5-溴-N3-甲基吡啶-2,3-二胺 | 166047-15-0

• 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
• 中文名称: 5-溴-N3-甲基吡啶-2,3-二胺
• 英文名称: 5-bromo-N³-methylpyridine-2,3-diamine
• 英文别名: 5-bromo-N3-methylpyridine-2,3-diamine；5-bromo-3-N-methylpyridine-2,3-diamine
• CAS: 166047-15-0
• 化学式: C₆H₈BrN₃
• 分子量: 202.054
• InChiKey: IEZBJIKJXNNYFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-溴-N3-甲基吡啶-2,3-二胺 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三乙胺 、 N,N-二异丙基乙胺 、 三环己基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.17h， 生成 N-methyl-3-(1-methyl-2-oxo-3-tritylimidazo[4,5-b]pyridin-6-yl)benzamide
  参考文献：
  名称：

  Structure Guided Development of Novel Thymidine Mimetics Targeting Pseudomonas aeruginosa Thymidylate Kinase: From Hit to Lead Generation

  摘要：

  Thymidylate kinase (TMK) is a potential chemotherapeutic target because it is directly involved in the synthesis of an essential component, thymidine triphosphate, in DNA replication. All reported TMK inhibitors are thymidine analogues, which might retard their development as potent therapeutics due to cell permeability and off-target activity against human TMK. A small molecule hit (1, IC(50) = 58 μM), which has reasonable inhibition potency against Pseudomonas aeruginosa TMK (PaTMK), was identified by the analysis of the binding mode of thymidine or TP(5)A in a PaTMK homology model. This hit (1) was cocrystallized with PaTMK, and several potent PaTMK inhibitors (leads, 46, 47, 48, and 56, IC(50) = 100-200 nM) were synthesized using computer-aided design approaches including virtual synthesis/screening, which was used to guide the design of inhibitors. The binding mode of the optimized leads in PaTMK overlaps with that of other bacterial TMKs but not with human TMK, which shares few common features with the bacterial enzymes. Therefore, the optimized TMK inhibitors described here should be useful for the development of antibacterial agents targeting TMK without undesired off-target effects. In addition, an inhibition mechanism associated with the LID loop, which mimics the process of phosphate transfer from ATP to dTMP, was proposed based on X-ray cocrystal structures, homology models, and structure-activity relationship results.

  DOI：

  10.1021/jm201349f
• 作为产物：
  描述：

  2,3-二氨基-5-溴吡啶 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.67h， 生成 5-溴-N3-甲基吡啶-2,3-二胺
  参考文献：
  名称：

  咪唑并吡啶并酮和7-氮杂恶唑的合成策略及其作为抗菌剂的评价

  摘要：

  已评估了各种合成方法和途径来制备高级咪唑并吡啶并酮和7-氮杂新多烯。研究靶分子作为大肠杆菌胸苷酸单磷酸激酶抑制剂。酶促测定表明咪唑并吡啶并酮是大肠杆菌胸苷单磷酸激酶的活性抑制剂。相反，目标7-氮杂恶唑具有较低的活性。

  DOI：

  10.1002/ejoc.202100172

文献信息

• GLP-1 Agonists and Uses Thereof
  申请人：Pfizer Inc.

  公开号：US20180170908A1

  公开（公告）日：2018-06-21

  Provided herein are 6-carboxylic acids of benzimidazoles and 4-aza-, 5-aza-, 7-aza- and 4,7-diaza-benzimidazoles as GLP-1R agonists, processes to make said compounds, and methods comprising administering said compounds to a mammal in need thereof.

  本文提供苯并咪唑的6-羧酸和4-氮杂、5-氮杂、7-氮杂和4,7-二氮杂苯并咪唑作为GLP-1R激动剂，制备该化合物的方法，以及包括将该化合物给予需要的哺乳动物的方法。
• Palladium(0)-catalyzed phenylation of imidazo[4,5-<i>b</i>]pyridines
  作者：Spiros Grivas、Stefan Lindström

  DOI：10.1002/jhet.5570320214

  日期：1995.3

  The tetrakis(triphenylphosphine)palladium(O)-catalyzed coupling of benzeneboronic acid with 2-chloro, 6-bromo and 6-bromo-2-chloro derivatives of 1- and 3-methylimidazo[4,5-b]pyridines to novel 2-phenyl-, 6-phenyl- and 2,6-diphenylimidazo[4,5-b]pyridines is described. The phenylation of imidazo[4,5-b]-pyridines containing labile hydrogens was not successful.

  四（三苯基膦）钯（O）催化的苯硼酸与1-和3-甲基咪唑并[4,5- b ]吡啶的2-氯，6-溴和6-溴-2-氯衍生物偶联至新型2描述了-苯基-，6-苯基-和2，6-二苯基咪唑并[4，5- b ]吡啶。含不稳定氢的咪唑并[4,5- b ]-吡啶的苯基化作用不成功。
• [EN] GCN2 MODULATING COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS MODULATEURS DE GCN2 ET LEURS UTILISATIONS
  申请人：HIBERCELL INC

  公开号：WO2022159745A1

  公开（公告）日：2022-07-28

  Provided herein are compounds, compositions, and methods useful for modulating the activity of GCN2 and for treating related conditions, diseases, and disorders (e.g., cancer and neurodegenerative diseases).

  本文提供了化合物、组合物和方法，有助于调节GCN2的活性，并用于治疗相关的疾病和疾病（例如癌症和神经退行性疾病）。
• GLP-1 receptor agonists and uses thereof
  申请人：Pfizer Inc.

  公开号：US10208019B2

  公开（公告）日：2019-02-19

  Provided herein are 6-carboxylic acids of benzimidazoles and 4-aza-, 5-aza-, 7-aza- and 4,7-diaza-benzimidazoles as GLP-1R agonists, processes to make said compounds, and methods comprising administering said compounds to a mammal in need thereof.

  本文提供了作为GLP-1R激动剂的苯并咪唑和4-氮杂-、5-氮杂-、7-氮杂-和4,7-二氮杂-苯并咪唑的6-羧酸，制造所述化合物的工艺，以及将所述化合物施用给需要的哺乳动物的方法。
• GLP-1 RECEPTOR AGONISTS AND USES THEREOF
  申请人：Pfizer Inc.

  公开号：EP3555064A1

  公开（公告）日：2019-10-23