2-n-butyl-3-methyl-1-oxo-1H,5H-pyrido[1,2-a]benzimidazole-4-carbonitrile | 577775-42-9

• 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-n-butyl-3-methyl-1-oxo-1H,5H-pyrido[1,2-a]benzimidazole-4-carbonitrile
• 英文别名: 2-butyl-3-methyl-1-oxo-5H-pyrido[1,2-a]benzimidazole-4-carbonitrile
• CAS: 577775-42-9
• 化学式: C₁₇H₁₇N₃O
• mdl: MFCD04127042
• 分子量: 279.341
• InChiKey: QKRFNJZLDFJRQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-n-butyl-3-methyl-1-oxo-1H,5H-pyrido[1,2-a]benzimidazole-4-carbonitrile 在 三氯氧磷 作用下， 以81%的产率得到2-n-butyl-1-chloro-3-methylpyrido[1,2-a]benzimidazole-4-carbonitrile
  参考文献：
  名称：

  Novel pyridobenzimidazole derivatives exhibiting antifungal activity by the inhibition of β-1,6-glucan synthesis

  摘要：

  Based on the HTS hit compound 1a, an inhibitor of beta-1,6-glucan synthesis, we synthesized novel pyridobenzimidazole derivatives and evaluated their antifungal activity. Among the compounds synthesized, we identified the potent compound 15e, which exhibits excellent activity superior to fluconazole against both Candida glabrata and Candida krusei. From the SAR study, we revealed essential moieties for antifungal activity. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.024
• 作为产物：
  描述：

  2-氰甲基苯并咪唑 、 2-正丁基乙酰乙酸乙酯 在 ammonium acetate 作用下， 以90%的产率得到2-n-butyl-3-methyl-1-oxo-1H,5H-pyrido[1,2-a]benzimidazole-4-carbonitrile
  参考文献：
  名称：

  Novel pyridobenzimidazole derivatives exhibiting antifungal activity by the inhibition of β-1,6-glucan synthesis

  摘要：

  Based on the HTS hit compound 1a, an inhibitor of beta-1,6-glucan synthesis, we synthesized novel pyridobenzimidazole derivatives and evaluated their antifungal activity. Among the compounds synthesized, we identified the potent compound 15e, which exhibits excellent activity superior to fluconazole against both Candida glabrata and Candida krusei. From the SAR study, we revealed essential moieties for antifungal activity. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.024

文献信息

• Imidazo[1,2-a]pyridine derivative
  申请人：Takemura Makoto

  公开号：US20050113397A1

  公开（公告）日：2005-05-26

  A compound reprsented by the following formula (I), its salts or nsolvates thereof capable of specifically or selectively expressig an antifungal activity in a broad spectrum based on the novel mechanism thereof of 1,6-β-glucan synthesis inhibition, and an antifungal agent containing any of them.

  以下化学式（I）所代表的化合物，其盐或无溶剂物，能够基于其新颖的机制——1,6-β-葡聚糖合成抑制，具有广谱的特异性或选择性抗真菌活性，以及含有其中任何一种的抗真菌剂。
• IMIDAZO(1,2-a)PYRIDINE DERIVATIVE
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1479681A1

  公开（公告）日：2004-11-24

  A compound reprsented by the following formula (I), its salts or nsolvates thereof capable of specifically or selectively expressig an antifungal activity in a broad spectrum based on the novel mechanism thereof of 1,6-β-glucan synthesis inhibition, and an antifungal agent containing any of them.

  下式(I)所代表的化合物、其盐类或溶液剂，根据其抑制 1，6-β-葡聚糖合成的新机理，能够特异性或选择性地表达广谱抗真菌活性，以及含有它们中任何一种的抗真菌剂。
• EP1479681
  申请人：——

  公开号：——

  公开（公告）日：——
• Novel pyridobenzimidazole derivatives exhibiting antifungal activity by the inhibition of β-1,6-glucan synthesis
  作者：Hiroshi Takeshita、Jun Watanabe、Yoichi Kimura、Katsuhiro Kawakami、Hisashi Takahashi、Makoto Takemura、Akihiro Kitamura、Kazuhiko Someya、Ryohei Nakajima

  DOI：10.1016/j.bmcl.2010.05.024

  日期：2010.7

  Based on the HTS hit compound 1a, an inhibitor of beta-1,6-glucan synthesis, we synthesized novel pyridobenzimidazole derivatives and evaluated their antifungal activity. Among the compounds synthesized, we identified the potent compound 15e, which exhibits excellent activity superior to fluconazole against both Candida glabrata and Candida krusei. From the SAR study, we revealed essential moieties for antifungal activity. (c) 2010 Elsevier Ltd. All rights reserved.