(E)-1-(4-azidophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol | 1194396-88-7

• 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)-1-(4-azidophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol
• CAS: 1194396-88-7
• 化学式: C₁₅H₁₈N₆O
• 分子量: 298.348
• InChiKey: SEFQFOMHFBLSRR-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-十一炔 、 (E)-1-(4-azidophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 (E)-4,4-dimethyl-1-(4-(4-nonyl-1H-1,2,3-triazol-1-yl)phenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
  参考文献：
  名称：

  Enlarged analogues of uniconazole, new azole containing inhibitors of ABA 8′-hydroxylase CYP707A

  摘要：

  We enlarged the uniconazole (UNI) molecule to find a specific inhibitor of abscisic acid (ABA) 8'-hydroxylase, and synthesized various UNI derivatives that were substituted with hydrophilic and hydrophobic groups at the 4-chlorine of the phenyl group of UNI using click chemistry. Considering its potency in ABA 8'-hydroxylase inhibition, its small effect on seedling growth, and its ease of application, UT4, the UNI derivative containing the C-4 alkyltriazole, was the best candidate for a highly selective inhibitor of ABA 8'-hydroxylase. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.137
• 作为产物：
  描述：

  在 盐酸 、 sodium azide 、 尿素 、 sodium nitrite 作用下， 以 水 为溶剂， 以75%的产率得到(E)-1-(4-azidophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol
  参考文献：
  名称：

  Enlarged analogues of uniconazole, new azole containing inhibitors of ABA 8′-hydroxylase CYP707A

  摘要：

  We enlarged the uniconazole (UNI) molecule to find a specific inhibitor of abscisic acid (ABA) 8'-hydroxylase, and synthesized various UNI derivatives that were substituted with hydrophilic and hydrophobic groups at the 4-chlorine of the phenyl group of UNI using click chemistry. Considering its potency in ABA 8'-hydroxylase inhibition, its small effect on seedling growth, and its ease of application, UT4, the UNI derivative containing the C-4 alkyltriazole, was the best candidate for a highly selective inhibitor of ABA 8'-hydroxylase. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.137

文献信息

• Abscinazole-E1, a novel chemical tool for exploring the role of ABA 8′-hydroxylase CYP707A
  作者：Mariko Okazaki、Hataitip Nimitkeatkai、Taku Muramatsu、Hikaru Aoyama、Kotomi Ueno、Masaharu Mizutani、Nobuhiro Hirai、Satoru Kondo、Toshiyuki Ohnishi、Yasushi Todoroki

  DOI：10.1016/j.bmc.2010.11.011

  日期：2011.1

  We developed abscinazole-E1 (Abz-E1), a specific inhibitor of abscisic acid (ABA) 8'-hydroxylase (CYP707A). This inhibitor was designed and synthesized as an enlarged analogue of uniconazole (UNI), a well-known plant growth retardant, which inhibits a gibberellin biosynthetic enzyme (ent-kaurene oxidase, CYP701A) as well as CYP707A. Our results showed that Abz-E1 functions as a potent inhibitor of CYP707A and a poor inhibitor of CYP701A both in vitro and in vivo. Abz-E1 application to plants resulted in improved desiccation tolerance and an increase in endogenous ABA. (C) 2010 Elsevier Ltd. All rights reserved.