4-(4-tert-butoxycarbonylaminopiperidine-1-sulfonyl)benzoic acid | 1251465-28-7

• 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-(4-tert-butoxycarbonylaminopiperidine-1-sulfonyl)benzoic acid
• 英文别名: 4-((4-((tert-butoxycarbonyl)amino)piperidin-1-yl)sulfonyl)benzoic acid；4-(4-tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-benzoic acid；4-[4-[(2-methylpropan-2-yl)oxycarbonylamino]piperidin-1-yl]sulfonylbenzoic acid
• CAS: 1251465-28-7
• 化学式: C₁₇H₂₄N₂O₆S
• 分子量: 384.453
• InChiKey: ONRPEZKMFSNBHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(4-tert-butoxycarbonylaminopiperidine-1-sulfonyl)benzoic acid 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 27.17h， 生成
  参考文献：
  名称：

  Irreversible 4-Aminopiperidine Transglutaminase 2 Inhibitors for Huntington's Disease

  摘要：

  A new series of potent TG2 inhibitors are reported that employ a 4-aminopiperidine core bearing an acrylamide warhead. We establish the structure activity relationship of this new series and report on the transglutaminase selectivity and in vitro ADME properties of selected compounds. We demonstrate that the compounds do not conjugate glutathione in an in vitro setting and have superior plasma stability over our previous series.

  DOI：

  10.1021/ml3001352
• 作为产物：
  描述：

  4-(氯磺酰)苯甲酸 、 4-叔丁氧羰基氨基哌啶 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 36.0h， 以70%的产率得到4-(4-tert-butoxycarbonylaminopiperidine-1-sulfonyl)benzoic acid
  参考文献：
  名称：

  腺苷 A2B 受体的不可逆拮抗剂

  摘要：

  腺苷 A 2B受体 (A 2B AR) 的阻断代表了一种潜在的癌症免疫治疗新策略。在本研究中，我们设计、合成并表征了基于 8-对磺基苯基黄嘌呤支架的不可逆 A 2B AR 拮抗剂。通过进行配体洗脱和动力学实验，在基于放射性配体结合和生物发光共振能量转移 (BRET) 的 Gα 15蛋白激活测定中证实了不可逆结合。p -(1-Propylxanthin-8-yl)benzene sulfonyl fluoride ( 6a , PSB-21500) 是本系列中最有效和选择性不可逆的 A 2B AR 拮抗剂，具有明显的 K人类 A 2B AR 的i值为 10.6 nM ，与其他 AR 亚型相比，选择性 > 38 倍。相应的 3-环丙基取代的黄嘌呤衍生物6c (PSB-21502) 具有类似的效力，但与 A 1 - 和 A 2A AR相比没有选择性。反应性磺酰氟基团与延长的黄嘌呤 8-取代基 (

  DOI：

  10.3390/molecules27123792

文献信息

• TRANSGLUTAMINASE TG2 INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF
  申请人：Prime Michael

  公开号：US20120302539A1

  公开（公告）日：2012-11-29

  Certain compounds and pharmaceutically acceptable salts are provided herein. Also provided are pharmaceutical compositions comprising at least one compound or pharmaceutically acceptable salt therein and one or more pharmaceutically acceptable vehicle. Methods of treating patients suffering from certain disease states responsive to the inhibition of transglutaminase TG2 activity are described. These disease states include neurodegenerative disorders such as Huntington's disease. Also described are methods of treatment include administering at least one compound or pharmaceutically acceptable salt thereof as a single active agent or administering at least one compound or pharmaceutically acceptable salt thereof in combination with one or more other therapeutic agents.

  本文提供了某些化合物和药用盐。还提供了包含至少一种化合物或药用盐以及一个或多个药用载体的药物组合物。描述了治疗对转谷氨酰胺酶TG2活性抑制敏感的某些疾病状态的方法。这些疾病状态包括亚型汉廷顿病等神经退行性疾病。还描述了治疗方法，包括单独使用至少一种化合物或药用盐作为单一活性剂或与一个或多个其他治疗剂结合使用至少一种化合物或药用盐。
• Transglutaminase TG2 inhibitors, pharmaceutical compositions, and methods of use thereof
  申请人：Prime Michael

  公开号：US08889716B2

  公开（公告）日：2014-11-18

  Certain compounds and pharmaceutically acceptable salts are provided herein. Also provided are pharmaceutical compositions comprising at least one compound or pharmaceutically acceptable salt therein and one or more pharmaceutically acceptable vehicle. Methods of treating patients suffering from certain disease states responsive to the inhibition of transglutaminase TG2 activity are described. These disease states include neurodegenerative disorders such as Huntington's disease. Also described are methods of treatment include administering at least one compound or pharmaceutically acceptable salt thereof as a single active agent or administering at least one compound or pharmaceutically acceptable salt thereof in combination with one or more other therapeutic agents.

  本文提供了某些化合物和药用可接受盐。还提供了制药组合物，其中包括至少一种化合物或药用可接受盐以及一个或多个药用可接受载体。描述了治疗对转谷氨酰胺酶TG2活性抑制有反应的某些疾病状态的方法。这些疾病状态包括神经退行性疾病，如亨廷顿病。还描述了治疗方法，包括单独使用至少一种化合物或药用可接受盐作为活性剂，或与一个或多个其他治疗剂联合使用至少一种化合物或药用可接受盐。
• [EN] ANTIVIRAL PYRIMIDINES<br/>[FR] PYRIMIDINES ANTIVIRALES
  申请人：PROGENICS PHARM INC

  公开号：WO2010118367A3

  公开（公告）日：2011-03-10
• US8889716B2
  申请人：——

  公开号：US8889716B2

  公开（公告）日：2014-11-18
• Irreversible 4-Aminopiperidine Transglutaminase 2 Inhibitors for Huntington's Disease
  作者：Michael E. Prime、Frederick A. Brookfield、Stephen M. Courtney、Simon Gaines、Richard W. Marston、Osamu Ichihara、Marie Li、Darshan Vaidya、Helen Williams、Anna Pedret-Dunn、Laura Reed、Sabine Schaertl、Leticia Toledo-Sherman、Maria Beconi、Douglas Macdonald、Ignacio Muñoz-Sanjuan、Celia Dominguez、John Wityak

  DOI：10.1021/ml3001352

  日期：2012.9.13

  A new series of potent TG2 inhibitors are reported that employ a 4-aminopiperidine core bearing an acrylamide warhead. We establish the structure activity relationship of this new series and report on the transglutaminase selectivity and in vitro ADME properties of selected compounds. We demonstrate that the compounds do not conjugate glutathione in an in vitro setting and have superior plasma stability over our previous series.