3-allyl-4-[(tetrahydro-2H-pyran-2-yl)oxy]benzaldehyde | 1548332-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-allyl-4-[(tetrahydro-2H-pyran-2-yl)oxy]benzaldehyde
• 英文别名: 4-(Oxan-2-yloxy)-3-prop-2-enylbenzaldehyde
• CAS: 1548332-73-5
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: AHGLKWMUKCBTCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-allyl-4-[(tetrahydro-2H-pyran-2-yl)oxy]benzaldehyde 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents

  摘要：

  Curcumin has been shown to possess anti-inflammatory activities but has been limited for its low stability and poor bioavailability. We have previously reported four series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MACs). In continuation of our ongoing research, we designed and synthesized 33 novel allylated or prenylated MACs here, and evaluated their anti-inflammatory effects in RAW 264.7 macrophages. A majority of them effectively inhibited the LPS-induced expression of TNF-alpha and IL-6, especially IL-6. The preliminary SAR and quantitative SAR analysis were conducted. Compound 14q is the most potent analog among them, and exhibits significant protection against LPS-induced death in septic mice. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.061
• 作为产物：
  描述：

  4-(3-甲基-2-丁烯氧基)苯甲醛 在 对甲苯磺酸 、 N,N-二乙基苯胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 3-allyl-4-[(tetrahydro-2H-pyran-2-yl)oxy]benzaldehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents

  摘要：

  Curcumin has been shown to possess anti-inflammatory activities but has been limited for its low stability and poor bioavailability. We have previously reported four series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MACs). In continuation of our ongoing research, we designed and synthesized 33 novel allylated or prenylated MACs here, and evaluated their anti-inflammatory effects in RAW 264.7 macrophages. A majority of them effectively inhibited the LPS-induced expression of TNF-alpha and IL-6, especially IL-6. The preliminary SAR and quantitative SAR analysis were conducted. Compound 14q is the most potent analog among them, and exhibits significant protection against LPS-induced death in septic mice. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.061

文献信息

• 一类含烯丙基的单羰基姜黄素类似物在制备抗 炎药物中的应用
  申请人：温州医科大学

  公开号：CN103524318B

  公开（公告）日：2016-04-13

  本发明提供了具有抗炎作用的含烯丙基的单羰基姜黄素类似物。另外，本发明还提供了这些化合物的药物组合物以及抗炎用途等。
• 一种含烯丙基取代的单羰基姜黄素类化合物 在制备抗肿瘤药物中的应用
  申请人：温州医科大学

  公开号：CN106214677B

  公开（公告）日：2019-04-23

  本发明公开了一种含烯丙基取代的单羰基姜黄素类化合物在制备抗肿瘤药物中的应用，所述的单羰基姜黄素类化合物为结构如式(Ⅰ)所示的化合物或其药用盐；式(I)中，A为C、S、O或‑NR1，其中R1独立地选自H、C1～C5烷基、苯砜基、苄基中的一种或者多种；n为0或1；R独立地选自一个或者多个H、羟基、烯丙基、C1～C4烷氧基、吡咯烷基、吗啉基或N‑甲基哌嗪基。试验结果表明，这类单羰基姜黄素类化合物具有较好的稳定性和抗肿瘤活性，可以作为一种潜在的抗肿瘤药物。
• Synthesis and optimization of novel allylated mono-carbonyl analogs of curcumin (MACs) act as potent anti-inflammatory agents against LPS-induced acute lung injury (ALI) in rats
  作者：Heping Zhu、Tingting Xu、Chenyu Qiu、Beibei Wu、Yali Zhang、Lingfeng Chen、Qinqin Xia、Chenglong Li、Bin Zhou、Zhiguo Liu、Guang Liang

  DOI：10.1016/j.ejmech.2016.05.041

  日期：2016.10

  allylated mono-carbonyl analogs of curcumin (MACs) were synthesized using an appropriate synthetic route and evaluated experimentally thru the LPS-induced expression of TNF-α and IL-6. Most of the obtained compounds exhibited improved water solubility as a hydrochloride salt compared to lead molecule 8f. The most active compound 7a was effective in reducing the Wet/Dry ratio in the lungs and protein

  使用适当的合成途径合成了一系列新的姜黄素对称和不对称烯丙基化单羰基类似物（MACs），并通过LPS诱导的TNF-α和IL-6表达进行了实验评估。与铅分子8f相比，大多数获得的化合物均显示出改善的水溶性，即盐酸盐形式的盐酸盐。活性最高的化合物7a可有效降低肺部的湿/干比和支气管肺泡灌洗液中的蛋白质浓度。同时，在脂多糖（LPS）攻击后，Bea-2B细胞中7a还抑制了包括TNF-α，IL-6，IL-1β和VCAM-1在内的几种炎性细胞因子的mRNA表达。这些结果表明7a 在急性肺损伤（ALI）的临床治疗中用作抗炎药可能在治疗上有益。
• 一种含哌啶酮结构的单羰基姜黄素类似物及 应用
  申请人：温州医科大学

  公开号：CN105541700B

  公开（公告）日：2018-05-04

  本发明公开了一种含哌啶酮结构的单羰基姜黄素类似物及应用，该单羰基姜黄素类似物的结构如式(I)或式(II)所示，式(I)中，R1可以为被不同的取代基任选取代的烷基、环烷基、苄基、芳酰基、取代芳酰基、磺酰基；式(II)中，R2可以为被不同的取代基任选取代的哌嗪基、吗啉基、吡咯烷基、N,N‑二取代烷基。本发明针对一类以取代哌啶酮为母核结构的单羰基姜黄素类似物技术领域进行大量实验研究，进行大量以取代哌啶酮为母核结构的单羰基姜黄素类似物设计、合成、药理活性筛选，得出一类以取代哌啶酮为母核结构的单羰基姜黄素类似物，并且本发明的单羰基姜黄素类似物具有高效、广谱的抗炎用途。
• Synthesis and biological evaluation of allylated mono-carbonyl analogues of curcumin (MACs) as anti-cancer agents for cholangiocarcinoma
  作者：Chenyu Qiu、Yan Hu、Ke Wu、Ke Yang、Nan Wang、Yue Ma、Heping Zhu、Yi Zhang、Yunfang Zhou、Chao Chen、Shanshan Li、Lili Fu、Xiuhua Zhang、Zhiguo Liu

  DOI：10.1016/j.bmcl.2016.10.080

  日期：2016.12

  A series of new allylated mono-carbonyl curcumin analogues (MACs) were designed and synthesized. In vitro cytotoxic activities of allylated MACs 6a-h together with previously reported analogues 4a-i and 7a-e, were tested against human cholangiocarcinoma cell lines including HUCCA, QBC-939 and RBE. Of all the compounds tested, 6c exhibited potent in vitro antiproliferative activity against the three tested cancer cell lines with IC50 values of 8.7, 9.3 and 8.9 mu M, respectively. Cell cycle analysis showed that 6c inhibited cell proliferation due to G2/M arrest. Furthermore, mechanistic studies revealed that 6c dose-dependently increased the level of Bax and inhibited the expression of Bcl-2, to induce cancer cell apoptosis. Taken together, this work provides a novel series of anti-cancer candidates for the treatment of cholangiocarcinoma. (C) 2016 Published by Elsevier Ltd.