tert-butyl (3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]propyl)carbamate | 894414-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: tert-butyl (3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]propyl)carbamate
• 英文别名: tert-Butyl (3-((1,3-dioxoisoindolin-2-yl)oxy)propyl)carbamate；tert-butyl N-[3-(1,3-dioxoisoindol-2-yl)oxypropyl]carbamate
• CAS: 894414-29-0
• 化学式: C₁₆H₂₀N₂O₅
• 分子量: 320.345
• InChiKey: FJHOAAXBCPGLOF-UHFFFAOYSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]propyl)carbamate 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 tert-butyl (3-((3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamido)oxy)propyl)carbamate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of RGD-Conjugated MEK1/2 Kinase Inhibitors for Integrin-Targeted Cancer Therapy

  摘要：

  两种源于MEK1/2激酶抑制剂PD0325901的新型RGD-MEKI偶联物系列已被开发用于整合素受体介导的癌症治疗。第一系列，烷氧基胺类似物RGD-MEKI偶联物9a-g通过与PD0325901相同的机制在黑色素瘤A375细胞中显示出抗增殖活性。PEGylation使9f在A375测定中的IC50值增加了三倍，而多cRGD肽负载则显著提高了9g在整合素高表达的U87细胞中的受体特异性抗增殖活性。在第二系列中，RGD-PD0325901 13相比烷氧基胺类似物，通过抑制ERK通路活性和癌细胞的DNA复制，显示出显著增强的抗肿瘤特性。此外，13在U87测定中比PD0325901显示出更强的抗增殖活性，且呈剂量依赖性。所有这些数据表明，带有酯键连接的RGD-MEKI偶联物提高了对整合素高表达肿瘤细胞的靶向能力，从而增强了抗癌疗效。

  DOI：

  10.3390/molecules181113957
• 作为产物：
  描述：

  N-(3-羟丙基)氨基甲酸叔丁酯 在 咪唑 、 碘 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 13.25h， 生成 tert-butyl (3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]propyl)carbamate
  参考文献：
  名称：

  Synthesis of fluorescent molecular probes based on cis-cinnamic acid and molecular imaging of lettuce roots

  摘要：

  We synthesized azo dye- and fluorescence-labeled cis-cinnamic acid analogues possessing inhibitory activity agaihst lettuce root growth and a trans-isomer without bioactivity as a control probe. The radicles incubated with the azo dye-labeled analogue were stained red, with their tips especially deeply dyed. The fluorescent images of the radicles incubated with each of these molecular probes depicted that the root cap was fluorescence-stained. However, images of the control radicles prepared by staining with the trans-isomer fluorescent probe did not show emission at the root cap. These contrasts suggest specific localization of the cis-cinnamate analogue at the columella cells. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.08.060

文献信息

• Structural basis of binding and inhibition of ornithine decarboxylase by 1-amino-oxy-3-aminopropane
  作者：X. Edward Zhou、Kelly Suino-Powell、Chad R. Schultz、Bilal Aleiwi、Joseph S. Brunzelle、Jared Lamp、Irving E. Vega、Edmund Ellsworth、André S. Bachmann、Karsten Melcher

  DOI：10.1042/bcj20210647

  日期：2021.12.10

  and its cofactor pyridoxal 5-phosphate (PLP) and functions by competing with the ODC substrate ornithine for binding to the catalytic site. We have revisited the mechanism of APA binding and ODC inhibition through a new crystal structure of APA-bound ODC, which we solved at 2.49 Å resolution. The structure unambiguously shows the presence of a covalent oxime between APA and PLP in the catalytic site

  鸟氨酸脱羧酶 (ODC) 是多胺 (PA) 合成的限速酶。PA 是增殖所需的癌代谢物，药物 ODC 抑制用于治疗过度增殖性疾病，包括癌症和传染病。最有效的 ODC 抑制剂是 1-氨基-氧基-3-氨基丙烷 (APA)。ODC-APA 复合物的先前晶体结构表明 APA 非共价结合 ODC 及其辅因子 5-磷酸吡哆醛 (PLP)，并通过与 ODC 底物鸟氨酸竞争结合催化位点发挥作用。我们通过 APA 结合的 ODC 的新晶体结构重新审视了 APA 结合和 ODC 抑制的机制，我们以 2.49 Å 的分辨率解决了这一问题。该结构清楚地表明在催化位点 APA 和 PLP 之间存在共价肟，我们通过质谱在溶液中证实了这一点。稳定的肟与 ODC 发生广泛的相互作用，但不能被分解代谢，这解释了 APA 在 ODC 抑制中的高效力。此外，我们解决了在底物结合袋处结合柠檬酸盐的 ODC/PLP 复合结构。这两种结构为开发更有效的药物
• Aqueous Self-Assembly of Purely Hydrophilic Block Copolymers into Giant Vesicles
  作者：Sarah M. Brosnan、Helmut Schlaad、Markus Antonietti

  DOI：10.1002/anie.201502100

  日期：2015.8.10

  self‐assembly of purely hydrophilic systems can be readily achieved with similar ease and success. We have synthesized double hydrophilic block copolymers from polysaccharides and poly(ethylene oxide) or poly(sarcosine) to yield high molar mass diblock copolymers through oxime chemistry. These hydrophilic materials can easily assemble into nanosized (<500 nm) and microsized (>5 μm) polymeric vesicles depending

  大分子的自组装是生命本身的基础，从历史上看，这些系统最初是由疏水作用驱动的两亲性系统发展所模仿。在此，我们证明，以类似的简便性和成功性，可以很容易地实现纯亲水性系统的自组装。我们已经从多糖和聚（环氧乙烷）或聚（肌氨酸）合成了双亲水嵌段共聚物，以通过肟化学生成高摩尔质量的二嵌段共聚物。根据浓度和二嵌段组成，这些亲水性材料可以轻松组装成纳米级（<500 nm）和微米级（> 5μm）聚合物囊泡。由于这些材料具有亲水性，
• COMPOSITIONS CONTAINING, METHODS INVOLVING, AND USES OF NON-NATURAL AMINO ACIDS AND POLYPEPTIDES
  申请人：Ambrx, Inc.

  公开号：EP1828224B1

  公开（公告）日：2016-04-06
• The synthesis and BK channel-opening activity of N- acylaminoalkyloxime derivatives of dehydroabietic acid
  作者：Yong-Mei Cui、Xin-Lan Liu、Wen-Ming Zhang、Hai-Xia Lin、Tomohiko Ohwada、Katsutoshi Ido、Kohei Sawada

  DOI：10.1016/j.bmcl.2015.12.038

  日期：2016.1

  A series of N-acylaminoalkyloxime derivatives of dehydroabietic acid were synthesized and evaluated for BK channel-opening activities in an assay system of CHO-K1 cells expressing hBK alpha channels. The structure-activity relationship study revealed that a non-covalent interaction between the S atom of the 2-thiophene and the carbonyl O atom may contribute to conformation restriction for interaction with the ion channel. This research could guide the design and synthesis of novel abietane-based BK channel opener. (C) 2015 Elsevier Ltd. All rights reserved.
• Compositions Containing, Methods Involving, and Uses of Non-Natural Amino Acids and Polypeptides
  申请人：MIAO Zhenwei

  公开号：US20080177027A1

  公开（公告）日：2008-07-24

  Disclosed herein are non-natural amino acids and polypeptides that include at least one non-natural amino acid, and methods for making such non-natural amino acids and polypeptides. The non-natural amino acids, by themselves or as a part of a polypeptide, can include a wide range of possible functionalities, but typical have at least one oxime, carbonyl, dicarbonyl, and/or hydroxylamine group. Also disclosed herein are non-natural amino acid polypeptides that are further modified post-translationally, methods for effecting such modifications, and methods for purifying such polypeptides. Typically, the modified non-natural amino acid polypeptides include at least one oxime, carbonyl, dicarbonyl, and/or hydroxylamine group. Further disclosed are methods for using such non-natural amino acid polypeptides and modified non-natural amino acid polypeptides, including therapeutic, diagnostic, and other biotechnology uses.