2'-hydroxy-4'-methoxy-4-(tetrahydropyran-2-yloxy)chalcone

• 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: 2'-hydroxy-4'-methoxy-4-(tetrahydropyran-2-yloxy)chalcone
• 英文别名: 2'-Hydroxy-4'-methoxy-4-(tetrahydropyran-2-yloxy)chalcone；1-(2-hydroxy-4-methoxyphenyl)-3-[4-(oxan-2-yloxy)phenyl]prop-2-en-1-one
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: BQIBHZRVLUUAES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-4'-methoxy-4-(tetrahydropyran-2-yloxy)chalcone 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到2',4-dihydroxy-4'-methoxychalcone
  参考文献：
  名称：

  Inhibition of prostaglandin E2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation

  摘要：

  The discovery of potent inhibitors of prostaglandin E2 (PGE2) synthesis in recent years has been proven to be an important game changer in pharmaceutical industry. It is known that excessive production of PGE2 triggers a vast array of biological signals and physiological events that contributes to inflammatory diseases such as rheumatoid arthritis, atherosclerosis, cancer, and pain. In this Letter, we report the synthesis of a series of minor prenylated chalcones and flavonoids which was found to be significantly active in suppressing the PGE2 production secreted by lipopolysaccharide-induced mouse macrophage cells (RAW 264.7). Among the compounds tested, 14b showed a dose-response inhibition of PGE2 production with an IC50 value of 2.1 μM. The suppression upon PGE2 secretion was not due to cell death since 14b did not reduce the cell viability in close proximity to the PGE2 inhibition concentration. The obtained atomic coordinates for the single-crystal XRD of 14b was then applied in the docking simulation to determine the potential important binding interactions with murine COX-2 and mPGES-1 putative binding sites.

  DOI：

  10.1016/j.bmcl.2014.06.061
• 作为产物：
  描述：

  丹皮酚 、 4-(四氢-吡喃-2-基氧基)-苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以63%的产率得到2'-hydroxy-4'-methoxy-4-(tetrahydropyran-2-yloxy)chalcone
  参考文献：
  名称：

  Inhibition of prostaglandin E2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation

  摘要：

  The discovery of potent inhibitors of prostaglandin E2 (PGE2) synthesis in recent years has been proven to be an important game changer in pharmaceutical industry. It is known that excessive production of PGE2 triggers a vast array of biological signals and physiological events that contributes to inflammatory diseases such as rheumatoid arthritis, atherosclerosis, cancer, and pain. In this Letter, we report the synthesis of a series of minor prenylated chalcones and flavonoids which was found to be significantly active in suppressing the PGE2 production secreted by lipopolysaccharide-induced mouse macrophage cells (RAW 264.7). Among the compounds tested, 14b showed a dose-response inhibition of PGE2 production with an IC50 value of 2.1 μM. The suppression upon PGE2 secretion was not due to cell death since 14b did not reduce the cell viability in close proximity to the PGE2 inhibition concentration. The obtained atomic coordinates for the single-crystal XRD of 14b was then applied in the docking simulation to determine the potential important binding interactions with murine COX-2 and mPGES-1 putative binding sites.

  DOI：

  10.1016/j.bmcl.2014.06.061

文献信息

• [EN] NOTCH INHIBITORS FOR USE IN THE TREATMENT OF T-CELL ACUTE LYMPHOBLASTIC LEUKEMIA<br/>[FR] INHIBITEURS DE NOTCH DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DE LA LEUCÉMIE LYMPHOBLASTIQUE AIGUË À LYMPHOCYTES T
  申请人：UNIV DEGLI STUDI ROMA LA SAPIENZA

  公开号：WO2018122689A1

  公开（公告）日：2018-07-05

  Compounds of formula (I) in the capacity of compounds with anti-tumor activity for the treatment of T-cell acute lymphoblastic leukemia (T-ALL).

  式（I）的化合物作为具有抗肿瘤活性的化合物，用于治疗T细胞急性淋巴细胞白血病（T-ALL）。
• NOTCH INHIBITORS FOR USE IN THE TREATMENT OF T-CELL ACUTE LYMPHOBLASTIC LEUKEMIA
  申请人：Università degli Studi di Roma "La Sapienza"

  公开号：EP3562803A1

  公开（公告）日：2019-11-06
• Inhibition of prostaglandin E2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation
  作者：Kamal Rullah、Mohd Fadhlizil Fasihi Mohd Aluwi、Bohari M. Yamin、Mohd Nazri Abdul Bahari、Leong Sze Wei、Syahida Ahmad、Faridah Abas、Nor Hadiani Ismail、Ibrahim Jantan、Lam Kok Wai

  DOI：10.1016/j.bmcl.2014.06.061

  日期：2014.8

  The discovery of potent inhibitors of prostaglandin E2 (PGE2) synthesis in recent years has been proven to be an important game changer in pharmaceutical industry. It is known that excessive production of PGE2 triggers a vast array of biological signals and physiological events that contributes to inflammatory diseases such as rheumatoid arthritis, atherosclerosis, cancer, and pain. In this Letter, we report the synthesis of a series of minor prenylated chalcones and flavonoids which was found to be significantly active in suppressing the PGE2 production secreted by lipopolysaccharide-induced mouse macrophage cells (RAW 264.7). Among the compounds tested, 14b showed a dose-response inhibition of PGE2 production with an IC50 value of 2.1 μM. The suppression upon PGE2 secretion was not due to cell death since 14b did not reduce the cell viability in close proximity to the PGE2 inhibition concentration. The obtained atomic coordinates for the single-crystal XRD of 14b was then applied in the docking simulation to determine the potential important binding interactions with murine COX-2 and mPGES-1 putative binding sites.