1-(6-羟基-4-甲氧基-1-苯并呋喃-5-基)-3-苯基丙-2-烯-1-酮 | 54437-44-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1-(6-羟基-4-甲氧基-1-苯并呋喃-5-基)-3-苯基丙-2-烯-1-酮
• 英文名称: 4-Methoxy-6-hydroxy-5-cinnamoyl-benzofuran
• 英文别名: 1-(6-hydroxy-4-methoxybenzo[b]furan-5-yl)-3-phenylprop-2-en-1-one；1-(6-hydroxy-4-methoxy-1-benzofuran-5-yl)-3-phenylprop-2-en-1-one；1-(6-hydroxy-4-methoxybenzofuran-5-yl)-3-phenylprop-2-en-1-one；1-(6-hydroxy-4-methoxy-benzofuran-5-yl)-3-phenyl-propenone；1-(6-Hydroxy-4-methoxy-1-benzofuran-5-yl)-3-phenylprop-2-en-1-one
• CAS: 54437-44-4
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: SPFCYLTZEFTMIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(6-羟基-4-甲氧基-1-苯并呋喃-5-基)-3-苯基丙-2-烯-1-酮 在 selenium(IV) oxide 作用下， 以 正丁醇 为溶剂， 生成 5H-呋喃并[3,2-g][1]苯并吡喃-5-酮,4-甲氧基-7-苯基-
  参考文献：
  名称：

  某些取代的呋喃色酮，苯并呋喃和黄酮衍生物的合成和抗惊厥活性。

  摘要：

  合成了呋喃色酮，2-苯基色酮（黄酮）和被硫代氨基脲或噻唑烷丁-4-酮取代的苯并呋喃衍生物。分别以丙戊酸和苯妥英钠为参考标准，对所有新合成的化合物在皮下戊四氮诱发的癫痫发作（scPTZ）和最大电击诱发的癫痫发作（MES）试验中均进行了抗惊厥活性的测试。scPTZ模型中活性最高的化合物为1c，2b，5a和7e，在腹膜内给药时在300 mg / kg时显示出100％的保护作用。此外，研究了三种活性最高的化合物（1c，2b，5a）的预处理对小鼠4-氨基吡啶诱导的致死性的影响。用这些化合物进行预处理显着增加了阵挛性和强直性惊厥的潜伏期，并防止了4-氨基吡啶诱发的死亡。因此，这提供了这些化合物的抗惊厥活性和对它们的神经保护活性的证据。基于获得的数据研究了构效关系。

  DOI：

  10.1248/cpb.58.1148
• 作为产物：
  描述：

  齿阿米素 在 水 、 potassium hydroxide 、 sodium hydroxide 作用下， 生成 1-(6-羟基-4-甲氧基-1-苯并呋喃-5-基)-3-苯基丙-2-烯-1-酮
  参考文献：
  名称：

  磷叶立德化学。第 34 部分 Chromenone Phosphanylidene 和 Cyclobutylidene 衍生物的合成

  摘要：

  摘要 亲核磷杂草烯叶立德与visnaginone 和khellinone 反应得到相应的亚膦基和呋喃色烯衍生物。此外，吡喃色烯是从色烯甲醛与磷枯草烯的反应中获得的。另一方面，亚膦基-亚环丁基及其二聚体是由呋喃色烯甲醛与相同的鏻试剂反应产生的。图形概要

  DOI：

  10.1080/10426507.2011.600741

文献信息

• Celecoxib analogs bearing benzofuran moiety as cyclooxygenase-2 inhibitors: Design, synthesis and evaluation as potential anti-inflammatory agents
  作者：Ghaneya Sayed Hassan、Sahar Mahmoud Abou-Seri、Gehan Kamel、Mamdouh Moawad Ali

  DOI：10.1016/j.ejmech.2014.02.033

  日期：2014.4

  The most potent and selective COX-2 inhibitors – compounds 3c, 3d, 3e, 9c and 9d – were assessed for their anti-inflammatory activity and ulcerogenic liability in vivo. The 3-(pyridin-3-yl)pyrazole derivatives 3c and 3e exhibited the highest anti-inflammatory activity, that is equipotent to celecoxib. Furthermore, the tested compounds proved to have better gastric safety profile compared to celecoxib

  合成了具有苯并呋喃部分3a - e和9a - d的新系列塞来昔布类似物，并对其体外COX-1 / COX-2抑制活性进行了评估。评估了最有效和选择性最强的COX-2抑制剂-化合物3c，3d，3e，9c和9d的体内抗炎活性和致溃疡作用。3-（吡啶-3-基）吡唑衍生物3c和3e具有最高的抗炎活性，相当于塞来昔布。此外，与塞来昔布相比，被测化合物具有更好的胃安全性。特别地，相对于参考药物，化合物3e显示出致溃疡的可能性降低了约40％。最后，在COX-2活性位点和药物相似性研究中对新化合物进行了分子对接模拟，结果与所获得的药理生物学结果吻合良好。
• Benzofuran–Morpholinomethyl–Pyrazoline Hybrids as a New Class of Vasorelaxant Agents: Synthesis and Quantitative Structure–Activity Relationship Study
  作者：Ghaneya Sayed Hassan、Doaa Ezzat Abdel Rahman、Dalia Osama Saleh、Gehad Abdel Raheem Abdel Jaleel

  DOI：10.1248/cpb.c14-00572

  日期：——

  The benzofuran–morpholinomethyl–pyrazoline hybrids 4a–e, 5a–e and 6a–j were synthesized via reaction of α,β-unsaturated carbonyl compounds 3a–e with hydrazine hydrate, semicarbazide or thiosemicarbazide. Applying the Mannich reaction to 5-(5-aryl-4,5-dihydro-1H-pyrazol-3-yl)-4-methoxybenzofuran-6-ols 7a–e with morpholine hydrochloride and paraformaldehyde afforded positional isomeric 7-morpholinomethyl derivatives 4a–e and N-morpholinomethyl derivatives 8a–e. All the synthesized compounds showed significant vasodilatation properties in isolated thoracic aortic rings of rats precontracted using the standard norepinephrine hydrochloride technique. Compounds 3d, 3e, 5a–c, 6b, 6c, 6f, 6h and 6i exhibited activity (IC50 0.3185–0.4577 mM) superior to that of prazocin (IC50 0.487 mM), while 5d, 6j and 8c showed comparable activity (IC50 0.4789–0.4951 mM). The quantitative structure–activity relationship study revealed a correlation between the observed vasorelaxant activities of the newly synthesized compounds and their different physicochemical parameters, especially solubility, in addition to structure connectivity and energetic quantities calculated from stored three dimensional (3D) conformations. Absorption, distribution, metabolism and elimination (ADME) evaluation showed good agreement with the biological results obtained.

  苯并呋喃-吗啉甲基吡唑啉杂化物 4a-e、5a-e 和 6a-j 是通过 α、β-不饱和羰基化合物 3a-e 与肼水合物、半肼或硫代氨基肼反应合成的。将 5-(5-芳基-4,5-二氢-1H-吡唑-3-基)-4-甲氧基苯并呋喃-6-醇 7a-e 与盐酸吗啉和多聚甲醛进行曼尼希反应，可得到位置异构的 7-吗啉甲基衍生物 4a-e 和 N-吗啉甲基衍生物 8a-e。在使用标准盐酸去甲肾上腺素技术预收缩大鼠离体胸主动脉环时，所有合成化合物都显示出明显的血管扩张特性。化合物 3d、3e、5a-c、6b、6c、6f、6h 和 6i 的活性（IC50 0.3185-0.4577 mM）优于普拉佐辛（IC50 0.487 mM），而 5d、6j 和 8c 的活性（IC50 0.4789-0.4951 mM）相当。定量结构-活性关系研究表明，新合成化合物的血管舒张活性与其不同的理化参数（尤其是溶解度）之间存在相关性，此外，根据储存的三维构象计算出的结构连接性和能量量也存在相关性。吸收、分布、代谢和消除（ADME）评估结果显示，新合成的化合物与所获得的生物学结果非常吻合。
• Reactions with Hydrazonoyl Halides 58: Synthesis of 2,3-Dihydro-1,3,4-thiadiazoles and 5-Arylazothiazoles
  作者：Abdou O. Abdelhamid、Zeineb H. Ismail、Anhar Abdel-Aziem

  DOI：10.1080/10426500701734190

  日期：2008.6.9

  1,3,4-Thiadiazolines containing a chromone moiety and 5-1-[4-substituted-5-phenyldiazenyl)(1,3-thiazol-2-yl]-5-phenyl-2-pyrazolin-3-yl)}-4-methoxybenzo[b]-furan-6-ol were synthetic from hydrazonoyl halide and alkyl carbodithioates and 5-[1-aminothiomethoxy)-5-phenyl-2-pyrazolin-3-yl)]-4-methoxybenzo[b]furan-6-ol, respectively. All structures of the newly synthesized compounds were elucidated by elemental

  含有色酮部分和 5-1-[4-取代-5-苯基二氮烯基)(1,3-噻唑-2-基]-5-苯基-2-吡唑啉-3-基)的 1,3,4-噻二唑啉}-4-甲氧基苯并[b]-呋喃-6-醇由腙酰卤和碳二硫代烷基酯和5-[1-氨基硫代甲氧基)-5-苯基-2-吡唑啉-3-基)]-4-甲氧基苯并[b]合成]呋喃-6-醇，分别。新合成化合物的所有结构都尽可能通过元素分析、光谱数据和替代合成方法阐明。
• Hishmat; Miky; Saleh, Pharmazie, 1989, vol. 44, # 12, p. 823 - 825
  作者：Hishmat、Miky、Saleh

  DOI：——

  日期：——
• Design, synthesis and structure–activity relationship of novel semi-synthetic flavonoids as antiproliferative agents
  作者：F.A. Ragab、T.A.A. Yahya、M.M. El-Naa、R.K. Arafa

  DOI：10.1016/j.ejmech.2014.06.007

  日期：2014.7

  Various flavonoid scaffold based derivatives viz furochalcones (3a-e, 6a-d and 9a-d), furoflavones (10a-d, 11a-d,12a-d,18a&b), flavones (21a-d), furoaurones (13a,b,14a-d and 15a-d) and 7-styrylfurochromones (22a-d and 25a-e) were designed and synthesized. The novel compounds were evaluated for their anti-proliferative activity against a panel of 60 cancer cell lines comprising 9 types of tumors. Ten compounds belonging to the major subgroups of flavonoids viz furochalcones (3a, 3d, 6b, 9a and 9b), furoflavones (12a and 12c), furoaurones (15d), styrylfurochromones (25b and 25e) showed very promising activity. These active compounds were also evaluated in vitro as kinase inhibitors against CDK2/cyclin E1, CDK4/cyclin D1 and GSK-3 beta and the best inhibition was displayed against GSK-3 beta with the allylfurochalcone derivative 9b exhibiting 80% decrease in GSK-3 beta catalytic activity. On the other hand, the styrylfurochromone 25e interestingly showed a 13% enhancement of GSK-3 beta catalytic power and a 12% reduction in CDK4/cyclin D1 activity. Finally, the in vivo anti-tumor activity of 25e was evaluated against breast cancer induced in mice. The results showed a profound anti-tumor effect of 25e that accompanies a significant increase and decrease in the levels of GSK-3 beta and cyclin D1, respectively. (C) 2014 Elsevier Masson SAS. All rights reserved.