2-((tert-butoxycarbonyl)amino)octadecanoic acid | 199448-67-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-((tert-butoxycarbonyl)amino)octadecanoic acid
• 英文别名: 2-[(2-Methylpropan-2-yl)oxycarbonylamino]octadecanoic acid
• CAS: 199448-67-4
• 化学式: C₂₃H₄₅NO₄
• 分子量: 399.615
• InChiKey: UGRVSCNUONHHST-UHFFFAOYSA-N

物化性质

• 沸点：
  517.2±33.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  28
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((tert-butoxycarbonyl)amino)octadecanoic acid 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 N-[α-D-glucopyranosyl-(1'''->4")-α-D-glucopyranosyl-(1"->4')-β-D-glucopyranosyl]-2-amino-D,L-octadecanamide
  参考文献：
  名称：

  Novel Liposaccharide Conjugates for Drug and Peptide Delivery

  摘要：

  Sugar-lipid conjugates with general structure 1-4 were prepared by coupling amino sugars with N-Boc-protected lipoamino acids and oligomers. Conjugates with general structure 5 were also prepared from glucuronic acid and methyl 2-aminohexadecanoate. The physicochemical properties of the conjugates were modified by varying the nature and number of sugars or the number of lipoamino acids or their alkyl chain length. The ability of the liposaccharides to aggregate was examined. These preliminary experiments have demonstrated the ability of the liposaccharides to form particulate systems per se and also their ability to be incorporated into conventional liposomal systems. The structure of the respective liposaccharides and the molar ratio of liposaccharide to dimyristoyl lecithin and cholesterol were found to have a profound effect on the type of colloidal systems produced.

  DOI：

  10.1021/js9702123
• 作为产物：
  描述：

  溴代十六烷 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 叔丁醇 为溶剂， 反应 73.0h， 生成 2-((tert-butoxycarbonyl)amino)octadecanoic acid
  参考文献：
  名称：

  非共价相互作用模仿共价：电极正交自组装层

  摘要：

  对于能量转换和存储以及分子传感至关重要的电荷转移事件发生在带电界面上。传统上，对界面的合成控制是通过分子的电极特异性共价束缚来实现的。共价键本质上限制了分子可调电极的范围和潜在稳定性窗口。在这里，我们报告了一种与电极表面化学无关的合成策略，以分子方式定义带电界面。我们将二茂铁氧化还原报告基团附加到两亲物上，利用非共价静电和范德华相互作用来制备在 2.9 V 范围内稳定的自组装层。该层的伏安响应和原位红外光谱模拟了类似的共价键合二茂铁的报道。该设计是电极正交的；层自组装是可逆的并且与底层电极材料的表面化学无关。我们证明该设计可用于多种电极材料类别（过渡金属、碳、碳复合材料）和形态（纳米结构、平面）。我们的工作将原子级精确的两亲物有机合成与极化电极上的原位非共价自组装相结合，为带电界面的预测性和无污染合成控制奠定了基础。

  DOI：

  10.1021/jacs.3c04387

文献信息

• Synthesis of a library of polycationic lipid core dendrimers and their evaluation in the delivery of an oligonucleotide with hVEGF inhibition
  作者：Harendra S. Parekh、Robert J. Marano、Elizabeth P. Rakoczy、Joanne Blanchfield、Istvan Toth

  DOI：10.1016/j.bmc.2006.03.029

  日期：2006.7.15

  This article follows on from our previous work in the area of non-viral gene delivery using polycationic dendrimers (PCDs). Herein we report on the synthesis and efficacy of a new library of lipid core PCDs in the delivery of the anti-angiogenic oligonucleotide (ODN-1) to retinal pigment epithelial cells. ELISA was used to monitor hVEGF levels in cells transfected with dendriplexes, Cytofectin GSV

  本文是基于我们先前在使用聚阳离子树状聚合物（PCD）进行非病毒基因递送方面的研究而得出的。在本文中，我们报道了脂质核心PCDs新文库在抗血管生成寡核苷酸（ODN-1）传递至视网膜色素上皮细胞中的合成和功效。ELISA用于监测用树突状复合体，细胞转染蛋白GSV和对照（未转染）转染的细胞中的hVEGF水平。在48小时时，hVEGF滴度回到细胞转染GSV的未转染对照的水平，但是，许多树突状复合体继续表现出hVEGF滴度的显着降低。
• Polycationic lipophilic-core dendrons as penetration enhancers for the oral administration of low molecular weight heparin
  作者：Patricia Y. Hayes、Benjamin P. Ross、Bradley G. Thomas、Istvan Toth

  DOI：10.1016/j.bmc.2005.08.004

  日期：2006.1

  Two polycationic lipophilic-core carbohydrate-based dendrons 2a-b and five polycationic lipophilic-core peptide dendrons 3-6, containing four arginine or lysine terminal residues, were synthesized and then tested in rats as penetration enhancers for the oral delivery of low molecular weight heparin. Better results were obtained with dendrons containing terminal lysine residues than terminal arginine. A significant anti-factor Xa activity was obtained when low molecular weight heparin was coadministered with dendron 5. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and in vitro evaluation of a library of modified endomorphin 1 peptides
  作者：Yasuko Koda、Mark Del Borgo、Susanne T. Wessling、Lawrence H. Lazarus、Yoshio Okada、Istvan Toth、Joanne T. Blanchfield

  DOI：10.1016/j.bmc.2008.04.020

  日期：2008.6

  Endomorphin 1 (Endo-1 = Tyr-Pro-Trp-Phe-NH(2)), an endogenous opioid with high affinity and selectivity for mu-opioid receptors, mediates acute and neuropathic pain in rodents. To overcome metabolic instability and poor membrane permeability, the N- and C-termini of Endo-1 were modified by lipoamino acids (Laa) and/or sugars, and 2',6'-dimethyltyrosine (Dmt) replacement of Tyr. Analogues were assessed for mu-opioid receptor affinity, inhibition of cAMP accumulation, enzymatic stability, and permeability across Caco-2 cell monolayers. C-Terminus modi. cation decreased receptor affinity, while N-terminus C8-Laa improved stability and permeability with slight change in receptor affinity. Dmt provided a promising lead compound: [C8Laa-Dmt[1]]-Endo-1 is nine times more stable (t(1/2) = 43.5 min), >8- fold more permeable in Caco-2 cell monolayers, and exhibits 140-fold greater mu-opioid receptor affinity (K(i mu) = 0.08 nM). (C) 2008 Elsevier Ltd. All rights reserved.
• In vitro bioevaluation and docking study of dihydrosphingosine and ethambutol analogues against sensitive and multi-drug resistant Mycobacterium tuberculosis
  作者：Leonardo Aquino Linhares、Aline dos Santos Peixoto、Luanna de Angelis Correia de Sousa、João Paulo Lucena Laet、Aline Caroline da Silva Santos、Valeria Rêgo Alves Pereira、Maria Madileuza Carneiro Neves、Luiz Felipe Gomes Rebello Ferreira、Marcelo Zaldini Hernandes、Jennifer de la Vega、Antônio Pereira-Neves、Arturo San Feliciano、Esther Del Olmo、Haiana Charifker Schindler、Lílian Maria Lapa Montenegro

  DOI：10.1016/j.ejmech.2023.115579

  日期：2023.10
• [EN] DELIVERY SYSTEMS<br/>[FR] SYSTEMES D'ADMINISTRATION
  申请人：ALCHEMIA PTY LTD

  公开号：WO2002053572A1

  公开（公告）日：2002-07-11

  The invention relates to compounds which are useful in the delivery of a wide variety of therapeutically useful molecules. In particular, the invention relates to compounds which are able to act as carriers for therapeutically useful molecules, and to pharmaceutical agents comprising these carriers. The compounds of the invention comprise a mono- or oligosaccharide, a lipidic moiety, and optionally a linker and/or a spacer. The pharmaceutical agents of the invention are particularly useful for oral administration.