2-(4-(tert-butyl)phenyl)-1H-imidazol | 1225882-59-6

• 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-(4-(tert-butyl)phenyl)-1H-imidazol
• 英文别名: 2-(4-tert-butylphenyl)-1H-imidazole
• CAS: 1225882-59-6
• 化学式: C₁₃H₁₆N₂
• 分子量: 200.283
• InChiKey: DARCFSYZWARYEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-(tert-butyl)phenyl)-1H-imidazol 在 四丁基氟化铵 、 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 、 正戊烷 为溶剂， 生成 C₂₃H₂₆N₂O₄
  参考文献：
  名称：

  Discovery of 4-Aryl-2-benzoyl-imidazoles as Tubulin Polymerization Inhibitor with Potent Antiproliferative Properties

  摘要：

  A series of 4-aryl-2-benzoyl-imidazoles were designed and synthesized based on our previously reported 2-aryl-4-benzoyl-imidazole (ABI) derivatives. The new structures reversed the aryl group and the benzoyl group of previous ABI structures and were named as reverse ABI (RABI) analogues. RABIs were evaluated for biological activity against eight cancer cell lines including multidrug-resistant cancer cell lines. In vitro assays indicated that several RABI compounds had excellent antiproliferative properties, with IC50 values in the low, nanomolar range. The average IC50 of the most active compound 12a is 14 nM. In addition, the mechanism of action of these new analogues was investigated by cell cycle analysis, tubulin polymerization assay, competitive mass spectrometry binding assay, and molecular docking studies. These studies confirmed that these new RABI analogues maintain their mechanisms of action by disrupting tubulin polymerization, similar to their parental ABI analogues.

  DOI：

  10.1021/jm4001117
• 作为产物：
  描述：

  草酸醛 、 对叔丁基苯甲醛 在 ammonium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 生成 2-(4-(tert-butyl)phenyl)-1H-imidazol
  参考文献：
  名称：

  Discovery of 4-Aryl-2-benzoyl-imidazoles as Tubulin Polymerization Inhibitor with Potent Antiproliferative Properties

  摘要：

  A series of 4-aryl-2-benzoyl-imidazoles were designed and synthesized based on our previously reported 2-aryl-4-benzoyl-imidazole (ABI) derivatives. The new structures reversed the aryl group and the benzoyl group of previous ABI structures and were named as reverse ABI (RABI) analogues. RABIs were evaluated for biological activity against eight cancer cell lines including multidrug-resistant cancer cell lines. In vitro assays indicated that several RABI compounds had excellent antiproliferative properties, with IC50 values in the low, nanomolar range. The average IC50 of the most active compound 12a is 14 nM. In addition, the mechanism of action of these new analogues was investigated by cell cycle analysis, tubulin polymerization assay, competitive mass spectrometry binding assay, and molecular docking studies. These studies confirmed that these new RABI analogues maintain their mechanisms of action by disrupting tubulin polymerization, similar to their parental ABI analogues.

  DOI：

  10.1021/jm4001117

文献信息

• Rh-Catalyzed Annulation of <i>ortho</i> -C−H Bonds of 2-Arylimidazoles with 1,4,2-Dioxazol-5-ones toward 5-Arylimidazo[1,2-<i>c</i> ]quinazolines
  作者：Xiaopeng Wu、Song Sun、Shengbo Xu、Jiang Cheng

  DOI：10.1002/adsc.201701331

  日期：2018.3.20

  A Rh‐catalyzed unique and direct approach for constructing a series of 5‐arylimidazo[1,2‐c]quinazolines in moderate to excellent yields from simple and readily available 2‐arylimidazoles and 3‐phenyl‐1,4,2‐dioxazol‐5‐ones was described. This procedure proceeds with sequential ortho‐C−H bond amidation and cyclization, which represents a facile and straightforward pathway to access such frameworks.

  用Rh催化的独特直接方法从简单易得的2芳基咪唑和3苯基-1,4,2-二恶唑-以中等到优异的收率构建一系列5芳基咪唑[1,2- c ]喹唑啉描述了5分。此过程以顺序的邻-C-H键酰胺化和环化进行，这代表了访问此类框架的便捷途径。
• Synthesis of benzoazepine derivatives <i>via</i> Rh(<scp>iii</scp>)-catalyzed inert C(sp²)–H functionalization and [4 + 3] annulation
  作者：Yuanshuang Xu、Linghua Zhang、Mengyang Liu、Xiaopeng Zhang、Xinying Zhang、Xuesen Fan

  DOI：10.1039/c9ob01830a

  日期：——

  In this paper, a novel and sustainable synthesis of the hitherto unreported 5H-benzo[c]imidazo[1,2-a]azepine-6-carboxylic acids via the cascade reactions of 2-arylimidazoles (1) with methylene-oxetanones (2) is presented. Mechanistically, the formation of the title compounds is triggered by a Rh(iii)-catalyzed C(sp2)-H alkenylation of 1 with 2 followed by an intramolecular N-nucleophilic substitution

  本文通过2-芳基咪唑（1）与亚甲基-氧杂环丁酮（2）的级联反应，合成了迄今未报道的5H-苯并[c]咪唑并[1,2-a]氮杂6-羧酸的新型且可持续的合成方法） 被表达。从机理上讲，Rh（iii）催化的C（sp2）-H烯基化反应为1与2，然后进行分子内N-亲核取代，触发了标题化合物的形成。用这种方法，以中等到良好的效率制备了一系列杂合化合物，这些杂合化合物结合了具有生物学前途的咪唑和苯并氮杂pine部分，并用合成的通用羧基修饰。此外，如此获得的产物的实用性通过将它们有效地转化为一些否则难以获得的五环化合物而得以显着展示。
• 一种5H-苯并[c]咪唑并[1,2-a]氮杂环庚烯- 6-羧酸类化合物的合成方法
  申请人：河南师范大学

  公开号：CN110372708B

  公开（公告）日：2021-07-09

  本发明公开了一种5H‑苯并[c]咪唑并[1,2‑a]氮杂环庚烯‑6‑羧酸类化合物的合成方法，该合成方法通过2‑芳基咪唑或2‑杂芳基咪唑类化合物和2‑甲烯基丙内酯类化合物之间的串联反应合成5H‑苯并[c]咪唑并[1,2‑a]氮杂环庚烯‑6‑羧酸类化合物，本发明具有操作简便、条件温和、底物适用范围广等优点，适合于工业化生产。
• PYRAZOLO[1,5-a]PYRIMIDINE COMPOUNDS AS mTOR INHIBITORS
  申请人：Siddiqui M. Arshad

  公开号：US20120322791A1

  公开（公告）日：2012-12-20

  The present invention provides Pyrazolopyrimidine Compounds of Formula (I): wherein L, T, Z, U, V, W, R 3 , R 6 , R 7 , R 8 , and m are as defined herein, and pharmaceutically acceptable salts of such Pyrazolopyrimidine Compounds. The Pyrazolopyrimidine Compounds are useful in the treatment of cancer and other diseases or disorders wherein mTOR is deregulated.

  本发明提供了式（I）的吡唑吡咯啉化合物：其中L、T、Z、U、V、W、R3、R6、R7、R8和m如本文所定义，并且这些吡唑吡咯啉化合物的药物可接受的盐。这些吡唑吡咯啉化合物在治疗癌症和其他mTOR失调的疾病或疾病中具有用处。
• FUSED TRICYCLIC COMPOUNDS AS mTOR INHIBITORS
  申请人：Meng Zhaoyang

  公开号：US20140171456A1

  公开（公告）日：2014-06-19

  The present invention relates to certain pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine and dipyrazolopyrimidine compounds of Formula (I) as inhibitors of mammalian Target Of Rapamycin (mTOR) kinase, which is also known as FRAP, RAFT, RAPT or SEP. The compounds may be used in the treatment of cancer and other disorders where mTOR is deregulated. The present invention further provides pharmaceutical compositions comprising the pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine or dipyrazolopyrimidine compounds.

  本发明涉及某些式（I）的吡唑并[1,5-a]吡咯并[3,2-e]嘧啶和二吡唑嘧啶化合物，作为哺乳动物雷帕霉素靶点（mTOR）激酶的抑制剂，该激酶也被称为FRAP、RAFT、RAPT或SEP。这些化合物可用于治疗癌症和其他mTOR失调的疾病。本发明还提供包含吡唑并[1,5-a]吡咯并[3,2-e]嘧啶或二吡唑嘧啶化合物的制药组合物。