(+)-9'-fluoroabscisic acid | 171867-81-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-9'-fluoroabscisic acid
• 英文别名: (1'R)-(+)-9'-fluoroabscisic acid；(2Z,4E)-5-[(1R,6R)-6-(fluoromethyl)-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid
• CAS: 171867-81-5
• 化学式: C₁₅H₁₉FO₄
• 分子量: 282.312
• InChiKey: OOKTZCMLEXZZTR-QOMXHDIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-9'-fluoroabscisic acid 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (2Z,4E)-5-((1R,2R,6S)-2-Hydroxy-1,3-dimethyl-5-oxo-bicyclo[4.1.0]hept-3-en-2-yl)-3-methyl-penta-2,4-dienoic acid
  参考文献：
  名称：

  环丙烷类似物探测的脱落酸的生物活性的环构象要求

  摘要：

  为了研究对脱落酸的生物活性构象环需求，环丙烷类似物6，7，9，和10被合成和它们在生物测定4的生物活性进行了测试。还检查了非手性环己二酮类似物8的活性。类似物7，其中6'β-取代基基本上被约束在轴向和二等分之间的轴向样取向上，没有活性，而6和8在C-6'β处无轴状取代基，而与构象偏好无关，其表现出与脱落酸同等的活性。该结果表明，在环的β侧的轴向取代基对活性是致命的。脱落酸的活性构象是C-9'是赤道的且侧链在假轴和双节之间的构象，即与假链的侧链接近的偏爱的半椅子而不是较少的构象。偏爱半椅子和侧链伪赤道仪。

  DOI：

  10.1016/0040-4020(96)00371-7
• 作为产物：
  描述：

  (+/-)-(2Z,4E and 2E,4E)-methyl 5-(6'-fluoromethyl-2',6'-dimethyl-3',4'-didehydro-1'-cyclohexen-1'-yl)-3-methyl-2,4-pentadioate 在 氧气 、 rose bengal 作用下， 生成 (-)-8'-fluoroabscisic acid 、 (+)-9'-fluoroabscisic acid 、 (+)-8'-fluoroabscisic acid 、 (2E,4E)-5-((1S,6R)-6-Fluoromethyl-1-hydroxy-2,6-dimethyl-4-oxo-cyclohex-2-enyl)-3-methyl-penta-2,4-dienoic acid
  参考文献：
  名称：

  1'-脱氧-1'-氟-和8'-氟脱落酸的合成及生物活性

  摘要：

  脱落酸 (ABA) 的解析类似物在水稻幼苗伸长、生菜种子发芽、大麦 α-淀粉酶诱导和叶黄素表皮条生物测定中的气孔开放中进行了测试。(1'S)-(+)-1'-Deoxy-1'-fluoroabscisic acid 的活性为 (1'S)-(+)-ABA 的 110 至 120，几乎与 (1'R)- 相当(+)-1'-脱氧脱落酸在这些测定中。这些结果表明氟原子不能模拟 C-1' 羟基。(1'R,6'S)-(+)-8'-氟脱落酸与(+)-ABA一样有效，对受试植物的影响与(+)-ABA没有区别。该结果表明高度不稳定的 8'-羟基脱落酸的活性与 (+)-ABA 的活性一样强。(-)-对映异构体的活性等于或小于(-)-ABA的活性。

  DOI：

  10.1016/0031-9422(95)00230-5

文献信息

• LANTHIONINE SYNTHETASE COMPONENT C-LIKE PROTEINS AS MOLECULAR TARGETS FOR PREVENTING AND TREATING DISEASES AND DISORDERS
  申请人：BASSAGANYA-RIERA Josep

  公开号：US20110275558A1

  公开（公告）日：2011-11-10

  The present invention relates to the field of medical treatments for diseases and disorders. More specifically, the present invention relates to the use of the lanthionine synthetase component C-like (LANCL) proteins as therapeutic targets for novel classes of anti-inflammatory, immune regulatory and antidiabetic drugs. This includes but it is not limited to abscisic acid (ABA), ABA analogs, benzimidazophenyls, repurposed drugs or drug combinations, including thiazolidinediones (TZDs); naturally occurring compounds such as conjugated diene fatty acids, conjugated triene fatty acids, isoprenoids, and natural and synthetic agonists of peroxisome proliferator-activated receptors that activate this receptor through an alternative mechanism of action involving LANCL2 or other membrane proteins to treat or prevent the common inflammatory pathogenesis underlying type 2 diabetes, atherosclerosis, cancer, some inflammatory infectious diseases such as influenza and autoimmune diseases including but not limited to inflammatory bowel disease (Crohn's disease and Ulcerative colitis), rheumatoid arthritis, multiple sclerosis and type 1 diabetes and other chronic inflammatory conditions.
• US9101573B2
  申请人：——

  公开号：US9101573B2

  公开（公告）日：2015-08-11
• Ring conformational requirement for biological activity of abscisic acid probed by the cyclopropane analogues
  作者：Yasushi Todoroki、Sei-ichi Nakano、Nobuhiro Hirai、Hajime Ohigashi

  DOI：10.1016/0040-4020(96)00371-7

  日期：1996.6

  requirement for the biological activity of abscisic acid, the cyclopropane analogues 6, 7, 9, and 10 were synthesized and their biological activities in four bioassays were tested. The activity of the achiral cyclohexadienone analogue 8 also was examined. Analogue 7 in which the 6′ β-substituent is constrained essentially to the axial-like orientation between axial and bisectional showed no activity, while 6

  为了研究对脱落酸的生物活性构象环需求，环丙烷类似物6，7，9，和10被合成和它们在生物测定4的生物活性进行了测试。还检查了非手性环己二酮类似物8的活性。类似物7，其中6'β-取代基基本上被约束在轴向和二等分之间的轴向样取向上，没有活性，而6和8在C-6'β处无轴状取代基，而与构象偏好无关，其表现出与脱落酸同等的活性。该结果表明，在环的β侧的轴向取代基对活性是致命的。脱落酸的活性构象是C-9'是赤道的且侧链在假轴和双节之间的构象，即与假链的侧链接近的偏爱的半椅子而不是较少的构象。偏爱半椅子和侧链伪赤道仪。
• Synthesis and biological activity of 1′-deoxy-1′-fluoro- and 8′-fluoroabscisic acids
  作者：Yasushi Todoroki、Nobuhiro Hirai、Koichi Koshimizu

  DOI：10.1016/0031-9422(95)00230-5

  日期：1995.10

  α-amylase induction and stomatal opening in spiderwort epidermal strip bioassays. (1′S)-(+)-1′-Deoxy-1′-fluoroabscisic acid showed 110 to 120 of the activity of (1′S)-(+)-ABA and was almost equal to (1′R)-(+)-1′-deoxyabscisic acid in these assays. These results suggest that the fluorine atom cannot mimic the C-1′ hydroxyl group. (1′R,6′S)-(+)-8′-fluoroabscisis acid was as effective as (+)-ABA, and the effect

  脱落酸 (ABA) 的解析类似物在水稻幼苗伸长、生菜种子发芽、大麦 α-淀粉酶诱导和叶黄素表皮条生物测定中的气孔开放中进行了测试。(1'S)-(+)-1'-Deoxy-1'-fluoroabscisic acid 的活性为 (1'S)-(+)-ABA 的 110 至 120，几乎与 (1'R)- 相当(+)-1'-脱氧脱落酸在这些测定中。这些结果表明氟原子不能模拟 C-1' 羟基。(1'R,6'S)-(+)-8'-氟脱落酸与(+)-ABA一样有效，对受试植物的影响与(+)-ABA没有区别。该结果表明高度不稳定的 8'-羟基脱落酸的活性与 (+)-ABA 的活性一样强。(-)-对映异构体的活性等于或小于(-)-ABA的活性。