5-Aminocarbonylpyridine-2-boronic acid | 1164100-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-Aminocarbonylpyridine-2-boronic acid
• 英文别名: (5-carbamoylpyridin-2-yl)boronic acid
• CAS: 1164100-83-7
• 化学式: C₆H₇BN₂O₃
• 分子量: 165.944
• InChiKey: AGBSBEROHUIBPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.14
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one 、 5-Aminocarbonylpyridine-2-boronic acid 在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成 6-(4-((S)-1-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)nicotinamide
  参考文献：
  名称：

  Discovery of BI 135585, an in vivo efficacious oxazinanone-based 11β hydroxysteroid dehydrogenase type 1 inhibitor

  摘要：

  A potent, in vivo efficacious 11 beta hydroxysteroid dehydrogenase type 1 (11 beta HSD1) inhibitor (11j) has been identified. Compound 11j inhibited 11 beta HSD1 activity in human adipocytes with an IC50 of 4.3 nM and in primary human adipose tissue with an IC80 of 53 nM. Oral administration of 11j to cynomolgus monkey inhibited 11 beta HSD1 activity in adipose tissue. Compound 11j exhibited >1000x selectivity over other hydroxysteroid dehydrogenases, displays desirable pharmacodynamic properties and entered human clinical trials in 2011. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.04.033

文献信息

• Identification of a Potential Antimalarial Drug Candidate from a Series of 2-Aminopyrazines by Optimization of Aqueous Solubility and Potency across the Parasite Life Cycle
  作者：Claire Le Manach、Aloysius T. Nchinda、Tanya Paquet、Diego Gonzàlez Cabrera、Yassir Younis、Ze Han、Sridevi Bashyam、Mohammed Zabiulla、Dale Taylor、Nina Lawrence、Karen L. White、Susan A. Charman、David Waterson、Michael J. Witty、Sergio Wittlin、Mariëtte E. Botha、Sindisiswe H. Nondaba、Janette Reader、Lyn-Marie Birkholtz、María Belén Jiménez-Díaz、María Santos Martínez、Santiago Ferrer、Iñigo Angulo-Barturen、Stephan Meister、Yevgeniya Antonova-Koch、Elizabeth A. Winzeler、Leslie J. Street、Kelly Chibale

  DOI：10.1021/acs.jmedchem.6b01265

  日期：2016.11.10

  Introduction of water-solubilizing groups on the 5-phenyl ring of a 2-aminopyrazine series led to the identification of highly potent compounds against the blood life-cycle stage of the human malaria parasite Plasmodium falciparum. Several compounds displayed high in vivo efficacy in two different mouse models for malaria, P. berghei-infected mice and P. falciparum-infected NOD-scid IL-2Rγnull mice

  在2-氨基吡嗪系列的5-苯基环上引入水溶性基团导致鉴定出针对人类疟疾寄生虫恶性疟原虫血液生命周期阶段的高效化合物。在两种不同的疟疾小鼠模型中，几种化合物在疟疾，伯氏疟原虫感染的小鼠和恶性疟原虫感染的NOD -scidIL-2Rγ无效小鼠中表现出很高的体内功效。领先者之一化合物3被确定为还具有良好的药代动力学，并且还具有针对肝脏和配子细胞寄生虫生命周期阶段的非常有效的活性。
• MST1 KINASE INHIBITORS AND METHODS OF THEIR USE
  申请人：Augeri David John

  公开号：US20120225857A1

  公开（公告）日：2012-09-06

  Compounds for the inhibition of mammalian Ste20-like kinase 1 (MST1) are disclosed, along with compositions comprising them and methods of their use in the treatment, management or prevention of an inflammatory or autoimmune diseases or disorders.

  本发明揭示了用于抑制哺乳动物Ste20样激酶1（MST1）的化合物，以及包含它们的组合物和它们在治疗、管理或预防炎症性或自身免疫性疾病或障碍中的使用方法。
• MST1 kinase inhibitors and methods of their use
  申请人：Augeri David John

  公开号：US08440652B2

  公开（公告）日：2013-05-14

  Compounds for the inhibition of mammalian Ste20-like kinase 1 (MST1) are disclosed, along with compositions comprising them and methods of their use in the treatment, management or prevention of an inflammatory or autoimmune diseases or disorders. Particular compounds are of the formula:

  本发明揭示用于抑制哺乳动物Ste20样激酶1（MST1）的化合物，以及包含它们的组合物和在治疗、管理或预防炎症或自身免疫疾病或紊乱方面使用它们的方法。特定的化合物的公式为：
• Discovery of BI 135585, an in vivo efficacious oxazinanone-based 11β hydroxysteroid dehydrogenase type 1 inhibitor
  作者：Linghang Zhuang、Colin M. Tice、Zhenrong Xu、Wei Zhao、Salvacion Cacatian、Yuan-Jie Ye、Suresh B. Singh、Peter Lindblom、Brian M. McKeever、Paula M. Krosky、Yi Zhao、Deepak Lala、Barbara A. Kruk、Shi Meng、Lamont Howard、Judith A. Johnson、Yuri Bukhtiyarov、Reshma Panemangalore、Joan Guo、Rong Guo、Frank Himmelsbach、Bradford Hamilton、Annette Schuler-Metz、Heike Schauerte、Richard Gregg、Gerard M. McGeehan、Katerina Leftheris、David A. Claremon

  DOI：10.1016/j.bmc.2017.04.033

  日期：2017.7

  A potent, in vivo efficacious 11 beta hydroxysteroid dehydrogenase type 1 (11 beta HSD1) inhibitor (11j) has been identified. Compound 11j inhibited 11 beta HSD1 activity in human adipocytes with an IC50 of 4.3 nM and in primary human adipose tissue with an IC80 of 53 nM. Oral administration of 11j to cynomolgus monkey inhibited 11 beta HSD1 activity in adipose tissue. Compound 11j exhibited >1000x selectivity over other hydroxysteroid dehydrogenases, displays desirable pharmacodynamic properties and entered human clinical trials in 2011. (C) 2017 Elsevier Ltd. All rights reserved.