2-imidazol-1-yl-1-phenyl-butan-1-one | 62514-37-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-imidazol-1-yl-1-phenyl-butan-1-one
• 英文别名: 2-Imidazol-1-yl-1-phenylbutan-1-one
• CAS: 62514-37-8
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: SBHYVRMBRSZXGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  咪唑 、 2-溴-1-苯基-1-丁酮 反应 2.0h， 生成 2-imidazol-1-yl-1-phenyl-butan-1-one
  参考文献：
  名称：

  Effects of anti-ecdysteroid azole analogues of metyrapone on the larval development of the fleshfly,Neobellieria bullata

  摘要：

  AbstractBased on our previous finding that PIM (phenyl‐imidazolyl‐metyra‐pon; 2‐(1‐imidazolyl)‐2‐methyl‐1‐phenylpropan‐1‐one, 1) is a strong inhibitor of ecdysone 20‐monooxygenase (IC50 = 7.89 × 10−7 M) from the fleshfly, Neobellieria bullata (Parker) and has also a good toxic action in vivo against this insect, 17 imidazole and 1,2,4‐triazole analogues of metyrapone were synthesized and evaluated for their action against N. bullata larvae in terms of toxicity, length of larval development, weight of the puparium as well as special symptoms, i.e. malformations of the anterior and posterior spiracles, and of the mandibles. The introduction of p‐methoxy (LC50 = 49 mg kg−1 in diet) or p‐chloro (LC50 = 97 mg kg−1) substituents on the benzene ring of PIM resulted in a significant increase in toxicity compared to that of metyrapone (LC50 = 561 mg kg−1) and PIM (LC50 = 148 mg kg−1). The hybridization state of the carbon atom adjacent to the benzene ring was not an important factor for toxicity because the acetoxy derivative (13) was almost as toxic as PIM. At least one methyl group was required on the carbon atom adjacent to the azole ring to maintain activity, while an ethyl group (4) enhanced the toxic effect. At the applied doses some compounds including metyrapone itself, extended the duration of the larval development. Only metyrapone and PIM decreased the puparium weight. Several derivatives induced lethal malformations of mandibles as well as the anterior and posterior spiracles.

  DOI：

  10.1002/ps.2780440304

文献信息

• Effects of anti-ecdysteroid azole analogues of metyrapone on the larval development of the fleshfly,<i>Neobellieria bullata</i>
  作者：Iván Bélai、Béla Darvas、Krisztina Bauer、Mahmoud H. Tag El-Din

  DOI：10.1002/ps.2780440304

  日期：1995.7

  AbstractBased on our previous finding that PIM (phenyl‐imidazolyl‐metyra‐pon; 2‐(1‐imidazolyl)‐2‐methyl‐1‐phenylpropan‐1‐one, 1) is a strong inhibitor of ecdysone 20‐monooxygenase (IC50 = 7.89 × 10−7 M) from the fleshfly, Neobellieria bullata (Parker) and has also a good toxic action in vivo against this insect, 17 imidazole and 1,2,4‐triazole analogues of metyrapone were synthesized and evaluated for their action against N. bullata larvae in terms of toxicity, length of larval development, weight of the puparium as well as special symptoms, i.e. malformations of the anterior and posterior spiracles, and of the mandibles. The introduction of p‐methoxy (LC50 = 49 mg kg−1 in diet) or p‐chloro (LC50 = 97 mg kg−1) substituents on the benzene ring of PIM resulted in a significant increase in toxicity compared to that of metyrapone (LC50 = 561 mg kg−1) and PIM (LC50 = 148 mg kg−1). The hybridization state of the carbon atom adjacent to the benzene ring was not an important factor for toxicity because the acetoxy derivative (13) was almost as toxic as PIM. At least one methyl group was required on the carbon atom adjacent to the azole ring to maintain activity, while an ethyl group (4) enhanced the toxic effect. At the applied doses some compounds including metyrapone itself, extended the duration of the larval development. Only metyrapone and PIM decreased the puparium weight. Several derivatives induced lethal malformations of mandibles as well as the anterior and posterior spiracles.