(S)-2-tert-Butoxycarbonylamino-pentanedioic acid 5-benzyl ester 1-(2-trimethylsilanyl-ethyl) ester | 172694-24-5

• 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: (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 5-benzyl ester 1-(2-trimethylsilanyl-ethyl) ester
• 英文别名: 5-O-benzyl 1-O-(2-trimethylsilylethyl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate
• CAS: 172694-24-5
• 化学式: C₂₂H₃₅NO₆Si
• 分子量: 437.608
• InChiKey: SQYJMSFWWNANGX-SFHVURJKSA-N

物化性质

• 沸点：
  518.0±50.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 5-benzyl ester 1-(2-trimethylsilanyl-ethyl) ester 在 palladium on activated charcoal 、 氢气 、 对甲苯磺酸 、 7-甲基-1,5,7-三氮杂二环[4.4.0]癸-5-烯 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 26.0h， 生成 α-[2-(trimethylsilyl)ethoxy]-2-N-[2-(trimethylsilyl)ethoxycarbonyl]folic acid
  参考文献：
  名称：

  A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes

  摘要：

  尽管有大量的文献描述了将叶酸与药效团反应，但这种方法无法有效地提供所需的共轭物的正确位置异构体。

  DOI：

  10.1039/c9ra01435g
• 作为产物：
  描述：

  2-(三甲硅基)乙醇 、 N-叔丁氧羰基-L-谷氨酸 5-苄酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到(S)-2-tert-Butoxycarbonylamino-pentanedioic acid 5-benzyl ester 1-(2-trimethylsilanyl-ethyl) ester
  参考文献：
  名称：

  Synthesis, characterization, and anticancer activity of folate γ-ferrocenyl conjugates

  摘要：

  通过一个特定的路线合成了新型的叶酸γ-二茂铁共轭物，并且表现出对Frα阳性的恶性细胞的选择性和增强的细胞毒性。

  DOI：

  10.1039/c9nj04954a

文献信息

• Synthesis, characterization, and anticancer activity of folate γ-ferrocenyl conjugates
  作者：Diego L. Bertuzzi、Gabriel Perli、Carolyne B. Braga、Catia Ornelas

  DOI：10.1039/c9nj04954a

  日期：——

  Novel folate γ-ferrocene conjugates were synthesized through a regiospecific route, and showed selectivity and enhanced cytotoxicity against Frα-positive malignant cells.

  通过一个特定的路线合成了新型的叶酸γ-二茂铁共轭物，并且表现出对Frα阳性的恶性细胞的选择性和增强的细胞毒性。
• A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes
  作者：Carlotta Figliola、Estelle Marchal、Brandon R. Groves、Alison Thompson

  DOI：10.1039/c9ra01435g

  日期：——

  Despite the vast literature that describes reacting folic acid with a pharmacophore, this route is ineffective in providing the correct regioisomer of the resulting conjugate.

  尽管有大量的文献描述了将叶酸与药效团反应，但这种方法无法有效地提供所需的共轭物的正确位置异构体。
• Cryptophane-Folate Biosensor for ¹²⁹Xe NMR
  作者：Najat S. Khan、Brittany A. Riggle、Garry K. Seward、Yubin Bai、Ivan J. Dmochowski

  DOI：10.1021/bc5005526

  日期：2015.1.21

  Folate-conjugated cryptophane was developed for targeting cryptophane to membrane-bound folate receptors that are overexpressed in many human cancers. The cryptophane biosensor was synthesized in 20 nonlinear steps, which included functionalization with folate recognition moiety, solubilizing peptide, and Cy3 fluorophore. Hyperpolarized Xe-129 NMR studies confirmed xenon binding to the folate-conjugated cryptophane. Cellular internalization of biosensor was monitored by confocal laser scanning microscopy and quantified by flow cytometry. Competitive blocking studies confirmed cryptophane endocytosis through a folate receptor-mediated pathway. Flow cytometry revealed 10-fold higher cellular internalization in KB cancer cells overexpressing folate receptors compared to HT-1080 cells with normal folate receptor expression. The biosensor was determined to be nontoxic in HT-1080 and KB cells by MTT assay at low micromolar concentrations typically used for hyperpolarized Xe-129 NMR experiments.
• Potent Dipeptide Inhibitors of the pp60<i>^c</i><i>^-</i><i>^src</i> SH2 Domain
  作者：Gregory J. Pacofsky、Karen Lackey、Krystal J. Alligood、Judd Berman、Paul S. Charifson、Renae M. Crosby、George F. Dorsey,、Paul L. Feldman、Tona M. Gilmer、Conrad W. Hummel、Steven R. Jordan、Christopher Mohr、Lisa M. Shewchuk、Daniel D. Sternbach、Marc Rodriguez

  DOI：10.1021/jm970853a

  日期：1998.5.1

  The design, synthesis, and evaluation of dipeptide analogues as ligands for the pp60(c-src) SH2 domain are described. The critical binding interactions between Ac-Tyr-Glu-N(n-C5H11)(2) (2) and the protein are established and form the basis for our structure-based drug design efforts. The effects of changes in both the C-terminal (11-27) and N-terminal (51-69) portions of the dipeptide are explored. Analogues with reduced overall charge (92-95) are also investigated. We demonstrate the feasibility of pairing structurally diverse subunits in a modest dipeptide framework with the goal of increasing the druglike attributes without sacrificing binding affinity.
• Folic acid functionalization for targeting self-assembled paclitaxel-based nanoparticles
  作者：Eleonora Colombo、Davide Andrea Coppini、Simone Maculan、Pierfausto Seneci、Benedetta Santini、Filippo Testa、Lucia Salvioni、Giovanni Maria Vanacore、Miriam Colombo、Daniele Passarella

  DOI：10.1039/d2ra06306a

  日期：——

  Hetero-nanoparticles self-assembled from a conjugate bearing folic acid as the targeting agent, and another bearing paclitaxel as the active agent are reported. Hetero-nanoparticles containing varying percentages of folic acid conjugates are characterised, and their biological activity is determined.

  报道了由以叶酸为靶向剂的缀合物和另一种以紫杉醇为活性剂的缀合物自组装的杂纳米颗粒。表征了含有不同百分比的叶酸缀合物的杂纳米颗粒，并确定了它们的生物活性。