苄基1,3-噻唑-2-基氨基甲酸酯 | 353255-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苄基1,3-噻唑-2-基氨基甲酸酯
• 英文名称: thiazol-2-yl-carbamic acid benzyl ester
• 英文别名: N-benzyloxycarbonyl-2-aminothiazole；benzyl N-(1,3-thiazol-2-yl)carbamate
• CAS: 353255-50-2
• 化学式: C₁₁H₁₀N₂O₂S
• mdl: MFCD01832948
• 分子量: 234.279
• InChiKey: QKWLYHRESAIPGB-UHFFFAOYSA-N

物化性质

• 熔点：
  124 °C
• 密度：
  1.359±0.06 g/cm3(Predicted)
• 溶解度：
  12.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苄基1,3-噻唑-2-基氨基甲酸酯 、 1,2-二(溴甲基)苯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以65%的产率得到benzyl N-[[2-[[phenylmethoxycarbonyl(1,3-thiazol-2-yl)amino]methyl]phenyl]methyl]-N-(1,3-thiazol-2-yl)carbamate
  参考文献：
  名称：

  由 2-氨基嘧啶、2-氨基噻唑和 2-氨基噻唑啉与溴化苄和二溴代苯的反应合成（杂芳基）烷基胺

  摘要：

  摘要 描述了 2-氨基嘧啶、2-氨基噻唑、2-氨基噻唑啉及其 Cbz 保护衍生物的烷基化反应。与苄基溴反应生成带有 2-氨基嘧啶和 2-氨基噻唑的单烷基化产物，但 2-氨基噻唑啉生成二烷基化产物。由于与邻二溴化物形成分子内环化产物以及与间二溴化物和对二溴化物形成不溶产物的趋势，与二溴化苯的反应变得复杂。

  DOI：

  10.1080/00397910701771074
• 作为产物：
  描述：

  2-氨基噻唑 、 氯甲酸苄酯 在 β-环糊精 作用下， 以 水 为溶剂， 反应 0.03h， 以92%的产率得到苄基1,3-噻唑-2-基氨基甲酸酯
  参考文献：
  名称：

  在β-环糊精存在下，胺和氨基酸作为N-苄氧基羰基衍生物的水相单保护

  摘要：

  在水相中，在室温下以高收率催化量的β-环糊精可以简单，选择性地用Cbz-Cl保护胺/氨基酸。该反应进行而没有任何副产物的形成，并且与现有方法相比具有优势。

  DOI：

  10.1016/j.tetlet.2006.06.162

文献信息

• MACROCYCLIC ANTAGONISTS OF THE MOTILIN RECEPTOR FOR TREATMENT OF GASTROINTESTINAL DYSMOTILITY DISORDERS
  申请人：Marsault Eric

  公开号：US20100093720A1

  公开（公告）日：2010-04-15

  The present invention provides conformationally-defined macrocyclic compounds that bind to and/or are functional modulators of the motilin receptor including subtypes, isoforms and/or variants thereof. These macrocyclic compounds, at a minimum, possess adequate pharmacological properties to be useful as therapeutics for a range of disease indications. In particular, these compounds are useful for treatment and prevention of disorders characterized by hypermotilinemia and/or gastrointestinal hypermotility, including, but not limited to, diarrhea, cancer treatment-related diarrhea, cancer-induced diarrhea, chemotherapy-induced diarrhea, radiation enteritis, radiation-induced diarrhea, stress-induced diarrhea, chronic diarrhea, AIDS-related diarrhea, C. difficile associated diarrhea, traveller's diarrhea, diarrhea induced by graph versus host disease, other types of diarrhea, dyspepsia, irritable bowel syndrome, chemotherapy-induced nausea and vomiting (emesis) and post-operative nausea and vomiting and functional gastrointestinal disorders. In addition, the compounds possess utility for the treatment of diseases and disorders characterized by poor stomach or intestinal absorption, such as short bowel syndrome, celiac disease and cachexia. The compounds also have use for the treatment of inflammatory diseases and disorders of the gastrointestinal tract, such as inflammatory bowel disease, ulcerative colitis, Crohn's disease and pancreatitis. Accordingly, methods of treating such disorders and pharmaceutical compositions including compounds of the present invention are also provided.

  本发明提供了与胃动素受体及其亚型、异构体和/或变体结合和/或是功能调节剂的构象定义明确的大环化合物。这些大环化合物至少具有足够的药理特性，可用作治疗一系列疾病指示的治疗药物。特别是，这些化合物对于治疗和预防以高胃动素血症和/或胃肠道高蠕动性为特征的疾病非常有用，包括但不限于腹泻、癌症治疗相关腹泻、癌症诱导腹泻、化疗诱导腹泻、放射性肠炎、放射性腹泻、压力诱导腹泻、慢性腹泻、艾滋病相关腹泻、C. difficile相关腹泻、旅行者腹泻、移植物宿主病引起的腹泻、其他类型的腹泻、消化不良、肠易激综合征、化疗诱导的恶心和呕吐（呕吐）以及术后恶心和呕吐和功能性胃肠道疾病。此外，这些化合物对于治疗以胃或肠道吸收不良为特征的疾病和疾病也具有用途，例如短肠综合征、乳糜泻和虚弱。这些化合物还可用于治疗胃肠道炎症性疾病和疾病，如炎症性肠病、溃疡性结肠炎、克罗恩病和胰腺炎。因此，本发明还提供了治疗此类疾病的方法和包括本发明化合物的药物组合物。
• A mild and efficient chemoselective <i>N</i>-benzyloxycarbonylation of amines using TBAB as a catalyst under solvent-free conditions
  作者：Kothamasu Suresh Babu、Vidadala Rama Subba Rao、Ravu Ranga Rao、Sakhamuri Sivaram Babu、Janaswami Madhusudana Rao

  DOI：10.1139/v08-169

  日期：2009.2

  We describe a mild and efficient method for the chemoselective N-benzyloxycarbonylation of amines by treatment of amines and aminoesters with benzyloxycarbonyl chloride (Cbz-Cl) in the presence of TBAB under solvent-free conditions in excellent yields. The method is general for the preparation of a wide variety of N-Cbz derivatives of aliphatic, aromatic amines, and aminoesters.

  我们介绍了一种温和、高效的胺化学选择性 N-苄氧羰基化方法，该方法是在无溶剂条件下，在 TBAB 存在下，用苄氧羰酰氯（Cbz-Cl）处理胺和氨基酯，收率极高。该方法适用于制备脂肪族胺、芳香族胺和氨基酯的各种 N-Cbz 衍生物。
• The Synthesis of Functionalized 3-Aryl- and 3-Heteroaryloxazolidin-2-ones and Tetrahydro-3-aryl-1,3-oxazin-2-ones via the Iodocyclocarbamation Reaction: Access to Privileged Chemical Structures and Scope and Limitations of the Method
  作者：Abbegail C. Bell、Alex B. Boomsma、Niecia E. Flikweert、Robert M. Hohlman、Shiyuan Zhang、Ronald L. Blankespoor、Shannon M. Biros、Richard J. Staples、Steven J. Brickner、Michael R. Barbachyn

  DOI：10.1021/acs.joc.9b03400

  日期：2020.5.15

  antibacterial agent. Herein, we report the results of our systematic investigation into the scope and limitations of this process and have identified some distinguishing characteristics within the aryl/heteroaryl series. We also describe the first preparation of 3-aryloxazolidin-2-ones bearing new functionalized C-5 substituents derived from conjugated 1,3-dienyl and cumulated 1,2-dienyl carbamate precursors

  3-芳基和3-杂芳基恶唑烷-2-酮由于其附加取代基的细微变化后表现出的多种药理活性，因此变得越来越重要，应被视为特权化学结构。碘代环氨基甲酸酯化反应已被广泛用于制备许多3-烷基-5-（卤代甲基）恶唑烷丁-2-酮，但是相应的芳族同类物尚未得到充分开发。我们建议外消旋的3-芳基和3-杂芳基-5-（碘甲基）恶唑烷-2-酮很容易通过N-烯丙基化的N-芳基或N-杂芳基氨基甲酸酯的碘代氨基甲酸酯化反应制备，可能是快速合成中间体。制备具有生物活性的潜在铅化合物。我们通过使用这种方法制备消旋利奈唑胺（一种抗菌剂）来说明这一点。在这里 我们报告了我们对该过程的范围和局限性进行系统研究的结果，并确定了芳基/杂芳基系列中的一些区别特征。我们还描述了第一种制备带有新的功能化C-5取代基的3-芳基恶唑烷-2-酮的方法，该取代基衍生自共轭的1,3-二烯基和累积的1,2-二烯基氨基甲酸酯前体。最后，我们描述了碘代氨基甲
• Macrocyclic antagonists of the motilin receptor for treatment of gastrointestinal dysmotility disorders
  申请人：Marsault Eric

  公开号：US09133235B2

  公开（公告）日：2015-09-15

  The present invention provides conformationally-defined macrocyclic compounds that bind to and/or are functional modulators of the motilin receptor including subtypes, isoforms and/or variants thereof. These macrocyclic compounds, at a minimum, possess adequate pharmacological properties to be useful as therapeutics for a range of disease indications. In particular, these compounds are useful for treatment and prevention of disorders characterized by hypermotilinemia and/or gastrointestinal hypermotility, including, but not limited to, diarrhea, cancer treatment-related diarrhea, cancer-induced diarrhea, chemotherapy-induced diarrhea, radiation enteritis, radiation-induced diarrhea, stress-induced diarrhea, chronic diarrhea, AIDS-related diarrhea, C. difficile associated diarrhea, traveller's diarrhea, diarrhea induced by graph versus host disease, other types of diarrhea, dyspepsia, irritable bowel syndrome, chemotherapy-induced nausea and vomiting (emesis) and post-operative nausea and vomiting and functional gastrointestinal disorders. In addition, the compounds possess utility for the treatment of diseases and disorders characterized by poor stomach or intestinal absorption, such as short bowel syndrome, celiac disease and cachexia. The compounds also have use for the treatment of inflammatory diseases and disorders of the gastrointestinal tract, such as inflammatory bowel disease, ulcerative colitis, Crohn's disease and pancreatitis. Accordingly, methods of treating such disorders and pharmaceutical compositions including compounds of the present invention are also provided.

  本发明提供了构象定义的大环化合物，它们结合并/或是运动素受体的功能调节剂，其中包括其亚型、同工型和/或变异体。这些大环化合物至少具有足够的药理学特性，可用于治疗一系列疾病指标。特别是，这些化合物对于治疗和预防以高动素血症和/或胃肠道高动力为特征的疾病，包括但不限于腹泻、癌症相关腹泻、化疗引起的腹泻、放射性肠炎、辐射性腹泻、压力性腹泻、慢性腹泻、艾滋病相关腹泻、C. difficile相关腹泻、旅行者腹泻、由移植物抗宿主病引起的腹泻、其他类型的腹泻、消化不良、肠易激综合症、化疗引起的恶心和呕吐（呕吐）以及术后恶心和呕吐和功能性胃肠疾病非常有用。此外，这些化合物还具有治疗胃或肠道吸收不良的疾病和疾病的作用，例如短肠综合症、乳糜泻和消耗症。这些化合物还可用于治疗胃肠道的炎症性疾病和疾病，例如炎症性肠病、溃疡性结肠炎、克罗恩病和胰腺炎。因此，本发明还提供了治疗这些疾病的方法和包含本发明化合物的制药组合物。
• Macrocyclic antagonist of the motilin receptor for treatment of gastrointestinal dysmotility disorders
  申请人：Tranzyme Pharma, Inc.

  公开号：EP2431380A2

  公开（公告）日：2012-03-21

  The present invention provides conformationally-defined macrocyclic compounds that bind to and/or are functional modulators of the motilin receptor including subtypes, isoforms and/or variants thereof. These macrocyclic compounds, at a minimum, possess adequate pharmacological properties to be useful as therapeutics for a range of disease indications. In particular, these compounds are useful for treatment and prevention of disorders characterized by hypermotilinemia and/or gastrointestinal hypermotility, including, but not limited to, diarrhea, cancer treatment-related diarrhea, cancer-induced diarrhea, chemotherapy-induced diarrhea, radiation enteritis, radiation-induced diarrhea, stress-induced diarrhea, chronic diarrhea, AIDS-related diarrhea, C. difficile associated diarrhea, traveller's diarrhea, diarrhea induced by graph versus host disease, other types of diarrhea, dyspepsia, irritable bowel syndrome, chemotherapy-induced nausea and vomiting (emesis) and post-operative nausea and vomiting and functional gastrointestinal disorders. In addition, the compounds possess utility for the treatment of diseases and disorders characterized by poor stomach or intestinal absorption, such as short bowel syndrome, celiac disease and cachexia. The compounds also have use for the treatment of inflammatory diseases and disorders of the gastrointestinal tract, such as inflammatory bowel disease, ulcerative colitis, Crohn's disease and pancreatitis. Accordingly, methods of treating such disorders and pharmaceutical compositions including compounds of the present invention are also provided.

  本发明提供了与动情素受体（包括其亚型、同工型和/或变体）结合和/或作为其功能调节剂的构象明确的大环化合物。这些大环化合物至少具有足够的药理特性，可作为一系列疾病适应症的治疗药物。特别是，这些化合物可用于治疗和预防以高胰岛素血症和/或胃肠道高运动性为特征的疾病，包括但不限于腹泻、癌症治疗相关性腹泻、癌症诱导性腹泻、化疗诱导性腹泻、放射性肠炎、放射性诱导性腹泻、压力诱导性腹泻、慢性腹泻、艾滋病相关性腹泻、艰难梭菌相关性腹泻、C.腹泻、艰难梭菌相关性腹泻、旅行者腹泻、图形对宿主疾病诱发的腹泻、其他类型的腹泻、消化不良、肠易激综合征、化疗诱发的恶心和呕吐（呃逆）、术后恶心和呕吐以及功能性胃肠功能紊乱。此外，这些化合物还可用于治疗以胃或肠吸收不良为特征的疾病和失调，如短肠综合征、乳糜泻和恶病质。这些化合物还可用于治疗胃肠道炎症性疾病和紊乱，如炎症性肠病、溃疡性结肠炎、克罗恩病和胰腺炎。因此，还提供了治疗此类疾病的方法和包括本发明化合物的药物组合物。