(+/-)-N^α-BOC-Tryptophan tert-butyl ester | 158008-94-7

• 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^α-BOC-Tryptophan tert-butyl ester
• 英文别名: Boc-(RS)-Trp-O^tBu；(2S)-2-(tert-butoxycarbonylamino)-3-(indol-3-yl)propionic acid tert-butyl ester；Boc-DL-tryptophan tert-butyl ester；tert-butyl 3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 158008-94-7
• 化学式: C₂₀H₂₈N₂O₄
• 分子量: 360.453
• InChiKey: IVXDHDUSJQBGMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-N^α-BOC-Tryptophan tert-butyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 (+/-)-Tryptophan tert-butyl ester hydrochloride
  参考文献：
  名称：

  Selective Removal of an N-BOC Protecting Group in the Presence of a tert-Butyl Ester and Other Acid-Sensitive Groups

  摘要：

  DOI：

  10.1021/jo00090a045
• 作为产物：
  描述：

  3-(2-tert-Butoxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-indole-1-carboxylic acid tert-butyl ester 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 50.0 ℃ 、26.66 Pa 条件下， 反应 7.0h， 以80%的产率得到(+/-)-N^α-BOC-Tryptophan tert-butyl ester
  参考文献：
  名称：

  在低压下使用硅胶选择性除去N -BOC保护基

  摘要：

  描述了使用硅胶从氮原子与芳族基团或羰基基团选择性地除去BOC基团。

  DOI：

  10.1016/0040-4039(95)02398-4

文献信息

• Discovery and Optimization of Novel Hydrogen Peroxide Activated Aromatic Nitrogen Mustard Derivatives as Highly Potent Anticancer Agents
  作者：Wenbing Chen、Heli Fan、Kumudha Balakrishnan、Yibin Wang、Huabing Sun、Yukai Fan、Varsha Gandhi、Leggy A. Arnold、Xiaohua Peng

  DOI：10.1021/acs.jmedchem.8b00559

  日期：2018.10.25

  We describe several new aromatic nitrogen mustards with various aromatic substituents and boronic esters that can be activated with H2O2 to efficiently cross-link DNA. In vitro studies demonstrated the anticancer potential of these compounds at lower concentrations than those of other clinically used chemotherapeutics, such as melphalan and chlorambucil. In particular, compound 10, bearing an amino

  我们描述了几种带有各种芳香族取代基和硼酸酯的新型芳香氮芥子，它们可以被H 2 O 2活化以有效地交联DNA。体外研究表明，与其他临床使用的化疗药物（例如美法仑和苯丁酸氮芥）相比，这些化合物的抗癌潜力较低。特别地，带有氨基酸酯链的化合物10对固有具有高水平活性氧物质的乳腺癌和白血病细胞具有选择性的细胞毒性。重要的是，10是10-14倍美法仑和苯丁酸氮芥对三阴性乳腺癌（TNBC）细胞更有效。同样，10与苯丁酸氮芥或先导化合物相比，对原发性慢性淋巴细胞白血病的毒性更大9。氨基酸侧链的引入提高了10的溶解度和渗透性。此外，10抑制异种移植小鼠中TNBC肿瘤的生长，而没有明显的一般毒性迹象，使该化合物成为临床开发的理想候选药物。
• Synthetic studies of 3-(3-fluorooxindol-3-yl)-l-alanine
  作者：Tomoya Fujiwara、Bin Yin、Meixiang Jin、Kenneth L. Kirk、Yoshio Takeuchi

  DOI：10.1016/j.jfluchem.2008.06.026

  日期：2008.9

  Oxidative fluorination of several protected tryptophans 8b-g with Selectfluor (TM) proceeded smoothly in aqueous media to give a diastereomeric mixture of the corresponding 3-fluorooxindoles 9b-g. Attempted deprotection of the 3-fluorooxindoles 9b-g under various conditions did not afford 3-(3-fluorooxindol-3-yl)-L-alanine (6). Reaction of the suitably protected tryptophan derivative 16 with Selectfluor (TM) produced the fluorinated product 17. Simultaneous cleavage of all protective groups of 17 under acidic conditions successfully gave the target compound 6 in excellent yield. (c) 2008 Elsevier B.V. All rights reserved.
• Microwave-Accelerated <i>O</i>-Alkylation of Carboxylic Acids with <i>O</i>-Alkylisoureas
  作者：Stefano Crosignani、Peter D. White、Bruno Linclau

  DOI：10.1021/ol0263705

  日期：2002.8.1

  Microwave-assisted beta-alkylations of several carboxylic acids have been performed with three different beta-alkylisoureas. All reactions are significantly faster compared to conventionally heated reactions, while retaining high chemoselectivity. The combination of microwave technology with the use of the solid-supported isourea 3 enables the synthetic chemist to obtain the pure methyl esters starting from the corresponding acids in less than an hour.
• Discovery of 7-[¹⁸F]Fluorotryptophan as a Novel Positron Emission Tomography (PET) Probe for the Visualization of Tryptophan Metabolism in Vivo
  作者：Boris D. Zlatopolskiy、Johannes Zischler、Dominique Schäfer、Elizaveta A. Urusova、Mehrab Guliyev、Olesia Bannykh、Heike Endepols、Bernd Neumaier

  DOI：10.1021/acs.jmedchem.7b01245

  日期：2018.1.11

  Tryptophan and its metabolites are involved in different physiological and pathophysiological processes. Consequently, positron emission tomography (PET) tracers addressing tryptophan metabolic pathways should allow the detection of different pathologies like neurological disorders and cancer. Herein we report an efficient method for the preparation of fluorotryptophans labeled in different positions with F-18 and their biological evaluation. 4-7-[F-18]Fluorotryptophans ([F-18]FTrps) were prepared according to a modified protocol of alcohol-enhanced Cu-mediated radiofluorination in 30-53% radiochemical yields. In vitro experiments demonstrated high cellular uptake of 4-7[F-18]FTrps in different tumor cell lines. 4, 5-, and 6-[F-18]FTrps, although stable in vitro, suffered from rapid in vivo defluorination. In contrast, 7-[F-18]FTrp demonstrated a high in vivo stability and enabled a clear delineation of serotonergic areas and melatonin-producing pineal gland in rat brains. Moreover 7-[F-18]FTrp accumulated in different tumor xenografts in a chick embryo CAM model. Thus, 7-[F-18]FTrp represents a highly promising PET probe for imaging of Trp metabolism.