(4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-5',6a,8a,9-tetramethyl-1,3,3',4,4',5,5',6,6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl (2-aminoethyl)carbamate | 1357020-17-7

• 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: (4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-5',6a,8a,9-tetramethyl-1,3,3',4,4',5,5',6,6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl (2-aminoethyl)carbamate
• CAS: 1357020-17-7
• 化学式: C₃₀H₄₈N₂O₄
• 分子量: 500.722
• InChiKey: WUYXRWXEIMEHNA-WLJSUUJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  36.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  82.81
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-5',6a,8a,9-tetramethyl-1,3,3',4,4',5,5',6,6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl (2-aminoethyl)carbamate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 [(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl] N-[2-[[(2S)-pyrrolidine-2-carbonyl]amino]ethyl]carbamate
  参考文献：
  名称：

  Water promoted enantioselective aldol Reaction by proline-cholesterol and -diosgenin based amphiphilic organocatalysts

  摘要：

  A series of proline-cholesterol and -diosgenin based amphiphilic organocatalysts were developed for the first time, and their catalytic activities for the enantioselective aldol reaction were investigated. The results indicated that water can significantly enhance the activity and stereoselectivity of the transformation via micelle formation. TEM and AFM analysis demonstrated that the diameter of the micelle particles ranged from 200 to 800 nm. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.078
• 作为产物：
  描述：

  薯蓣皂素 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-5',6a,8a,9-tetramethyl-1,3,3',4,4',5,5',6,6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl (2-aminoethyl)carbamate
  参考文献：
  名称：

  L-脯氨酸/胆固醇和薯os皂甙元为基础的硫脲协同系统，用于在水存在下直接不对称羟醛反应

  摘要：

  合成了一系列胆固醇和基于疏水性的尿素和硫脲化合物，并成功地将其作为水存在下L-脯氨酸催化的羟醛反应的助催化剂。获得抗构型产物，具有良好的产率（高达94％），高的非对映选择性（高达95∶5）和高的对映体过量（高达93％ee）。L-脯氨酸在水存在下催化效率的成功结果表明，胆固醇和硫脲的薯os皂苷元部分的疏水性对在水存在下的反应性和选择性至关重要。

  DOI：

  10.3906/kim-2003-36

文献信息

• Biotinylated Cyclen-Contained Cationic Lipids as Non-Viral Gene Delivery Vectors
  作者：Qiang Liu、Wen-Jing Yi、Yi-Mei Zhang、Ji Zhang、Liandi Guo、Xiao-Qi Yu

  DOI：10.1111/cbdd.12159

  日期：2013.10

  A series of 1, 4, 7, 10‐tetraazacyclododecane (cyclen)‐based cationic lipids, namely 5a–c bearing a biotin moiety and a variety of end groups (cholesterol, diosgenin, and α‐tocopherol) via biodegradable carbamate bond linkage were prepared and applied as non‐viral gene delivery vectors. The liposomes formed from 5 and dioleoylphosphatidylethanolamine could bind and condense plasmid DNA into nanoparticles

  通过可生物降解的氨基甲酸酯键连接的一系列基于1，4，7，10-四氮杂十二烷（环）的阳离子脂质，即5a–c，带有生物素部分和各种端基（胆固醇，薯os皂素和α-生育酚）。制备并用作非病毒基因传递载体。由5和二油酰基磷脂酰乙醇胺形成的脂质体可以将质粒DNA结合并浓缩成具有适当大小和zeta电位的纳米颗粒。所有生物素化的周期蛋白阳离子脂质即使在高N / P比下也比市售lipofectamine 2000具有更高的细胞活力，而其转染效率相对较低。此外，结果表明，在这三种脂质中，含α-生育酚的化合物5c具有更高的DNA结合能力，更低的细胞毒性和更高的转染效率。在两种不同细胞系中的转染显示这些脂质复合物对肿瘤细胞具有更高的基因传递效率。
• Design, synthesis of methotrexate-diosgenin conjugates and biological evaluation of their effect on methotrexate transport-resistant cells
  作者：Bangrong Cai、Aimei Liao、Kyung-Ku Lee、Jae-Sam Ban、Hyun-Sam Yang、Young Jun Im、ChangJu Chun

  DOI：10.1016/j.steroids.2016.10.006

  日期：2016.12

  A series of methotrexate-diosgenin conjugates was designed and synthesized to enhance the passive internalization of methotrexate (MTX) into transport-resistant cells. The inhibitory effects of these conjugates on dihydrofolate reductase (DHFR), and their anti-proliferation behaviors against a transport resistant breast cancer cell line, MDA-MB-231, were investigated. All of the synthesized conjugates retained an ability to inhibit DHFR after the diosgenin substitution. The MTX conjugates were much more potent against methotrexate-resistant MDA-MB-231 cells than MTX. Conjugate 18, containing a disulfide bond, exhibited the most potent anti-proliferative and DHFR inhibitory effects (IC50 = 4.1 mu M and 17.21 nM, respectively). Anti-proliferative activity was higher in the conjugate with a longer space linker (conjugate 21) than those with shorter linkers (conjugates 19 and 20). These results suggest that diosgenin conjugation of MTX may be an effective way to overcome its transport resistance in cancer cells. (C) 2016 Elsevier Inc. All rights reserved.