2-methoxy-5-(3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-5-yl)phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-methoxy-5-(3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-5-yl)phenol
• 英文别名: 5-(4,5-dihydro-3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)-2-methoxyphenol；2-Methoxy-5-(3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1h-pyrazol-5-yl) phenol；2-methoxy-5-[3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-5-yl]phenol
• 化学式: C₁₉H₂₂N₂O₅
• 分子量: 358.394
• InChiKey: QKLBZUPEFOPJFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-methoxy-5-(3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-5-yl)phenol 、 异氰酸2-甲氧苯酯 以 乙醇 为溶剂， 反应 1.0h， 以92%的产率得到5-(3-hydroxy-4-methoxyphenyl)-N-(2-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Pyrazoline and Pyrimidine Analogs of Combretastatin-A4 as Anticancer, Anti-inflammatory and Antioxidant Agents

  摘要：

  A library of 3,5-diaryl-1-carbothioamide-pyrazoline (5a-j), N-1-phenyl sulfonyl pyrazoline (6a-e) and pyrimidine (7a) analogs of combretastatin-A4 were synthesized and evaluated for their in vitro anticancer, anti-inflammatory and antioxidant activity. Results of in vitro assay against human breast cancer cell line (MCF-7) showed several compounds endowed with significant cytotoxicity compared to the adriamycin, a standard anticancer drug. Among the compounds synthesized, 7a was found to possess significant antiproliferative activity (Gl(50) <0.1 mu M) against the MCF-7 cell line as good as adriamycin (Gl(50) < 0.1 mu M) whereas, compounds 6c, 5j and 5g also displayed good cytotoxicity (Gl(50) = 25.3-42.6 mu M). Besides this, most active compound 7a was also evaluated against human myeloid leukemia cell line K562 and the remarkable result was obtained with Gl(50)< 0.1 mu M, comparable to that of adriamycin (Gl(50)< 0.1 mu M). In addition, all the synthesized compounds were evaluated for their anti-inflammatory and antioxidant activity. The percent inhibition studies revealed that most of the compounds were found to possess substantial anti-inflammatory and antioxidant activities.

  DOI：

  10.5562/cca3393
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 在 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 40.0h， 生成 2-methoxy-5-(3-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-5-yl)phenol
  参考文献：
  名称：

  吡唑啉和吡啶衍生物作为抗癌，消炎和抗氧化剂的康维他汀-A4类似物的合成和药理评价

  摘要：

  合成了康美他汀-A4的三类N 1-苯基吡唑啉（5a - e），N 1-苯基磺酰基吡唑啉（6a - e）和吡啶类似物（8a - d）。化合物的结构通过光谱技术验证。筛选了所有化合物对MCF-7细胞系的抗癌活性，抗氧化剂（DPPH，NO，SOR和H 2 O 2）以及抗炎活性，而化合物（8a – d）还针对K562细胞系进行了测试。化合物8a和8b显示针对MCF-7细胞系（GI实质性的抗癌活性50  = 5.59和11.70μM），虽然没有阿霉素（GI可比50  ⩽0.1μM）。然而，没有一种化合物对K562细胞系具有活性。尽管如此，化合物8a的抑癌活性（TGI = 69.2 µM）比标准药物阿霉素（TGI = 75.8 µM）更好。与标准抗坏血酸相比，大多数化合物5a，5b，5c，5e，6a，6b，6c，6d，6e 8a和8b具有更好的抑制所有自由基的作用，而化合物5c和5b 与标准的消炎药双氯芬酸钠相当，它具有明显的消炎活性。

  DOI：

  10.1007/s00044-018-2142-8

文献信息

• BENZOTHIAZOLE HYBRIDS USEFUL AS ANTICANCER AGENTS AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Kamal Ahmed

  公开号：US20140039190A1

  公开（公告）日：2014-02-06

  Compounds of general formula A useful as potential anticancer agents against human cancer cell lines and a process for the preparation thereof.

  一般式为A的化合物可作为潜在的抗人癌细胞系癌症药物，并提供其制备方法。
• [EN] BENZOTHIAZOLE HYBRIDS USEFUL AS ANTICANCER AGENTS AND PROCESS FOR THE PREPARATION THEREOF<br/>[FR] HYBRIDES DE BENZOTHIAZOLE UTILISÉS EN TANT QU'AGENTS ANTICANCÉREUX ET PROCÉDÉ DE PRÉPARATION CORRESPONDANT
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2012104875A1

  公开（公告）日：2012-08-09

  The present invention provides compounds of general formula A useful as potential anticancer agents against human cancer cell lines and provides a process for the preparation thereof.

  本发明提供了一种通用公式A的化合物，可作为潜在的抗人类癌细胞系的抗癌剂，并提供了其制备方法。
• Design, synthesis, and biological testing of pyrazoline derivatives of combretastatin-A4
  作者：Marlie Johnson、Brent Younglove、Lauren Lee、Regan LeBlanc、Herman Holt、Patrice Hills、Hilary Mackay、Toni Brown、Susan L. Mooberry、Moses Lee

  DOI：10.1016/j.bmcl.2007.07.105

  日期：2007.11

  Fourteen N-acetylated and non-acetylated 3,4,5-tri- or 2,5-dimethoxypyrazoline analogs of combretastatin-A4 (1) were synthesized. A non-acetylated derivative (5a) with the same substituents as CA-4 (1) was the most active compound in the series, with IC50 values of 2.1 and 0.5 mu M in B16 and L1210 cell lines, respectively. In contrast, a similar compound with an acetyl group at N1 of the pyrazoline ring (6g) showed poor activity in the cell lines studied. A cell-based assay indicated that compound 5a caused extensive microtubule depolymerization with an EC50 value of 7.1 mu M in A-10 cells while no activity was seen with the acetylated compound. Molecular modeling studies showed that these compounds possess a twisted conformation similar to CA-4 (1). (c) 2007 Elsevier Ltd. All rights reserved.
• AMIDOBENZOTHIAZOLES AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Council of Scientific and Industrial Research

  公开号：EP2670740B1

  公开（公告）日：2015-12-30
• US8921552B2
  申请人：——

  公开号：US8921552B2

  公开（公告）日：2014-12-30