2-((4-chloro-6-methylpyrimidin-2-ylthio)methyl)-1H-benzimidazole | 1601469-47-9

• 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: 2-((4-chloro-6-methylpyrimidin-2-ylthio)methyl)-1H-benzimidazole
• 英文别名: 2-{[(4-chloro-6-methylpyrimidin-2-yl)thio]methyl}-1H-benzo[d]imidazole；2-[(4-chloro-6-methylpyrimidin-2-yl)sulfanylmethyl]-1H-benzimidazole
• CAS: 1601469-47-9
• 化学式: C₁₃H₁₁ClN₄S
• 分子量: 290.776
• InChiKey: BAHXZCICUXIHFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((4-chloro-6-methylpyrimidin-2-ylthio)methyl)-1H-benzimidazole 、 二乙醇胺 以 异丙醇 为溶剂， 反应 2.0h， 以81.1%的产率得到2,2'-{{2-{[(1H-benzo[d]imidazol-2-yl)methyl]thio}-6-methylpyrimidin-4-yl}azanediyl}diethanol
  参考文献：
  名称：

  Synthesis, in vitro antimicrobial and cytotoxic activities of novel pyrimidine–benzimidazol combinations

  摘要：

  A series of novel 4-substituted-2-{[(1H-benzo[d] imidazol-2-yl)methyl] thio}-6-methylpyrimidine derivatives were designed, synthesized and evaluated for their cytotoxic activities against four human cancer cell lines and inhibitory activities against five type culture strains in vitro. Some of synthetic pyrimidine-benzimidazol combinations showed good inhibitory activities against Stenotrophomonas maltophilia, especially compounds 7b and 7c. Compounds 7a and 7d exhibited enhanced activities against MGC-803 in vitro, when compared to 5-Fu. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.04.037
• 作为产物：
  描述：

  2-{[(1H-benzo[d]imidazol-2-yl)methyl]thio}-6-methylpyrimidin-4-ol 在 三氯氧磷 、 三氯化磷 作用下， 反应 2.0h， 以96.5%的产率得到2-((4-chloro-6-methylpyrimidin-2-ylthio)methyl)-1H-benzimidazole
  参考文献：
  名称：

  4位含查尔酮结构单元的6-取代-2-(苯并咪 唑-2-亚甲硫基)嘧啶类化合物及其制备方法 和用途

  摘要：

  本发明属于药物化学领域，公开了具有抗肿瘤活性的4位含查尔酮结构单元的6‑取代‑2‑(苯并咪唑‑2‑亚甲硫基)嘧啶类化合物及其制备方法和用途。其具有通式Ⅰ结构，其中：R1为甲基、苯基；R2为3,4,5‑三甲氧基苯基、4‑溴苯基、4‑氟苯基、3‑氟苯基、3‑硝基苯基、3‑溴苯基、3,5‑二氟苯基、2‑氟‑4‑溴苯基、3‑溴‑4‑氟苯基、3‑羟基苯基、2‑噻吩基、2‑呋喃基、3,5‑二氟苯基、3,5‑二氯苯基。初步的体外抗肿瘤活性评价发现该系列化合物对多种肿瘤细胞具有明显的抑制和杀伤作用。开发成为新药后可作为活性成分应用于临床预防和癌症治疗。

  公开号：

  CN106243089B

文献信息

• Synthesis, antimicrobial and cytotoxic activities of pyrimidinyl benzoxazole, benzothiazole and benzimidazole
  作者：D. Seenaiah、P. Ramachandra Reddy、G. Mallikarjuna Reddy、A. Padmaja、V. Padmavathi、N. Siva krishna

  DOI：10.1016/j.ejmech.2014.02.050

  日期：2014.4

  A variety of pyrimidinyl benzoxazoles, benzothiazoles and benzimidazoles linked by thio, methylthio and amino moieties were prepared and studied their antimicrobial and cytotoxic activities. The compound pyrimidinyl bis methylthio benzimidazole 22 was a potent antimicrobial agent particularly against Staphylococcus aureus (29 mm, MIC 12.5 mu g/mL) and Penicillium chrysogenum (38 mm, MIC 12.5 mu g/mL). The amino linked pyrimidinyl bis benzothiazole 24 exhibited cytotoxic activity on A549 cells with IC50 value of 10.5 mu M. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis, in vitro antimicrobial and cytotoxic activities of novel pyrimidine–benzimidazol combinations
  作者：Peng-Ju Chen、Ang Yang、Yi-Fei Gu、Xiao-Song Zhang、Kun-Peng Shao、Deng-Qi Xue、Peng He、Teng-Fei Jiang、Qiu-Rong Zhang、Hong-Min Liu

  DOI：10.1016/j.bmcl.2014.04.037

  日期：2014.6

  A series of novel 4-substituted-2-[(1H-benzo[d] imidazol-2-yl)methyl] thio}-6-methylpyrimidine derivatives were designed, synthesized and evaluated for their cytotoxic activities against four human cancer cell lines and inhibitory activities against five type culture strains in vitro. Some of synthetic pyrimidine-benzimidazol combinations showed good inhibitory activities against Stenotrophomonas maltophilia, especially compounds 7b and 7c. Compounds 7a and 7d exhibited enhanced activities against MGC-803 in vitro, when compared to 5-Fu. (C) 2014 Published by Elsevier Ltd.
• 4位含查尔酮结构单元的6-取代-2-(苯并咪 唑-2-亚甲硫基)嘧啶类化合物及其制备方法 和用途
  申请人：郑州大学

  公开号：CN106243089B

  公开（公告）日：2018-05-15

  本发明属于药物化学领域，公开了具有抗肿瘤活性的4位含查尔酮结构单元的6‑取代‑2‑(苯并咪唑‑2‑亚甲硫基)嘧啶类化合物及其制备方法和用途。其具有通式Ⅰ结构，其中：R1为甲基、苯基；R2为3,4,5‑三甲氧基苯基、4‑溴苯基、4‑氟苯基、3‑氟苯基、3‑硝基苯基、3‑溴苯基、3,5‑二氟苯基、2‑氟‑4‑溴苯基、3‑溴‑4‑氟苯基、3‑羟基苯基、2‑噻吩基、2‑呋喃基、3,5‑二氟苯基、3,5‑二氯苯基。初步的体外抗肿瘤活性评价发现该系列化合物对多种肿瘤细胞具有明显的抑制和杀伤作用。开发成为新药后可作为活性成分应用于临床预防和癌症治疗。