2-(4-甲氧基苯甲酰基)-1-苯并呋喃-5-甲醛 | 300664-77-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(4-甲氧基苯甲酰基)-1-苯并呋喃-5-甲醛
• 英文名称: 2-(4-Methoxybenzoyl)-1-benzofuran-5-carbaldehyde
• CAS: 300664-77-1
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: IKRGAQSOLZHDGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 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：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl)ethanone 、 2-(4-甲氧基苯甲酰基)-1-苯并呋喃-5-甲醛 以82%的产率得到(E)-1-(5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl)-3-(2-(4-methoxybenzoyl)benzofuran-5-yl)prop-2-en-1-one
  参考文献：
  名称：

  al作为抗疟药的结构与活性关系的合成与认识

  摘要：

  从中国甘草的根中分离得到的Licochalcone A（I）是迄今为止报道的最有前途的抗疟化合物。在继续我们的药物发现计划时，我们从猪屎豆属中分离了两个类似的查耳酮，medicageninin（II）和munchiwarin（III），它们对恶性疟原虫具有抗疟活性。合成了88个查耳酮的文库，并对其体外抗疟活性进行了评估。在这些中，67，68，74，77，和78显示出在体外对抗疟疾活性良好恶性疟原虫具有低细胞毒性的3D7和K1菌株。这些查耳酮还显示出寄生虫约瑟氏疟原虫（N-67株）感染的瑞士小鼠的寄生虫病减少和存活时间增加。药代动力学研究表明，不良的ADME特性导致口服生物利用度低。分子对接研究揭示了这些抑制剂在falcipain-2（FP-2）酶的活性位点的结合方向。化合物67，68，和78显示出对主要血红蛋白降解半胱氨酸适度抑制活性蛋白酶FP-2。

  DOI：

  10.1021/jm300588j
• 作为产物：
  描述：

  对羟基苯甲醛 在 乌洛托品 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 28.0h， 生成 2-(4-甲氧基苯甲酰基)-1-苯并呋喃-5-甲醛
  参考文献：
  名称：

  Design, synthesis, and evaluation of benzofuran-based chromenochalcones for antihyperglycemic and antidyslipidemic activities

  摘要：

  合成了新型双效苯并呋喃类铬喹酮，并对其体内外抗高血糖和抗血脂活性进行了评估。

  DOI：

  10.1039/d2md00341d

文献信息

• Synthesis and Insight into the Structure–Activity Relationships of Chalcones as Antimalarial Agents
  作者：Narender Tadigoppula、Venkateswarlu Korthikunta、Shweta Gupta、Papireddy Kancharla、Tanvir Khaliq、Awakash Soni、Rajeev Kumar Srivastava、Kumkum Srivastava、Sunil Kumar Puri、Kanumuri Siva Rama Raju、Wahajuddin、Puran Singh Sijwali、Vikash Kumar、Imran Siddiqi Mohammad

  DOI：10.1021/jm300588j

  日期：2013.1.10

  licorice, is the most promising antimalarial compound reported so far. In continuation of our drug discovery program, we isolated two similar chalcones, medicagenin (II) and munchiwarin (III), from Crotalaria medicagenia, which exhibited antimalarial activity against Plasmodium falciparum. A library of 88 chalcones were synthesized and evaluated for their in vitro antimalarial activity. Among these, 67,

  从中国甘草的根中分离得到的Licochalcone A（I）是迄今为止报道的最有前途的抗疟化合物。在继续我们的药物发现计划时，我们从猪屎豆属中分离了两个类似的查耳酮，medicageninin（II）和munchiwarin（III），它们对恶性疟原虫具有抗疟活性。合成了88个查耳酮的文库，并对其体外抗疟活性进行了评估。在这些中，67，68，74，77，和78显示出在体外对抗疟疾活性良好恶性疟原虫具有低细胞毒性的3D7和K1菌株。这些查耳酮还显示出寄生虫约瑟氏疟原虫（N-67株）感染的瑞士小鼠的寄生虫病减少和存活时间增加。药代动力学研究表明，不良的ADME特性导致口服生物利用度低。分子对接研究揭示了这些抑制剂在falcipain-2（FP-2）酶的活性位点的结合方向。化合物67，68，和78显示出对主要血红蛋白降解半胱氨酸适度抑制活性蛋白酶FP-2。
• Agonists and Antagonists of the S1P5 Receptor, and Methods of Use Thereof
  申请人：Harris Christopher M.

  公开号：US20100216762A1

  公开（公告）日：2010-08-26

  Disclosed are compounds that are agonists or antagonists of the S1P 5 receptor, compositions comprising said compounds, and methods of using said compounds and compositions. In certain embodiments, said compounds are 1-benzylazetidine-3-carboxylic acid derivatives. In certain embodiments, said methods relate to the treatment of neuropatic pain and/or a neurodegenerative disorder. In certain embodiments, said compounds may be used in combination with a second therapeutic agent.

  本发明涉及一种作为S1P5受体激动剂或拮抗剂的化合物，包括该化合物的组合物以及使用该化合物和组合物的方法。在某些实施例中，该化合物是1-苄基氮杂环丙氨酸衍生物。在某些实施例中，该方法涉及神经病性疼痛和/或神经退行性疾病的治疗。在某些实施例中，该化合物可以与第二种治疗药物联合使用。
• Synthesis, Structure–Activity Relationships, and Biological Studies of Chromenochalcones as Potential Antileishmanial Agents
  作者：Rahul Shivahare、Venkateswarlu Korthikunta、Hardik Chandasana、Manish K. Suthar、Pragati Agnihotri、Preeti Vishwakarma、Telaprolu K. Chaitanya、Papireddy Kancharla、Tanvir Khaliq、Shweta Gupta、Rabi Sankar Bhatta、J. Venkatesh Pratap、Jitendra K. Saxena、Suman Gupta、Narender Tadigoppula

  DOI：10.1021/jm401893j

  日期：2014.4.24

  Antileishmanial activities of a library of synthetic chalcone analogues have been examined. Among them, five compounds (11, 14, 16, 17, 22, and 24) exhibited better activity than the marketed drug miltefosine in in vitro studies against the intracellular amastigotes form of Leishmania donovani. Three promising compounds, 16, 17, and 22, were tested in a L. donovani/hamster model. Oral administration of chalcone 16, at a concentration of 100 mg/kg of body weight per day for 5 consecutive days, resulted in >84% parasite inhibition at day 7 post-treatment and it retained the activity until day 28. The molecular and immunological studies revealed that compound 16 has a dual nature to act as a direct parasite killing agent and as a host immunostimulant. Pharmacokinetics and serum albumin binding studies also suggest that compound 16 has the potential to be a candidate for the treatment of the nonhealing form of leishmaniasis.
• Design, synthesis, and evaluation of benzofuran-based chromenochalcones for antihyperglycemic and antidyslipidemic activities
  作者：Venkateswarlu Korthikunta、Rohit Singh、Rohit Srivastava、Jyotsana Pandey、Atul Srivastava、Upma Chaturvedi、Akansha Mishra、Arvind K. Srivastava、Akhilesh K. Tamrakar、Narender Tadigoppula

  DOI：10.1039/d2md00341d

  日期：——

  Novel dual acting benzofuran-based chromenochalcones were synthesized and assessed for in vitro and in vivo antihyperglycemic and antidyslipidemic activities.

  合成了新型双效苯并呋喃类铬喹酮，并对其体内外抗高血糖和抗血脂活性进行了评估。