tert-butyl (2-((4-methoxyphenyl)amino)-2-oxoethyl)carbamate | 34885-75-1

• 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: tert-butyl (2-((4-methoxyphenyl)amino)-2-oxoethyl)carbamate
• 英文别名: Tert-butyl (4-methoxyphenylcarbamoyl)methylcarbamate；tert-butyl N-[2-(4-methoxyanilino)-2-oxoethyl]carbamate
• CAS: 34885-75-1
• 化学式: C₁₄H₂₀N₂O₄
• mdl: MFCD24391777
• 分子量: 280.324
• InChiKey: CWKPOVBPJLDVRJ-UHFFFAOYSA-N

物化性质

• 熔点：
  143-144 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  480.2±30.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-((4-methoxyphenyl)amino)-2-oxoethyl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到氨基-N-(4-甲氧基苯基)乙酰胺
  参考文献：
  名称：

  基于酰胺的二足探针，用于超灵敏和选择性地检测水溶液中的3,5-二硝基水杨酸

  摘要：

  合成了构象刚度不同的带有-的二足探针（探针1和2），用于灵敏检测水溶液中的3,5-二硝基水杨酸（DNSA）。两个二脚架探针均具有两个pyr单元，并且在高DMSO中的高水分含量（> 60％）下表现出由聚集（ACQ）引起的猝灭。由于the二聚体（例如，受激准分子）是在99％水溶液中的主要构象，因此激发后，两个探针在486 nm（探针1）或480 nm（探针2）上均显示出足够的准分子发射强度。探针（探针1和2）的准分子发射在DNSA存在下被灵敏地淬灭。探针1在各种羧酸（CA）中对DNSA有选择性的响应，而探针2对DNSA和5-NSA都有响应。密度泛函理论（DFT）计算表明，在存在DNSA的情况下，探针会发生结构变化，从而导致探针的每个pyr单元与客体分子的苯环之间形成新的π - π相互作用。这种新的π - π相互作用使能量能够从to转移到非辐射客体分子（DNSA），从而导致探针中的荧光猝灭。探针

  DOI：

  10.1016/j.dyepig.2017.08.039
• 作为产物：
  描述：

  N-(2-hydroxyethyl)-4-[[1-(4-methoxyanilino)-1-oxopropan-2-yl]amino]-3,5-dinitrobenzamide 在 N-甲基咪唑 、 氰基磷酸二乙酯 、 丙酮 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 4.5h， 生成 tert-butyl (2-((4-methoxyphenyl)amino)-2-oxoethyl)carbamate
  参考文献：
  名称：

  N-Substituted 2-(2,6-Dinitrophenylamino)propanamides:  Novel Prodrugs That Release a Primary Amine via Nitroreduction and Intramolecular Cyclization

  摘要：

  A series of N-dinitrophenylamino acid amides [(4-CONHZ-2,6-diNO(2)Ph)N(R)C(X,Y)CONHPhOMe] were prepared as potential bioreductive prodrugs and reduced radiolytically to study their rates of subsequent intramolecular cyclization. Compounds bearing a free NH group (R = H) underwent rapid cyclization in neutral aqueous buffers (t(1/2) < 1 min) following 4-electron reduction, with the generation of a N-hydroxydihydroquinoxalinone and concomitant release of 4-methoxyaniline. Amine release from analogous N-methyl analogues (R = Me) was relatively slow. These results are consistent-with intramolecular cyclization of a monohydroxylamine intermediate. The high rates of cyclization/extrusion by these very electron-deficient hydroxylamines suggest that the process is greatly accelerated by the presence of an H-bonding "conformational lock" between the anilino NH group and the adjacent o-nitro group (Kirk and Cohen, 1972). Changes in the phenylcarboxamide side chain or in C-methylation in the linking chain had little effect-on the rate of cyclization. The model compounds had 1-electron reduction potentials in the range appropriate for cellular reduction (-373 mV for a measured example) and appeared suitable for development as prodrugs that release amine-based effecters following enzymic or radiolytic reduction. Prodrug examples containing 4-aminoaniline mustard and 5-amino-1-(chloromethyl)benz[e]indoline alkylating units were evaluated but were not activated efficiently by cellular nitroreductases. However, cell killing by the radiation-induced reduction of the latter prodrug was demonstrated.

  DOI：

  10.1021/jm960783s

文献信息

• New isoleucine derived dipeptides as antiprotozoal agent: Synthesis, in silico and in vivo studies.
  作者：Ogechi C. Ekoh、Uchechukwu C. Okoro、Rafat Ali、David I. Ugwu、Sunday N. Okafor、James A. Ezugwu

  DOI：10.1016/j.molstruc.2021.130017

  日期：2021.5

  aceturate. In the antimalarial study, 11b was the most active compound, even better than the standard. Molecular docking result suggests good interaction between the reported compounds and the target protein. The results of haematological analysis, liver and kidney function tests showed that the compounds had no adverse effect on the blood and organs. Compound 11b stands out among the derivatives haven shown

  疟疾耐药性寄生虫的出现越来越多，锥虫病的有效化学疗法不足，代表了热带地区传染病治疗的巨大挑战。关于开发有效的抗原生动物剂，通过使用肽偶联剂将化合物（10）与（8a-j）缩合，合成了十种新的甘草二肽磺酰胺衍生物。化合物11b，11i和11j最能清除11b小鼠的锥虫布氏锥虫，并具有与醋酸二米那嗪相当的活性。在抗疟疾研究中，11b是活性最高的化合物，甚至优于标准化合物。分子对接结果表明所报道的化合物与靶蛋白之间具有良好的相互作用。血液学分析，肝和肾功能测试的结果表明该化合物对血液和器官没有不良影响。化合物11b在衍生物中脱颖而出，这些衍生物在抗疟和抗锥虫试验中均显示出更好的活性。
• Aggregation induced emission enhancement behavior of conformationally rigid pyreneamide-based probe for ultra-trace detection of picric acid (PA)
  作者：Ashwani Kumar、Pil Seok Chae

  DOI：10.1016/j.dyepig.2018.04.014

  日期：2018.9

  (PA) detection. These probes commonly contain a central rigid core, but probe 1 contains relatively short linkers/spacers compared to probes 2 and 3. The dipodal probes produced dominant pyrene excimer fluorescence in an aqueous solution, and aggregation-induced emission enhancement (AIEE) was observed. The fluorescence emission of probe 1 was significantly quenched only by the presence of PA, while probes

  在这项研究中，我们设计并制备了具有pyr柔韧性的pic酸二甲双胍探针，用于苦味酸（PA）检测。这些探针通常包含中央刚性核，但与探针2和3相比，探针1包含相对较短的接头/间隔子。二脚架探针在水溶液中产生主要的pyr准分子荧光，并且观察到聚集诱导的发射增强（AIEE）。仅当存在PA时，探针1的荧光发射才被猝灭，而探针2和3则对4-硝基苯酚或2,4-二硝基苯酚以及PA产生响应。在三种二脚架探针中，探针的结合强度最高1与PA的结合常数为K a  = 3.96×10 7  M -1。1 H NMR测量和DFT计算表明，添加PA后，这些双脚探针通过the环和PA在水溶液中的π-π相互作用形成单个的探针-PA络合物。这种复合物的形成使得能量在激发时能从富电子的to转移到贫电子的PA上，从而导致荧光猝灭。探针1提供了水中PA的超痕量检测，观察和计算的检出限（LOD）分别为1 nM和0.13 pM，是报告的
• COMPOUNDS WHICH HAVE A PROTECTIVE ACTIVITY WITH RESPECT TO THE ACTION OF TOXINS AND OF VIRUSES WITH AN INTRACELLULAR MODE OF ACTION
  申请人：Commissariat A L'Energie Atomique Et Aux Energies Alternatives

  公开号：US20160083355A1

  公开（公告）日：2016-03-24

  The subject matter of the present invention is novel families of compounds which are aromatic amine, imine, aminoadamantane and benzodiazepine derivatives, medicaments comprising same and the use thereof as inhibitors of the toxic effects of toxins with intracellular activity, such as, for example, ricin, and of viruses that use the internalization pathway for infecting cells.

  本发明的主题是新型化合物家族，其中包括芳香胺、亚胺、氨基金刚烷和苯二氮卓衍生物，包括相同的药物和将其用作抑制具有细胞内活性的毒素（例如蓖麻毒素）以及利用内化途径感染细胞的病毒的药物。
• BIARYL-SUBSTITUTED TETRAHYDRO-PYRAZOLO-PYRIDINE MODULATORS OF CATHEPSIN S
  申请人：Allen Darin

  公开号：US20080207683A1

  公开（公告）日：2008-08-28

  Biaryl-substituted tetrahydro-pyrazolo-pyridine compounds are described, which are useful as cathepsin S modulators. Such compounds may be used in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by cathepsin S activity, such as psoriasis, pain, multiple sclerosis, atherosclerosis, and rheumatoid arthritis.

  所述的双芳基取代的四氢吡唑吡啶化合物被描述为对半胱氨酸蛋白酶S的调节剂。这些化合物可用于制备药物组合物和治疗由半胱氨酸蛋白酶S活性介导的疾病状态、疾病和病况的方法，如银屑病、疼痛、多发性硬化、动脉粥样硬化和类风湿性关节炎。
• Synthesis and anticonvulsant activity of some N-(benzoyl)glycinanilide derivatives
  作者：Zeynep Soyer、Ozlem Akgul、Ayse H. Tarikogullari、Unsal Calis

  DOI：10.1007/s00044-013-0474-y

  日期：2013.10

  certain lipophilic glycine derivatives demonstrate anticonvulsant activity in animal epilepsy models. On the other hand, anilide is another fruitful structure for designing potential anticonvulsant agents. Ameltolide, ralitoline and some phthalimide derivatives are the examples of anilide analogs with potent anticonvulsant activity. In this study, two key structural pharmacophores were combined and a

  甘氨酸是主要的抑制性神经递质，最近的研究表明，某些亲脂性甘氨酸衍生物在动物癫痫模型中表现出抗惊厥活性。另一方面，苯胺是设计潜在的抗惊厥剂的另一种富有成果的结构。苯乙内酯，雷洛托林和一些邻苯二甲酰亚胺衍生物是具有有效抗惊厥活性的苯胺类似物的实例。在这项研究中，结合了两个关键的结构药效团和一系列N设计了-苯甲酰基甘氨酰苯胺衍生物。他们的抗惊厥活性针对最大电击（MES）和皮下注射的甲硝唑癫痫试验进行了评估，而其神经毒性通过旋转脚踏试验进行了检验。初步筛选结果表明，大多数化合物在MES测试中均有效。根据研究的剂量，根据旋转试验，没有一种化合物显示出神经毒性。该系列中最具活性的化合物是N-（2-（（（4-甲氧基苯基）氨基）-2-氧代乙基）苯甲酰胺（化合物8），其在N-苯基环上带有4-甲氧基取代基。