2-甲基-2-丙基[2-(二乙基氨基)乙基]氨基甲酸酯 | 497834-53-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-甲基-2-丙基[2-(二乙基氨基)乙基]氨基甲酸酯
• 英文名称: tert-butyl N-[2-(diethylamino)ethyl]carbamate
• 英文别名: tert-butyloxylcarbonyl-N,N-diethylethylenediamine；(N-Boc)-N’,N’-diethylethylenediamine
• CAS: 497834-53-4
• 化学式: C₁₁H₂₄N₂O₂
• 分子量: 216.324
• InChiKey: KWOWDSDUNUBMGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丙基[2-(二乙基氨基)乙基]氨基甲酸酯 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 diethyl-[2-[[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbonyl]amino]ethyl]-methylazanium;chloride
  参考文献：
  名称：

  Cationic lipid-conjugated dexamethasone as a selective antitumor agent

  摘要：

  Dexamethasone (Dex) is one of the highly potent synthetic glucocorticoids. It exhibits prominent anti-inflammatory but moderate anti-proliferative activities. It is widely used along side chemotherapy to alleviate toxic side effects. Additionally, Dex is also a potent inducer of gluconeogenesis. However, its overuse critically desensitizes cells against chemotherapy. Herein, we report on the development of a new class of cationic lipid-Dex conjugates in which the C-8 carbon chain analogue (DX8) exhibited glucocorticoid receptor (GR)-mediated, caspase-3-assisted, cancer cell-selective anti-proliferative activity. Melanoma tumors in DX8-treated mice exhibited significantly reduced tumor aggressiveness with respect to tumors in Dex-treated mice. Tumor lysates prepared from DX8-treated group showed elevated levels of p53. DX8-treated cancer cells showed clear degradation of kinase JAK3/STAT3 protein levels. Additionally, DX8-treatment decreased the level of VEGFR2 in tumor-endothelial cells implying DX8's anti-proliferative roles in both tumor cells and tumor neovascular cells. Collectively, our results demonstrate potent anti-angiogenic, and selective JAK3/STAT3 down-regulating anticancer characteristics of DX8, a new dexamethasone-based antitumor molecule.

  DOI：

  10.1016/j.ejmech.2014.06.051
• 作为产物：
  描述：

  溴乙烷 、 N-叔丁氧羰基-1,2-乙二胺 在 potassium carbonate 作用下， 以 乙酸乙酯 为溶剂， 反应 48.0h， 以55%的产率得到2-甲基-2-丙基[2-(二乙基氨基)乙基]氨基甲酸酯
  参考文献：
  名称：

  Cationic lipid-conjugated dexamethasone as a selective antitumor agent

  摘要：

  Dexamethasone (Dex) is one of the highly potent synthetic glucocorticoids. It exhibits prominent anti-inflammatory but moderate anti-proliferative activities. It is widely used along side chemotherapy to alleviate toxic side effects. Additionally, Dex is also a potent inducer of gluconeogenesis. However, its overuse critically desensitizes cells against chemotherapy. Herein, we report on the development of a new class of cationic lipid-Dex conjugates in which the C-8 carbon chain analogue (DX8) exhibited glucocorticoid receptor (GR)-mediated, caspase-3-assisted, cancer cell-selective anti-proliferative activity. Melanoma tumors in DX8-treated mice exhibited significantly reduced tumor aggressiveness with respect to tumors in Dex-treated mice. Tumor lysates prepared from DX8-treated group showed elevated levels of p53. DX8-treated cancer cells showed clear degradation of kinase JAK3/STAT3 protein levels. Additionally, DX8-treatment decreased the level of VEGFR2 in tumor-endothelial cells implying DX8's anti-proliferative roles in both tumor cells and tumor neovascular cells. Collectively, our results demonstrate potent anti-angiogenic, and selective JAK3/STAT3 down-regulating anticancer characteristics of DX8, a new dexamethasone-based antitumor molecule.

  DOI：

  10.1016/j.ejmech.2014.06.051

文献信息

• Microwave assisted mild, rapid, solvent-less, and catalyst-free chemoselective N-tert-butyloxycarbonylation of amines
  作者：Satish N. Dighe、Hemant R. Jadhav

  DOI：10.1016/j.tetlet.2012.08.089

  日期：2012.10

  Microwave assisted simple, rapid, solventless, and catalyst-free chemoselective method for the protection of amino group in aromatic, aliphatic, heterocyclic, aralkyl amines, phenyl hydrazine, and amino acid esters in good to excellent isolated yield (83–98%) in short reaction time (2–12 min) has been reported.

  微波辅助的简单，快速，无溶剂和无催化剂的化学选择性方法可保护芳香族，脂肪族，杂环，芳烷基胺，苯基肼和氨基酸酯中的氨基，具有良好的分离效果（83-98％）据报道反应时间短（2–12分钟）。
• Cooperative Intramolecular Hydrogen Bonding Strongly Enforces <i>cis</i>-Peptoid Folding
  作者：Andrew W. Wijaya、Andy I. Nguyen、Leah T. Roe、Glenn L. Butterfoss、Ryan K. Spencer、Nan K. Li、Ronald N. Zuckermann

  DOI：10.1021/jacs.9b10497

  日期：2019.12.11

  side-chains demonstrates significant enforcement of the cis-amide backbone (Kcis/trans up to 70) using an unexpected ensemble of weak intramolecular CH-O and/or NH-O hydrogen bonds between the side-chain and the backbone carbonyl moieties. These interactions are evidenced by X-ray crystallography, variable-temperature NMR spectroscopy, and DFT calculations. Moreover, these side-chains are inexpensive

  序列定义的 peptoids 或 N 取代的甘氨酸，由于其生物稳定性和高效合成，是一类有吸引力的生物衍生聚合物。然而，具有精确三维结构的折叠 peptoids 的从头设计受到了有限的手段来确定性地控制骨架构象的阻碍。Peptoid 折叠通常会因顺式/反式骨架-酰胺异构化而不稳定，并且很少有侧链能够强制执行特定的酰胺构象。在这里，我们展示了一类新型的阳离子烷基铵乙基侧链使用一种意想不到的弱分子内 CH-O 和/或 NH-O 氢的组合，证明了顺式酰胺主链（Kcis/trans 高达 70）的显着增强侧链和骨架羰基部分之间的键。X 射线晶体学证明了这些相互作用，变温 NMR 光谱和 DFT 计算。此外，这些侧链价格低廉、结构多样、亲水，并且可以通过固相合成整合到更长的拟肽序列中。值得注意的是，我们扩展了这些概念以合成一种水溶性 peptoid 10 聚体，它在溶液中采用一个主要折叠，由多维 NMR
• Controlling the Chameleonic Behavior and Membrane Permeability of Cyclosporine Derivatives via Backbone and Side Chain Modifications
  作者：Dongjae Lee、Jieun Choi、Min June Yang、Chin-Ju Park、Jiwon Seo

  DOI：10.1021/acs.jmedchem.3c01140

  日期：2023.9.28

  permeability through conformational switching in different environmental polarities, a trait known as chameleonic behavior. In this study, we demonstrate specific backbone and side chain modifications that can control chameleonic behavior and passive membrane permeability using a cyclosporin O (CsO) scaffold. To quantify chameleonic behavior, we used a ratio of the population of the closed conformation obtained

  一些大环化合物通过不同环境极性下的构象转换表现出增强的膜渗透性，这种特性被称为变色龙行为。在这项研究中，我们展示了特定的主链和侧链修饰，可以使用环孢菌素 O (CsO) 支架控制变色行为和被动膜通透性。为了量化变色行为，我们使用了每种 CsO 衍生物在极性溶剂和非极性溶剂中获得的闭合构象的总体比率。我们发现1位（ 1和3）的β-羟基化可以编码变色性并提高通透性。然而，通过添加额外的跨环氢键（2和5）引起的构象稳定导致膜渗透速率减慢得多。我们的 CsO 支架为系统研究构象、膜通透性、溶解度和蛋白质结合之间的关系提供了一个平台。这些知识有助于发现能够靶向不可成药靶标的强效超越五规则（bRo5）大环化合物。
• Cationic lipid-conjugated dexamethasone as a selective antitumor agent
  作者：Samaresh Sau、Rajkumar Banerjee

  DOI：10.1016/j.ejmech.2014.06.051

  日期：2014.8

  Dexamethasone (Dex) is one of the highly potent synthetic glucocorticoids. It exhibits prominent anti-inflammatory but moderate anti-proliferative activities. It is widely used along side chemotherapy to alleviate toxic side effects. Additionally, Dex is also a potent inducer of gluconeogenesis. However, its overuse critically desensitizes cells against chemotherapy. Herein, we report on the development of a new class of cationic lipid-Dex conjugates in which the C-8 carbon chain analogue (DX8) exhibited glucocorticoid receptor (GR)-mediated, caspase-3-assisted, cancer cell-selective anti-proliferative activity. Melanoma tumors in DX8-treated mice exhibited significantly reduced tumor aggressiveness with respect to tumors in Dex-treated mice. Tumor lysates prepared from DX8-treated group showed elevated levels of p53. DX8-treated cancer cells showed clear degradation of kinase JAK3/STAT3 protein levels. Additionally, DX8-treatment decreased the level of VEGFR2 in tumor-endothelial cells implying DX8's anti-proliferative roles in both tumor cells and tumor neovascular cells. Collectively, our results demonstrate potent anti-angiogenic, and selective JAK3/STAT3 down-regulating anticancer characteristics of DX8, a new dexamethasone-based antitumor molecule.