3,4-(bis-allyloxy)benzoic acid allyl ester | 664334-20-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-(bis-allyloxy)benzoic acid allyl ester
• 英文别名: 3,4-di-O-allylprotocatechuic acid；3,4-(bis-allyloxy)benzoic acid；3,4-Bis[(prop-2-en-1-yl)oxy]benzoic acid；3,4-bis(prop-2-enoxy)benzoic acid
• CAS: 664334-20-7
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: GSMUNBJHYOTUHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-(bis-allyloxy)benzoic acid allyl ester 在 吗啉 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2R,3R,4S)-3-acetamido-4-(diaminomethylideneamino)-2-[(1R,2R)-1-[3-(3,4-dihydroxybenzoyl)oxypropylcarbamoyloxy]-2,3-dihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
  参考文献：
  名称：

  Enhanced Anti-influenza Agents Conjugated with Anti-inflammatory Activity

  摘要：

  Influenza therapy with a single targeted compound is often limited in efficacy due to the rapidly developed drug resistance. Moreover, the uncontrolled virus-induced cytokines could cause the high mortality of human infected by H5N1 avian influenza virus. In this study, we explored the novel dual-targeted bifunctional anti-influenza drugs formed by conjugation with anti-inflammatory agents. In particular, the caffeic acid (CA)-bearing zanamivir (ZA) conjugates ZA-7-CA (1) and ZA-7-CA-amide (7) showed simultaneous inhibition of influenza virus neuraminidase and suppression of pro-inflammatory cytokines. These ZA conjugates provided remarkable protection of cells and mice against influenza infections. Intranasal administration of low dosage (<1.2 mu mol/kg/day) of ZA conjugates exhibited much greater effect than the combination therapy with ZA and the anti-inflammatory agents in protection of the lethally infected mice by H1N1 or H5N1 influenza viruses.

  DOI：

  10.1021/jm3009844
• 作为产物：
  描述：

  原儿茶酸 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 8.0h， 生成 3,4-(bis-allyloxy)benzoic acid allyl ester
  参考文献：
  名称：

  ENHANCED ANTI-INFLUENZA AGENTS CONJUGATED WITH ANTI-INFLAMMATORY ACTIVITY

  摘要：

  新型双靶向、双功能抗流感药物通过与抗炎药物结合形成。根据本发明的示例药物包括咖啡酸（CA）基底的扎那米韦（ZA）共轭物ZA-7-CA（1）、ZA-7-CA酰胺（7）和ZA-7-Nap（43），用于同时抑制流感病毒神经氨基酸酶和抑制促炎细胞因子。提供了用于制备这些增强型抗流感共轭药物的合成方法。合成的双功能ZA共轭物对保护由H1N1或H5N1流感病毒致命感染的小鼠具有协同作用。ZA-7-CA、ZA-7-CA酰胺和ZA-7-Nap共轭物的疗效远远优于ZA与抗炎药物的联合治疗。

  公开号：

  US20130274229A1

文献信息

• Controlled Reversible Anchoring of η6-Arene/TsDPEN- Ruthenium(II) Complex onto Magnetic Nanoparticles: A New Strategy for Catalyst Separation and Recycling
  作者：Lei Wu、Yan-Mei He、Qing-Hua Fan

  DOI：10.1002/adsc.201100317

  日期：2011.11

  A new catalyst separation and recycling protocol combining magnetic nanoparticles and host-guest assembly was developed. The catalyst, (η6-arene)[N-(para-toluenesulfonyl)-1,2-diphenylethylenediamine]ruthenium trifluoromethanesulfonate [Ru(OTf)(TsDPEN)(η6-arene)] bearing a dialkylammonium salt tag, was easily separated from the reaction mixtures by magnet-assisted decantation, on basis of the formation

  开发了一种新的催化剂分离和回收方案，该方案结合了磁性纳米颗粒和客体组装。的催化剂，（η 6 -arene）ñ - （对甲苯磺酰）-1,2-二苯基乙二胺]合钌三氟甲磺酸酯的[Ru（OTF）（TsDPEN）（η 6 -arene）]轴承二烷基铵盐标签，被容易地分离二苯并[24]冠-8修饰的Fe 3 O 4形成假轮烷配合物的基础上，通过磁辅助倾析法从反应混合物中分离得到纳米粒子。钌催化剂已经成功地重复使用了至少5次，同时保留了对映体选择性，但以2-甲基喹啉的不对称氢化中相对较低的催化活性为代价。
• Synthesis and biological evaluation of bergenin analogues as mushroom tyrosinase inhibitors
  作者：Yusei Kashima、Mitsuo Miyazawa

  DOI：10.1007/s12272-012-0903-3

  日期：2012.9

  the standard tyrosinase inhibitors of arbutin (IC50 value = 221.8 ± 1.9 μM) and kojic acid (IC50 value = 46.6 ± 3.8 μM). The bergenin moiety, the ester linkage, and benzoic acid moiety of bergenin derivatives affected two biologic activities. Tyrosinase inhibitory activity was affected by substituents of benzoic acid moiety. This manuscript provides a good foundation for the design and development of

  在这份手稿中，我们合成了一系列 bergenin 类似物，分析了它们对两种生物活性（抗氧化活性 (ORAC) 和蘑菇酪氨酸酶抑制活性）的结构重要性。其中，含有儿茶酚部分的化合物 5 表现出最大的抗氧化活性（3.75 μmol Trolox 当量/μmol 5）。此外，与熊果苷（IC50 值 = 221.8 ± 1.9 μM）和曲酸（IC50 值 = 46.6 ± 3.8 μM）的标准酪氨酸酶抑制剂相比，发现化合物 5 最有效（IC50 值 = 17.5 ± 0.04 μM） . bergenin 衍生物的 bergenin 部分、酯键和苯甲酸部分影响两种生物活性。酪氨酸酶抑制活性受苯甲酸部分取代基的影响。
• Identification and Semi-Synthesis of 3-O-Protocatechuoylceanothic Acid, a Novel and Natural GPR120 Agonist †
  作者：Changjin Lim、Jung Gyu Park、Kyo Bin Kang、Young-Ger Suh

  DOI：10.3390/molecules24193487

  日期：——

  The identification and three step synthesis of 3-O-protocatechuoylceanothic acid, a novel and natural GPR120 agonist, is described. This ceanothane-type triterpenoid was identified from the components of Ziziphus jujuba roots and was found to be a new GPR120 agonist with a novel structure. We synthetically converted ceanothic acid, which does not have GPR120 agonist activity, into 3-O-protocatechuoylceanothic

  描述了 3-O-protocatechuoylceanothic 酸（一种新型天然 GPR120 激动剂）的鉴定和三步合成。这种ceanothane 型三萜是从Ziziphus jujuba 根的成分中鉴定出来的，并被发现是一种具有新颖结构的新型GPR120 激动剂。我们通过三个步骤将不具有 GPR120 激动剂活性的鲸蜡酸合成转化为 3-O-原儿茶酰鲸蜡酸。此外，我们还提供了基于我们的合成的 3-O-原儿茶酰ceanothic 酸的校正 NMR 谱。
• Enhanced anti-influenza agents conjugated with anti-inflammatory activity
  申请人：Academia Sinica

  公开号：US10130714B2

  公开（公告）日：2018-11-20

  Novel dual-targeted, bifunctional anti-influenza drugs formed by conjugation with anti-inflammatory agents are disclosed. Exemplary drugs according to the invention include caffeic acid (CA)-bearing zanamivir (ZA) conjugates ZA-7-CA (1), ZA-7-CA-amide (7) and ZA-7-Nap (43) for simultaneous inhibition of influenza virus neuraminidase and suppression of proinflammatory cytokines. Synthetic methods for preparation of these enhanced anti-influenza conjugate drugs are provided. The synthetic bifunctional ZA conjugates act synergistically towards protection of mice lethally infected by H1N1 or H5N1 influenza viruses. The efficacy of ZA-7-CA, ZA-7-CA-amide and ZA-7-Nap conjugates is much greater than the combination therapy of ZA with anti-inflammatory agents.

  本发明公开了通过与抗炎剂共轭形成的新型双靶向、双功能抗流感药物。根据本发明，示例药物包括含咖啡酸（CA）的扎那米韦（ZA）共轭物ZA-7-CA（1）、ZA-7-CA-酰胺（7）和ZA-7-Nap（43），用于同时抑制流感病毒神经氨酸酶和抑制促炎细胞因子。本文提供了制备这些增强型抗流感共轭药物的合成方法。合成的双功能ZA共轭物能协同保护被H1N1或H5N1流感病毒致命感染的小鼠。ZA-7-CA、ZA-7-CA-酰胺和ZA-7-Nap共轭物的疗效远远高于ZA与消炎药的联合疗法。
• Structure-activity relationships of bergenin derivatives effect on α-glucosidase inhibition
  作者：Yusei Kashima、Hidehiko Yamaki、Takuya Suzuki、Mitsuo Miyazawa

  DOI：10.3109/14756366.2012.719503

  日期：2013.12.1

  The alpha-glucosidase inhibitory activities of bergenin derivatives were evaluated. Bergenin derivatives were synthesized from bergenin which is a characteristic compound of B. ligulata. A new bergenin derivative, 11-O-(3',4'-dimethoxybenzoyl)-bergenin showed the highest potent inhibitory activity among those of bergenin derivatives. The presence of substituents at 3',4'-position in bergenin derivatives altered the alpha-glucosidase inhibitory activity. 11-O-(3', 4'-dimethoxybenzoyl)-bergenin was noncompetitive inhibitor for alpha-glucosidase. The present study reveals that bergenin derivatives could be classified as a new group of alpha-glucosidase inhibitors.