(E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylaldehyde | 261913-24-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylaldehyde
• 英文别名: 3-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)propenal；(E)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-enal
• CAS: 261913-24-0
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: QLMGOPJBUUNBHB-OWOJBTEDSA-N

物化性质

• 沸点：
  343.9±21.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylaldehyde 在 双(三甲基硅烷基)氨基钾 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 4.17h， 生成 5-(2,3-dihydrobenzo[1,4]dioxin-6-yl)penta-2,4-dienoic acid
  参考文献：
  名称：

  Naphthalene and 2,3-dihydrobenzo[b][1,4]dioxine derivatives with extended side chains as new scaffolds of CB₂-selective ligands

  摘要：

  在这里，我们报告了合成具有延长侧链的萘、二氢苯并二恶烷和芴衍生物，并对它们进行了作为CB₁和CB₂受体配体的生物评价。

  DOI：

  10.1039/c4md00232f
• 作为产物：
  描述：

  1,4-苯并二恶烷-6-丙烯酸 在 manganese(IV) oxide 、 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylaldehyde
  参考文献：
  名称：

  含异恶唑啉/吡唑啉支架的胡椒碱类似物的合成及其杀虫活性

  摘要：

  为了继续发现新的潜在杀虫剂，我们制备了31个含有异恶唑啉/吡唑啉支架的胡椒碱类似物，并通过红外光谱，质子/碳13核磁共振光谱和高分辨率质谱进行了证实。通过1 H– 1 H COZY光谱进一步确定化合物VIIb和VIIIc的结构。特别是通过单晶X射线衍射明确地确认了化合物VIIIc的构型。针对三种严重且通常威胁农作物的农业害虫，Tetranychus cinnabarinus Boisduval（蜘蛛螨），Mythimna separata，对它们的杀虫活性进行了评估。沃克（东方夜蛾）和小菜蛾（小菜蛾）。化合物VIIIb的和VIIIC呈现出大于不是对铅化合物胡椒碱40倍更有效的杀螨活性朱砂叶螨。值得注意的是，化合物VIa – c对小菜蛾的口服毒性比太生丹宁更明显。化合物VIb和VIc显示出对分离支原体的更有希望的生长抑制活性，而不是tossendanin。结果表明，亚甲二氧基和异恶唑啉支架对

  DOI：

  10.1021/acs.jafc.8b03690

文献信息

• 2-Acyl-3-carboxyl-tetrahydroisoquinoline Derivatives: Mixed-Type PTP1B Inhibitors without PPARγ Activation
  作者：Ko Morishita、Yoshimichi Shoji、Masaki Fukui、Yuma Ito、Tatsuya Kitao、Shin-ichiro Ozawa、Shuichi Hirono、Hiroaki Shirahase

  DOI：10.1248/cpb.c18-00571

  日期：2018.12.1

  oquinoline derivatives were synthesized and biologically evaluated. Among them, (S)-2-(E)-3-furan-2-ylacryloyl}-7-[(2E,4E)-5-(2,4,6-trifluorophenyl)penta-2,4-dienyloxy]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (compound 17u) was identified as a potent protein tyrosine phosphatase 1B (PTP1B) inhibitor without peroxisome proliferator-activated receptor (PPAR) γ activation: PTP1B inhibition IC50=0

  合成了一系列新颖的2-酰基-3-羧基-四氢异喹啉衍生物，并对其进行了生物学评估。其中，（S）-2-（（E）-3-呋喃-2-基丙烯酰基）-7-[（2E，4E）-5-（2,4,6-三氟苯基）戊-2,4-二烯氧基] -1,2,3,4-四氢异喹啉-3-羧酸（化合物17u）被确定为有效的蛋白酪氨酸磷酸酶1B（PTP1B）抑制剂，无过氧化物酶体增殖物激活受体（PPAR）γ激活：PTP1B抑制作用IC50 = 0.19 µM，PPARγEC50> 10 µM。化合物17u对PTP1B表现出混合型抑制作用，这种抑制模式通过计算配体对接到PTP1B的催化位点和变构位点而得以合理化。化合物17u在大鼠中也表现出较高的口服吸收，剂量为10 mg / kg（每os（口服），Cmax = 4.67 µM），在以db的最终给药后24小时进行的口服葡萄糖耐量试验中，在30 mg / kg / d（po）下连续4周显着
• [EN] HETEROCYCLIC AMIDES AS KINASE INHIBITORS<br/>[FR] AMIDES HÉTÉROCYCLIQUES UTILISÉS EN TANT QU'INHIBITEURS DE KINASE
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2016185423A1

  公开（公告）日：2016-11-24

  Disclosed are compounds having the formula: (I) wherein R1, R2, and R3 are as defined herein, and methods of making and using the same.

  揭示的是具有以下式的化合物：(I) 其中R1、R2和R3如本文所定义，并且制备和使用这些化合物的方法。
• Therapeutic compounds and methods of use thereof
  申请人：KUALITY HERBCEUTICS LLC

  公开号：US10584108B2

  公开（公告）日：2020-03-10

  The invention provides compounds that are useful for treating or preventing cancer.

  本发明提供了可用于治疗或预防癌症的化合物。
• Heterocyclic amides as kinase inhibitors
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：US10590085B2

  公开（公告）日：2020-03-17

  Disclosed are compounds having the formula (I): wherein R1, R2, and R3 are as defined herein, and methods of making and using the same.

  公开了具有式 (I) 的化合物： 其中 R1、R2 和 R3 如本文所定义，以及制造和使用它们的方法。
• Structure–activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities
  作者：Surrinder Koul、Jawahir L. Koul、Subhash C. Taneja、Kanaya L. Dhar、Deshvir S. Jamwal、Kuldeep Singh、Rashmeet K. Reen、Jaswant Singh

  DOI：10.1016/s0968-0896(99)00273-4

  日期：2000.1

  Inhibitors of drug metabolism have important implications in pharmaco-toxicology and agriculture. We have reported earlier that piperine, a major alkaloid of black and long peppers inhibits both constitutive and inducible cytochrome P450 (CYP)dependent drug metabolising enzymes. In the present study, an attempt has been made to prepare several novel synthetic analogues so as to relate various modifications in the parent molecule to the inhibition of CYP activities. Two types of mono-oxygenase reactions arylhydrocarbon hydroxylase (AHH) and 7-methoxycoumarin-O-demethylase (MOCD) have been studied. Inhibition studies were investigated in rat microsomal fraction prepared from untreated, 3MC- and PB- treated rat liver in vitro. Modifications were introduced into the piperine molecule: (i) in the phenyl nucleus, (ii) in the side chain and (iii) in the basic moiety. Thus, 38 compounds have been subjected to such studies, and simultaneously an attempt has also been made to arrive at the structure-activity relationship of synthetic analogues. In general, most of the inhibitory potential of the parent molecule is lost with modification in either of the three components of piperine. Saturation of the side chain resulted in significantly enhanced inhibition of CYP while modifications in the phenyl and basic moieties in few analogues offered maximal selectivity in inhibiting either constitutive or inducible CYP activities. Thus Few novel analogues as CYP inactivators have been synthesized which may have important consequences in pharmacokinetics and bioavailability of drugs. (C) 2000 Elsevier Science Ltd. All rights reserved.