benzyl N-{tris[2-(ethoxycarbonyl)ethoxymethyl]methyl}carbamate | 220431-66-3

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl N-{tris[2-(ethoxycarbonyl)ethoxymethyl]methyl}carbamate
• 英文别名: 3-[2-benzyloxycarbonylamino-3-(2-ethoxycarbonylethoxy)-2-(2-ethoxycarbonyl-ethoxymethyl)propoxy]propionic acid ethyl ester；Benzyl N-[Tris[2-(ethoxycarbonyl)ethoxymethyl]methyl]carbamate；ethyl 3-[3-(3-ethoxy-3-oxopropoxy)-2-[(3-ethoxy-3-oxopropoxy)methyl]-2-(phenylmethoxycarbonylamino)propoxy]propanoate
• CAS: 220431-66-3
• 化学式: C₂₇H₄₁NO₁₁
• 分子量: 555.623
• InChiKey: PUGQUJMKWXZXSP-UHFFFAOYSA-N

物化性质

• 沸点：
  634.2±55.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  39
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  benzyl N-{tris[2-(ethoxycarbonyl)ethoxymethyl]methyl}carbamate 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 144.0h， 生成 benzyl N-tris{[2-[((N-hydroxy-N-methylcarbamoyl)methyl)aminocarbonyl]ethoxy]methyl}methylcarbamate
  参考文献：
  名称：

  A new route to trihydroxamate-containing artificial siderophores and synthesis of a new fluorescent probe

  摘要：

  A fluorescent labelled artificial siderophore 1 was synthesized by coupling a 7-nitrobenz-2-oxa-1,3-diazole (NBD) derivative to the terminal amino group of a new trihydroxamate-containing amine 2, a ferrichrome-type siderophore that was obtained from tris(hydroxymethyl) amino methane. Compound I was shown to be a suitable tool for experiments on siderophore transport and uptake processes in various organisms cells and particularly in Candida albicans cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.053
• 作为产物：
  描述：

  三[[2-(叔-丁氧羰基)乙氧基]甲基]甲胺 在 甲酸 、 sodium carbonate 、 对甲苯磺酸 作用下， 以 水 、 苯 为溶剂， 生成 benzyl N-{tris[2-(ethoxycarbonyl)ethoxymethyl]methyl}carbamate
  参考文献：
  名称：

  Self-Association of Protected Newkome-Type Second-Generation Dendrimers at Nanomolar Level Concentrations in Aqueous Solution

  摘要：

  Protected Newkome-type second-generation dendrimers (based on Lin's amine) were synthesized with a pyrene moiety attached to the core. The photophysical property in aqueous solution of the protected dendrimers shows self-association behavior in water. Pyrene excimer emission at 475 nm is observed in water even at very low concentrations of protected dendrimer (ca. 5 x 10(-8) M). This emission band is absent in other solvents even up to a concentration of 10(-5) M. The corresponding unprotected dendrimer does not show the pyrene excimer fluorescence. The amide of pyrene butyric acid with tert-butylamine shows the formation of excimer, albeit with very low intensity. Quenching studies on the dendrimer with hydrophilic quencher iodide anion (I-) reveal that there is significant quenching of fluorescence intensity in the case of N-tert-butyl-4-pyren-1-ylbutyramide as compared to that of the pyrene-attached second-generation protected dendrimer. This shows that the pyrene moiety in the case of the protected dendrimer is significantly shielded from the surrounding.

  DOI：

  10.1021/ma0498215

文献信息

• [EN] CONJUGATED ANTISENSE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS ANTISENS CONJUGUÉS ET LEUR UTILISATION
  申请人：ISIS PHARMACEUTICALS INC

  公开号：WO2014179620A1

  公开（公告）日：2014-11-06

  Provided herein are oligomeric compounds with conjugate groups. In certain embodiments, the oligomeric compounds are conjugated to N-Acetylgalactosamine.

  本文提供了具有共轭基团的寡聚化合物。在某些实施例中，这些寡聚化合物与N-乙酰半乳糖结合。
• [EN] TARGETED THERAPEUTIC NUCLEOSIDES AND THEIR USE<br/>[FR] NUCLÉOSIDES THÉRAPEUTIQUES CIBLÉES ET LEUR UTILISATION
  申请人：ISIS PHARMACEUTICALS INC

  公开号：WO2015042447A1

  公开（公告）日：2015-03-26

  Provided herein are compounds comprising one or more therapeutic nucleosides and one or more targeting groups. In certain embodiments, the compounds further comprise one or more oligonucleotides. In certain embodiments, a targeting group comprises one or more N-Acetylgalactosamine.

  本文提供的化合物包括一个或多个治疗性核苷和一个或多个靶向基团。在某些实施例中，这些化合物进一步包括一个或多个寡核苷酸。在某些实施例中，一个靶向基团包括一个或多个N-乙酰半乳糖胺。
• [EN] COMPOSITIONS AND METHODS FOR ENHANCED INTESTINAL ABSORPTION OF CONJUGATED OLIGOMERIC COMPOUNDS<br/>[FR] COMPOSITIONS ET MÉTHODES ASSURANT UNE MEILLEURE ABSORPTION INTESTINALE DE COMPOSÉS OLIGOMÈRES CONJUGUÉS
  申请人：ISIS PHARMACEUTICALS INC

  公开号：WO2015188194A1

  公开（公告）日：2015-12-10

  Provided herein are compositions and methods for non-parenteral delivery of conjugated oligomeric compounds. In certain embodiments, compositions and methods are provided for oral delivery of conjugated oligomeric compounds. In certain embodiments, the oligomeric compounds are conjugated to one or more N-acetylgalactosamines or N-acetylgalactosamine analogues.

  本文提供了用于非肠内递送共轭寡聚化合物的组合物和方法。在某些实施方式中，提供了用于口服递送共轭寡聚化合物的组合物和方法。在某些实施方式中，这些寡聚化合物与一个或多个N-乙酰半乳糖胺或N-乙酰半乳糖胺类似物共轭。
• Dendrimers as molecular translocators
  申请人：Goodman Murray

  公开号：US20060216265A1

  公开（公告）日：2006-09-28

  Transport molecules include a dendrimer and a biologically active molecule. The dendrimer of such transport molecules includes at least one guanidine group, at least one protonated guanidine group, at least one protected guanidine group, at least one amidine group, at least one protonated amidine group, at least one protected amidine group, at least one ureido group, at least one protonated ureido group, at least one protected ureido group, at least one thioureido group, at least one protonated thioureido group, or at least one protected thioureido group. The biologically active molecule is bonded to the dendrimer. A method of increasing the bioavailability of a drug includes bonding the drug to a dendrimer of the invention.

  转运分子包括一种树枝状聚合物和一种生物活性分子。这些转运分子的树枝状聚合物包括至少一个胍基团、至少一个质子化的胍基团、至少一个保护的胍基团、至少一个酰胺基团、至少一个质子化的酰胺基团、至少一个保护的酰胺基团、至少一个脲基团、至少一个质子化的脲基团、至少一个保护的脲基团、至少一个硫脲基团、至少一个质子化的硫脲基团，或至少一个保护的硫脲基团。生物活性分子与树枝状聚合物结合。一种增加药物生物利用度的方法包括将药物与本发明的树枝状聚合物结合。
• Receptor-Specific Delivery of Peptide Nucleic Acids Conjugated to Three Sequentially Linked <i>N</i>-Acetyl Galactosamine Moieties into Hepatocytes
  作者：Pramod Bhingardeve、Bharath Raj Madhanagopal、Hemanth Naick、Prashant Jain、Muthiah Manoharan、Krishna Ganesh

  DOI：10.1021/acs.joc.0c00601

  日期：2020.7.17

  Peptide nucleic acids (PNAs) are DNA analogs that bind with high affinity to DNA and RNA in a sequence-specific manner but have poor cell permeability, limiting use as therapeutic agents. The work described here is motivated by recent reports of efficient gene silencing specifically in hepatocytes by small interfering RNAs conjugated to triantennary N-acetyl galactosamine (GalNAc), the ligand recognized

  肽核酸（PNA）是DNA类似物，它们以序列特异性方式与DNA和RNA高亲和力结合，但细胞通透性差，限制了其作为治疗剂的用途。此处描述的工作是受最近报道的，即通过与三触角N-乙酰半乳糖胺（GalNAc）（脱唾液酸糖蛋白受体（ASGPR）识别的配体）缀合的小干扰RNA在肝细胞中有效进行基因沉默所激发。的PNA缀合到在N末端或者三触角的GalNAc（支化结构），或位于C锚定的单体的GalNAc部分γ的三个连续的PNA单体的ñ - （2-氨基乙基）甘氨酸（AEG在固相上合成支架（顺序结构）。如紫外和圆二色光谱法所示，它们与互补的DNA和RNA形成双链体。GalNAc偶联的PNA的荧光标记类似物被表达ASGPR的HepG2细胞内在化，但缺少该受体的HEK-293细胞却不吸收。如共聚焦显微镜所证实的，相继缀合物比分支缀合物更有效地内化到HepG2细胞中，大约13倍。此处提出的结果突出了GalNAc偶联