2-(4-Hexylphenyl)-4-oxochromene-6-carboxylic acid | 72739-22-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-Hexylphenyl)-4-oxochromene-6-carboxylic acid
• CAS: 72739-22-1
• 化学式: C₂₂H₂₂O₄
• 分子量: 350.414
• InChiKey: WIFDTMIXLQLAEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-N-己基苯甲醛 在 氢氧化钾 、 溴 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 2-(4-Hexylphenyl)-4-oxochromene-6-carboxylic acid
  参考文献：
  名称：

  Inhibition of histamine-induced gastric secretion by flavone-6-carboxylic acids

  摘要：

  Twenty-five flavone-6-carboxylic acids were synthesized and tested as to their ability to inhibit histamine-induced gastric acid secretion in the rat. 3-Isopropoxy-4'-methoxyflavone-6-carboxylic acid (41) showed consistent oral activity while being devoid of any other noteworthy pharmacological effects. In vitro, this compound was found to be inactive as a histamine H2 antagonist, and its mode of action remains unknown.

  DOI：

  10.1021/jm00177a029

文献信息

• Novel Baicalein-Derived Inhibitors of Plasmodium falciparum
  作者：Chandra Sekhar Gudla、Vignesh Selvam、Siva Shanmugam Selvaraj、Renu Tripathi、Prince Joshi、Salique Hassan Shaham、Mayas Singh、Radha Krishan Shandil、Saman Habib、Shridhar Narayanan

  DOI：10.3390/pathogens12101242

  日期：——

  Malaria, a life-threatening mosquito-borne disease caused by Plasmodium parasites, continues to pose a significant global health burden. Despite notable progress in combating the disease in recent years, malaria remains prevalent in many regions, particularly in Southeast Asia and most of sub-Saharan Africa, where it claims hundreds of thousands of lives annually. Flavonoids, such as the baicalein class of compounds, are known to have antimalarial properties. In this study, we rationally designed and synthesized a series of baicalein derivatives and identified a lead compound, FNDR-10132, that displayed potent in vitro antimalarial activity against Plasmodium falciparum (P. falciparum), both chloroquine-sensitive (60 nM) and chloroquine-resistant (177 nM) parasites. FNDR-10132 was evaluated for its antimalarial activity in vivo against the chloroquine-resistant strain Plasmodium yoelii N67 in Swiss mice. The oral administration of 100 mg/kg of FNDR-10132 showed 44% parasite suppression on day 4, with a mean survival time of 13.5 ± 2.3 days vs. 8.4 ± 2.3 days of control. Also, FNDR-10132 displayed equivalent activity against the resistant strains of P. falciparum in the 200–300 nM range. This study offers a novel series of antimalarial compounds that could be developed into potent drugs against chloroquine-resistant malarial parasites through further chemistry and DMPK optimization.

  疟疾是一种由疟原虫引起的威胁生命的蚊媒疾病，继续对全球健康造成重大负担。尽管近年来在防治疟疾方面取得了显著进展，但疟疾仍在许多地区流行，尤其是在东南亚和撒哈拉以南非洲的大部分地区，每年有数十万人因此而丧生。众所周知，黄酮类化合物（如黄芩素类）具有抗疟特性。在这项研究中，我们合理地设计和合成了一系列黄芩苷衍生物，并确定了一种先导化合物 FNDR-10132，该化合物对恶性疟原虫（P. falciparum）、氯喹敏感寄生虫（60 nM）和氯喹抗性寄生虫（177 nM）均显示出强大的体外抗疟活性。FNDR-10132 在瑞士小鼠体内对耐氯喹的yoelii N67 株疟原虫的抗疟活性进行了评估。口服 100 毫克/千克 FNDR-10132 后，第 4 天的寄生虫抑制率为 44%，平均存活时间为 13.5 ± 2.3 天（对照组为 8.4 ± 2.3 天）。此外，FNDR-10132 在 200-300 nM 范围内对恶性疟原虫耐药菌株显示出同等的活性。这项研究提供了一系列新型抗疟化合物，通过进一步的化学和 DMPK 优化，可将其开发成抗耐氯喹疟原虫的强效药物。
• PFISTER J. R.; WYMANN W. E.; SCHULER M. E.; ROSZKOWSKI A. P., J. MED. CHEM., 1980, 23, NO 3, 335-338
  作者：PFISTER J. R.、 WYMANN W. E.、 SCHULER M. E.、 ROSZKOWSKI A. P.

  DOI：——

  日期：——
• Inhibition of histamine-induced gastric secretion by flavone-6-carboxylic acids
  作者：Juerg R. Pfister、Walter E. Wymann、Margery E. Schuler、Adolph P. Roszkowski

  DOI：10.1021/jm00177a029

  日期：1980.3

  Twenty-five flavone-6-carboxylic acids were synthesized and tested as to their ability to inhibit histamine-induced gastric acid secretion in the rat. 3-Isopropoxy-4'-methoxyflavone-6-carboxylic acid (41) showed consistent oral activity while being devoid of any other noteworthy pharmacological effects. In vitro, this compound was found to be inactive as a histamine H2 antagonist, and its mode of action remains unknown.