(S,E)-1-(4-(4-((2-(2-butoxyethoxy)ethoxy)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate | 1376980-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S,E)-1-(4-(4-((2-(2-butoxyethoxy)ethoxy)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 1376980-09-4
• 化学式: C₃₆H₄₅F₃N₆O₆
• 分子量: 714.785
• InChiKey: YCJKYBODIXOMFZ-PANZOTHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  51.0
• 可旋转键数：
  19.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  124.64
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (S,E)-1-(4-(4-((2-(2-butoxyethoxy)ethoxy)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 以72%的产率得到(+)-(S)-abscinazole-E2B
  参考文献：
  名称：

  Abscinazole-E2B, a practical and selective inhibitor of ABA 8′-hydroxylase CYP707A

  摘要：

  We developed abscinazole-E2B (Abz-E2B), a practical and specific inhibitor of abscisic acid (ABA) 80hydroxylase (CYP707A), by structural modification of abscinazole-E1 (Abz-E1), another compound we developed. A butoxy group was introduced to Abz-E2B instead of the tosylate group of Abz-E1, in expectation of better water solubility, because the calculated log P value of Abz-E2B is 3.47, which is smaller than that of Abz-E1 (4.02). The water solubility of Abz-E2B was greater than 90% at a concentration of 100 mu M, at which the solubility of Abz-E1 was 20%. The enzyme specificity was improved significantly. In in vitro assays constructed using recombinant enzymes, (+/-)-Abz-E2B was a considerably weaker inhibitor than (+/-)-Abz-E1 for CYP701A, a GA biosynthetic enzyme, which is a target of S-uniconazole (S-UNI), a lead compound of Abz-E1. (+/-)-Abz-E2B application to plants resulted in improved desiccation tolerance and an increase in endogenous ABA, with little retardation of growth. We also prepared optically pure Abz-E2B and determined its absolute configuration. The R-enantiomer of Abz-E2B was the more potent inhibitor of CYP707A, unlike UNI, whereas both enantiomers were markedly less effective than S-UNI in inhibiting CYP701A. Because S-Abz-E2B arrested the growth of rice seedlings at 100 mu M, probably because of off-target effects, R-Abz-E2B should be used as a chemical tool for research focusing on CYP707A when 100 mu M or higher concentration is required, although (+/-)-Abz-E2B may be useful as an alternative option at a lower concentration. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.068
• 作为产物：
  描述：

  (E)-2-(2-((1-(4-(3-hydroxy-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-1-yl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)ethoxy)ethyl 4-methylbenzenesulfonate 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 oil 为溶剂， 反应 25.25h， 生成 (S,E)-1-(4-(4-((2-(2-butoxyethoxy)ethoxy)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Abscinazole-E2B, a practical and selective inhibitor of ABA 8′-hydroxylase CYP707A

  摘要：

  We developed abscinazole-E2B (Abz-E2B), a practical and specific inhibitor of abscisic acid (ABA) 80hydroxylase (CYP707A), by structural modification of abscinazole-E1 (Abz-E1), another compound we developed. A butoxy group was introduced to Abz-E2B instead of the tosylate group of Abz-E1, in expectation of better water solubility, because the calculated log P value of Abz-E2B is 3.47, which is smaller than that of Abz-E1 (4.02). The water solubility of Abz-E2B was greater than 90% at a concentration of 100 mu M, at which the solubility of Abz-E1 was 20%. The enzyme specificity was improved significantly. In in vitro assays constructed using recombinant enzymes, (+/-)-Abz-E2B was a considerably weaker inhibitor than (+/-)-Abz-E1 for CYP701A, a GA biosynthetic enzyme, which is a target of S-uniconazole (S-UNI), a lead compound of Abz-E1. (+/-)-Abz-E2B application to plants resulted in improved desiccation tolerance and an increase in endogenous ABA, with little retardation of growth. We also prepared optically pure Abz-E2B and determined its absolute configuration. The R-enantiomer of Abz-E2B was the more potent inhibitor of CYP707A, unlike UNI, whereas both enantiomers were markedly less effective than S-UNI in inhibiting CYP701A. Because S-Abz-E2B arrested the growth of rice seedlings at 100 mu M, probably because of off-target effects, R-Abz-E2B should be used as a chemical tool for research focusing on CYP707A when 100 mu M or higher concentration is required, although (+/-)-Abz-E2B may be useful as an alternative option at a lower concentration. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.068