1-(3-bromophenethyl)-1H-imidazole | 912962-94-8

• 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: 1-(3-bromophenethyl)-1H-imidazole
• 英文别名: 1-[2-(3-bromophenyl)ethyl]-1H-imidazole；1-[2-(3-bromophenyl)ethyl]imidazole
• CAS: 912962-94-8
• 化学式: C₁₁H₁₁BrN₂
• 分子量: 251.126
• InChiKey: XZKCJKLTIMFTAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 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：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-bromophenethyl)-1H-imidazole 在 四(三苯基膦)钯 三氯化硼 、 sodium carbonate 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 7.0h， 生成 N-butyloxycarbonyl-3-[3-(2-benzoimidazol-1-ylethyl)phenyl]-5-iso-butyl-thiophene-2-sulfonamide
  参考文献：
  名称：

  WO2006/109048

  摘要：

  公开号：
• 作为产物：
  描述：

  在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 反应 3.67h， 以72%的产率得到1-(3-bromophenethyl)-1H-imidazole
  参考文献：
  名称：

  From the First Selective Non-Peptide AT₂ Receptor Agonist to Structurally Related Antagonists

  摘要：

  A para substitution pattern of the phenyl ring is a characteristic feature of the first reported selective AT(2) receptor agonist M024/C21 (1) and all the nonpeptidic AT(2) receptor agonists described so far. Two series of compounds structurally related to 1 but with a meta substitution pattern have now been synthesized and biologically evaluated for their affinity to the AT(1) and AT(2) receptors. A high AT(2)/AT(1) receptor selectivity was obtained with all 41 compounds synthesized, and the majority exhibited K-i ranging from 2 to 100 nM. Five compounds were evaluated for their functional activity at the AT(2) receptor, applying a neurite outgrowth assay in NG108-15 cells.. Notably, four of the five compounds, with representatives from both series, acted as potent AT(2) receptor antagonists. These compounds were found to be considerably more effective than PD 123,319, the standard AT(2) receptor antagonist used in most laboratories. No AT(2) receptor antagonists were previously reported among the derivatives with a para substitution pattern. Hence, by a minor modification of the agonist 1 it could be transformed into the antagonist, compound 38. These compounds should serve as valuable tools in the assessment of the role of the AT(2) receptor in more complex physiological models.

  DOI：

  10.1021/jm2015099

文献信息

• New Arylethanolimidazole Derivatives as HO-1 Inhibitors with Cytotoxicity against MCF-7 Breast Cancer Cells
  作者：Valeria Ciaffaglione、Sebastiano Intagliata、Valeria Pittalà、Agostino Marrazzo、Valeria Sorrenti、Luca Vanella、Antonio Rescifina、Giuseppe Floresta、Ameera Sultan、Khaled Greish、Loredana Salerno

  DOI：10.3390/ijms21061923

  日期：——

  In this paper, a novel series of imidazole-based heme oxygenase-1 (HO-1) inhibitors is reported. These compounds were obtained by modifications of previously described high potent and selective arylethanolimidazoles. In particular, simplification of the central linker and repositioning of the hydrophobic portion were carried out. Results indicate that a hydroxyl group in the central region is crucial for the potency as well as the spatial distribution of the hydrophobic portion. Docking studies revealed a similar interaction of the classical HO-1 inhibitors with the active site of the protein. The most potent and selective compound (5a) was tested for its potential cytotoxic activity against hormone-sensitive and hormone-resistant breast cancer cell lines (MCF-7 and MDA-MB-231).

  在这篇论文中，报道了一系列新型的咪唑基血红素氧合酶-1（HO-1）抑制剂。这些化合物是通过对先前描述的高效和选择性芳基乙醇咪唑进行修改而获得的。特别是，对中心连接物的简化和疏水部分的重新定位进行了。结果表明，中心区域的羟基对于药效以及疏水部分的空间分布至关重要。对接研究揭示了经典HO-1抑制剂与蛋白质活性位点的类似相互作用。最有效和选择性的化合物（5a）被测试其对激素敏感和激素抵抗性乳腺癌细胞系（MCF-7和MDA-MB-231）的潜在细胞毒活性。
• Tricyclic Angiotensin II Agonists
  申请人：Alterman Mathias

  公开号：US20090042931A1

  公开（公告）日：2009-02-12

  There is provided compounds of formula I, wherein A, X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , R 4 and R 5 have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful as selective agonists of the AT2 receptor, and thus, in particular, in the treatment of inter alia gastrointestinal conditions, such as dyspepsia, IBS and MOF, and cardiovascular disorders.

  提供了公式I的化合物，其中A、X1、X2、X3、X4、Y1、Y2、Y3、Y4、Z1、Z2、R4和R5的含义在说明中给出，并且其药物可接受的盐，这些化合物可作为AT2受体的选择性激动剂使用，因此，特别是在治疗胃肠道疾病，如消化不良、肠易激综合症和多器官功能障碍等方面，以及心血管疾病方面具有用途。
• Tricyclic angiotensin II agonists
  申请人：Vicore Pharma AB

  公开号：US08080571B2

  公开（公告）日：2011-12-20

  There is provided compounds of formula I, wherein A, X1, X2, X3, X4, Y1, Y2, Y3, Y4, Z1, Z2, R4 and R5 have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful as selective agonists of the AT2 receptor, and thus, in particular, in the treatment of inter alia gastrointestinal conditions, such as dyspepsia, IBS and MOF, and cardiovascular disorders.

  提供了I式化合物，其中A、X1、X2、X3、X4、Y1、Y2、Y3、Y4、Z1、Z2、R4和R5的含义在描述中给出，并且其药学上可接受的盐，这些化合物可用作AT2受体的选择性激动剂，因此特别适用于治疗胃肠道疾病，如消化不良、肠易激综合征和MOF，以及心血管疾病。
• NEW TRICYCLIC ANGIOTENSIN II AGONISTS
  申请人：Vicore Pharma AB

  公开号：EP1869023B1

  公开（公告）日：2012-01-11
• US8080571B2
  申请人：——

  公开号：US8080571B2

  公开（公告）日：2011-12-20