6-hydroxy-6-(2-methoxy-6-naphthyl)hexanoic acid | 134754-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-hydroxy-6-(2-methoxy-6-naphthyl)hexanoic acid
• 英文别名: 6-hydroxy-6-(6-methoxynaphth-2-yl)hexanoic acid；6-Hydroxy-6-(6-methoxynaphthalen-2-yl)hexanoic acid
• CAS: 134754-90-8
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: NUOITRBHWCQUPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-萘甲醚 在 氢氧化钾 、 sodium tetrahydroborate 、 三氯化铝 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 6-hydroxy-6-(2-methoxy-6-naphthyl)hexanoic acid
  参考文献：
  名称：

  Novel 6-oxo-6-naphthylhexanoic acid derivatives with anti-inflammatory and 5-lipoxygenase inhibitory activity

  摘要：

  A series of novel 6-(6-alkoxy-2-naphthyl)oxoalkanoates and alkanamides were synthesized as inhibitors of inflammation and 5-lipoxygenase. They were evaluated in vivo for anti-inflammatory activity in the established adjuvent arthritis assay in rats and in vitro as inhibitors of 5-lipoxygenase in rat basophilic leukemia (RBL) cells. N-Hydroxy-N-methyl-6-(6-methoxy-2-naphthyl)-6-oxohexanamide, compound 28, which is representative of the more potent anti-inflammatory / 5-lipoxygenase inhibitors in the series was approximately twice as potent as the standard, ibuprofen in the adjuvent rat and exhibited an IC50 of 0.25 micromolar in the RBL assay.

  DOI：

  10.1016/0223-5234(91)90025-i

文献信息

• Distant Functionalization via Incorporation of Thiophene Moieties in Electrophilic Reactions Promoted by Samarium Diiodide
  作者：Shyh-Ming Yang、Sandip Kumar Nandy、Anandakathir Robinson Selvakumar、Jim-Min Fang

  DOI：10.1021/ol006628w

  日期：2000.11.1

  [GRAPHICS]Methyl thiophene-2-carboxylate, methyl 3-(thien-2-yl)acrylate, and methyl 5,2'-bithiophene-2-carboxylate were utilized as the synthetic equivalents of pentanoate 5-anion, pentanoate 4,5-dianion, heptanoate 7-anion, and nonanoate-8,9-dianion. By the promotion of samarium diiodide, these thiophene incorporating compounds reacted with aldehydes, ketones, and conjugated esters regioselectively at the thienyl rings, Long-chain esters with remote hydroxyl and carboxyl groups, including an antiarthritis agent, a shellac component, and an inhibitory agent of spore germination, were prepared after reductive desulfurizatian on Raney nickel.
• Novel 6-oxo-6-naphthylhexanoic acid derivatives with anti-inflammatory and 5-lipoxygenase inhibitory activity
  作者：WV Murray、MP Wachter、AM Kasper、DC Argentieri、RJ Capetola、DM Ritchie

  DOI：10.1016/0223-5234(91)90025-i

  日期：1991.3

  A series of novel 6-(6-alkoxy-2-naphthyl)oxoalkanoates and alkanamides were synthesized as inhibitors of inflammation and 5-lipoxygenase. They were evaluated in vivo for anti-inflammatory activity in the established adjuvent arthritis assay in rats and in vitro as inhibitors of 5-lipoxygenase in rat basophilic leukemia (RBL) cells. N-Hydroxy-N-methyl-6-(6-methoxy-2-naphthyl)-6-oxohexanamide, compound 28, which is representative of the more potent anti-inflammatory / 5-lipoxygenase inhibitors in the series was approximately twice as potent as the standard, ibuprofen in the adjuvent rat and exhibited an IC50 of 0.25 micromolar in the RBL assay.