abscinazole-F1 | 1192842-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: abscinazole-F1
• 英文别名: (E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[2,1-c][1,4]oxazin-8-ol
• CAS: 1192842-92-4
• 化学式: C₁₇H₁₉ClN₂O₂
• 分子量: 318.803
• InChiKey: JANXIJBMSWPGJW-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  47.28
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (E)-6-tert-butyl-5-(4-chlorobenzylidene)-5H-imidazo[2,1-c][1,4]oxazin-8(6H)-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以38%的产率得到abscinazole-F1
  参考文献：
  名称：

  Abscinazole-F1, a conformationally restricted analogue of the plant growth retardant uniconazole and an inhibitor of ABA 8′-hydroxylase CYP707A with no growth-retardant effect

  摘要：

  To develop a specific inhibitor of abscisic acid (ABA) 8'-hydroxylase, a key enzyme in the catabolism of ABA, a plant hormone involved in stress tolerance, seed dormancy, and other various physiological events, we designed and synthesized conformationally restricted analogues of uniconazole (UNI), a well-known plant growth retardant, which inhibits a biosynthetic enzyme (ent-kaurene oxidase) of gibberellin as well as ABA 8'-hydroxylase. Although most of these analogues were less effective than UNI in inhibition of ABA 8'-hydroxylase and rice seedling growth, we found that a lactol-bridged analogue with an imidazole is a potent inhibitor of ABA 8'-hydroxylase but not of plant growth. This compound, abscinazole-F1, induced drought tolerance in apple seedlings upon spray treatment with a 10 mu M solution. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.070