhao

  DOI：10.1055/s-2007-992357

  日期：2007.12

  Several 1,2,3-triazole-fused oligonucleoside and oligosaccharide analogues were synthesized by involving a Cu(I)-catalyzed 1,3-dipolar cycloaddition as the key step. The structures of the products were confirmed on the basis of the 1H NMR and ESI-MS methods.

  以 Cu(I) 催化的 1,3 二极环化反应为关键步骤，合成了多种 1,2,3-三唑融合寡核苷酸和寡糖类似物。通过 1H NMR 和 ESI-MS 方法确认了产物的结构。