5-bromo-2-(pyridin-2-yl)-1H-benzo[d]imidazole | 1304458-60-3

• 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-2-(pyridin-2-yl)-1H-benzo[d]imidazole
• 英文别名: 5-bromo-2-(pyridin-2-yl)-1H-1,3-benzodiazole；6-bromo-2-pyridin-2-yl-1H-benzimidazole
• CAS: 1304458-60-3
• 化学式: C₁₂H₈BrN₃
• mdl: MFCD20403487
• 分子量: 274.12
• InChiKey: UPORMWWQCXNWOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-二(溴甲基)苯 、 5-bromo-2-(pyridin-2-yl)-1H-benzo[d]imidazole 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Cu(I)-benzimidazole complexes with triphenylphosphine as coligand: DNA lesion and reactive oxygen-dependent mitochondrial dysfunction inducing apoptosis

  摘要：

  DOI：

  10.1016/j.ica.2022.121333
• 作为产物：
  描述：

  2-吡啶甲酸 、 4-溴邻苯二胺 生成 5-bromo-2-(pyridin-2-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Cu(I)-benzimidazole complexes with triphenylphosphine as coligand: DNA lesion and reactive oxygen-dependent mitochondrial dysfunction inducing apoptosis

  摘要：

  DOI：

  10.1016/j.ica.2022.121333

文献信息

• Synthesis of Pyridinyl-benzo[d]imidazole/Pyridinyl-benzo[d]thiazole Derivatives and their Yeast Glucose Uptake Activity In Vitro
  作者：Momin Khan、Riaz Ahmad、Gauhar Rehman、Naeem Gul、Sana Shah、Uzma Salar、Shahnaz Perveen、Khalid Mohammed Khan

  DOI：10.2174/1570180815666181004102209

  日期：2019.9.11

  Diabetes is the primary cause of fatality and disability all over the world, in recent past, we have reported various classes of compounds as anti-glycating agents and we have also reported benzimidazole and benzothiazole derivatives as a potential class of anti-glycating agents. This encouraged us to evaluate the pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 for yeast glucose uptake activity.

  In the present study, an equimolar mixture of pyridine carboxaldehyde derivatives (1 mmol) and sodium metabisulphite (1 mmol) in DMF (10 mL) was stirred for 10 to 15 min, followed by addition of o-phenylene diamine/2-aminothiophenol (1 mmol) into it and refluxed for 3 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was poured into crushed ice. Precipitates were formed which were collected by filtration to produce compounds 1-27 in good yields. Recrystallization from methanol yielded pure crystals.

  Our present study showed that all compounds showed a varying degree of yeast glucose uptake activity in the range IC50 = 36.43-272.20 µM, compared to standard metronidazole (IC50 = 41.86 ± 0.09 µM). Compounds 5 (IC50 = 38.14 ± 0.17 µM), 6 (IC50 = 40.23 ± 0.20 µM), and 7 (IC50 = 36.43 ± 0.02 µM) showed an excellent yeast glucose uptake activity better than the standard.

  Pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 were synthesized, structurally characterized, and evaluated for in vitro yeast glucose uptake activity. Compounds 5 (IC50 = 38.14 ± 0.17 µM), 6 (IC50 = 40.23 ± 0.20 µM), and 7 (IC50 = 36.43 ± 0.02 µM) demonstrated potent yeast glucose uptake activity as compared to standard metronidazole (IC50 = 41.86 ± 0.09 µM). This study identified a number of potential lead molecules which can be helpful in lowering the blood glucose level in hyperglycemia.

  背景：糖尿病是全球致死和致残的主要原因，最近，我们已报告各种类别的化合物作为抗糖基化剂，并且我们还报告苯并咪唑和苯并噻唑衍生物作为一种潜在的抗糖基化剂类。这激励我们评估吡啶基苯并咪唑/吡啶基苯并噻唑衍生物1-27对酵母葡萄糖摄取活性的作用。 方法：在本研究中，将吡啶羧醛衍生物（1 mmol）和亚硫酸钠（1 mmol）在DMF（10 mL）中等摩尔混合物搅拌10至15分钟，然后加入邻苯二胺/2-氨基硫酚（1 mmol）并回流3小时。通过薄层色谱监测反应进展。反应完成后，将反应混合物倒入碎冰中。形成沉淀，通过过滤收集，产生产率良好的化合物1-27。用甲醇再结晶得到纯晶体。 结果：我们的研究表明，所有化合物在酵母葡萄糖摄取活性范围内显示出不同程度的活性，IC50 = 36.43-272.20 µM，与标准甲硝唑（IC50 = 41.86 ± 0.09 µM）相比。化合物5（IC50 = 38.14 ± 0.17 µM）、6（IC50 = 40.23 ± 0.20 µM）和7（IC50 = 36.43 ± 0.02 µM）显示出优异的酵母葡萄糖摄取活性，优于标准物质。 结论：合成了吡啶基苯并咪唑/吡啶基苯并噻唑衍生物1-27，进行了结构表征，并评估了体外酵母葡萄糖摄取活性。化合物5（IC50 = 38.14 ± 0.17 µM）、6（IC50 = 40.23 ± 0.20 µM）和7（IC50 = 36.43 ± 0.02 µM）表现出强大的酵母葡萄糖摄取活性，与标准甲硝唑（IC50 = 41.86 ± 0.09 µM）相比。该研究确定了一系列潜在的先导分子，有助于降低高血糖水平。
• ARYL AND HETEROARYL SULFONES AS MGLUR4 ALLOSTERIC POTENTIATORS, COMPOSITIONS, AND METHODS OF TREATING NEUROLOGICAL DYSFUNCTION
  申请人：Conn P. Jeffrey

  公开号：US20120245185A1

  公开（公告）日：2012-09-27

  In one aspect, the invention relates to sulfone compounds which are useful as allosteric potentiators/positive allosteric modulators of the metabotropic glutamate receptor subtype 4 (mGluR4); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds, for example, in treating neurological and psychiatric disorders or other disease state associated with glutamate dysfunction.

  在一个方面，本发明涉及用作代谢型谷氨酸受体亚型4（mGluR4）的变构剂/正变构调节剂的磺酮化合物；制备该化合物的合成方法；包含该化合物的制药组合物；以及使用该化合物的方法，例如，用于治疗神经系统和精神疾病或与谷氨酸功能障碍相关的其他疾病状态。
• Aryl and heteroaryl sulfones as mGluR4 allosteric potentiators, compositions, and methods of treating neurological dysfunction
  申请人：Conn P. Jeffrey

  公开号：US08912336B2

  公开（公告）日：2014-12-16

  In one aspect, the invention relates to sulfone compounds which are useful as allosteric potentiators/positive allosteric modulators of the metabotropic glutamate receptor subtype 4 (mGluR4); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds, for example, in treating neurological and psychiatric disorders or other disease state associated with glutamate dysfunction.

  在一个方面，本发明涉及作为代谢型谷氨酸受体亚型4（mGluR4）的变构剂/正变构调节剂有用的磺酮化合物；制备该化合物的合成方法；包含该化合物的药物组合物；以及使用该化合物的方法，例如用于治疗神经系统和精神障碍或与谷氨酸功能障碍相关的其他疾病状态。
• US8912336B2
  申请人：——

  公开号：US8912336B2

  公开（公告）日：2014-12-16
• CN117024451
  申请人：——

  公开号：——

  公开（公告）日：——