(S)-2-amino-6-tert-butoxycarbonylaminohexanoic acid 4-methoxybenzyl ester | 1045709-85-0

• 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-amino-6-tert-butoxycarbonylaminohexanoic acid 4-methoxybenzyl ester
• 英文别名: 2-amino-6-tert –butoxycarbonylaminohexanoic acid 4-methoxybenzyl ester
• CAS: 1045709-85-0
• 化学式: C₁₉H₃₀N₂O₅
• 分子量: 366.458
• InChiKey: MQBLSRCOYIIQIM-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  99.88
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Bis[(4-methoxyphenyl)methyl] 2-aminopentanedioate;hydrochloride 、 (S)-2-amino-6-tert-butoxycarbonylaminohexanoic acid 4-methoxybenzyl ester 在 Bis[(4-methoxyphenyl)methyl] 2-aminopentanedioate;hydrochloride 作用下， 以62.3的产率得到(10S,14S)-tris(4-methoxybenzyl) 2,2-dimethyl-4,12-dioxo-3-oxa-5,11,13-triazahexadecane-10,14,16-tricarboxylate
  参考文献：
  名称：

  Clin Cancer Res 2011, 17, 7645-7653

  摘要：

  DOI：
• 作为产物：
  描述：

  N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 在 哌啶 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (S)-2-amino-6-tert-butoxycarbonylaminohexanoic acid 4-methoxybenzyl ester
  参考文献：
  名称：

  Targeted Biocompatible Nanoparticles for the Delivery of (−)-Epigallocatechin 3-Gallate to Prostate Cancer Cells

  摘要：

  Molecular targeted cancer therapy mediated by nanoparticles (NPs) is a promising strategy to overcome the lack of specificity of conventional chemotherapeutic agents. In this context, the prostate-specific membrane antigen (PSMA) has demonstrated a powerful potential for the management of prostate cancer (PCa). Cancer chemoprevention by phytochemicals is emerging as a suitable approach for the treatment of early carcinogenic processes. Since (-)-epigallocatechin 3-gallate (EGCG) has shown potent chemopreventive efficacy for PCa, we designed and developed novel targeted NPs in order to selectively deliver EGCG to cancer cells. Herein, to explore the recent concept of "nanochemoprevention", we present a study on EGCG-loaded NPs consisting of biocompatible polymers, functionalized with small molecules targeting PSMA, that exhibited a selective in vitro efficacy against PSMA-expressing PCa cells. This approach could be beneficial for high risk patients and would fulfill a significant therapeutic need, thus opening new perspectives for novel and effective treatment for PCa.

  DOI：

  10.1021/jm1013715

文献信息

• Synthesis and Evaluation of Technetium-99m- and Rhenium-Labeled Inhibitors of the Prostate-Specific Membrane Antigen (PSMA)
  作者：Sangeeta R. Banerjee、Catherine A. Foss、Mark Castanares、Ronnie C. Mease、Youngjoo Byun、James J. Fox、John Hilton、Shawn E. Lupold、Alan P. Kozikowski、Martin G. Pomper

  DOI：10.1021/jm800111u

  日期：2008.8.1

  The prostate- specific membrane antigen (PSMA) is increasingly recognized as a viable target for imaging and therapy of cancer. We prepared seven 99'Tc/Re-labeled compounds by attaching known Tc/Re chelating agents to an amino-functionalized PSMA inhibitor (lys-NHCONH-glu) with or without a variable length linker moiety. Ki values ranged from 0.17 to 199 nM. Ex vivo biodistribution and in vivo imaging demonstrated the degree of specific binding to engineered PSMA+ PC3 PIP tumors. PC3-PIP cells are derived from PO that have been transduced with the gene for PSMA. Despite demonstrating nearly the lowest PSMA inhibitory potency of this series, [99`Tc(COXLI)]+ (LI = (2-pyridylmethVI)2N(CH,,)4CH(COH)NHCO-(CH2)6CO-NH-lys-NHCONH-glu) showed the highest, most selective PIP tumor uptake, at 7.9 4.0% injected dose per gram of tissue at 30 min postinjection. Radioactivity cleared from nontarget tissues to produce a PIP to flu (PSMA-PC3) ratio of 44:1 at 120 min postinjection. PSMA can accommodate the steric requirements of 99"Tc/Re complexes within PSMA inhibitors, the best results achieved with a linker moiety between the e amine of the urea lysine and the chelator.
• Development of targeted nanoparticles loaded with antiviral drugs for SARS-CoV-2 inhibition
  作者：Vanna Sanna、Sandro Satta、Tzung Hsiai、Mario Sechi

  DOI：10.1016/j.ejmech.2022.114121

  日期：2022.3
• J. Med. Chem. 2010, 53, 1732-1740
  作者：

  DOI：——

  日期：——
• J. Med. Chem. 2008, 51, 4504-4517
  作者：

  DOI：——

  日期：——