(E)-1-(3-azidophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one | 1314006-60-4

• 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
• 英文名称: (E)-1-(3-azidophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
• CAS: 1314006-60-4
• 化学式: C₁₆H₁₃N₃O₃
• 分子量: 295.298
• InChiKey: AWOKXMNJSAFMCM-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-azidophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one 、 2-甲基-1-丁烯-3-炔 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 5.0h， 以64%的产率得到(E)-3-(4-hydroxy-3-methoxyphenyl)-1-[3-(4-prop-1-en-2-yltriazol-1-yl)phenyl]prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of substituted triazolyl curcumin mimics that inhibit RANKL-induced osteoclastogenesis

  摘要：

  Some promising new antiresorptive agents of potential utility for treating osteoporosis were uncovered in a curcumin mimics library possessing a substituted triazole moiety, which is synthesized by the Cu(I)-catalyzed Huisgen 1,3-cycloaddition reaction between two azido intermediates (9 and 10) and various alkynes (a-k). A tartarate-resistant acid phosphatase (TRAP) activity assay was carried out with RANKL-induced osteoclastogenesis of mouse monocyte/macrophage RAW264.7 cells; the results indicated that the curcumin mimics derived from intermediate 10 exhibited stronger inhibitory activity than 9. In particular, curcumin mimics 12h, 13c, and 13e strongly inhibited osteoclast differentiation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.106
• 作为产物：
  描述：

  间氨基苯乙酮 在 盐酸 、 potassium hydroxide 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 (E)-1-(3-azidophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of substituted triazolyl curcumin mimics that inhibit RANKL-induced osteoclastogenesis

  摘要：

  Some promising new antiresorptive agents of potential utility for treating osteoporosis were uncovered in a curcumin mimics library possessing a substituted triazole moiety, which is synthesized by the Cu(I)-catalyzed Huisgen 1,3-cycloaddition reaction between two azido intermediates (9 and 10) and various alkynes (a-k). A tartarate-resistant acid phosphatase (TRAP) activity assay was carried out with RANKL-induced osteoclastogenesis of mouse monocyte/macrophage RAW264.7 cells; the results indicated that the curcumin mimics derived from intermediate 10 exhibited stronger inhibitory activity than 9. In particular, curcumin mimics 12h, 13c, and 13e strongly inhibited osteoclast differentiation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.106

文献信息

• The TRAIL Sensitization Effect of Substituted Triazolyl Curcumin Mimics Against Brain Cancer Cells
  作者：Daeho Kwon、Sangtae Oh、Ji-Hye Park、Seoul Lee、Seokjoon Lee

  DOI：10.5012/bkcs.2014.35.11.3339

  日期：2014.11.20
• Synthesis of substituted triazolyl curcumin mimics that inhibit RANKL-induced osteoclastogenesis
  作者：Sang-Kyu Park、Sangtae Oh、Hye Kyoung Shin、Seong Hwan Kim、Jungyeob Ham、Jae-Seok Song、Seokjoon Lee

  DOI：10.1016/j.bmcl.2011.04.106

  日期：2011.6

  Some promising new antiresorptive agents of potential utility for treating osteoporosis were uncovered in a curcumin mimics library possessing a substituted triazole moiety, which is synthesized by the Cu(I)-catalyzed Huisgen 1,3-cycloaddition reaction between two azido intermediates (9 and 10) and various alkynes (a-k). A tartarate-resistant acid phosphatase (TRAP) activity assay was carried out with RANKL-induced osteoclastogenesis of mouse monocyte/macrophage RAW264.7 cells; the results indicated that the curcumin mimics derived from intermediate 10 exhibited stronger inhibitory activity than 9. In particular, curcumin mimics 12h, 13c, and 13e strongly inhibited osteoclast differentiation. (C) 2011 Elsevier Ltd. All rights reserved.