2-bromo-1-(5-(2-hydroxyphenyl)-3-methyl-4,5-dihydropyrazol-1-yl)ethanone | 1355956-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-bromo-1-(5-(2-hydroxyphenyl)-3-methyl-4,5-dihydropyrazol-1-yl)ethanone
• 英文别名: 2-Bromo-1-[3-(2-hydroxyphenyl)-5-methyl-3,4-dihydropyrazol-2-yl]ethanone；2-bromo-1-[3-(2-hydroxyphenyl)-5-methyl-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 1355956-62-5
• 化学式: C₁₂H₁₃BrN₂O₂
• 分子量: 297.151
• InChiKey: RXVRGFJGYZHQSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(5-(2-hydroxyphenyl)-3-methyl-4,5-dihydropyrazol-1-yl)ethanone 在 碳酸氢钠 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以87%的产率得到2-Methyl-1,11b-dihydropyrazolo[1,5-d][1,4]benzoxazepin-5-one
  参考文献：
  名称：

  Design and synthesis of novel 2-methyl-4,5-substitutedbenzo[f]-3,3a,4,5-tetrahydro-pyrazolo[1,5-d][1,4]oxazepin-8(7H)-one derivatives as telomerase inhibitors

  摘要：

  Eight novel 4,5-tetrahydropyrazolo[1,5-d][1,4] oxazepine derivatives have been synthesized and purified to be screened for anticancer activity. By a modified TRAP assay, some titled compounds were tested against telomerase, and compound 4a showed the most potent inhibitory activity with IC50 value at 0.78 +/- 0.22 mu M. Western blot assays showed that compounds 4a and 4b could inhibit expression of Cyclin D1, TERT, phospho-AKT and PI3K/AKT pathway. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.101
• 作为产物：
  描述：

  4-(2-hydroxyphenyl)but-3-en-2-one 在 4-二甲氨基吡啶 、 一水合肼 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 7.0h， 生成 2-bromo-1-(5-(2-hydroxyphenyl)-3-methyl-4,5-dihydropyrazol-1-yl)ethanone
  参考文献：
  名称：

  Identification of human telomerase inhibitors having the core of N -acyl-4,5-dihydropyrazole with anticancer effects

  摘要：

  Eight human telomerase inhibitors (5a-5h) having the core of N-acyl-4,5-dihydropyrazole with anticancer effects were identified in this study. Biological results revealed that a few compounds had potent anticancer activities against three common tumor cell lines (SGC-7901, HepG2 and MGC-803). Among them, compound 5c, with a molecular weight of only 272.2 Da, had antiproliferative activities against SGC-7901 and MGC-803 with EC50 values of 2.06 +/- 0.17 and 2.89 +/- 0.62 mu M, respectively, better than 5-Fluorouracil. Compound 5c inhibited the enzyme of telomerase with an IC50 value of 1.86 +/- 0.51 mu M, surpassing the control compound, ethidium bromide. Modeling study showed that this compound can reside in the binding pocket of the telomerase/TNA: DNA hairpin complex. When the moiety of N-acyl was changed to N-sulfonyl, the gotten compounds (8a-8i) had deteriorative activities against both these three cancer cell lines and the enzyme of telomerase. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.02.025

文献信息

• Novel 2-(benzo[d]thiazol-2-yl)-1-(3-methyl-5-substituted-phenyl-4,5-dihydropyrazol-1-yl)ethanone Derivatives: Synthesis and Antibacterial Activity
  作者：Chun-Xiu Pan、Jun Li、Xin-Hua Liu

  DOI：10.2174/157018011795514212

  日期：2011.6.1

  A series of novel 2-(benzo[d]thiazol-2-yl)-1-(3-methyl-5-substituted-phenyl-4,5-dihydropyrazol-1-yl)ethanone derivatives were synthesized and characterized by NMR, ESI-MS. Biological activity tests results show that compounds 4a, 4b, 4d and 4g displayed activity with MIC of 1.562 μg/mL against B. subtilis ATCC 6633, compound 4d displayed significant activity with MIC of 1.562 μg/mL against S. aureus

  合成了一系列新型的2-（苯并[d]噻唑-2-基）-1-（3-甲基-5-取代-苯基-4,5-二氢吡唑-1-基）乙酮衍生物，并进行了NMR表征， ESI-MS。生物活性测试结果表明，化合物4a，4b，4d和4g对枯草芽孢杆菌ATCC 6633的活性为MIC为1.562μg/ mL，化合物4d对金黄色葡萄球菌ATCC 6538的活性为MIC为1.562μg/ mL。具有有效抗菌活性的4a强烈抑制金黄色葡萄球菌DNA促旋酶和枯草芽孢杆菌DNA促旋酶，对金黄色葡萄球菌DNA促旋酶和枯草芽孢杆菌DNA促旋酶的IC50为0.5μg/ ml。
• Design and synthesis of novel 5-phenyl-N-piperidine ethanone containing 4,5-dihydropyrazole derivatives as potential antitumor agents
  作者：Xin-Hua Liu、Jun Li、Jing Bo Shi、Bao-An Song、Xing-Bao Qi

  DOI：10.1016/j.ejmech.2012.02.040

  日期：2012.5

  A series of novel 5-phenyl-N-piperidine ethanone-4,5-dihydropyrazole derivatives as potential telomerase inhibitors were synthesized. The bioassays demonstrated that compounds 4d, 4f, 7a and 7h occupied high antiproliferative activities against SGC-7901, MGC-803 and Bcap-37 cell lines. By a modified TRAP assay, some titled compounds were tested against telomerase, and compound 7b showed the most potent inhibitory activity with IC50 value at 2.00 +/- 0.40 mu M. The active compound 4d was also docked into the telomerase TERT active site to determine the probable binding model. The results indicated that conserved residues Lys189, Asp254 and Gln308 were important for ligand binding via hydrogen bond interactions. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Design and synthesis of novel 2-methyl-4,5-substitutedbenzo[f]-3,3a,4,5-tetrahydro-pyrazolo[1,5-d][1,4]oxazepin-8(7H)-one derivatives as telomerase inhibitors
  作者：Xin-Hua Liu、Ying-Ming Jia、Bao-An Song、Zhi-xiang Pang、Song Yang

  DOI：10.1016/j.bmcl.2012.11.101

  日期：2013.2

  Eight novel 4,5-tetrahydropyrazolo[1,5-d][1,4] oxazepine derivatives have been synthesized and purified to be screened for anticancer activity. By a modified TRAP assay, some titled compounds were tested against telomerase, and compound 4a showed the most potent inhibitory activity with IC50 value at 0.78 +/- 0.22 mu M. Western blot assays showed that compounds 4a and 4b could inhibit expression of Cyclin D1, TERT, phospho-AKT and PI3K/AKT pathway. (c) 2012 Elsevier Ltd. All rights reserved.
• Identification of human telomerase inhibitors having the core of N -acyl-4,5-dihydropyrazole with anticancer effects
  作者：Xuan Xiao、Yong Ni、Ying-Ming Jia、Min Zheng、Han-Fei Xu、Jun Xu、Chenzhong Liao

  DOI：10.1016/j.bmcl.2016.02.025

  日期：2016.3

  Eight human telomerase inhibitors (5a-5h) having the core of N-acyl-4,5-dihydropyrazole with anticancer effects were identified in this study. Biological results revealed that a few compounds had potent anticancer activities against three common tumor cell lines (SGC-7901, HepG2 and MGC-803). Among them, compound 5c, with a molecular weight of only 272.2 Da, had antiproliferative activities against SGC-7901 and MGC-803 with EC50 values of 2.06 +/- 0.17 and 2.89 +/- 0.62 mu M, respectively, better than 5-Fluorouracil. Compound 5c inhibited the enzyme of telomerase with an IC50 value of 1.86 +/- 0.51 mu M, surpassing the control compound, ethidium bromide. Modeling study showed that this compound can reside in the binding pocket of the telomerase/TNA: DNA hairpin complex. When the moiety of N-acyl was changed to N-sulfonyl, the gotten compounds (8a-8i) had deteriorative activities against both these three cancer cell lines and the enzyme of telomerase. (C) 2016 Elsevier Ltd. All rights reserved.