(5-(4-methoxybenzyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate | 898045-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5-(4-methoxybenzyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate
• 英文别名: 5-[(4-Methoxyphenyl)methoxy]-2-[[(methylsulfonyl)oxy]methyl]-4H-pyran-4-one；[5-[(4-methoxyphenyl)methoxy]-4-oxopyran-2-yl]methyl methanesulfonate
• CAS: 898045-00-6
• 化学式: C₁₅H₁₆O₇S
• 分子量: 340.354
• InChiKey: PGBVNCQVQFHUAE-UHFFFAOYSA-N

物化性质

• 沸点：
  600.9±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5-(4-methoxybenzyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate 在 sodium azide 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 2-(叠氮甲基)-5-羟基吡喃-4-酮
  参考文献：
  名称：

  신규한 코직산 컨쥬게이트 화합물 및 그의 용도

  摘要：

  本发明涉及通过点击反应使辅酶A和抗氧化剂诱导体共轭的新型辅酶A共轭化合物，以及含有该化合物的抗氧化健康辅助食品和具有美白、抗氧化和抗衰老效果的皮肤外用制剂组合物。根据本发明，辅酶A共轭化合物有效地抑制酪氨酸酶，因此可用作抗氧化健康辅助食品组合物和具有抗氧化、抗衰老和美白功能的皮肤外用制剂的有效成分。

  公开号：

  KR20160046136A
• 作为产物：
  描述：

  4-甲氧基氯苄 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 (5-(4-methoxybenzyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate
  参考文献：
  名称：

  신규한 코직산 컨쥬게이트 화합물 및 그의 용도

  摘要：

  本发明涉及通过点击反应使辅酶A和抗氧化剂诱导体共轭的新型辅酶A共轭化合物，以及含有该化合物的抗氧化健康辅助食品和具有美白、抗氧化和抗衰老效果的皮肤外用制剂组合物。根据本发明，辅酶A共轭化合物有效地抑制酪氨酸酶，因此可用作抗氧化健康辅助食品组合物和具有抗氧化、抗衰老和美白功能的皮肤外用制剂的有效成分。

  公开号：

  KR20160046136A

文献信息

• Design, synthesis and antibacterial activity of novel pleuromutilin derivatives with 4 H -pyran-4-one and pyridin-4-one substitution in the C-14 side chain
  作者：Chen-Yu Ling、Yun-Liang Tao、Wen-Jing Chu、Hui Wang、Hai-Dong Wang、Yu-She Yang

  DOI：10.1016/j.cclet.2015.09.019

  日期：2016.2

  H -pyran-4-one and pyridin-4-one substitution in the C-14 side chain have been designed and synthesized. In vitro antibacterial activity evaluation showed that most of the derivatives exhibited potent antibacterial activity against drug resistant Gram-positive strains. Compounds 12a , 12d , and 28 are the most active derivatives in this series, displaying activity comparable to that of retapamulin

  摘要设计合成了一系列新颖的截短侧耳素衍生物，其在C-14侧链上具有4个H-吡喃-4-酮和吡啶-4-酮取代基。体外抗菌活性评估表明，大多数衍生物对耐药革兰氏阳性菌株均表现出有效的抗菌活性。化合物12a，12d和28是该系列中活性最高的衍生物，其活性与雷帕米林和BC-3781相当。由于该系列的代谢稳定性不令人满意，因此正在进行进一步的修饰以改善其药代动力学特性。
• Synthesis of Tyrosinase Inhibitory Kojic Acid Derivative
  作者：Yong Sup Lee、Jang Hyun Park、Min Hwan Kim、Seon Hee Seo、Hyoung Ja Kim

  DOI：10.1002/ardp.200500213

  日期：2006.3

  Kojic acid derivative 2 was synthesized by joining two pyrone rings through an ethylene linkage by Horner‐Emmons reaction of phosphonate 6 with aldehyde 7. The intermediates 6 and 7 were derived from kojic acid. The tyrosinase inhibitory activity of 2 was about 8 times more potent (IC50 = 3.63 μM) than that of kojic acid (IC50 = 30.61 μM). Compound 2 also exhibited potent melanin synthesis inhibitory

  通过膦酸酯 6 与醛 7 的霍纳-埃蒙斯反应，通过乙烯键连接两个吡喃酮环合成曲酸衍生物 2。中间体 6 和 7 衍生自曲酸。2 的酪氨酸酶抑制活性 (IC50 = 3.63 μM) 比曲酸 (IC50 = 30.61 μM) 强约 8 倍。化合物 2 还表现出有效的黑色素合成抑制活性（5 μg 时抑制率为 19.53%），表明曲酸的两个吡喃酮环通过合适的接头连接可以是鉴定有效酪氨酸酶抑制剂的有用策略。
• Synthesis of kojic acid derivatives as secondary binding site probes of d-amino acid oxidase
  作者：Mithun Raje、Niyada Hin、Bridget Duvall、Dana V. Ferraris、James F. Berry、Ajit G. Thomas、Jesse Alt、Camilo Rojas、Barbara S. Slusher、Takashi Tsukamoto

  DOI：10.1016/j.bmcl.2013.04.062

  日期：2013.7

  A series of kojic acid (5-hydroxy-2-hydroxymethyl-4H-pyran-4-one) derivatives were synthesized and tested for their ability to inhibit D-amino acid oxidase (DAAO). Various substituents were incorporated into kojic acid at its 2-hydroxymethyl group. These analogs serve as useful molecular probes to explore the secondary binding site, which can be exploited in designing more potent DAAO inhibitors. (c) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of kojic acid-derived copper-chelating apoptosis inducing agents
  作者：Yu-Hua Chen、Pei-Jung Lu、Christopher Hulme、Arthur Y. Shaw

  DOI：10.1007/s00044-012-0094-y

  日期：2013.2

  Three classes of kojic acid derivatives were synthesized and examined for their antiproliferative activity against HeLa cells. Both 8b and 11 co-treated with copper ion exhibited synergistic effect on the HeLa cell growth inhibition with GI(50) values of 11.9 and 7.1 mu M, respectively. Flow cytometric analysis of HeLa cells revealed that 11-Cu co-treatment induced the sub-G1 arrest in a dose-dependent manner, suggesting that the growth-inhibitory effect is attributed to DNA fragmentation. Moreover, western blot of HeLa cells cytosolic extracts displayed the cleavage of the 116-kDa protein poly(ADP-ribose) polymerase and activation of caspase-3 by the reduced level of the 32-kDa proenzyme, indicating that the caspase-dependent apoptotic pathway was involved. We further demonstrated that MAPK pathway regulators such as ERK and p38 were activated in response to 11-Cu co-treatment, suggesting that the intracellular oxidative stress was dramatically stimulated by the copper ion. Taken together, we have successfully synthesized kojic acid-derived copper-induced apoptotic agents.
• DNA METHYLATION INHIBITORS
  申请人：Chen Ching-Shih

  公开号：US20120157465A1

  公开（公告）日：2012-06-21

  A number of DNA methylation inhibitors are described. The DNA methylation inhibitors were identified using a two-component enhanced green fluorescent protein reporter system to screen a compound library containing procainamide derivatives. The DNA methylation inhibitors can be used for cancer therapy and prevention.