N-benzyloxycarbonyl-glycine trimethylsilylethyl ester | 65057-56-9

• 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
• 英文名称: N-benzyloxycarbonyl-glycine trimethylsilylethyl ester
• 英文别名: N-carboxybenzyloxy 2-trimethylsilylethyl glycinate；2-(trimethylsilyl)ethyl N-[(benzyloxy)carbonyl]glycinate；2-(trimethylsilyl)ethyl 2-(((benzyloxy)carbonyl)amino)acetate；2-trimethylsilylethyl 2-(phenylmethoxycarbonylamino)acetate
• CAS: 65057-56-9
• 化学式: C₁₅H₂₃NO₄Si
• 分子量: 309.437
• InChiKey: BHMRJMOJAUUOIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-glycine trimethylsilylethyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 N,N-dibenzylglycine 2-trimethylsilylethyl ester
  参考文献：
  名称：

  N，N-二苄基甘氨酸酯的烷基化和缩合反应：α-氨基酸衍生物的合成

  摘要：

  N脱质子后，N-二苄基甘氨酸酯会在α-碳原子上与各种亲电试剂发生烷基化和缩合反应。

  DOI：

  10.1039/c39870001329
• 作为产物：
  描述：

  2-(三甲硅基)乙醇 、 N-苄氧羰基甘氨酸 在 N,N'-羰基二咪唑 作用下， 生成 N-benzyloxycarbonyl-glycine trimethylsilylethyl ester
  参考文献：
  名称：

  合成复杂的δ-炔基氨基酸作为潜在的甲基转移酶的多底物加合物抑制剂。

  摘要：

  描述了两种类型的δ-炔基氨基酸的合成。关键中间体是通过两种不同的途径从末端乙炔衍生而来的：（1）钯介导的Heck型芳基化反应，和（2）Simmons-Smith同源化反应，然后使生成的炔丙基有机金属与苯甲酰基三甲基硅烷反应。对所需氨基酸的进一步加工涉及将衍生自N-亚苄基甘氨酸酯的碳负离子与复杂的烷基卤化物偶合。使用该化学方法成功地完成了非核苷δ-炔属氨基酸的合成。在含有核苷的氨基酸的情况下，通过该途径合成了潜在的邻苯二酚O-甲基转移酶的多底物加合物抑制剂。不幸的是，5'-脱氧，5'对酸的敏感性

  DOI：

  10.1016/0968-0896(96)00139-3

文献信息

• Partially saturated nitrogen-containing heterocyclic compound
  申请人：TAISHO PHARMACEUTICAL CO., LTD

  公开号：US09422240B2

  公开（公告）日：2016-08-23

  There are provided compounds having a superior PHD2 inhibitory effect that are represented by general formula (I′): (in the above-mentioned general formula (I′), W, Y, R2, R3, R4, and Y4 are as described hereinabove), or pharmaceutically acceptable salts thereof.

  提供了具有优越的PHD2抑制效果的化合物，其通式表示为(I'):(在上述通式(I')中，W、Y、R2、R3、R4和Y4如上所述)，或其药学上可接受的盐。
• EP3705471
  申请人：——

  公开号：——

  公开（公告）日：——
• PARTIALLY SATURATED NITROGEN-CONTAINING HETEROCYCLIC COMPOUND
  申请人：Taisho Pharmaceutical Co., Ltd.

  公开号：EP2881384B1

  公开（公告）日：2018-05-30
• Synthesis of chemically functionalized superparamagnetic nanoparticles as delivery vectors for chemotherapeutic drugs
  作者：Stephen Hanessian、Justyna A. Grzyb、Feride Cengelli、Lucienne Juillerat-Jeanneret

  DOI：10.1016/j.bmc.2007.12.051

  日期：2008.3.15

  Superparamagnetic iron oxide nanoparticles (SPIONs) are in clinical use for disease detection by MRI. A major advancement would be to link therapeutic drugs to SPIONs in order to achieve targeted drug delivery combined with detection. In the present work, we studied the possibility of developing a versatile synthesis protocol to hierarchically construct drug-functionalized-SPIONs as potential anti-cancer agents. Our model biocompatible SPIONs consisted of an iron oxide core (9-10 nm diameter) coated with polyvinylalcohols (PVA/aminoPVA), which can be internalized by cancer cells, depending on the positive charges at their surface. To develop drug-functionalized-aminoPVA-SPIONs as vectors for drug delivery, we first designed and synthesized bifunctional linkers of varied length and chemical composition to which the anti-cancer drugs 5-fluorouridine or doxorubicin were attached as biologically labile esters or peptides, respectively. These functionalized linkers were in turn coupled to aminoPVA by amide linkages before preparing the drug-functionalized-SPIONs that were characterized and evaluated as anti-cancer agents using human melanoma cells in culture. The 5-fluorouridine-SPIONs with an optimized ester linker were taken up by cells and proved to be efficient anti-tumor agents. While the doxorubicin-SPIONs linked with a Gly-Phe-Leu-Gly tetrapeptide were cleaved by lysosomal enzymes, they exhibited poor uptake by human melanoma cells in culture. (C) 2008 Elsevier Ltd. All rights reserved.
• Highly Selective Aldose Reductase Inhibitors. 3. Structural Diversity of 3-(Arylmethyl)-2,4,5-trioxoimidazolidine-1-acetic Acids
  作者：Takayuki Kotani、Yasuhiro Nagaki、Akira Ishii、Yukari Konishi、Hisashi Yago、Seishi Suehiro、Nobuhisa Okukado、Kaoru Okamoto

  DOI：10.1021/jm960594+

  日期：1997.2.1

  Accumulation of intracellular sorbitol, the reduced product of glucose, catalyzed by aldose reductase (AR) (EC 1.1.1.21), is thought to be the cause of the development of diabetic complications. Our attention is focused on finding compounds which inhibit AR without significantly inhibiting aldehyde reductase (ALR) (EC 1.1.1.2). The uracil or 2,4-dioxoimidazolidine skeleton having the benzothiazolyl or 4-chloro-3-nitrophenyl group as an aryl part indicated not only extremely high AR inhibitory activity but also AR selectivity. The ratio of IC50(ALR)/IC50(AR) of 3-[(5-chlorobenzothiazol-2-yl)methyl]-1,2,3,4-tetrahydro-2,4-dioxopyrim-idine-1-acetic acid (47d) was more than 17 500. The uracil skeleton with the benzothiazolyl moiety seemed to be the best combination for selective AR inhibition.