(E)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol | 76714-97-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol
• CAS: 76714-97-1
• 化学式: C₁₅H₁₈N₄O₃
• 分子量: 302.333
• InChiKey: SJAVRFGXUPEVEA-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.08
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (E)-6-tert-butyl-5-(4-nitrobenzylidene)-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-8-ol
  参考文献：
  名称：

  A conformationally restricted uniconazole analogue as a specific inhibitor of rice ent-kaurene oxidase, CYP701A6

  摘要：

  The plant growth retardant uniconazole (UNI), which has been used as an effective inhibitor of ent-kaurene oxidase (CYP701A) involved in gibberellin biosynthesis, also strongly inhibits ABA 8'-hydroxylase (CYP707A), a key enzyme in abscisic acid catabolism. Azole P450 inhibitors bind to the P450 active site by both coordinating to the heme-iron atom via an sp(2) nitrogen and interacting with surrounding protein residues through a lipophilic region. We hypothesized that poor selectivity of UNI may result from its small molecular size and flexible conformation that allows it to fit into active sites differing in size and shape. To find a selective inhibitor of CYP701A based on this hypothesis, we examined inhibitory activities of three types of UNI analogues, which were conformationally constrained, enlarged in width, and enlarged in length, against recombinant rice CYP701A6 and Arabidopsis CYP707A3. Conformationally restricted analogues, UFAP2 and UFAP2N, inhibited CYP701A6 as strongly as UNI, whereas it inhibited CYP707A3 less than UNI. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.028