6-bromo-5-methoxythiazolo[5,4-b]pyridin-2-amine | 1198319-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-bromo-5-methoxythiazolo[5,4-b]pyridin-2-amine
• 英文别名: 6-bromo-5-methoxy-[1,3]thiazolo[5,4-b]pyridin-2-amine
• CAS: 1198319-50-4
• 化学式: C₇H₆BrN₃OS
• 分子量: 260.114
• InChiKey: ZPEHTDHWSSYHKY-UHFFFAOYSA-N

物化性质

• 沸点：
  363.2±52.0 °C(Predicted)
• 密度：
  1.832±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  89.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-bromo-5-methoxythiazolo[5,4-b]pyridin-2-amine 在 偶氮二甲酸二异丙酯 、 氢溴酸 、 二正丁基氧化锡 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 1-[6-bromo-5-(tetrahydro-2H-pyran-4-yloxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]-3-ethylurea
  参考文献：
  名称：

  Thiazolopyridine Ureas as Novel Antitubercular Agents Acting through Inhibition of DNA Gyrase B

  摘要：

  A pharmacophore-based search led to the identification of thiazolopyridine ureas as a novel scaffold with antitubercular activity acting through inhibition of DNA Gyrase B (GyrB) ATPase. Evaluation of the binding mode of thiazolopyridines in a Mycobacterium tuberculosis (Mtb) GyrB homology model prompted exploration of the side chains at the thiazolopyridine ring C-5 position to access the ribose/solvent pocket. Potent compounds with GyrB IC50 ≤ 1 nM and Mtb MIC ≤ 0.1 μM were obtained with certain combinations of side chains at the C-5 position and heterocycles at the C-6 position of the thiazolopyridine core. Substitutions at C-5 also enabled optimization of the physicochemical properties. Representative compounds were cocrystallized with Streptococcus pneumoniae (Spn) ParE; these confirmed the binding modes predicted by the homology model. The target link to GyrB was confirmed by genetic mapping of the mutations conferring resistance to thiazolopyridine ureas. The compounds are bactericidal in vitro and efficacious in vivo in an acute murine model of tuberculosis.

  DOI：

  10.1021/jm401268f
• 作为产物：
  描述：

  5-氨基-2-甲氧基-3-溴吡啶 、 potassium thioacyanate 在 溴 、 溶剂黄146 作用下， 反应 2.0h， 生成 6-bromo-5-methoxythiazolo[5,4-b]pyridin-2-amine
  参考文献：
  名称：

  [EN] 7-AZAINDOLE COMPOUNDS FOR INHIBITION OF BCR-ABL TYROSINE KINASES
  [FR] COMPOSÉS DE 7-AZAINDOLE POUR L'INHIBITION DE TYROSINE KINASES BCR-ABL

  摘要：

  本公开涉及抑制Bcr-Abl酪氨酸激酶的化合物和组合物，制备该化合物和组合物的方法，以及它们在治疗各种癌症，如慢性髓细胞白血病（CML）中的使用。

  公开号：

  WO2022076973A1

文献信息

• [EN] THIAZOLO [5, 4-B] PYRIDINE AND OXAZOLO [5, 4-B] PYRIDINE DERIVATIVES AS ANTIBACTERIAL AGENTS<br/>[FR] DÉRIVÉS DE THIAZOLO [5, 4-B] PYRIDINE ET D'OXAZOLO [5,4-B] COMME AGENTS ANTIBACTÉRIENS
  申请人：ASTRAZENECA AB

  公开号：WO2009147431A1

  公开（公告）日：2009-12-10

  Compounds of formula (I) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.

  描述了化学式（I）的化合物及其药用可接受的盐。还描述了它们的制备方法、含有它们的药物组合物、它们作为药物的用途以及它们在治疗细菌感染中的用途。
• NEW COMPOUND 255
  申请人：Ghorpade Sandeep Raghunath

  公开号：US20100137303A1

  公开（公告）日：2010-06-03

  Compounds of formula (I) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.

  本文描述了化学式(I)的化合物及其药物可接受的盐。还描述了制备它们的过程，包含它们的制药组合物，以及它们作为药物用于治疗细菌感染的用途。
• [EN] 7-AZAINDOLE COMPOUNDS FOR INHIBITION OF BCR-ABL TYROSINE KINASES<br/>[FR] COMPOSÉS DE 7-AZAINDOLE POUR L'INHIBITION DE TYROSINE KINASES BCR-ABL
  申请人：ENLIVEN THERAPEUTICS INC

  公开号：WO2022076973A1

  公开（公告）日：2022-04-14

  The present disclosure relates to compounds and compositions for inhibition of Bcr-Abl tyrosine kinases, methods of preparing said compounds and compositions, and their use in the treatment of various cancers, such as chronic myeloid leukemia (CML).

  本公开涉及抑制Bcr-Abl酪氨酸激酶的化合物和组合物，制备该化合物和组合物的方法，以及它们在治疗各种癌症，如慢性髓细胞白血病（CML）中的使用。
• [EN] ANTIBACTERIAL COMBINATIONS COMPRISING POLYMYXIN<br/>[FR] COMPOSÉS ANTIBACTÉRIENS
  申请人：BIOTA EUROPE LTD

  公开号：WO2015114452A3

  公开（公告）日：2015-11-12
• THIAZOLO [5, 4-B] PYRIDINE AND OXAZOLO [5, 4-B] PYRIDINE DERIVATIVES AS ANTIBACTERIAL AGENTS
  申请人：AstraZeneca AB

  公开号：EP2303894A1

  公开（公告）日：2011-04-06