diosgenin chloroacetate | 1234312-40-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diosgenin chloroacetate
• 英文别名: 3β,25R-spirost-5-en-3yl 2-chloroacetate；3β-25R-spirost-5-en-3yl 2-chloroacetate
• CAS: 1234312-40-3
• 化学式: C₂₉H₄₃ClO₄
• 分子量: 491.111
• InChiKey: OSACJGGRTYJGMS-WLGKAUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  diosgenin chloroacetate 在 sodium carbonate 、 potassium iodide 作用下， 以 氯仿 、 二甲基亚砜 、 乙腈 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Cationic Lipids Containing Cyclen and Ammonium Moieties as Gene Delivery Vectors

  摘要：

  In this study, two novel cationic lipids containing protonated cyclen and quaternary ammonium moieties were designed and synthesized as non‐viral gene delivery vectors. The structures of the two lipids differ in their hydrophobic region (cholesterol or diosgenin). Cationic liposomes were easily prepared from the lipids individually or from the mixtures of each cationic lipid and dioleoylphosphatidylethanolamine. Several studies including DLS, gel retardation assay, and ethidium bromide intercalation assay suggest that these amphiphilic molecules are able to bind and compact DNA into nanometer particles which can be used as non‐viral gene delivery agents. Our results from in vitro transfection show that in association with dioleoylphosphatidylethanolamine, two cationic lipids can induce effective gene transfection in human embryonic kidney 293 cells, although the gene transfection efficiencies of two cationic lipids were found to be lower than that of lipofectamine 2000TM. Besides, different cytotoxicity was found for two lipoplexes. This study demonstrates that the title cationic lipids have large potential to be efficient non‐viral gene vectors.

  DOI：

  10.1111/j.1747-0285.2012.01355.x
• 作为产物：
  描述：

  氯乙酸 、 薯蓣皂素 在 1-甲基吡咯烷-2-酮硫酸盐 作用下， 反应 0.5h， 以89%的产率得到diosgenin chloroacetate
  参考文献：
  名称：

  使用 Mizoroki-Heck 反应合成新型类固醇、它们的光谱分析、抗宫颈癌的抗癌活性和 DFT 研究

  摘要：

  摘要 两种新型类固醇，3β, 25R-spirost-5-en-3yl 3-(4-propionylphenyl)but-2-enoate(3a) 和 3β, 25R-spirost-5-en-3yl 3-(4-nitrophenyl) but-2-enoate (3b) 已经使用钯催化的 Mizoroki-Heck 反应在两步合成中合成，使用薯蓣皂苷元作为起始材料。采用了一种新策略，涉及将薯蓣皂苷元（化合物 1）转化为化合物、3β, 25R-spirost-5-en-3yl 2-chloroacetate（化合物 2）、3β, 25R-spirost-5-en-3yl trans-but- 2-烯酸（化合物 3）和 3β, 25R-spirost-5-en-3yl-trans-cinnamate（化合物 4）通过使用离子液体 (NMP+HSO4) 的 Steglich 酯化。然后在DMF

  DOI：

  10.1016/j.molstruc.2019.127512

文献信息

• Synthesis of furostanol glycosides: discovery of a potent α-glucosidase inhibitor
  作者：Peng Wang、Jiejie Hao、Xiuli Zhang、Cong Wang、Huashi Guan、Ming Li

  DOI：10.1039/c6ob01766e

  日期：——

  A convenient approach to the synthesis of furostanol glycosides has been developed with the features of both highly efficient incorporation of a 26-O-β-D-glucopyranosyl unit and ready formation of hemiketal ring E. The total syntheses of seven furostanol saponins including funlioside B, lilioglycoside, protobioside I, protodioscin, pallidifloside I, coreajaponins A and parisaponin I are efficiently

  已经开发了一种方便的合成糠醛甾醇糖苷的方法，该方法具有高效掺入26- O- β- D-吡喃葡萄糖基单元和易于形成半缩酮环E的特点。七种糠醛甾醇皂苷的总合成包括fun素B使用容易获得的16β-乙酰氧基-22-氧代-26-羟基胆甾醇衍生物作为有效的构建基块可有效地获得，，，，，、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、还评估了合成皂苷的α-葡萄糖苷酶抑制活性，这表明fun药苷B是开发α-葡萄糖苷酶抑制剂的高度潜在的先导。
• First synthesis of furostans bearing a 1, 3-dioxane ring at C-26. XRD, Hirshfeld surfaces analysis, DFT studies
  作者：Arun Sethi、Praveer Singh、Priyanka Yadav、Rohit Prakash、Ranvijay Pratap Singh

  DOI：10.1016/j.molstruc.2021.131364

  日期：2022.1

  (∇2ρ(rBCP)), energy parameters-kinetic electron energy density (GBCP), potential electron density (VBCP) and the total electron energy density (HBCP) at the bond critical points (BCP) were analyzed by ‘Atoms in molecules’ AIM theory. The Hirshfeld surface analysis helped in identifying important intermolecular interactions in 2e. Global reactivity descriptors and molecular electrostatic potential for compounds

  在 2-取代的 1,3-丙二醇存在下，薯蓣皂苷元衍生物中的环 F 的区域选择性打开，产生了在 C-26 处带有 1,3-二恶烷环的新呋喃坦。这些合成的化合物1e、2a、2b、2c、2d和2e 的结构是在光谱数据的基础上建立的，包括 1D 和 2D NMR 以及 ESI-HRMS。2e (22R,25R)-26-(5-broMO-5-nitro-1,3-dioxanyl)furost-5-en-3-yl acetate 的单晶 X 射线衍射分析不仅有助于结构鉴定，还有助于确定其立体化学。这些化合物的分子几何形状是通过密度泛函理论 (DFT/B3LYP) 使用 6–31 G (d, p) 基组在基态下计算的。使用时间相关密度泛函理论（TD-DFT）计算电子特性，例如 HOMO 和 LUMO 能量。拓扑参数-电子密度（ρBCP），电子密度的拉普拉斯算子（∇2 ρ ( r BCP ))、能量参数-动能电子能量密度
• Novel cationic lipids possessing protonated cyclen and imidazolium salt for gene delivery
  作者：Qing-Dong Huang、Wen-Jing Ou、Hong Chen、Zhi-Hua Feng、Jing-Yi Wang、Ji Zhang、Wen Zhu、Xiao-Qi Yu

  DOI：10.1016/j.ejpb.2011.03.017

  日期：2011.8

  In this study, two novel protonated cyclen and imidazolium salt-containing cationic lipids differing only in their hydrophobic region (cholesterol or diosgenin) have been designed and synthesized for gene delivery. Cationic liposomes were easily prepared from each of these lipids individually or from the mixtures of each cationic lipid and dioleoylphosphatidyl ethanolamine (DOPE). Several studies including DLS, gel retardation assay, ethidium bromide intercalation assay, and TEM demonstrated that these amphiphilic molecules are able to bind and compact DNA into nanometer particles that could be used as non-viral gene delivery agents. Our results from in vitro transfection showed that in association with DOPE, two cationic lipids can induce effective gene transfection in HEK293 cells. Furthermore, the gene transfection efficiencies of two cationic lipids were dramatically increased in the presence of calcium ion (Ca2+). It is notable that the gene transfection abilities of two cationic lipids were maintained in the presence of 10% serum. Besides, different cytotoxicity was found for two lipoplexes. This study demonstrates that the title cationic lipids have large potential to be efficient non-viral gene vector. (C) 2011 Elsevier B.V. All rights reserved.