1-(3,5-dimethylbenzyl)-1,3-dihydro-2H-benzimidazole-2-thione | 1562664-70-3

• 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: 1-(3,5-dimethylbenzyl)-1,3-dihydro-2H-benzimidazole-2-thione
• 英文别名: 1-(3,5-dimethylbenzyl)-1,3-dihydro-2H-benzo[d]imidazole-2-thione；3-[(3,5-dimethylphenyl)methyl]-1H-benzimidazole-2-thione
• CAS: 1562664-70-3
• 化学式: C₁₆H₁₆N₂S
• 分子量: 268.382
• InChiKey: YHCNXUIMCPJIRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  47.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3,5-dimethylbenzyl)-1,3-dihydro-2H-benzimidazole-2-thione 、 N1-(2-氯苯基)-2-氯乙酰胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以72%的产率得到2-{[1-(3,5-dimethylbenzyl)-1H-benzimidazol-2-yl]sulfanyl}-N-2-chlorophenylacetamide
  参考文献：
  名称：

  Design and synthesis of N1-aryl-benzimidazoles 2-substituted as novel HIV-1 non-nucleoside reverse transcriptase inhibitors

  摘要：

  A series of novel N-1-aryl-2-arylthioacetamido-benzimidazoles were synthesized and evaluated as inhibitors of human immunodeficiency virus type-1 (HIV-1). Some of them proved to be effective in inhibiting HIV-1 replication at submicromolar and nanomolar concentration acting as HIV-1 non-nucleoside RT inhibitors (NNRTIs), with low cytotoxicity. The preliminary structure-activity relationship (SAR) of these new derivatives was discussed and rationalized by docking studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.045
• 作为产物：
  描述：

  3,5-二甲基溴苄 在 盐酸 、 sodium hydride 、 锌 作用下， 以 吡啶 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 1-(3,5-dimethylbenzyl)-1,3-dihydro-2H-benzimidazole-2-thione
  参考文献：
  名称：

  Design and synthesis of N1-aryl-benzimidazoles 2-substituted as novel HIV-1 non-nucleoside reverse transcriptase inhibitors

  摘要：

  A series of novel N-1-aryl-2-arylthioacetamido-benzimidazoles were synthesized and evaluated as inhibitors of human immunodeficiency virus type-1 (HIV-1). Some of them proved to be effective in inhibiting HIV-1 replication at submicromolar and nanomolar concentration acting as HIV-1 non-nucleoside RT inhibitors (NNRTIs), with low cytotoxicity. The preliminary structure-activity relationship (SAR) of these new derivatives was discussed and rationalized by docking studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.045

文献信息

• Design and synthesis of N1-aryl-benzimidazoles 2-substituted as novel HIV-1 non-nucleoside reverse transcriptase inhibitors
  作者：Anna-Maria Monforte、Stefania Ferro、Laura De Luca、Giuseppa Lo Surdo、Francesca Morreale、Christophe Pannecouque、Jan Balzarini、Alba Chimirri

  DOI：10.1016/j.bmc.2013.12.045

  日期：2014.2

  A series of novel N-1-aryl-2-arylthioacetamido-benzimidazoles were synthesized and evaluated as inhibitors of human immunodeficiency virus type-1 (HIV-1). Some of them proved to be effective in inhibiting HIV-1 replication at submicromolar and nanomolar concentration acting as HIV-1 non-nucleoside RT inhibitors (NNRTIs), with low cytotoxicity. The preliminary structure-activity relationship (SAR) of these new derivatives was discussed and rationalized by docking studies. (C) 2014 Elsevier Ltd. All rights reserved.