(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-ol | 1376979-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (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-ol
• 英文别名: abscinazole-E2B；(E)-1-[4-[4-[2-(2-butoxyethoxy)ethoxymethyl]triazol-1-yl]phenyl]-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol
• CAS: 1376979-91-7
• 化学式: C₂₆H₃₈N₆O₄
• 分子量: 498.626
• InChiKey: GIJQJYWPDPMZCQ-LFVJCYFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (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-ol 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (+)-(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 、 正丁醇 在 sodium hydride 作用下， 以 oil 为溶剂， 反应 19.25h， 以85%的产率得到(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-ol
  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

文献信息

• ABSCINAZOLE
  申请人：NATIONAL UNIVERSITY CORPORATION SHIZUOKA UNIVERSITY

  公开号：US20170290335A1

  公开（公告）日：2017-10-12

  A compound represented by formula (I) or a salt thereof has an inhibitory action on abscisic acid 8′-hydroxylase CYP707A. The compound or a salt thereof can be used as a plant growth regulator. wherein R is a C1-6 alkyl group, and the C1-6 alkyl group optionally have a substituent selected from the group consisting of a halogen atom and a C1-6 alkoxy group.

  由公式（I）表示的化合物或其盐对脱落酸8'-羟基化酶CYP707A具有抑制作用。该化合物或其盐可用作植物生长调节剂。其中R为C1-6烷基基团，C1-6烷基基团可选择地具有来自卤原子和C1-6烷氧基团的取代基。
• US9820487B2
  申请人：——

  公开号：US9820487B2

  公开（公告）日：2017-11-21
• [EN] ABSCINAZOLE<br/>[FR] ABSCINAZOLE<br/>[JA] アブシナゾール
  申请人：UNIV SHIZUOKA NAT UNIV CORP

  公开号：WO2016047533A1

  公开（公告）日：2016-03-31

  　式（Ｉ）で表される化合物又はその塩は、アブシジン酸８'位水酸化酵素ＣＹＰ７０７Ａの阻害作用を有する。かかる化合物又はその塩は、植物成長調節剤として利用可能である。［ＲはＣ１－６アルキル基であり、Ｃ１－６アルキル基はハロゲン原子及びＣ１－６アルコキシ基からなる群から選択される置換基を有していてもよい。］