5-(2-bromo-1,3-thiazol-5-yl)-2H-tetrazole | 1241897-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2-bromo-1,3-thiazol-5-yl)-2H-tetrazole
• 英文别名: 2-bromo-5-(2H-tetrazol-5-yl)-1,3-thiazole
• CAS: 1241897-91-5
• 化学式: C₄H₂BrN₅S
• 分子量: 232.063
• InChiKey: PMPNTKQJPALBKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  溴乙酸叔丁酯 、 5-(2-bromo-1,3-thiazol-5-yl)-2H-tetrazole 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 tert-butyl [5-(2-bromo-1,3-thiazol-5-yl)-2H-tetrazol-2-yl]acetate
  参考文献：
  名称：

  [EN] NOVEL SPIRO COMPOUNDS USEFUL AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE
  [FR] NOUVEAUX COMPOSÉS SPIRO UTILES EN TANT QU'INHIBITEURS DE LA STÉAROYL-COENZYME A DELTA-9 DÉSATURASE

  摘要：

  结构式（I）的杂环芳香化合物相对于其他已知的硬脂酰辅酶A去饱和酶（SCD1）具有选择性抑制作用。本发明的化合物可用于预防和治疗与异常脂质合成和代谢相关的疾病，包括心血管疾病（如动脉粥样硬化）、肥胖、糖尿病、神经系统疾病、代谢综合征、胰岛素抵抗和肝脂肪变性。

  公开号：

  WO2011011872A1
• 作为产物：
  描述：

  2-溴-5-氰基噻唑 在 zinc dibromide sodium azide 、 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 5.0h， 生成 5-(2-bromo-1,3-thiazol-5-yl)-2H-tetrazole
  参考文献：
  名称：

  [EN] HETEROCYCLIC COMPOUNDS AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE
  [FR] COMPOSÉS HÉTÉROCYCLIQUES INHIBITEURS DE LA STÉAROYL-COENZYME A DELTA-9 DÉSATURASE

  摘要：

  结构式I的杂环化合物是硬脂酰辅酶A Δ-9去饱和酶（SCD）的抑制剂。本发明的化合物对于预防和治疗与异常脂质合成和代谢相关的疾病非常有用，包括心血管疾病；动脉粥样硬化；肥胖；糖尿病；神经系统疾病；代谢综合征；胰岛素抵抗；癌症；肝脂肪变性；以及非酒精性脂肪性肝炎。

  公开号：

  WO2010108268A1

文献信息

• HETEROCYCLIC DERIVATIVES AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE
  申请人：Isabel Elise

  公开号：US20110301143A1

  公开（公告）日：2011-12-08

  Heterocyclic compounds of structural formula (I), or a pharmaceutically acceptable salt thereof, wherein W is a R 1 — substituted heteroaryl, R 1 is an heteroaryl ring substituted with an ester or carboxylic acid containing radical, X-T is N—CR 5 R 6 , C═CR 5 or CR 13 —CR 5 R 6 , Y is a bond or —C(O)—, a and b represent an integer selected from 1 to 4, and Ar is an optionally substituted phenyl or naphtyl, are inhibitors of stearoyl-coenzyme A delta-9 desaturase (SCD) The heterocyclic compounds are useful for the prevention and treatment of conditions related to abnormal lipid synthesis and metabolism, including cardiovascular disease, atherosclerosis, obesity, diabetes, neurological disease, Metabolic Syndrome, insulin resistance, cancer, liver steatosis, and non-alcoholic steatohepatitis.

  结构式（I）的杂环化合物，或其药学上可接受的盐，其中W是R1-取代的杂芳基，R1是取代有酯基或羧基的杂芳基环，X-T是N—CR5R6，C═CR5或CR13—CR5R6，Y是键或—C(O)—，a和b代表选自1到4的整数，Ar是可选择取代的苯基或萘基，是硬脂酰辅酶A 9-脱饱和酶（SCD）的抑制剂。这些杂环化合物对于预防和治疗与异常脂质合成和代谢有关的疾病非常有用，包括心血管疾病、动脉粥样硬化、肥胖症、糖尿病、神经系统疾病、代谢综合征、胰岛素抵抗、癌症、肝脂肪变性和非酒精性脂肪肝。
• [EN] NOVEL SPIRO COMPOUNDS USEFUL AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE<br/>[FR] NOUVEAUX COMPOSÉS SPIRO UTILES COMME INHIBITEURS DE LA STÉAROYL-COENZYME A DELTA-9 DÉSATURASE
  申请人：MERCK FROSST CANADA LTD

  公开号：WO2010094120A1

  公开（公告）日：2010-08-26

  Heteroaromatic compounds of structural formula (I) are selective inhibitors of stearoyl-coenzyme A delta-9 desaturase (SCD1) relative to other known stearoyl-coenzyme A desaturases. The compounds of the present invention are useful for the prevention and treatment of conditions related to abnormal lipid synthesis and metabolism, including cardiovascular disease, such as atherosclerosis; obesity; diabetes; neurological disease; metabolic syndrome; insulin resistance; and liver steatosis.

  结构式（I）的杂环芳香化合物相对于其他已知的硬脂酰辅酶A去饱和酶（SCD1）具有选择性抑制作用。本发明的化合物可用于预防和治疗与异常脂质合成和代谢相关的疾病，包括心血管疾病，如动脉粥样硬化；肥胖；糖尿病；神经系统疾病；代谢综合征；胰岛素抵抗；以及肝脂肪变性。
• HETEROCYCLIC COMPOUNDS AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE
  申请人：Lachance Nicolas

  公开号：US20120010186A1

  公开（公告）日：2012-01-12

  Heterocyclic compounds of structural formula I are inhibitors of stearoyl-coenzyme A delta-9 desaturase (SCD). The compounds of the present invention are useful for the prevention and treatment of conditions related to abnormal lipid synthesis and metabolism, including cardiovascular disease; atherosclerosis; obesity; diabetes; neurological disease; Metabolic Syndrome; insulin resistance; cancer, liver steatosis; and non-alcoholic steatohepatitis.

  结构式I的杂环化合物是硬脂酰辅酶A delta-9去饱和酶（SCD）的抑制剂。本发明的化合物可用于预防和治疗与异常脂质合成和代谢有关的疾病，包括心血管疾病；动脉粥样硬化；肥胖症；糖尿病；神经系统疾病；代谢综合征；胰岛素抵抗；癌症；肝脂肪变性和非酒精性脂肪性肝炎。
• [EN] HETEROCYCLIC DERIVATIVES AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE<br/>[FR] DÉRIVÉS HÉTÉROCYCLIQUES COMME INHIBITEURS DE LA STÉAROYL-COENZYME A DELTA-9 DÉSATURASE
  申请人：MERCK CANADA INC

  公开号：WO2010094126A8

  公开（公告）日：2012-03-08
• Discovery of potent and liver-targeted stearoyl-CoA desaturase (SCD) inhibitors in a bispyrrolidine series
  作者：Nicolas Lachance、Yves Gareau、Sébastien Guiral、Zheng Huang、Elise Isabel、Jean-Philippe Leclerc、Serge Léger、Evelyn Martins、Christian Nadeau、Renata M. Oballa、Stéphane G. Ouellet、David A. Powell、Yeeman K. Ramtohul、Geoffrey K. Tranmer、Thao Trinh、Hao Wang、Lei Zhang

  DOI：10.1016/j.bmcl.2011.12.002

  日期：2012.1

  Inhibition of stearoyl-CoA desaturase (SCD) activity represents a potential novel mechanism for the treatment of metabolic disorders including obesity and type II diabetes. To circumvent skin and eye adverse events observed in rodents with systemically-distributed SCD inhibitors, our research efforts have been focused on the search for new and structurally diverse liver-targeted SCD inhibitors. This work has led to the discovery of novel, potent and structurally diverse liver-targeted bispyrrolidine SCD inhibitors. These compounds possess suitable cellular activity and pharmacokinetic properties to inhibit liver SCD activity in a mouse pharmacodynamic model. (C) 2011 Elsevier Ltd. All rights reserved.