3-(2,2-Dimethylchroman-6-yl)-1H-pyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(2,2-Dimethylchroman-6-yl)-1H-pyrazole
• 英文别名: 5-(2,2-dimethyl-3,4-dihydrochromen-6-yl)-1H-pyrazole
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: NTXYUGGSGPFFBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  对叔丁基苯磺酰氯 、 3-(2,2-Dimethylchroman-6-yl)-1H-pyrazole 在 吡啶 作用下， 反应 1.0h， 以35%的产率得到1-(4-Tert-butylphenyl)sulfonyl-3-(2,2-dimethyl-3,4-dihydrochromen-6-yl)pyrazole
  参考文献：
  名称：

  Identification of anticancer agents based on the thieno[2,3-b]pyridine and 1H-pyrazole molecular scaffolds

  摘要：

  Structural similarity search of commercially available analogues of thieno[2,3-b]pyridine and 1H-pyrazole derivatives, known anticancer agents, resulted in 717 hits. These were docked into the phosphoinositide specific-phospholipase C (PLC) binding pocket, the putative target of the compounds, to further focus the selection. Thirteen derivatives of the thieno[2,3-b]pyridines were identified and tested against the NCI60 panel of human tumour cell lines. The most active derivative 1 was most potent against the MDA-MB-435 melanoma cell line with GI(50) at 30 nM. Also, it was found that a piperidine moiety is tolerated on the thieno[2,3-b]pyridine scaffold with GI(50) = 296 nM (MDA-MB-435) for derivative 10 considerably expanding the structure activity relationship for the series. For the 1H-pyrazoles four derivatives were identified using the in silico approach and additionally ten were synthesised with various sub-stituents on the phenyl moiety to extend the structural activity relationship but only modest anticancer activity was found. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.05.061
• 作为产物：
  描述：

  2,2-二甲基-6-乙酰基-2H-1-苯并吡喃 在 palladium 10% on activated carbon 、 氢气 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.75h， 生成 3-(2,2-Dimethylchroman-6-yl)-1H-pyrazole
  参考文献：
  名称：

  Identification of anticancer agents based on the thieno[2,3-b]pyridine and 1H-pyrazole molecular scaffolds

  摘要：

  Structural similarity search of commercially available analogues of thieno[2,3-b]pyridine and 1H-pyrazole derivatives, known anticancer agents, resulted in 717 hits. These were docked into the phosphoinositide specific-phospholipase C (PLC) binding pocket, the putative target of the compounds, to further focus the selection. Thirteen derivatives of the thieno[2,3-b]pyridines were identified and tested against the NCI60 panel of human tumour cell lines. The most active derivative 1 was most potent against the MDA-MB-435 melanoma cell line with GI(50) at 30 nM. Also, it was found that a piperidine moiety is tolerated on the thieno[2,3-b]pyridine scaffold with GI(50) = 296 nM (MDA-MB-435) for derivative 10 considerably expanding the structure activity relationship for the series. For the 1H-pyrazoles four derivatives were identified using the in silico approach and additionally ten were synthesised with various sub-stituents on the phenyl moiety to extend the structural activity relationship but only modest anticancer activity was found. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.05.061

文献信息

• Identification of anticancer agents based on the thieno[2,3-b]pyridine and 1H-pyrazole molecular scaffolds
  作者：Chatchakorn Eurtivong、Inga Reynisdóttir、Stephanie Kuczma、Daniel P. Furkert、Margaret A. Brimble、Jóhannes Reynisson

  DOI：10.1016/j.bmc.2016.05.061

  日期：2016.8

  Structural similarity search of commercially available analogues of thieno[2,3-b]pyridine and 1H-pyrazole derivatives, known anticancer agents, resulted in 717 hits. These were docked into the phosphoinositide specific-phospholipase C (PLC) binding pocket, the putative target of the compounds, to further focus the selection. Thirteen derivatives of the thieno[2,3-b]pyridines were identified and tested against the NCI60 panel of human tumour cell lines. The most active derivative 1 was most potent against the MDA-MB-435 melanoma cell line with GI(50) at 30 nM. Also, it was found that a piperidine moiety is tolerated on the thieno[2,3-b]pyridine scaffold with GI(50) = 296 nM (MDA-MB-435) for derivative 10 considerably expanding the structure activity relationship for the series. For the 1H-pyrazoles four derivatives were identified using the in silico approach and additionally ten were synthesised with various sub-stituents on the phenyl moiety to extend the structural activity relationship but only modest anticancer activity was found. (C) 2016 Elsevier Ltd. All rights reserved.