3-(2,3-dimethoxyphenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one | 940810-89-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(2,3-dimethoxyphenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one
• 英文别名: DMFP；3-(2,3-Dimethoxyphenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one
• CAS: 940810-89-9
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: RKFUYVPHYBKMSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2,3-dimethoxyphenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到
  参考文献：
  名称：

  杂环查尔酮衍生物的合成及其对2,2-二苯基-1-苦基肼(DPPH)自由基的清除能力

  摘要：

  精心制备了一系列杂环杂环查耳酮衍生物，如苯环的等排体噻吩或呋喃环，并系统研究了杂环对2,2-二苯基-1-苦基肼（DPPH）自由基清除活性的影响。构效关系（SAR）分析表明，含噻吩环的查尔酮的活性高于含呋喃环的查尔酮，并且与未取代的杂环相比，杂环甲基取代基的存在对活性的影响明显相反。 , 噻吩环的 4'-甲基基团活性增加，呋喃环的 3'-甲基基团活性降低。杂环的独特等排效应（即，

  DOI：

  10.5012/bkcs.2012.33.8.2585
• 作为产物：
  描述：

  5-甲基-2-乙酰基呋喃 、 2,3-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以91%的产率得到3-(2,3-dimethoxyphenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  杂环查尔酮衍生物的合成及其对2,2-二苯基-1-苦基肼(DPPH)自由基的清除能力

  摘要：

  精心制备了一系列杂环杂环查耳酮衍生物，如苯环的等排体噻吩或呋喃环，并系统研究了杂环对2,2-二苯基-1-苦基肼（DPPH）自由基清除活性的影响。构效关系（SAR）分析表明，含噻吩环的查尔酮的活性高于含呋喃环的查尔酮，并且与未取代的杂环相比，杂环甲基取代基的存在对活性的影响明显相反。 , 噻吩环的 4'-甲基基团活性增加，呋喃环的 3'-甲基基团活性降低。杂环的独特等排效应（即，

  DOI：

  10.5012/bkcs.2012.33.8.2585

文献信息

• Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent
  作者：Kok Wai Lam、Reaz Uddin、Choi Yi Liew、Chau Ling Tham、Daud A. Israf、Ahmad Syahida、Mohd. Basyaruddin Abdul Rahman、Zaheer Ul-Haq、Nordin H. Lajis

  DOI：10.1007/s00044-011-9706-1

  日期：2012.8

  In this study, thirty-eight chalcone analogs were synthesized and evaluated for nitric oxide (NO) inhibition activity on RAW 264.7 cells. Among these compounds, chalcones bearing furanyl group showed remarkable anti-inflammatory activity. Both compounds 2d and 2j were identified as the most potent NO inhibitor on IFN-gamma/LPS-activated RAW 264.7 cells. In order to examine the structure-activity relationship, a 3D QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method on the selected chalcones. Partial least square analysis produced a statistically coherent model with good predictive value, r (2) = 0.989 and a good cross validated value, q (2) = 0.583.
• Synthesis and Evaluation of Chalcone Derivatives as Inhibitors of Neutrophils' Chemotaxis, Phagocytosis and Production of Reactive Oxygen Species
  作者：Syed N. A. Bukhari、Yasmin Tajuddin、Vannessa J. Benedict、Kok W. Lam、Ibrahim Jantan、Juriyati Jalil、Malina Jasamai

  DOI：10.1111/cbdd.12226

  日期：2014.2

  Inhibitory effects on neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species (ROS) are among the important targets in developing anti‐inflammatory agents and immunosuppressants. Eight series of chalcone derivatives including five newly synthesized series were assessed for their inhibitory effects on chemotaxis, phagocytosis and ROS production in human polymorphonuclear neutrophils (PMNs). Inhibition of PMNs' chemotaxis and phagocytosis abilities were investigated using the Boyden chamber technique and the Phagotest kit, respectively, while ROS production was evaluated using luminol‐ and lucigenin‐based chemiluminescence assay. The new derivatives (4d and 8d), which contain 4‐methylaminoethanol functional group were active in all the assays performed. It was also observed that some of the compounds were active in inhibiting chemotaxis while others suppressed phagocytosis and ROS production. The information obtained gave new insight into chalcone derivatives with the potential to be developed as immunomodulators.
• Synthesis of Heterocyclic Chalcone Derivatives and Their Radical Scavenging Ability Toward 2,2-Diphenyl-1-Picrylhydrazyl (DPPH) Free Radicals
  作者：Ki-Jun Hwang、Ho-Seok Kim、In-Cheol Han、Beom-Tae Kim

  DOI：10.5012/bkcs.2012.33.8.2585

  日期：2012.8.20

  A series of heterocyclic chalcone derivatives bearing heterocycles such as thiophene or furan ring as an isostere of benzene ring were carefully prepared, and the influence of heterocycles on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities was systematically investigated. Structure-activity relationships (SAR) analysis showed that the activities of thiophene ring-containing chalcones

  精心制备了一系列杂环杂环查耳酮衍生物，如苯环的等排体噻吩或呋喃环，并系统研究了杂环对2,2-二苯基-1-苦基肼（DPPH）自由基清除活性的影响。构效关系（SAR）分析表明，含噻吩环的查尔酮的活性高于含呋喃环的查尔酮，并且与未取代的杂环相比，杂环甲基取代基的存在对活性的影响明显相反。 , 噻吩环的 4'-甲基基团活性增加，呋喃环的 3'-甲基基团活性降低。杂环的独特等排效应（即，
• Antinociceptive Effect of 3-(2,3-Dimethoxyphenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one in Mice Models of Induced Nociception
  作者：Nur Ismail、Lee Ming-Tatt、Nordin Lajis、Muhammad Akhtar、Ahmad Akira、Enoch Perimal、Daud Israf、Mohd Sulaiman

  DOI：10.3390/molecules21081077

  日期：——

  The antinociceptive effects produced by intraperitoneal administration of a novel synthetic chalcone, 3-(2,3-dimethoxyphenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one (DMFP), were investigated in several mouse models of induced nociception. The administration of DMFP (0.1, 0.5, 1.0 and 5.0 mg/kg) produced significant attenuation on the acetic acid-induced abdominal-writhing test. It also produced a significant increase in response latency time in the hot-plate test and a marked reduction in time spent licking the injected paw in both phases of the formalin-induced paw-licking test. In addition, it was also demonstrated that DMFP exhibited significant inhibition of the neurogenic nociceptive response induced by intraplantar injections of capsaicin and glutamate. Moreover, the antinociceptive effect of DMFP in the acetic acid-induced abdominal-writhing test and the hot-plate test was not antagonized by pretreatment with a non-selective opioid receptor antagonist, naloxone. Finally, DMFP did not show any toxic effects and/or mortality in a study of acute toxicity and did not interfere with motor coordination during the Rota-rod test. Our present results show that DMFP exhibits both peripheral and central antinociceptive effects. It was suggested that its peripheral antinociceptive activity is associated with attenuated production and/or release of NO and various pro-inflammatory mediators, while central antinociceptive activity seems to be unrelated to the opioidergic system, but could involve, at least in part, an interaction with the inhibition of capsaicin-sensitive fibers and the glutamatergic system.

  研究了腹腔注射新型合成查尔酮 3-(2,3-二甲氧基苯基)-1-(5-甲基呋喃-2-基)丙-2-en-1-酮 (DMFP) 产生的镇痛作用。几种诱导伤害感受的小鼠模型。 DMFP（0.1、0.5、1.0 和 5.0 mg/kg）的施用对乙酸引起的腹部扭动试验产生显着减弱。它还显着增加了热板测试中的响应延迟时间，并显着减少了福尔马林诱导的舔爪测试的两个阶段中舔注射爪子所花费的时间。此外，还证明DMFP对足底注射辣椒素和谷氨酸引起的神经源性伤害性反应具有显着的抑制作用。此外，DMFP 在乙酸引起的腹部扭动试验和热板试验中的抗伤害作用不会被非选择性阿片受体拮抗剂纳洛酮预处理所拮抗。最后，DMFP 在急性毒性研究中没有表现出任何毒性作用和/或死亡率，并且在 Rota-rod 测试期间不会干扰运动协调。我们目前的结果表明 DMFP 具有外周和中枢抗伤害作用。有人认为，其外周抗伤害活性与 NO 和各种促炎介质的产生和/或释放减弱有关，而中枢抗伤害活性似乎与阿片系统无关，但可能至少部分涉及相互作用抑制辣椒素敏感纤维和谷氨酸能系统。