Tert-butyl N-[1-(phenylcarbamoyl)ethyl]carbamate | 126787-11-9

• 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 N-[1-(phenylcarbamoyl)ethyl]carbamate
• 英文别名: N-Phenyl 2-(BOC-amino)propanamide；tert-butyl N-(1-anilino-1-oxopropan-2-yl)carbamate
• CAS: 126787-11-9
• 化学式: C₁₄H₂₀N₂O₃
• 分子量: 264.324
• InChiKey: OUOCJOYAOSCKKP-UHFFFAOYSA-N

物化性质

• 沸点：
  450.3±28.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Tert-butyl N-[1-(phenylcarbamoyl)ethyl]carbamate 在 盐酸 、 三乙胺 、 异丙醇 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 2-((1-(2-chlorophenyl)-4-hydroxy-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-N-phenylpropanamide
  参考文献：
  名称：

  Structure-Based Discovery of Highly Selective Phosphodiesterase-9A Inhibitors and Implications for Inhibitor Design

  摘要：

  A new series of phosphodiesterase-9 (PDE9) inhibitors that contain a scaffold of 6-amino-pyrazolopyrimidinone have been discovered by a combination of structure-based design and computational docking. This procedure significantly saved the load of chemical synthesis and is an effective method for the discovery of inhibitors. The best compound 28 has an IC50 of 21 nM and 3.3 mu M, respectively, for PDE9 and PDE5 and about 3 orders of magnitude of selectivity against other PDE families. The crystal structure of the PDE9 catalytic domain in complex with 28 has been determined and shows a hydrogen bond between 28 and Tyr424. This hydrogen bond may account for the 860-fold selectivity of 28 against PDE1B, in comparison with about 30-fold selectivity of BAY73-6691. Thus, our studies suggest that Tyr424, a unique residue of PDE8 and PDE9, is a potential target for improvement of selectivity of PDE9 inhibitors.

  DOI：

  10.1021/jm301189c
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 0.17h， 生成 Tert-butyl N-[1-(phenylcarbamoyl)ethyl]carbamate
  参考文献：
  名称：

  氨基酸衍生物与未活化烯烃的对映选择性脱氨烷基化

  摘要：

  在此，我们报道了第一个镍催化的氨基酸和肽衍生物与未活化烯烃的对映选择性脱氨烷基化反应。成功的关键是发现了一种新的空间阻碍双（恶唑啉）配体主链，从而提供了一种通过sp 3 C-N 功能化获得对映体富集的sp 3 – sp 3连接的从头技术。我们的协议以其广泛的范围和广泛的通用性而著称，即使在后期功能化的背景下也是如此。此外，未活化内烯烃的对映选择性脱氨远程加氢烷基化反应也已触手可及，从而为在远程sp 3 C-H位点上形成对映体富集的sp 3 – sp 3中心提供了有用的切入点。

  DOI：

  10.1021/jacs.1c12350

文献信息

• New sulphonamide pyrolidine carboxamide derivatives: Synthesis, molecular docking, antiplasmodial and antioxidant activities
  作者：Efeturi A. Onoabedje、Akachukwu Ibezim、Uchechukwu C. Okoro、Sanjay Batra

  DOI：10.1371/journal.pone.0243305

  日期：——

  Here we report the synthesis of thirty-two new drug-like sulphonamide pyrolidine carboxamide derivatives and their antiplasmodial and antioxidant capabilities. In addition, molecular docking was used to check their binding affinities for homology modelled P. falciparum N-myristoyltransferase, a confirmed drug target in the pathogen. Results revealed that sixteen new derivatives killed the parasite

  带有磺酰胺功能的羧酰胺已显示出对人类疟疾的病原体恶性疟原虫具有显着的致死作用。在这里，我们报告了三十二种新的药物样磺酰胺吡咯烷羧酰胺衍生物的合成及其抗血浆和抗氧化能力。此外，分子对接用于检查它们与恶性疟原虫N-肉豆蔻酰基转移酶（病原体中已确认的药物靶标）同源性的结合亲和力。结果显示，有16种新衍生物以单位微摩尔浓度（IC50 = 2.40-8.30μM）杀死了该寄生虫，化合物10b，10c，10d，10j和10o在IC50处清除了DPPH自由基（6.48、8.49、3.02、6.44和4.32μg） / mL）与抗坏血酸的1.06μg/ mL相当。与理论配体吡唑-磺酰胺（Ki = 0.01μM）相比，化合物10o以与理论配体抑制常数（Ki = 0.09μM）结合PfNMT的活性最高。这项研究确定了化合物10o（通常是该系列化合物）是具有抗氧化活性的潜在抗疟疾候选药物，需要进一步关注以优化其活性。
• Visible Light Induced Copper‐Catalyzed Enantioselective Deaminative Arylation of Amino Acid Derivatives Assisted by Phenol
  作者：Yue Jia、Zhihan Zhang、Guo‐Ming Yu、Xuan Jiang、Liang‐Qiu Lu、Wen‐Jing Xiao

  DOI：10.1002/anie.202312102

  日期：2023.12.18

  A visible light induced enantioselective deaminative arylation of amino acid derivatives by bifunctional copper catalysis is disclosed. A variety of α-aryl-N-phenylamides are prepared with good efficiency and high enantioselectivity. A possible reaction mechanism and an asymmetric induction mode have been proposed based on experimental and computational evidence.

  公开了通过双功能铜催化的可见光诱导的氨基酸衍生物的对映选择性脱氨芳基化。多种α-芳基-N-苯基酰胺的制备具有良好的效率和高对映选择性。基于实验和计算证据，提出了一种可能的反应机制和不对称诱导模式。
• [EN] ARYLAMIDE DERIVATIVES USEFUL IN THE TREATMENT OF DISEASES ASSOCIATED WITH SERCA ACTIVITY<br/>[FR] PROCÉDÉS DE TRAITEMENT DE MALADIES ASSOCIÉES À LA MODULATION DE SERCA
  申请人：CELLADON CORP

  公开号：WO2010088450A3

  公开（公告）日：2010-12-23
• Discovery of KOH/BrCH ₂ SO ₂ F as Water‐Removable System for Clean, Mild and Robust Synthesis of Amides and Peptides
  作者：Qi‐Xin Wu、Tao Shu、Wan‐Yin Fang、Hua‐Li Qin

  DOI：10.1002/ejoc.202200719

  日期：2022.7.21

  AbstractHerein we described an efficient, practical, and robust protocol for amides and peptides synthesis from carboxylic acids and amines using the combination of bromomethanesulfonyl fluoride (BMSF) with inorganic base KOH as a water‐removable system. This method is featured with broad substrate scope, excellent functional group compatibility, high yields, operational simplicity, and easy purification, which will exert great potential in amide and peptide synthesis.
• New sulphonamide-peptide hybrid molecules as potential PBP 2a ligands and methicillin resistant <i>Staphylococcus aureus</i> actives
  作者：Akachukwu Ibezim、Raphael Onuku、Chidalu Ottih、Ifeoma Ezeonu、Efeturi Onoabedje、Karuppasamy Ramanathan、Ngozi Nwodo

  DOI：10.1080/07391102.2022.2111359

  日期：——