(1R,3S,6R)-(3'Z)-1,5,5-trimethyl-6-(3'-methyl-5'-(phenylthio)pent-3'-en-1'-ynyl)-7-oxabicyclo[4.1.0]heptan-3-ol | 1159072-34-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1R,3S,6R)-(3'Z)-1,5,5-trimethyl-6-(3'-methyl-5'-(phenylthio)pent-3'-en-1'-ynyl)-7-oxabicyclo[4.1.0]heptan-3-ol
• 英文别名: (1R,3S,6R)-1,5,5-trimethyl-6-[(Z)-3-methyl-5-phenylsulfanylpent-3-en-1-ynyl]-7-oxabicyclo[4.1.0]heptan-3-ol
• CAS: 1159072-34-0
• 化学式: C₂₁H₂₆O₂S
• 分子量: 342.502
• InChiKey: CXSZEXSUNNJPIF-STDAQHLQSA-N

物化性质

• 沸点：
  472.6±45.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  58.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,3S,6R)-(3'Z)-6-(5'-hydroxy-3'-methylpent-3'-en-1'-ynyl)-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol 、 二苯二硫醚 在 三丁基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以54%的产率得到(1R,3S,6R)-(3'Z)-1,5,5-trimethyl-6-(3'-methyl-5'-(phenylthio)pent-3'-en-1'-ynyl)-7-oxabicyclo[4.1.0]heptan-3-ol
  参考文献：
  名称：

  Inhibitors of a 9-cis epoxycarotenoid dioxygenase

  摘要：

  公式（I）的化合物：其中：R1为—SR10，—O—C（O）—R11，—NR12R13，其中R10为C1-8-烷基或苯基，未取代或取代为C1-4-烷基；R11为噻吩基、呋喃基或吡咯基；R12为H或C1-4-烷基，R13为C1-8-烷基或苯基，未取代或取代为C1-4-烷基；R2为H或C1-4-烷基；R3和R4分别为H或C1-4-烷基；R5和R6分别为H、OH或OR14，或者一起为═O，其中R14为保护基；R7为H或C1-4-烷基；R8为H，R9为OH，R15为H，或者R15为H，R8和R9一起为—O—，或者R9为OH，R8和R15一起形成键；R18和R19均为H，或者R18和R19一起形成键，或其植物生理学上可接受的盐对于抑制植物或种子中的9-顺式-环氧类胡萝卜二氧化酶（NCED）是有用的，因此对于调节植物或种子中的ABA生物合成是有用的。

  公开号：

  US20100160166A1

文献信息

• Sesquiterpene-like inhibitors of a 9-cis-epoxycarotenoid dioxygenase regulating abscisic acid biosynthesis in higher plants
  作者：Jason Boyd、Yuanzhu Gai、Ken M. Nelson、Erica Lukiwski、James Talbot、Mary K. Loewen、Stacey Owen、L. Irina Zaharia、Adrian J. Cutler、Suzanne R. Abrams、Michele C. Loewen

  DOI：10.1016/j.bmc.2009.01.076

  日期：2009.4

  Abscisic acid (ABA) is a carotenoid-derived plant hormone known to regulate critical functions in growth, development and responses to environmental stress. The key enzyme which carries out the first committed step in ABA biosynthesis is the carotenoid cleavage 9-cis-epoxycarotenoid dioxygenase (NCED). We have developed a series of sulfur and nitrogen-containing compounds as potential ABA biosynthesis inhibitors of the NCED, based on modification of the sesquiterpenoid segment of the 9-cis-xanthophyll substrates and product. In in vitro assays, three sesquiterpene-like carotenoid cleavage dioxygenase (SLCCD) inhibitor compounds 13, 17 and 18 were found to act as inhibitors of Arabidopsis thaliana NCED 3 (AtNCED3) with K-i'S of 93, 57 and 87 mu M, respectively. Computational docking to a model of AtNCED3 supports a mechanism of inhibition through coordination of the heteroatom with the non-heme iron in the enzyme active site. In pilot studies, pretreatment of osmotically stressed Arabidopsis plants with compound 13 resulted lower levels of ABA and catabolite accumulation compared to levels in mannitol-stressed plant controls. This same inhibitor moderated known ABA-induced gene regulation effects and was only weakly active in inhibition of seed germination. Interestingly, all three inhibitors led to moderation of the stress-induced transcription of AtNCED3 itself, which could further contribute to lowering ABA biosynthesis in planta. Overall, these sesquiterpenoid-like inhibitors present new tools for controlling and investigating ABA biosynthesis and regulation. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.
• US8283481B2
  申请人：——

  公开号：US8283481B2

  公开（公告）日：2012-10-09