2-(2-chlorophenyl)-1H-imidazole-4-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-chlorophenyl)-1H-imidazole-4-carbaldehyde
• 英文别名: 2-(2-chlorophenyl)-1H-imidazole-5-carbaldehyde
• 化学式: C₁₀H₇ClN₂O
• 分子量: 206.631
• InChiKey: ZEODDIHUVAIOTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-叔丁基羟胺盐酸盐 、 2-(2-chlorophenyl)-1H-imidazole-4-carbaldehyde 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以73%的产率得到(Z)-α-[2-(2-Chlorophenyl)-1H-imidazol-4-yl]-N-tert-butylnitrone
  参考文献：
  名称：

  Synthesis, Structure, and Neuroprotective Properties of Novel Imidazolyl Nitrones

  摘要：

  A new series of imidazolyl nitrones spin traps has been synthesized and evaluated pharmacologically. The salient structural feature of these molecules is the presence of an imidazole moiety substituted by aromatic or heteroaromatic cycles. This connectivity imparts to the nitrone superior neuroprotective properties in vivo and in parallel reduced side effects and toxicity. Thus compound 6a (a 2-phenylimidazolyl nitrone) administered intraperitoneally protects (80%) mice from lethality induced by an intracerebroventricular administration of tert-butyl hydroperoxide (t-BHP) an oxidant capable of inducing neurodegenerative processes. Administration of the archetypal nitrone phenyl-tert-butyl nitrone (PBN) at an equimolar dose also affords some protection (60%) in this test. However, this activity is accompanied by hypothermia, whereas no such effect is apparent for 6a. Moreover, previously prepared nonsubstituted or alkyl-substituted imidazolyl nitrones were shown to be extremely toxic to rats in contrast to the compounds prepared in this study. The observed activities in vivo correlate well with the calculated partition coefficients (ClogP) and HOMO energy level.

  DOI：

  10.1021/jm991154w
• 作为产物：
  描述：

  2-(邻氯苯基)-2-咪唑啉 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 2-(2-chlorophenyl)-1H-imidazole-4-carbaldehyde
  参考文献：
  名称：

  设计，合成，结构-活性关系研究和X射线晶体学的3-取代的吲哚-2-二-5-羧酸酰胺衍生物作为PAK4抑制剂

  摘要：

  先前我们已经描述了将吲哚啉-2-一-5-羧酰胺确定为有效的PAK4抑制剂。这项研究通过对先导化合物2和3进行一些修饰，扩展了我们原始系列的构效关系。在生化和细胞分析中设计，合成和评估了一系列新型衍生物。该系列中的大多数显示出针对A549和HCT116细胞的纳摩尔生化活性和有效的抗增殖活性。代表性化合物10a表现出优异的酶抑制作用（PAK4 IC 50  = 25 nM）和细胞效价（A549 IC 50  = 0.58μM，HCT116 IC 50  = 0.095μM）。化合物的X射线结构获得与PAK4结合的10a。晶体学分析证实了分子模型的预测，并有助于改进SAR结果。另外，化合物10a显示出集中的多靶点激酶抑制作用，良好的计算药物相似性。化合物10a的进一步分析表明，它对人细胞色素P450的各种同工型均显示出弱的抑制活性。

  DOI：

  10.1016/j.ejmech.2018.05.051

文献信息

• [EN] INHIBITORS OF HCV NS5B POLYMERASE<br/>[FR] INHIBITEURS DE LA POLYMERASE NS5B DU VHC
  申请人：UPJOHN CO

  公开号：WO2004002977A1

  公开（公告）日：2004-01-08

  The present invention porivdes compounds of Formula I, compositons and methods that are useful for treating viral infections and associated diseases, particularly HCV infections and associated diseases.

  本发明提供了式I化合物、组合物及方法，这些化合物、组合物及方法对于治疗病毒感染及相关疾病具有效用，特别是HCV感染及相关疾病。
• Inhibitors of HCV NS5B polymerase
  申请人：Finzel Craig Barry

  公开号：US20060004063A1

  公开（公告）日：2006-01-05

  The present invention provides compounds of Formula I, compositions and methods that are useful for treating viral infections and associated diseases, particularly HCV infections and associated diseases.

  本发明提供了I式化合物、组合物和方法，用于治疗病毒感染和相关疾病，特别是HCV感染和相关疾病。
• Bi-functional complexes and methods for making and using such complexes
  申请人：Gouliaev Alex Haahr

  公开号：US11225655B2

  公开（公告）日：2022-01-18

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.

  本发明涉及一种合成双功能复合物的方法，该复合物包括分子部分和识别分子部分的识别寡核苷酸部分。根据本发明的合成方法的一部分优选在一种或多种有机溶剂中进行，此时包含可选保护标签或寡核苷酸标识符的新生双功能复合物与固体支持物相连接，合成方法的另一部分优选在适合于将寡核苷酸标签酶加到溶液中的新生双功能复合物的条件下进行。
• Highly Efficient, Environment-Friendly, One-Pot Synthesis of 2-Substituted 4-Formylimidazoles from 4-Acylaminoisoxazoles
  作者：Feng Gao、Xin-Chuan Tian、Xiao-Xia Qu、Dan Wang、Dong Pu

  DOI：10.1055/s-0034-1379201

  日期：——

  A highly efficient and environment-friendly one-pot synthesis of 2-substituted 4-formylimidazoles was accomplished. Raney nickel catalyzed hydrogenation of 4-acylaminoisoxazoles in ethanol, followed by sodium hydroxide promoted recyclization of the ring-opened intermediates, afforded the functionalized imidazoles.
• INHIBITORS OF HCV NS5B POLYMERASE
  申请人：Pharmacia & Upjohn Company LLC

  公开号：EP1532128A1

  公开（公告）日：2005-05-25