methyl imidazo<2,1-b>benzothiazole-2-carboxylate | 114094-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: methyl imidazo<2,1-b>benzothiazole-2-carboxylate
• 英文别名: methyl benzo[d]imidazo[2,1-b]thiazole-2-carboxylate；Methyl imidazo[2,1-b][1,3]benzothiazole-2-carboxylate
• CAS: 114094-95-0
• 化学式: C₁₁H₈N₂O₂S
• 分子量: 232.263
• InChiKey: RWSOTXIEORKMLT-UHFFFAOYSA-N

物化性质

• 熔点：
  156-157 °C(Solv: ethyl acetate (141-78-6))
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-乙基-(9ci)-2-氨基苯并噻唑 在 sodium hydroxide 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 32.0h， 生成 methyl imidazo<2,1-b>benzothiazole-2-carboxylate
  参考文献：
  名称：

  (Imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones and related compounds as potential nonsedative anxiolytics

  摘要：

  Several series of heterocyclic carboxylic esters were found to be active in the benzodiazepine receptor binding assay, a typical example being ethyl 7-ethyl-5-methoxyimidazo[1,2-a]quinoline-2-carboxylate (4b) with an IC50 of 150 nM. The corresponding phenylmethanone 5d was more potent with an IC50 of 14 nM and was orally active in animal models thought to predict anxiolytic effects. The synthesis of a large number of compounds resulted in the optimization of this activity in a series of (imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones of which compounds 7e, 8b, 8h, 8j, and 8k were equipotent with chlordiazepoxide while exhibiting reduced anticonvulsant activity, little or no muscle relaxation, and negligible sedative effects.

  DOI：

  10.1021/jm00401a025

文献信息

• Copper-Promoted Cycloaddition of α-Methylenyl Isocyanides with Benzothiazoles: Tunable Access to Benzo[<i>d</i>]imidazothiazoles
  作者：Jian Wang、Jing Li、Qiang Zhu

  DOI：10.1021/acs.orglett.5b02694

  日期：2015.11.6

  benzothiazoles. When the C2 position of benzothiazole is linked to a C–H or C–C bond, benzo[d]imidazo[2,1-b]thiazoles are obtained through a novel rearrangement via C–S bond cleavage and formation of a new C–S bond. When 2-chloro- or 2-bromobenzothiazoles are used under the same reaction conditions, the isomeric benzo[d]imidazo[5,1-b]thiazoles are formed selectively. These reactions proceed smoothly in moderate

  通过α-亚甲基异氰化物与苯并噻唑的铜促进的环加成反应，已开发出可调谐途径生成苯并[ d ]咪唑并噻唑的两种异构体。当苯并噻唑的C2位置与C–H或C–C键相连时，通过C–S键的裂解和新C的形成，通过新颖的重排可以获得苯并[ d ]咪唑基[2,1- b ]噻唑–S键。当在相同反应条件下使用2-氯-或2-溴苯并噻唑时，选择性地形成异构体苯并[ d ]咪唑并[5，1- b ]噻唑。这些反应在室温下以中等至极好的收率顺利进行，并且可以容忍各种官能团。
• Imidazo[2,1-B]thiazole and 5,6-dihydroimidazo[2,1-B]thiazole derivatives useful as S100-inhibitors
  申请人：Active Biotech AB

  公开号：US10385069B2

  公开（公告）日：2019-08-20

  A compound of formula (I) or a pharmaceutically acceptable salt thereof. The compound is useful for use in the treatment of cancer, an inflammatory disorder, an autoimmunity disorder or a neurodegenerative disorder.

  式 (I) 的化合物或其药学上可接受的盐。该化合物可用于治疗癌症、炎症性疾病、自身免疫性疾病或神经退行性疾病。
• CLEMENTS-JEWERY, STEPHEN;DANSWAN, GEOFFREY;GARDNER, COLIN R.;MATHARU, SAR+, J. MED. CHEM., 31,(1988) N 6, 1220-1226
  作者：CLEMENTS-JEWERY, STEPHEN、DANSWAN, GEOFFREY、GARDNER, COLIN R.、MATHARU, SAR+

  DOI：——

  日期：——
• IMIDAZO[2,1-B]THIAZOLE AND 5,6-DIHYDROIMIDAZO[2,1-B]THIAZOLE DERIVATIVES USEFUL AS S100-INHIBITORS
  申请人：Active Biotech AB

  公开号：US20180282348A1

  公开（公告）日：2018-10-04

  A compound of formula (I) or a pharmaceutically acceptable salt thereof. The compound is useful for use in the treatment of cancer, an inflammatory disorder, an autoimmunity disorder or a neurodegenerative disorder.
• (Imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones and related compounds as potential nonsedative anxiolytics
  作者：Stephen Clements-Jewery、Geoffrey Danswan、Colin R. Gardner、Saroop S. Matharu、Robert Murdoch、W. Roger Tully、Robert Westwood

  DOI：10.1021/jm00401a025

  日期：1988.6

  Several series of heterocyclic carboxylic esters were found to be active in the benzodiazepine receptor binding assay, a typical example being ethyl 7-ethyl-5-methoxyimidazo[1,2-a]quinoline-2-carboxylate (4b) with an IC50 of 150 nM. The corresponding phenylmethanone 5d was more potent with an IC50 of 14 nM and was orally active in animal models thought to predict anxiolytic effects. The synthesis of a large number of compounds resulted in the optimization of this activity in a series of (imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones of which compounds 7e, 8b, 8h, 8j, and 8k were equipotent with chlordiazepoxide while exhibiting reduced anticonvulsant activity, little or no muscle relaxation, and negligible sedative effects.