2-benzyl-1H-naphth[2,3-d]imidazole | 519019-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-benzyl-1H-naphth[2,3-d]imidazole
• 英文别名: 2-benzylnaphth[2,3-d]imidazole；2-benzyl-1H-benzo[f]benzimidazole
• CAS: 519019-32-0
• 化学式: C₁₈H₁₄N₂
• 分子量: 258.323
• InChiKey: LUWXAOJBEKBFMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  硫酸二甲酯 、 2-benzyl-1H-naphth[2,3-d]imidazole 在 氢氧化钾 作用下， 以 苯 为溶剂， 反应 2.0h， 以20%的产率得到2-benzyl-1-methyl-1H-naphth[2,3-d]imidazole
  参考文献：
  名称：

  Synthesis and cytotoxicity of substituted 2-benzylnaphth[2,3-d]imidazoles

  摘要：

  Designed as a new series of so called "bivalent ligand" containing the proposed 2-benzylnaphthimidazole-type structure, a number of 2-benzylnaphth[2,3-d]imidazoles, bearing various substituents, have been prepared by a synthetic approach involving an heterocyclization of 2,3-diaminonaphthalene 4 with appropriate imidates 3 (for 1b-i) followed by alkylation (for 1j-1) with the desired alkylating agent. Compounds 1b-f, h-1 were subjected to primary biological evaluation for cancer cell growth inhibition (one-dose, three-cell assay), and the four most active terms, 1c, h, i and j, were then evaluated for their cytotoxic profiles in the National Cancer Institute's (NCI) human disease-oriented, 60 cell line, in vitro antitumor screening protocol. Among them, two compounds (1h and 1i) are the most representatives demonstrating not only high growth-inhibitory activities against some leukemia cancer cells, but also fairly good activities against the growth of certain cell lines of some solid tumors. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(03)00197-0
• 作为产物：
  描述：

  2,3-二氨基萘 、 ethyl 2-phenylacetimidate hydrochloride 以 甲醇 为溶剂， 反应 1.0h， 以81%的产率得到2-benzyl-1H-naphth[2,3-d]imidazole
  参考文献：
  名称：

  Synthesis and cytotoxicity of substituted 2-benzylnaphth[2,3-d]imidazoles

  摘要：

  Designed as a new series of so called "bivalent ligand" containing the proposed 2-benzylnaphthimidazole-type structure, a number of 2-benzylnaphth[2,3-d]imidazoles, bearing various substituents, have been prepared by a synthetic approach involving an heterocyclization of 2,3-diaminonaphthalene 4 with appropriate imidates 3 (for 1b-i) followed by alkylation (for 1j-1) with the desired alkylating agent. Compounds 1b-f, h-1 were subjected to primary biological evaluation for cancer cell growth inhibition (one-dose, three-cell assay), and the four most active terms, 1c, h, i and j, were then evaluated for their cytotoxic profiles in the National Cancer Institute's (NCI) human disease-oriented, 60 cell line, in vitro antitumor screening protocol. Among them, two compounds (1h and 1i) are the most representatives demonstrating not only high growth-inhibitory activities against some leukemia cancer cells, but also fairly good activities against the growth of certain cell lines of some solid tumors. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(03)00197-0

文献信息

• Naphthimidazolyl neuropeptide Y receptor antagonists
  申请人：Eli Lilly and Company

  公开号：US05776931A1

  公开（公告）日：1998-07-07

  This invention provides a series of substituted 1H-naphth\x9b2,3-d!imidazoles which are useful in treating a condition associated with an excess of neuropeptide Y. This invention also provides methods employing these substituted 1H-naphth\x9b2,3-d!imidazoles as well as pharmaceutical formulations with comprise as an active ingredient one or more of these compounds.

  这项发明提供了一系列替代的1H-萘\x9b2,3-d!咪唑，可用于治疗与神经肽Y过量有关的疾病。该发明还提供了利用这些替代的1H-萘\x9b2,3-d!咪唑的方法，以及包含这些化合物中一个或多个作为活性成分的药物配方。
• Microwave-assisted one step high-throughput synthesis of benzimidazoles
  作者：Shou-Yuan Lin、Yuko Isome、Ethan Stewart、Ji-Feng Liu、Daniel Yohannes、Libing Yu

  DOI：10.1016/j.tetlet.2006.02.127

  日期：2006.4

  One-pot synthesis of benzimidazoles from diamines and carboxylic acids was developed under microwave irradiation condition, which provided a practical and efficient method for high-throughput synthesis of this important class of heterocyclic compounds. (c) 2006 Elsevier Ltd. All rights reserved.