tert-butyl {2-[(methylsulfonyl)amino]benzyl}carbamate | 1227486-33-0

• 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: tert-butyl {2-[(methylsulfonyl)amino]benzyl}carbamate
• 英文别名: Tert-butyl{2-[(methylsulfonyl)amino]benzyl}carbamate；tert-butyl N-[[2-(methanesulfonamido)phenyl]methyl]carbamate
• CAS: 1227486-33-0
• 化学式: C₁₃H₂₀N₂O₄S
• 分子量: 300.379
• InChiKey: KMFNGCKFDKKUOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl {2-[(methylsulfonyl)amino]benzyl}carbamate 在 potassium carbonate 、 二异丙胺 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Selectivity switch between FAK and Pyk2: Macrocyclization of FAK inhibitors improves Pyk2 potency

  摘要：

  Herein, we describe the synthesis of Pyk2 inhibitors via macrocyclization of FAR and dual Pyk2-FAK inhibitors. We identified macrocycle 25a as a highly potent Pyk2 inhibitor (IC50 = 0.7 nM), with similar to 175-fold improvement in Pyk2 potency as compared to its acyclic counterpart. In many cases, macrocyclization improved Pyk2 potency while weakening FAK potency, thereby improving the Pyk2/FAIC selectivity ratio for this structural class of inhibitors. Various macrocyclic linkers were studied in an attempt to optimize Pyk2 selectivity. We observed macrocyclic atropisomerism during the synthesis of 19-membered macro cycles 10a-d, and successfully obtained crystallographic evidence of one atropisomer (10a-AtropB) preferentially bound to Pyk2. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.10.092
• 作为产物：
  描述：

  甲基磺酰氯 、 (2-氨基苄基)-氨基甲酸叔丁酯 在 吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 tert-butyl {2-[(methylsulfonyl)amino]benzyl}carbamate
  参考文献：
  名称：

  EP2361902

  摘要：

  公开号：

文献信息

• 4,6-DIAMINONICOTINAMIDE COMPOUND
  申请人：Shirakami Shohei

  公开号：US20110230467A1

  公开（公告）日：2011-09-22

  [Problem] The present invention provides a 4,6-diaminonicotinamide compound which is useful as an active ingredient of a pharmaceutical composition, in particular, a pharmaceutical composition for treating diseases caused by undesirable and/or abnormal cytokine signal transduction. [Means for Solution] The present inventors have extensively studied compounds having a JAK3 inhibitory action, and as a result, they have found that a 4,6-diaminonicotinamide compound which is the compound of the present invention has an excellent JAK3 inhibitory action and is useful as an agent for preventing or treating diseases caused by undesirable and/or abnormal cytokine signal transduction, thereby completing the present invention.

  [问题] 本发明提供了一种4,6-二氨基烟酰胺化合物，该化合物可用作制药组合物的活性成分，特别是用于治疗由不良和/或异常的细胞因子信号传导引起的疾病的制药组合物。 [解决方法] 本发明人广泛研究了具有JAK3抑制作用的化合物，结果发现本发明的4,6-二氨基烟酰胺化合物具有出色的JAK3抑制作用，并且可用作预防或治疗由不良和/或异常的细胞因子信号传导引起的疾病的药剂，从而完成了本发明。
• [EN] 4,6-DIAMINONICOTINAMIDE COMPOUND<br/>[FR] 4,6-DIAMINONICOTINAMIDE
  申请人：ASTELLAS PHARMA INC

  公开号：WO2010058846A1

  公开（公告）日：2010-05-27

  【課題】 　本発明は医薬組成物、殊に、望ましくないおよび／または異常なサイトカインシグナル伝達により引き起こされる疾患の治療用医薬組成物の有効成分として有用な４，６-ジアミノニコチンアミド化合物を提供する。 【課題を解決するための手段】 　本発明者らは、JAK3阻害作用を有する化合物について鋭意検討した結果、本発明化合物である４，６-ジアミノニコチンアミド化合物が優れたJAK3阻害作用を有し、望ましくないおよび／または異常なサイトカインシグナル伝達異常により引き起こされる疾患の予防あるいは治療剤として有用であることを見出して本発明を完成した。
• EP2361902
  申请人：——

  公开号：——

  公开（公告）日：——
• Selectivity switch between FAK and Pyk2: Macrocyclization of FAK inhibitors improves Pyk2 potency
  作者：Julie Farand、Nicholas Mai、Jayaraman Chandrasekhar、Zachary E. Newby、Josh Van Veldhuizen、Jennifer Loyer-Drew、Chandrasekar Venkataramani、Juan Guerrero、Amy Kwok、Ning Li、Yelena Zherebina、Sibylle Wilbert、Jeff Zablocki、Gary Phillips、William J. Watkins、Robert Mourey、Gregory T. Notte

  DOI：10.1016/j.bmcl.2016.10.092

  日期：2016.12

  Herein, we describe the synthesis of Pyk2 inhibitors via macrocyclization of FAR and dual Pyk2-FAK inhibitors. We identified macrocycle 25a as a highly potent Pyk2 inhibitor (IC50 = 0.7 nM), with similar to 175-fold improvement in Pyk2 potency as compared to its acyclic counterpart. In many cases, macrocyclization improved Pyk2 potency while weakening FAK potency, thereby improving the Pyk2/FAIC selectivity ratio for this structural class of inhibitors. Various macrocyclic linkers were studied in an attempt to optimize Pyk2 selectivity. We observed macrocyclic atropisomerism during the synthesis of 19-membered macro cycles 10a-d, and successfully obtained crystallographic evidence of one atropisomer (10a-AtropB) preferentially bound to Pyk2. (C) 2016 Elsevier Ltd. All rights reserved.