3-[3-methoxy-4-[(tetrahydropyran-2-yl)oxy]phenyl]-2-propenal | 909281-82-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 3-[3-methoxy-4-[(tetrahydropyran-2-yl)oxy]phenyl]-2-propenal
• 英文别名: (E)-3-(3-methoxy-4-(tetrahydropyran-2-yloxy)phenyl)acrylaldehyde；4-(tetrahydro-2H-pyran-2-yloxy)-3-methoxycinnamic aldehyde；(E)-3-[3-methoxy-4-(oxan-2-yloxy)phenyl]prop-2-enal
• CAS: 909281-82-9
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: NFJSESLKVOMFOI-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 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：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[3-methoxy-4-[(tetrahydropyran-2-yl)oxy]phenyl]-2-propenal 在 palladium on activated charcoal 氢气 、 sodium hydrogensulfite 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 12.5h， 生成 4-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one
  参考文献：
  名称：

  一种作为 TRPV1 受体激动剂的辣椒素类化合物的有效和简便合成

  摘要：

  描述了一种新的通用合成路线，用于制备辣椒素样分子，该分子含有模拟辣椒素结构中酰胺官能团的 α-羟基酮官能团。该合成中的关键反应是形成作为中间体的 α-（二甲氨基）烷腈。通过与二甲胺和氰化钠水溶液反应，由脂肪醛和芳香醛成功地制备了这些腈。用二异丙基氨基锂 (LDA) 处理腈，然后与各种醛反应导致形成 α-羟基酮化合物，其例子包括 2-羟基-1-(4-羟基-3-甲氧基苯基)dodecan-3-一，(5R)-和(5S)-2-羟基-1-(4-羟基-3-甲氧基苯基)-5,9-二甲基dec-8-en-3-one，代表新型辣椒素样分子。(4-苄氧基-3-甲氧基苯基)乙醛的形成也由4-苄氧基-3-甲氧基苯甲醛与叶立德试剂(甲氧基甲基)三苯基溴化鏻的Wittig反应描述，然后酸水解形成标题化合物。这种醛是合成辣椒素样结构的有用前体。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  DOI：

  10.1002/ejoc.200600135
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 0.83h， 生成 3-[3-methoxy-4-[(tetrahydropyran-2-yl)oxy]phenyl]-2-propenal
  参考文献：
  名称：

  Synthesis, cytotoxicity against human oral cancer KB cells and structure–activity relationship studies of trienone analogues of curcuminoids

  摘要：

  A general method for the synthesis of substituted (1E,4E,6E)-1,7-diphenylhepta-1,4,6-trien-3-ones, based on the aldol condensations of substituted 4-phenylbut-3-en-2-ones and substituted 3-phenylacrylaldehydes, was achieved. The natural trienones 4 and 5 have been synthesized by this method, together with the trienone analogues 9-20. These analogues were evaluated for their cytotoxic activity against human oral cancer KB cell line. The structure-activity relationship study has indicated that the analogues with the 1,4,6-trien-3-one function are more potent than the curcuminoid-type function. Analogues with meta-oxygen function on the aromatic rings are more potent than those in the ortho- and para-positions. Free phenolic hydroxy group is more potent than the corresponding methyl ether analogues. Among the potent trienones, compounds 11, 18 and 20 were more active than the anticancer drug ellipticine. All compounds were also evaluated against the non-cancerous Vero cells and it was found that compounds 11, 12 and 17 were much less toxic than curcumin (1); they showed high selectivity indices of 35.46, 33.46 and 31.68, respectively. These analogues are regarded as the potent trienones for anti-oral cancer study. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.105

文献信息

• Neuroprotective effect of synthetic chalcone derivatives as competitive dual inhibitors against μ-calpain and cathepsin B through the downregulation of tau phosphorylation and insoluble Aβ peptide formation
  作者：Kyung-Hwa Jeon、Eunyoung Lee、Kyu-Yeon Jun、Ji-Eun Eom、Soo Yeon Kwak、Younghwa Na、Youngjoo Kwon

  DOI：10.1016/j.ejmech.2016.06.008

  日期：2016.10

  A series of chalcone derivatives were synthesized and evaluated for their μ-calpain and cathepsin B inhibitory activities. Among the tested chalcone derivatives, two compounds, 7 and 11, showed potent inhibitory activities against μ-calpain and cathepsin B and were selected for further evaluation. Compounds 7 and 11 showed enzyme inhibitory activities at the cellular level and displayed neuroprotective

  合成了一系列查尔酮衍生物，并评估了它们的μ-钙蛋白酶和组织蛋白酶B抑制活性。在测试的查耳酮衍生物中，两种化合物7和11显示出对μ-钙蛋白酶和组织蛋白酶B的有效抑制活性，因此选择进行进一步评估。化合物7和11在人的神经母细胞瘤细胞系SH-SY5Y细胞中显示出在细胞水平上的酶抑制活性，并显示出对氧化应激诱导的细胞凋亡的神经保护作用。此外，化合物7和11减少了p25的形成，tau磷酸化和不溶性Aβ肽的形成。酶动力学实验和对接研究表明，这些化合物7和11竞争性抑制μ-钙蛋白酶和组织蛋白酶B酶。
• [EN] CONJUGATED TLR7 AND NOD2 AGONISTS<br/>[FR] AGONISTES CONJUGUÉS DE TLR7 ET DE NOD2
  申请人：UNIV LJUBLJANI

  公开号：WO2022084417A1

  公开（公告）日：2022-04-28

  This invention provides covalent conjugates of TLR7 and NOD2 agonists, processes for preparing such compounds and the use of such compounds in medicine.

  这项发明提供了TLR7和NOD2激动剂的共价结合物，制备这种化合物的方法以及在医学中使用这种化合物的用途。
• Synthesis, cytotoxicity against human oral cancer KB cells and structure–activity relationship studies of trienone analogues of curcuminoids
  作者：Thipphawan Chuprajob、Chatchawan Changtam、Ratchanaporn Chokchaisiri、Warangkana Chunglok、Nilubon Sornkaew、Apichart Suksamrarn

  DOI：10.1016/j.bmcl.2014.04.105

  日期：2014.7

  A general method for the synthesis of substituted (1E,4E,6E)-1,7-diphenylhepta-1,4,6-trien-3-ones, based on the aldol condensations of substituted 4-phenylbut-3-en-2-ones and substituted 3-phenylacrylaldehydes, was achieved. The natural trienones 4 and 5 have been synthesized by this method, together with the trienone analogues 9-20. These analogues were evaluated for their cytotoxic activity against human oral cancer KB cell line. The structure-activity relationship study has indicated that the analogues with the 1,4,6-trien-3-one function are more potent than the curcuminoid-type function. Analogues with meta-oxygen function on the aromatic rings are more potent than those in the ortho- and para-positions. Free phenolic hydroxy group is more potent than the corresponding methyl ether analogues. Among the potent trienones, compounds 11, 18 and 20 were more active than the anticancer drug ellipticine. All compounds were also evaluated against the non-cancerous Vero cells and it was found that compounds 11, 12 and 17 were much less toxic than curcumin (1); they showed high selectivity indices of 35.46, 33.46 and 31.68, respectively. These analogues are regarded as the potent trienones for anti-oral cancer study. (C) 2014 Elsevier Ltd. All rights reserved.
• An Efficient and Facile Synthesis of Capsaicin-Like Compounds as Agonists of the TRPV1 Receptor
  作者：Van H. Tran、Ravi Kantharaj、Basil D. Roufogalis、Colin C. Duke

  DOI：10.1002/ejoc.200600135

  日期：2006.7

  this synthesis was the formation of α-(dimethylamino)alkanenitriles as intermediates. These nitriles were successfully prepared from both aliphatic and aromatic aldehydes by reaction with dimethylamine and aqueous sodium cyanide. Treatment of the nitriles with lithium diisopropylamide (LDA) followed by reaction with various aldehydes led to the formation of α-hydroxy ketone compounds, examples of which

  描述了一种新的通用合成路线，用于制备辣椒素样分子，该分子含有模拟辣椒素结构中酰胺官能团的 α-羟基酮官能团。该合成中的关键反应是形成作为中间体的 α-（二甲氨基）烷腈。通过与二甲胺和氰化钠水溶液反应，由脂肪醛和芳香醛成功地制备了这些腈。用二异丙基氨基锂 (LDA) 处理腈，然后与各种醛反应导致形成 α-羟基酮化合物，其例子包括 2-羟基-1-(4-羟基-3-甲氧基苯基)dodecan-3-一，(5R)-和(5S)-2-羟基-1-(4-羟基-3-甲氧基苯基)-5,9-二甲基dec-8-en-3-one，代表新型辣椒素样分子。(4-苄氧基-3-甲氧基苯基)乙醛的形成也由4-苄氧基-3-甲氧基苯甲醛与叶立德试剂(甲氧基甲基)三苯基溴化鏻的Wittig反应描述，然后酸水解形成标题化合物。这种醛是合成辣椒素样结构的有用前体。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451