2-bromomethyl-1-(toluene-4-sulfonyl)-1H-imidazole | 191982-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromomethyl-1-(toluene-4-sulfonyl)-1H-imidazole
• 英文别名: 2-(bromomethyl)-1-(4-methylphenyl)sulfonylimidazole
• CAS: 191982-64-6
• 化学式: C₁₁H₁₁BrN₂O₂S
• 分子量: 315.191
• InChiKey: OQRBCUIGWGXELL-UHFFFAOYSA-N

物化性质

• 沸点：
  462.0±55.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromomethyl-1-(toluene-4-sulfonyl)-1H-imidazole 、 (6aR,9aS)-2-(phenylmethyl)-5,6a,7,8,9,9a-hexahydro-5-methylcyclopent[4,5]imidazo[2,1-b]purin-4(3H)-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-2-(phenylmethyl)-3-{[1-(tolylsulfonyl)imidazol-2-yl]methyl}cyclopent[4,5]imidazo[2,1-b]purin-4(3H)-one
  参考文献：
  名称：

  Potent Tetracyclic Guanine Inhibitors of PDE1 and PDE5 Cyclic Guanosine Monophosphate Phosphodiesterases with Oral Antihypertensive Activity

  摘要：

  Tetracyclic guanines have been shown to be potent and selective inhibitors of the cGMP-hydrolyzing enzymes PDE1 and PDE5. In general, these compounds are inactive or only weakly active as inhibitors of PDE3, which is a major isozyme involved in cAMP hydrolysis. Structure-activity relationships are developed at N-1, C-2, N-3, and N-5 on the core nucleus. Compound 31, with an IC50 of 70 pM, is the most potent inhibitor of PDE1, while 50, with an IC50 of 4 nM, is the most potent inhibitor of PDE5. Compounds 20, 22, 30, and 50 are potent dual inhibitors with IC50 values below 30 nM for both PDE1 and PDE5. Compounds 12, 20, and 28 reduced blood pressure by more than 45 mmHg when administered orally at 10 mg/kg to the spontaneously hypertensive rat (SHR).

  DOI：

  10.1021/jm9608467
• 作为产物：
  描述：

  1-tosyl-1H-imidazole-2-carbaldehyde 在 三乙基硅烷 、 四溴化碳 、 三苯基膦 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-bromomethyl-1-(toluene-4-sulfonyl)-1H-imidazole
  参考文献：
  名称：

  Potent Tetracyclic Guanine Inhibitors of PDE1 and PDE5 Cyclic Guanosine Monophosphate Phosphodiesterases with Oral Antihypertensive Activity

  摘要：

  Tetracyclic guanines have been shown to be potent and selective inhibitors of the cGMP-hydrolyzing enzymes PDE1 and PDE5. In general, these compounds are inactive or only weakly active as inhibitors of PDE3, which is a major isozyme involved in cAMP hydrolysis. Structure-activity relationships are developed at N-1, C-2, N-3, and N-5 on the core nucleus. Compound 31, with an IC50 of 70 pM, is the most potent inhibitor of PDE1, while 50, with an IC50 of 4 nM, is the most potent inhibitor of PDE5. Compounds 20, 22, 30, and 50 are potent dual inhibitors with IC50 values below 30 nM for both PDE1 and PDE5. Compounds 12, 20, and 28 reduced blood pressure by more than 45 mmHg when administered orally at 10 mg/kg to the spontaneously hypertensive rat (SHR).

  DOI：

  10.1021/jm9608467

文献信息

• Methods of making 2,6-diaryl piperidine derivatives
  申请人：Chen Gang

  公开号：US20050154201A1

  公开（公告）日：2005-07-14

  Methods for preparing 2,6-diaryl piperidine derivatives are described. More particularly, 2,6-diaryl piperidines having formula 1-4 are prepared by cyclocondensation of an aryl or heteroaryl aldehyde with 1,3-acetonedicarboxylic acid.

  描述了制备2,6-二芳基哌啶衍生物的方法。更具体地，通过芳基或杂环芳基醛与1,3-乙二酸二甲酯进行环缩合反应制备具有1-4式的2,6-二芳基哌啶。
• Chemokine receptor binding heterocyclic compounds with enhanced efficacy
  申请人：Bridger J. Gary

  公开号：US20050059702A1

  公开（公告）日：2005-03-17

  Compounds that interact with the CXCR4 receptor are described. These compounds are useful in treating, for Example, HIV infection and inflammatory conditions such as rheumatoid arthritis, as well as asthma or cancer, and are useful in methods to elevate progenitor and stem cell counts as well as methods to elevate white blood cell counts.

  描述了与CXCR4受体相互作用的化合物。这些化合物在治疗HIV感染和炎症性疾病（如类风湿性关节炎）、哮喘或癌症方面非常有用，并且在提高祖细胞和干细胞计数以及提高白细胞计数的方法中也非常有用。
• CHEMOKINE RECEPTOR BINDING HETEROCYCLIC COMPOUNDS WITH ENHANCED EFFICACY
  申请人：BRIDGER Gary J.

  公开号：US20090281308A1

  公开（公告）日：2009-11-12

  Compounds that interact with the CXCR4 receptor are described. These compounds are useful in treating, for Example, HIV infection and inflammatory conditions such as rheumatoid arthritis, as well as asthma or cancer, and are useful in methods to elevate progenitor and stem cell counts as well as methods to elevate white blood cell counts.

  描述了与CXCR4受体相互作用的化合物。这些化合物在治疗HIV感染和炎症疾病，如类风湿性关节炎、哮喘或癌症方面非常有用，并且在提高祖细胞和干细胞计数以及提高白细胞计数的方法中也非常有用。
• Method of making a 2,6-diaryl piperidine derivative
  申请人：Genzyme Corporation

  公开号：EP2664617A1

  公开（公告）日：2013-11-20

  Methods for preparing 2,6-diaryl piperidine derivatives are described. More particularly, 2,6-diaryl piperidines having specific formulae are prepared by cyclocondensation of an aryl or heteroaryl aldehyde with 1,3-acetonedicarboxylic acid.

  描述了制备 2,6-二芳基哌啶衍生物的方法。更具体地说，具有特定分子式的 2,6-二芳基哌啶是通过芳基或杂芳基醛与 1,3-丙酮二羧酸的环缩合反应制备的。
• EP1615633A2
  申请人：——

  公开号：EP1615633A2

  公开（公告）日：2006-01-18