(E)-1-(2-hydroxy-5-fluorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one | 391-94-6

• 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
• 英文名称: (E)-1-(2-hydroxy-5-fluorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 5'-fluoro-2'-hydroxy-4-methoxy-trans-chalcone；5'-Fluor-2'-hydroxy-4-methoxy-trans-chalkon；5'-Fluoro-2'-hydroxy-4-methoxychalcone；(E)-1-(5-fluoro-2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 391-94-6
• 化学式: C₁₆H₁₃FO₃
• 分子量: 272.276
• InChiKey: JOAXGODDHKAEDJ-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-hydroxy-5-fluorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 以 乙醇 为溶剂， 以29%的产率得到6-Fluor-4'-methoxy-flavanon
  参考文献：
  名称：

  Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold

  摘要：

  通过紫外/可见光谱和核磁共振谱，研究了替代对一种新型比色动态共价开关支架的影响。

  DOI：

  10.1039/c4ob00398e
• 作为产物：
  描述：

  6-Fluor-4'-methoxy-flavanon 以 乙醇 为溶剂， 生成 (E)-1-(2-hydroxy-5-fluorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold

  摘要：

  通过紫外/可见光谱和核磁共振谱，研究了替代对一种新型比色动态共价开关支架的影响。

  DOI：

  10.1039/c4ob00398e

文献信息

• [EN] HETEROCYCLIC COMPOUNDS THAT BLOCK THE EFFECTS OF ADVANCED GLYCATION END PRODUCTS (AGE)<br/>[FR] COMPOSES HETEROCYCLIQUES BLOQUANT LES EFFETS DES PRODUITS TERMINAUX AVANCES DE GLYCATION
  申请人：REDDYS LAB LTD DR

  公开号：WO2005040163A1

  公开（公告）日：2005-05-06

  The present invention relates to novel compounds of Formula (Ia) or (Ib), their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. Formula (Ia), or Formula (Ib) in the above formulae L represents Formula (I), Formula (II) or -(CH2)1- Q represents Formula (III), or Formula (IV). The present invention also relates to a process for the preparation of the above said novel compounds, their pharmaceutically acceptable salts and pharmaceutical compositions containing them. The present invention also relates to methods and compositions comprising compounds that treat pathophysiological conditions arising from inflammatory responses. In particular, the present invention is directed to compounds that inhibit or block glycated protein produced induction of the signaling-associated inflammatory responses in tissues, including endothelial cells. The present invention relates to compounds that inhibit smooth muscle proliferation. The present invention also relates to compounds that act as modulators of Perlecan activity and expression. In particular, the present invention is directed to compounds that inhibit smooth muscle cell proliferation by modulating heparan sulfate proteoglycans (HSPG) such as Perlecan. The present invention further relates to the use of compounds to treat vascular occlusive conditions characterized by smooth muscle proliferation such as stenosis, restenosis, neointimal hyperplasia, and atherosclerosis. The compounds of Formula (I) are also useful for the treatment and/or prevention of cancer. The types of cancers include melanoma, prostate, leukemia, lymphoma, non-small lung cancers, cancer of the central nervous system, breast, colon, ovarian or renal cancer.

  本发明涉及公式（Ia）或（Ib）的新化合物，它们的药学上可接受的盐以及含有它们的药学上可接受的组合物。在上述公式中，公式（Ia）或公式（Ib）中的L代表公式（I）、公式（II）或-(CH2)1-，Q代表公式（III）或公式（IV）。本发明还涉及制备上述新化合物、其药学上可接受的盐和含有它们的药物组合物的方法。本发明还涉及包括治疗由炎症反应引起的病理生理条件的化合物的方法和组合物。具体而言，本发明涉及抑制或阻断组织中糖化蛋白诱导的与信号相关的炎症反应的化合物。本发明涉及抑制平滑肌增殖的化合物。本发明还涉及作为Perlecan活性和表达调节剂的化合物。具体而言，本发明涉及通过调节肝素硫酸蛋白聚糖（HSPG）如Perlecan来抑制平滑肌细胞增殖的化合物。本发明进一步涉及利用化合物治疗由平滑肌增殖特征的血管闭塞性疾病，如狭窄、再狭窄、新内膜增生和动脉粥样硬化。公式（I）的化合物也可用于治疗和/或预防癌症。癌症类型包括黑色素瘤、前列腺癌、白血病、淋巴瘤、非小细胞肺癌、中枢神经系统癌症、乳腺癌、结肠癌、卵巢癌或肾癌。
• Heterocyclic compounds and methods of making and using thereof
  申请人：Rao Koteswar Yeleswarapu

  公开号：US20050119269A1

  公开（公告）日：2005-06-02

  Compounds of formula (I), and methods and/or compositions comprising compounds that are effective in modulating inflammatory responses, such as those resulting from AGE and glycated protein accumulation are provided. Methods and/or compositions comprising compounds that are effective in modulating smooth muscle cell proliferation and the diseases or conditions related thereto are also provided.

  提供化学式(I)的化合物，以及包含这些化合物的方法和/或组合物，这些化合物对调节由AGE和糖基化蛋白堆积引起的炎症反应有效。还提供了有效调节平滑肌细胞增殖及其相关疾病或病况的方法和/或组合物。
• Synthesis and biological evaluation of flavonoid-based IP6K2 inhibitors
  作者：Myunghwan Ahn、Seung Eun Park、Jiyeon Choi、Jiahn Choi、Doyoung Choi、Dongju An、Hayoung Jeon、Soowhan Oh、Kiho Lee、Jaehoon Kim、Jaebong Jang、Seyun Kim、Youngjoo Byun

  DOI：10.1080/14756366.2023.2193866

  日期：2023.12.31

  and obesity. In this study, we designed, synthesised, and evaluated flavonoid-based compounds as new inhibitors of IP6K2. Structure-activity relationship studies identified compound 20s as the most potent IP6K2 inhibitor with an IC50 value of 0.55 μM, making it 5-fold more potent than quercetin, the reported flavonoid-based IP6K2 inhibitor. Compound 20s showed higher inhibitory potency against IP6K2

  摘要 肌醇多磷酸盐 (IPs) 是一组肌醇代谢物，可作为外部信号线索的第二信使。它们发挥着多种生理作用，例如胰岛素释放、端粒长度维持、细胞代谢和衰老。肌醇六磷酸激酶 2 (IP6K2) 是产生 5-二磷酸肌醇 1,2,3,4,6-五磷酸 (5-IP7) 的关键酶，它影响葡萄糖诱导的胞吐作用的早期阶段。因此，IP6Ks 的调控可能成为治疗糖尿病和肥胖等疾病的一种有前途的策略。在这项研究中，我们设计、合成和评估了基于类黄酮的化合物作为 IP6K2 的新抑制剂。构效关系研究确定化合物20s是最有效的 IP6K2 抑制剂，IC 为50值为 0.55 μM，使其比槲皮素强 5 倍，槲皮素是已报道的基于类黄酮的 IP6K2 抑制剂。化合物20s对 IP6K2 的抑制效力高于 IP6K1 和 IP6K3。化合物20s可用作命中化合物，用于 IP6K2 抑制剂的进一步结构修饰。
• Chen; Yang, Taiwan Yaoxue Zazhi, 1951, vol. 3, p. 39
  作者：Chen、Yang

  DOI：——

  日期：——
• HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING THEREOF
  申请人：Reddy US Therapeutics, Inc.

  公开号：EP1678157A2

  公开（公告）日：2006-07-12