eicosyl 3α-azido-7α,12α-di-[N-(t-butyloxycarbonyl)amino]-5β-cholan-24-oate | 391256-01-2

• 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: eicosyl 3α-azido-7α,12α-di-[N-(t-butyloxycarbonyl)amino]-5β-cholan-24-oate
• 英文别名: eicosanoyl 3α-azido-7α,12α-di[N-(t-butoxycarbonyl)amino]-5β-cholan-24-oate
• CAS: 391256-01-2
• 化学式: C₅₄H₉₇N₅O₆
• 分子量: 912.394
• InChiKey: PIMFFGXRSNLWBF-WTOVGBGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.33
• 重原子数：
  65.0
• 可旋转键数：
  26.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  151.72
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  eicosyl 3α-azido-7α,12α-di-[N-(t-butyloxycarbonyl)amino]-5β-cholan-24-oate 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 、 三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 126.0h， 生成 (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-10,13-dimethyl-7,12-bis-(3-phenyl-ureido)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester
  参考文献：
  名称：

  Substrate Discrimination by Cholapod Anion Receptors:  Geometric Effects and the “Affinity−Selectivity Principle”

  摘要：

  Cholapod anion receptors can achieve high affinities while maintaining compatibility with nonpolar media. Previously they have been shown to transport anions across cell and vesicle membranes. In the present work, the scope of the architecture is expanded and structure-selectivity relationships are investigated. Eight new receptors have been synthesized, with up to six H-bond donor centers. Using Cram's extraction method, these compounds plus five known examples have been tested for binding to seven monovalent anions (tetraethylammonium salts, wet chloroform as solvent). Association constants in excess of 10(10) M-1 have been measured for several pairings. Selectivities vary with receptor geometry, as expected. More remarkably, they also depend on receptor strength: more powerful receptors show a wider range of binding free energies, and therefore a greater spread of Ka(X-)/K-a(Y-). This "affinity-selectivity" effect can be derived from empirical relationships for H-bond strengths, and could prove widely operative in supramolecular chemistry.

  DOI：

  10.1021/ja0524144
• 作为产物：
  描述：

  methyl 3β-methanesulfonyl-7α,12α-di[N-(t-butyloxycarbonyl)amino]-5β-cholan-24-oate 在 sodium hydroxide 、 sodium azide 、 caesium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 216.95h， 生成 eicosyl 3α-azido-7α,12α-di-[N-(t-butyloxycarbonyl)amino]-5β-cholan-24-oate
  参考文献：
  名称：

  新的“足纲”阴离子载体；来自胆酸的高亲和力卤化物受体。

  摘要：

  DOI：

  10.1021/ja016796z

文献信息

• Facilitated Phosphatidylserine (PS) Flip-Flop and Thrombin Activation Using A Synthetic PS Scramblase
  作者：J. Middleton Boon、Timothy N. Lambert、Adam L. Sisson、Anthony P. Davis、Bradley D. Smith

  DOI：10.1021/ja029670q

  日期：2003.7.1

  A cationic steroid with a hydrogen-bonding pocket that has an affinity for anionic phospholipid headgroups was synthesized and shown to strongly promote the translocation or flip-flop of a fluorescent, C(6)NBD-labeled phosphatidylserine probe (C(6)NBD-PS) across vesicle membranes. In addition, the synthetic PS scramblase increases the levels of endogenous PS on the surface of erythrocytes as monitored

  合成了一种带有氢键口袋的阳离子类固醇，该类固醇对阴离子磷脂头基具有亲和力，并显示出强烈促进荧光、C(6)NBD 标记的磷脂酰丝氨酸探针 (C(6)NBD- PS) 跨囊泡膜。此外，合成的 PS 加扰酶增加了红细胞表面内源性 PS 的水平，如通过膜联蛋白 V-FITC 结合的流式细胞术分析所监测的。当细胞用 N-乙基马来酰亚胺 (NEM)（一种内源性氨基磷脂翻转酶的抑制剂）进行预处理时，PS 扰乱效应会增强。NEM 和合成 PS 加扰酶的组合使红细胞促进凝血酶原转化为凝血酶的能力提高了 4 倍。
• Contra-Hofmeister anion extraction by cyclosteroidal receptors
  作者：Adam L. Sisson、John P. Clare、Anthony P. Davis

  DOI：10.1039/b510768g

  日期：——

  Steroid-based receptors with enclosed binding sites, formed from quaternary ammonium and macrocyclic bis-urea units, can substantially override the Hofmeister series in anion phase transfer experiments.

  基于类固醇的受体，其封闭的结合位点由季铵盐和大环双脲单元构成，可以在阴离子相转移实验中显著超越霍夫迈斯特系列。
• High-Affinity Anion Binding by Steroidal Squaramide Receptors
  作者：Sophie J. Edwards、Hennie Valkenier、Nathalie Busschaert、Philip A. Gale、Anthony P. Davis

  DOI：10.1002/anie.201411805

  日期：2015.4.7

  Exceptionally powerful anion receptors have been constructed by placing squaramide groups in axial positions on a steroidal framework. The steroid preorganizes the squaramide NH groups such that they can act cooperatively on a bound anion, while maintaining solubility in nonpolar media. The acidic NH groups confer higher affinities than previously‐used ureas or thioureas. Binding constants exceeding 1014 M−1

  通过将方酰胺基团放置在类固醇框架的轴向位置，构建了异常强大的阴离子受体。该类固醇预先组织方酰胺 NH 基团，以便它们可以协同作用于结合的阴离子，同时保持在非极性介质中的溶解度。酸性 NH 基团比以前使用的脲或硫脲具有更高的亲和力。通过采用克拉姆萃取程序的变型，已经测量了氯仿中四乙基铵盐的超过10 14  M -1的结合常数。这些受体还作为单层囊泡中的跨膜阴离子载体进行了研究。不同寻常的是，它们的活性与阴离子亲和力不相关，因此表明阴离子载体设计中结合强度的上限。