4-carbamoylbenzoic acid tert-butyl ester | 1307310-12-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-carbamoylbenzoic acid tert-butyl ester
• 英文别名: Tert-butyl 4-carbamoylbenzoate
• CAS: 1307310-12-8
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: CYQFJLUPQMMIEN-UHFFFAOYSA-N

物化性质

• 沸点：
  360.7±25.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-carbamoylbenzoic acid tert-butyl ester 在 劳森试剂 、 potassium hydrogencarbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.5h， 生成
  参考文献：
  名称：

  Development of Amidine-Based Sphingosine Kinase 1 Nanomolar Inhibitors and Reduction of Sphingosine 1-Phosphate in Human Leukemia Cells

  摘要：

  Sphingosine 1-phosphate (S1P) is a bioactive lipid that has been identified as an accelerant of cancer progression. The sphingosine kinases (SphKs) are the sole producers of S1P, and thus, SphK inhibitors may prove effective in cancer mitigation and chemosensitization. Of the two SphKs, SphK1 overexpression has been observed in a myriad of cancer cell lines and tissues and has been recognized as the presumptive target over that of the poorly characterized SphK2. Herein, we present the design and synthesis of amidine-based nanomolar SphK1 subtype-selective inhibitors. A homology model of SphK1, trained with this library of amidine inhibitors, was then used to predict the activity of additional, more potent, inhibitors. Lastly, select amidine inhibitors were validated in human leukemia U937 cells, where they significantly reduced endogenous S1P levels at nanomolar concentrations.

  DOI：

  10.1021/jm2001053
• 作为产物：
  描述：

  4-(叔丁氧羰基)苯甲 酸 在 三乙胺 、 氯甲酸异丁酯 、 氨 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 7.0h， 以66%的产率得到4-carbamoylbenzoic acid tert-butyl ester
  参考文献：
  名称：

  Development of Amidine-Based Sphingosine Kinase 1 Nanomolar Inhibitors and Reduction of Sphingosine 1-Phosphate in Human Leukemia Cells

  摘要：

  Sphingosine 1-phosphate (S1P) is a bioactive lipid that has been identified as an accelerant of cancer progression. The sphingosine kinases (SphKs) are the sole producers of S1P, and thus, SphK inhibitors may prove effective in cancer mitigation and chemosensitization. Of the two SphKs, SphK1 overexpression has been observed in a myriad of cancer cell lines and tissues and has been recognized as the presumptive target over that of the poorly characterized SphK2. Herein, we present the design and synthesis of amidine-based nanomolar SphK1 subtype-selective inhibitors. A homology model of SphK1, trained with this library of amidine inhibitors, was then used to predict the activity of additional, more potent, inhibitors. Lastly, select amidine inhibitors were validated in human leukemia U937 cells, where they significantly reduced endogenous S1P levels at nanomolar concentrations.

  DOI：

  10.1021/jm2001053

文献信息

• Hydration of nitriles using a metal–ligand cooperative ruthenium pincer catalyst
  作者：Beibei Guo、Johannes G. de Vries、Edwin Otten

  DOI：10.1039/c9sc04624k

  日期：——

  Nitrile hydration provides access to amides that are important structural elements in organic chemistry. Here we report catalytic nitrile hydration using ruthenium catalysts based on a pincer scaffold with a dearomatized pyridine backbone. These complexes catalyze the nucleophilic addition of H2O to a wide variety of aliphatic and (hetero)aromatic nitriles in tBuOH as solvent. Reactions occur under

  腈水合提供了获得酰胺的途径，酰胺是有机化学中重要的结构元素。在这里，我们报告了使用基于具有脱芳构化吡啶骨架的钳形支架的钌催化剂催化腈水合。这些配合物在作为溶剂的t BuOH 中催化 H 2 O 与多种脂肪族和（杂）芳香族腈的亲核加成。反应在没有添加剂的温和条件（室温）下发生。提出了一种腈水合机制，该机制由腈的金属-配体协同结合引发。
• Mechanistic Studies of Palladium-Catalyzed Aminocarbonylation of Aryl Chlorides with Carbon Monoxide and Ammonia
  作者：Justin Y. Wang、Alexandra E. Strom、John F. Hartwig

  DOI：10.1021/jacs.8b04073

  日期：2018.6.27

  synthesized, and kinetic measurements of the formation and reactions of these intermediates were undertaken to determine the mechanism of the oxidative addition of aryl bromides and chlorides to a Pd(0) dicarbonyl compound in the presence of CO and the mechanism of the reaction of ammonia with a Pd(II) phenacyl complex to form benzamide. The oxidative addition of aryl chlorides and aryl bromides was determined

  报道了可靠的、钯催化的芳基氯化物与氨的氨基羰基化的机理信息。该反应以乙烯络合物 1 作为催化剂发生，通过分离催化中间体和动力学测量获得了机理信息，包括在 CO 存在下将芳基氯氧化加成钯 (0) 络合物的第一个机理数据。合成和苯酰基卤化钯中间体，并对这些中间体的形成和反应进行动力学测量，以确定在 CO 存在下芳基溴化物和氯化物与 Pd(0) 二羰基化合物的氧化加成机理和氨与 Pd(II) 苯甲酰络合物反应形成苯甲酰胺。芳基氯化物和芳基溴化物的氧化加成被确定发生在卤代芳烃与带有二齿膦和一个 CO 配体的三配位 Pd(0) 物质的限速反应中。初级 13C 动力学同位素效应表明该步骤涉及碳-卤素键的断裂。我们的数据表明，苯酰卤化钯络合物与氨反应形成苯甲酰胺的途径包括用氨将氯化物从苯酰钯氯化物络合物中可逆置换，结合的氨去质子化形成苯酰钯酰氨基络合物，然后还原消除到形成CN键。与该机制一致，芳基钯酰胺络合物与
• NOVEL CYCLOSPORIN DERIVATIVES AND USES THEREOF
  申请人：S&T Global Inc.

  公开号：US20190151403A1

  公开（公告）日：2019-05-23

  A compound of the Formula (I) is disclosed: (I) or pharmaceutically acceptable salt thereof, wherein the symbols are as defined in the specification. Also described are a pharmaceutical composition comprising the same and a method for treating or preventing viral infections, inflammation, dry eye, central nervous disorders, cardiovascular diseases, cancer, obesity, diabetes, muscular dystrophy, lung, and liver, and kindey diseases, and hair loss using the same.
• Development of Amidine-Based Sphingosine Kinase 1 Nanomolar Inhibitors and Reduction of Sphingosine 1-Phosphate in Human Leukemia Cells
  作者：Andrew J. Kennedy、Thomas P. Mathews、Yugesh Kharel、Saundra D. Field、Morgan L. Moyer、James E. East、Joseph D. Houck、Kevin R. Lynch、Timothy L. Macdonald

  DOI：10.1021/jm2001053

  日期：2011.5.26

  Sphingosine 1-phosphate (S1P) is a bioactive lipid that has been identified as an accelerant of cancer progression. The sphingosine kinases (SphKs) are the sole producers of S1P, and thus, SphK inhibitors may prove effective in cancer mitigation and chemosensitization. Of the two SphKs, SphK1 overexpression has been observed in a myriad of cancer cell lines and tissues and has been recognized as the presumptive target over that of the poorly characterized SphK2. Herein, we present the design and synthesis of amidine-based nanomolar SphK1 subtype-selective inhibitors. A homology model of SphK1, trained with this library of amidine inhibitors, was then used to predict the activity of additional, more potent, inhibitors. Lastly, select amidine inhibitors were validated in human leukemia U937 cells, where they significantly reduced endogenous S1P levels at nanomolar concentrations.