ethyl 1-methyl-2-sulphanyl-1H-imidazole-5-carbpxylate | 108905-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-methyl-2-sulphanyl-1H-imidazole-5-carbpxylate
• 英文别名: Ethyl 1-methyl-2-sulfanylimidazole-5-carboxylate；ethyl 3-methyl-2-sulfanylidene-1H-imidazole-4-carboxylate
• CAS: 108905-74-4
• 化学式: C₇H₁₀N₂O₂S
• 分子量: 186.235
• InChiKey: IYPAKZVEOSENBN-UHFFFAOYSA-N

物化性质

• 沸点：
  257.7±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)
• 溶解度：
  >27.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-methyl-2-sulphanyl-1H-imidazole-5-carbpxylate 在 吡啶 、 三乙基硼氢化锂 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 [1-methyl-2-(methylsulphinyl)-1H-imidazol-5-yl]methyl 4-nitrophenyl carbonate
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Imidazolylmethyl Carbamate Prodrugs of Alkylating Agents

  摘要：

  Two approaches to prodrugs of alkylating agents based on an imidazolylmethyl carbamate nucleus were explored. A 2-azido analogue (3) of the bis-carbamate carmethizole (1) displayed similar aerobic cytotoxicity to 1 in a panel of human and murine cell lines. Approaches to the 2-amino and 2-carbamoyl analogues are described. In the second approach an imidazolylmethanol was used as a 'trigger' linked via a carbamate to the alkylating agent N,N-bis(2-chlorethyl)amine (BCEA). Nitroimidazole and methylsulphinylimidazole carbamate prodrugs 6-8 were 5-20-fold less toxic than BCEA. Despite this deactivation in the prodrug form, little increase in cytotoxicity was observed under hypoxia. The data suggest that BCEA released on bioreduction is not sufficiently potent to contribute significant additional cytotoxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01031-5
• 作为产物：
  描述：

  2-[甲酰基(甲基)氨基]乙酸乙酯 在 盐酸 、 sodium ethanolate 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 ethyl 1-methyl-2-sulphanyl-1H-imidazole-5-carbpxylate
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Imidazolylmethyl Carbamate Prodrugs of Alkylating Agents

  摘要：

  Two approaches to prodrugs of alkylating agents based on an imidazolylmethyl carbamate nucleus were explored. A 2-azido analogue (3) of the bis-carbamate carmethizole (1) displayed similar aerobic cytotoxicity to 1 in a panel of human and murine cell lines. Approaches to the 2-amino and 2-carbamoyl analogues are described. In the second approach an imidazolylmethanol was used as a 'trigger' linked via a carbamate to the alkylating agent N,N-bis(2-chlorethyl)amine (BCEA). Nitroimidazole and methylsulphinylimidazole carbamate prodrugs 6-8 were 5-20-fold less toxic than BCEA. Despite this deactivation in the prodrug form, little increase in cytotoxicity was observed under hypoxia. The data suggest that BCEA released on bioreduction is not sufficiently potent to contribute significant additional cytotoxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01031-5

文献信息

• [EN] HETEROARYL-UREAS AND THEIR USE AS GLUCOKINASE ACTIVATORS<br/>[FR] HETEROARYL-UREES ET LEUR UTILISATION EN TANT QU'ACTIVATEURS DE GLUCOKINASE
  申请人：NOVO NORDISK AS

  公开号：WO2005066145A1

  公开（公告）日：2005-07-21

  This invention relates to compounds that are of formula (I) wherein A is heteroaryl and R1 and R2 are both cyclic residues, that are activators of glucokinase and thus may be useful for the management, treatment, control, or adjunct treatment of diseases, where increasing glucokinase activity is beneficial .

  这项发明涉及具有以下结构的化合物（I），其中A是杂环烷基，R1和R2都是环状残基，这些化合物是葡萄糖激酶的激活剂，因此可能对管理、治疗、控制或辅助治疗需要增加葡萄糖激酶活性的疾病有益。
• Nematicidal trifluorobutenyl imidazole thioether derivatives
  申请人：Watanabe Yukiyoshi

  公开号：US20050080123A1

  公开（公告）日：2005-04-14

  The present invention relates to novel trifluorobutenyl imidazole thioether derivatives of the following formula (1) wherein R 1 represents hydrogen or halogen, R 2 represents hydrogen, halogen or alkoxycarbonyl, R 3 represents hydrogen, alkyl, alkenyl, cycloalkyl or aralkyl, and n represents 0,1 or 2, with the proviso that R 1 , R 2 and R 3 do not all represent hydrogen at the same time to a process for their preparation and to their use as nematicides.

  本发明涉及以下式(1)的新型三氟丁烯基咪唑硫醚衍生物，其中R1代表氢或卤素，R2代表氢、卤素或烷氧羰基，R3代表氢、烷基、烯基、环烷基或芳基烷基，n代表0、1或2，但R1、R2和R3不同时均代表氢，以及其制备方法和作为杀线虫剂的用途。
• Heteroaryl-Ureas and Their Use as Glucokinase Activators
  申请人：Murray Anthony

  公开号：US20090216013A1

  公开（公告）日：2009-08-27

  This invention relates to compounds of formula (I) which are activators of glucokinase and thus may be useful for the management, treatment, control, or adjunct treatment of diseases, where increasing glucokinase activity is beneficial.

  本发明涉及公式（I）的化合物，其为葡萄糖激酶激活剂，因此可能对增加葡萄糖激酶活性有益的疾病的管理、治疗、控制或辅助治疗有用。
• Heteroaryl-ureas and their use as glucokinase activators
  申请人：Murray Anthony

  公开号：US20070054897A1

  公开（公告）日：2007-03-08

  This invention relates to compounds of formula (I) which are activators of glucokinase and thus may be useful for the management, treatment, control, or adjunct treatment of diseases, where increasing glucokinase activity is beneficial.

  本发明涉及式（I）的化合物，它们是葡萄糖激酶的激活剂，因此可能对增加葡萄糖激酶活性有益的疾病的管理、治疗、控制或辅助治疗有用。
• HETEROARYL-UREAS AND THEIR USE AS GLUCOKINASE ACTIVATORS
  申请人：Murray Anthony

  公开号：US20110060019A1

  公开（公告）日：2011-03-10

  This invention relates to compounds of formula (I) which are activators of glucokinase and thus may be useful for the management, treatment, control, or adjunct treatment of diseases, where increasing glucokinase activity is beneficial.

  本发明涉及式（I）化合物，其为葡萄糖激酶的激活剂，因此可能有助于治疗、控制或辅助治疗增加葡萄糖激酶活性有益的疾病。