1-(2-amino-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-yl)ethan-1-one | 124458-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-amino-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-yl)ethan-1-one
• 英文别名: 5-acetyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylamine；5-Acetyl-2-amino-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine；1-(2-Amino-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl)-ethanone；1-(2-amino-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridin-5-yl)ethanone
• CAS: 124458-11-3
• 化学式: C₈H₁₁N₃OS
• 分子量: 197.261
• InChiKey: FNPABBLKLMLVLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  1-(2-amino-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-yl)ethan-1-one 在 sodium hydroxide 、 ammonium chloride 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 4,5,6,7-四氢噻唑[5,4-C]吡啶-2-胺
  参考文献：
  名称：

  Heterocycylic-substituted quinoline-carboxylic acids

  摘要：

  1-取代-6-氟-7-杂环-1,4-二氢喹诺-1-(或二氢萘啉)-4-酮羧酸具有抗菌性能。7-杂环基团是一个双环基团，其中一个环是饱和的，另一个环是不饱和的。

  公开号：

  US05037834A1
• 作为产物：
  描述：

  N-乙酰基-4-哌啶酮 、 氰胺 在 吡啶 、 sulfur 作用下， 反应 2.0h， 生成 1-(2-amino-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-yl)ethan-1-one
  参考文献：
  名称：

  鉴定用于目标生物学评估的新型GPR81激动剂前导系列。

  摘要：

  GPR81是一种新型药物靶标，与葡萄糖和脂质代谢的控制有关。缺乏适用于体内研究的强效GPR81调节剂，限制了该乳酸传感受体的药理学表征。我们进行了高通量筛选（HTS），并确定了一个GPR81激动剂化学系列，其中包含一个中央酰基尿素支架接头。在SAR探索过程中，又开发了两个新系列，其中一个包含环状酰基脲生物等位基因，另一个包含中央酰胺键。这三个系列提供了适用于体内研究的不同选择性和理化性质。

  DOI：

  10.1016/j.bmcl.2020.126953

文献信息

• Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1
  申请人：——

  公开号：US20030199501A1

  公开（公告）日：2003-10-23

  The present invention relates to using a compound having the formula (I) wherein T is I) thienyl, which optionally is substituted with halogen, or II) phenyl optionally substituted with halogen and/or C 1-6 -alkyl; E is a bond, —CH 2 — or —CO—; L is a bond, —CH 2 —, —CHR 4 — or —NR 3 —; R 3 is H, C 1-6 -alkyl, C 1-6 -acyl or —COR 4 ; R 4 is morpholino or C 1-6 -amido; R 6 and R 7 are independently hydrogen or C 1-6 -alkyl; and R 8 and R 9 are independently hydrogen or C 1-6 -alkyl, as well as pharmaceutically acceptable salts, hydrates and solvates thereof, in the manufacture of a medicament for the treatment or prevention of diabetes, syndrome X, obesity, glaucoma, hyperlipidemia, hyperglycemia, hyperinsulinemia, osteoporosis, tuberculosis, dementia, depression, virus diseases and inflammatory disorders.

  本发明涉及使用具有以下化学式（I）的化合物，其中T是（I）噻吩基，它可以用卤素取代，或者（II）苯基，它可以用卤素和/或C1-6烷基取代；E是键，-CH2-或-CO-;L是键，-CH2-，-CHR4-或-NR3-;R3是H，C1-6烷基，C1-6酰基或-COR4;R4是吗啡基或C1-6酰胺基;R6和R7独立地是氢或C1-6烷基;R8和R9独立地是氢或C1-6烷基，以及其药学上可接受的盐，水合物和溶剂化物，在制造用于治疗或预防糖尿病，X综合症，肥胖症，青光眼，高脂血症，高血糖，高胰岛素血症，骨质疏松症，结核病，痴呆症，抑郁症，病毒病和炎症性疾病的药物。
• Thiazolyl and oxazolyl[5,4-c]piperidyl-substituted quinolone-carboxylic
  申请人：Pfizer Inc.

  公开号：US05214051A1

  公开（公告）日：1993-05-25

  Thiazolyl and oxazolyl [5,4-c] piperidyl-substituted quinolone-carboxylic acids and related analogs thereof having antibacterial properties are disclosed.

  本发明揭示了具有抗菌性的噻唑基和氧唑基[5,4-c]哌啶取代的喹诺酸羧酸及其相关类似物。
• Inhibitors of 11-β-hydroxy steroid dehydrogenase type 1
  申请人：Biovitrum AB

  公开号：US07030135B2

  公开（公告）日：2006-04-18

  The present invention relates to using a compound having the formula (I) wherein T is I) thienyl, which optionally is substituted with halogen, or II) phenyl optionally substituted with halogen and/or C1-6-alkyl; E is a bond, —CH2— or —CO—; L is a bond, —CH2—, —CHR4— or —NR3—; R3 is H, C1-6-alkyl, C1-6-acyl or —COR4; R4 is morpholino or C1-6-amido; R6 and R7 are independently hydrogen or C1-6-alkyl; and R8 and R9 are independently hydrogen or C1-6-alkyl, as well as pharmaceutically acceptable salts, hydrates and solvates thereof, in the manufacture of a medicament for the treatment or prevention of diabetes, syndrome X, obesity, glaucoma, hyperlipidemia, hyperglycemia, hyperinsulinemia, osteoporosis, tuberculosis, dementia, depression, virus diseases and inflammatory disorders.

  本发明涉及使用具有以下式子（I）的化合物，其中T是I）噻吩基，可以用卤素取代，或II）苯基，可以用卤素和/或C1-6烷基取代；E是键，-CH2-或-CO-；L是键，-CH2-，-CHR4-或-NR3-；R3是H，C1-6烷基，C1-6酰基或-COR4；R4是吗啡环或C1-6酰胺基；R6和R7分别是氢或C1-6烷基；R8和R9分别是氢或C1-6烷基，以及其药学上可接受的盐、水合物和溶剂合物，用于制备治疗或预防糖尿病、综合征X、肥胖症、青光眼、高脂血症、高血糖、高胰岛素血症、骨质疏松症、结核病、痴呆症、抑郁症、病毒性疾病和炎症性疾病的药物。
• [EN] N-SUBSTITUTED-3,5-DISUBSTITUTED BENZAMIDE COMPOUND AND PREPARATION METHOD AND APPLICATION THEREOF<br/>[FR] COMPOSÉ BENZAMIDE N-SUBSTITUÉ-3,5-DISUBSTITUÉ ET SES PROCÉDÉ DE PRÉPARATION ET APPLICATION<br/>[ZH] N-取代-3,5-二取代苯甲酰胺类化合物及其制备方法和应用
  申请人：SHANGHAI INST MATERIA MEDICA

  公开号：WO2016112863A1

  公开（公告）日：2016-07-21

  本发明公开一种N-取代-3,5-二取代苯甲酰胺类化合物及其制备方法和应用，该化合物结构如通式I所示，式中，m、X、Y、R1、R2和R3如权利要求书和说明书所示。本发明还公开了包含通式I所示化合的药物组合物。本发明的化合物可以作为葡萄糖激酶激动剂，用于预防和/或治疗与葡萄糖代谢异常相关的疾病。
• Discovery of cycloalkyl-fused N-thiazol-2-yl-benzamides as tissue non-specific glucokinase activators: Design, synthesis, and biological evaluation
  作者：Zhengyu Wang、Xiaofan Shi、Huan Zhang、Liang Yu、Yanhua Cheng、Hefeng Zhang、Huibin Zhang、Jinpei Zhou、Jing Chen、Xu Shen、Wenhu Duan

  DOI：10.1016/j.ejmech.2017.07.051

  日期：2017.10

  Glucokinase (GK) activators are being developed for the treatment of type 2 diabetes mellitus (T2DM). However, existing GK activators have risks of hypoglycemia caused by over-activation of GK in islet cells and dyslipidemia caused by over-activation of intrahepatic GK. In the effort to mitigate risks of hypoglycemia and dyslipidemia while maintaining the promising efficacy of GK activator, we investigated a series of cycloalkyl-fused N-thiazol-2-yl-benzamides as tissue non-specific partial GK activators, which led to the identification of compound 72 that showed a good balance between in vitro potency and enzyme kinetic parameters, and protected beta-cells from streptozotocin-induced apoptosis. Chronic treatment of compound 72 demonstrated its potent activity in regulation of glucose homeostasis and low risk of dyslipidemia with diabetic db/db mice in oral glucose tolerance test (OGTT). Moreover, acute treatment of compound 72 did not induce hypoglycemia in C57BL/6J mice even at 200 mg/kg via oral administration. (C) 2017 Elsevier Masson SAS. All rights reserved.