5-bromo-1-(2-phenylethyl)-1H-benzimidazole | 679794-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-bromo-1-(2-phenylethyl)-1H-benzimidazole
• 英文别名: 5-bromo-1-phenethyl-1H-benzo[d]imidazole；5-bromo-1-(2-phenylethyl)benzimidazole
• CAS: 679794-09-3
• 化学式: C₁₅H₁₃BrN₂
• 分子量: 301.186
• InChiKey: YDDIMGWUJMBBNV-UHFFFAOYSA-N

物化性质

• 沸点：
  443.5±47.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  5-bromo-1-(2-phenylethyl)-1H-benzimidazole 、 3,5-二甲基异恶唑-4-硼酸频哪醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 以21%的产率得到3,5-dimethyl-4-(1-phenethyl-1H-benzo[d]imidazol-5-yl)isoxazole
  参考文献：
  名称：

  CBP/p300 溴结构域小分子配体的发现和优化

  摘要：

  缺乏针对溴结构域和末端外 (BET) 亚家族之外的溴结构域的小分子抑制剂。在这里，我们描述了人类赖氨酸乙酰转移酶 CBP/p300 溴结构域模块的高效和选择性配体，由一系列 5-异恶唑基苯并咪唑开发而成。我们的出发点是片段命中，使用 Suzuki 偶联、苯并咪唑形成反应和还原胺化的平行合成将其优化为更有效和选择性更强的先导化合物。使用热稳定性测定法研究了先导化合物对其他溴结构域家族成员的选择性，结果显示对结构相关的 BET 家族成员有一些抑制作用。为了解决 BET 选择性问题，与 CREB ​​结合蛋白 (CBP) 和 BRD4 的第一个溴结构域 (BRD4(1)) 结合的先导化合物的 X 射线晶体结构用于指导更具选择性的化合物的设计。获得的晶体结构揭示了两种不同的结合模式。通过改变芳基取代模式和开发构象受限的类似物，增加了 CBP 超过 BRD4(1) 的选择性。优化后的化合物具有高效 (Kd

  DOI：

  10.1021/ja412434f
• 作为产物：
  描述：

  甲酸 、 4-bromo-N1-(2-phenylethyl)-1,2-benzenediamine 反应 1.0h， 生成 5-bromo-1-(2-phenylethyl)-1H-benzimidazole
  参考文献：
  名称：

  LPA RECEPTOR ANTAGONISTS

  摘要：

  公开号：

  EP1553075B1

文献信息

• LPA Receptor Antagonists
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP2565178A1

  公开（公告）日：2013-03-06

  A compound of the general formula (I): (wherein the symbols are as defined in the description), or a non-toxic salt thereof This compound engages in LPA receptor bonding and antagonism and hence is useful in the prevention and/or treatment of urinary system disease (symptom with prostatic hypertrophy or neurogenic bladder dysfunction disease, symptom to be caused by spinal cord neoplasm, nucleous hernia, spinal canal stenosis or diabetes, occlusion disease of lower urinary tract, inflammatory disease of lower urinary tract, polyuria), carcinoma-associated disease (solid tumor, solid tumor metastasis, angiofibroma, myeloma, multiple myeloma, Kaposi's sarcoma, leucemia and carcinomatous infiltration transition), proliferative disease (disorder with aberrant angiogenesis, artery obstruction and pulmonary fibrosis), inflammation / immune system disease (psoriasis, nephropathy, hepatitis and pneumonitis symptom), disease caused by secretory dysfunction (Sjogren syndrome), brain-related disease (brain infarction, cerebral apoplexy and brain or peripheral neuropathy) or chronic disease (chronic asthma, glomerulonephritis, obesity, prostate hyperplasia, diseases caused by arteriosclerosis process, rheumatism or atopic dermatitis).

  通式(I)的化合物： (其中符号如描述中所定义），或其无毒盐 该化合物参与 LPA 受体的结合和拮抗作用，因此可用于预防和/或治疗泌尿系统疾病（症状为前列腺肥大或神经源性膀胱功能障碍疾病、脊髓肿瘤、核疝、椎管狭窄或糖尿病、下尿路闭塞症、下尿路炎症、多尿）、癌症相关疾病（实体瘤、实体瘤转移、血管纤维瘤、骨髓瘤、多发性骨髓瘤卡波西肉瘤、白血病和癌浸润转变）、增殖性疾病（血管异常生成障碍、动脉阻塞和肺纤维化）、炎症/免疫系统疾病（银屑病、肾病、肝炎和肺炎症状）、分泌功能障碍引起的疾病（Sjogren 综合症）、与脑有关的疾病（脑梗塞、脑中风、脑或周围神经病）或慢性疾病（慢性哮喘、肾小球肾炎、肥胖症、前列腺增生、动脉硬化过程引起的疾病、风湿病或特应性皮炎）。
• Lpa receptor antagonist
  申请人：Terakado Masahiko

  公开号：US20060148830A1

  公开（公告）日：2006-07-06

  A compound of the general formula (I): (wherein the symbols are as defined in the description), or a non-toxic salt thereof. This compound engages in LPA receptor bonding and antagonism and hence is useful in the prevention and/or treatment of urinary system disease (symptom with prostatic hypertrophy or neurogenic bladder dysfunction disease, symptom to be caused by spinal cord neoplasm, nucleous hernia, spinal canal stenosis or diabetes, occlusion disease of lower urinary tract, inflammatory disease of lower urinary tract, polyuria), carcinoma-associated disease (solid tumor, solid tumor metastasis, angiofibroma, myeloma, multiple myeloma, Kaposi's sarcoma, leucemia and carcinomatous infiltration transition), proliferative disease (disorder with aberrant angiogenesis, artery obstruction and pulmonary fibrosis), inflammation/immune system disease (psoriasis, nephropathy, hepatitis and pneumonitis symptom), disease caused by secretory dysfunction (Sjogren syndrome), brain-related disease (brain infarction, cerebral apoplexy and brain or peripheral neuropathy) or chronic disease (chronic asthma, glomerulonephritis, obesity, prostate hyperplasia, diseases caused by arteriosclerosis process, rheumatism or atopic dermatitis).
• LPA RECEPTOR ANTAGONIST
  申请人：Terakado Masahiko

  公开号：US20080293764A1

  公开（公告）日：2008-11-27

  A compound of the general formula (I): (wherein the symbols are as defined in the description), or a non-toxic salt thereof. This compound engages in LPA receptor bonding and antagonism and hence is useful in the prevention and/or treatment of urinary system disease (symptom with prostatic hypertrophy or neurogenic bladder dysfunction disease, symptom to be caused by spinal cord neoplasm, nucleous hernia, spinal canal stenosis or diabetes, occlusion disease of lower urinary tract, inflammatory disease of lower urinary tract, polyuria), carcinoma-associated disease (solid tumor, solid tumor metastasis, angiofibroma, myeloma, multiple myeloma, Kaposi's sarcoma, leucemia and carcinomatous infiltration transition), proliferative disease (disorder with aberrant angiogenesis, artery obstruction and pulmonary fibrosis), inflammation/immune system disease (psoriasis, nephropathy, hepatitis and pneumonitis symptom), disease caused by secretory dysfunction (Sjogren syndrome), brain-related disease (brain infarction, cerebral apoplexy and brain or peripheral neuropathy) or chronic disease (chronic asthma, glomerulonephritis, obesity, prostate hyperplasia, diseases caused by arteriosclerosis process, rheumatism or atopic dermatitis).
• US7820682B2
  申请人：——

  公开号：US7820682B2

  公开（公告）日：2010-10-26
• US8124645B2
  申请人：——

  公开号：US8124645B2

  公开（公告）日：2012-02-28