1-(3-(4-chlorophenyl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone | 212577-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(3-(4-chlorophenyl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone
• 英文别名: 1-[5-(4-Chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 212577-21-4
• 化学式: C₁₈H₁₇ClN₂O₃
• 分子量: 344.798
• InChiKey: DDBOVZJFZPFQFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-(4-chlorophenyl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 1-(5-(4-((1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-3-methoxyphenyl)-3(4 chlorophenyl)-4,5-dihydropyrazol-1-yl)ethanone
  参考文献：
  名称：

  通过点击化学合成1,2,3-三唑系留双功能杂化物及其细胞毒性研究

  摘要：

  考虑到目前使用的大多数抗癌药物的耐药性，已合成了吡唑基查耳酮和由三唑环束缚的对硝基苄基官能团的分子杂合物，并评估了其对三种人类癌细胞系（THP，COLO-205）的细胞毒性研究，A-549）。初步研究的结果显示出细胞毒性活性对电子因子的显着依赖性。萘基（JGPT-11）和三甲氧基苯基环（JGPT-6）作为环A的放置被证明对增强细胞毒性潜力极为有利。因此，我们在本文中报道了新型分子杂合体的合成和细胞毒性研究。对JGPT-11和6的生物学机理的详细研究正在进行中。

  DOI：

  10.1007/s00044-012-0312-7
• 作为产物：
  描述：

  香草醛 在 硫酸 、 一水合肼 、 溶剂黄146 作用下， 反应 52.0h， 生成 1-(3-(4-chlorophenyl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone
  参考文献：
  名称：

  通过点击化学合成1,2,3-三唑系留双功能杂化物及其细胞毒性研究

  摘要：

  考虑到目前使用的大多数抗癌药物的耐药性，已合成了吡唑基查耳酮和由三唑环束缚的对硝基苄基官能团的分子杂合物，并评估了其对三种人类癌细胞系（THP，COLO-205）的细胞毒性研究，A-549）。初步研究的结果显示出细胞毒性活性对电子因子的显着依赖性。萘基（JGPT-11）和三甲氧基苯基环（JGPT-6）作为环A的放置被证明对增强细胞毒性潜力极为有利。因此，我们在本文中报道了新型分子杂合体的合成和细胞毒性研究。对JGPT-11和6的生物学机理的详细研究正在进行中。

  DOI：

  10.1007/s00044-012-0312-7

文献信息

• Synthesis and cytotoxicity studies of 3,5-diaryl N-acetyl pyrazoline—isatin hybrids
  作者：Manmohan Sharma、Sahil Sharma、Abhishek Buddhiraja、A. K. Saxena、Kunal Nepali、P. M. S. Bedi

  DOI：10.1007/s00044-014-1001-5

  日期：2014.10

  Numerous reports highlighting the cytotoxic effects of 3,5-diaryl N-acetyl-pyrazolines and isatin tempted us to synthesise conjugates of the functionalities via alkyl armed triazole tetheration. The hybrids were synthesized by click chemistry approach and were evaluated against a panel of cell lines i.e. viz HeLa (cervix cancer), CAKI-I (Renal cancer), PC-3 (Prostate cancer) and Miapaca-2 (pancreatic cancer). The hybrids were classified into right-handed and left-handed conjugates on the basis of the placement of the isatin ring. The length of the alkyl armed triazole linker was varied from 2 to 6. Structure activity relationship has also been presented. A preliminary cytotoxic assay was performed on the series of 3,5-diaryl N-acetyl-pyrazolines and only the potent 3,5-diaryl N-acetyl-pyrazolines were selected for their inclusion in the hybrid scaffold. Among the cell lines employed, HeLa cell line was the most sensitive towards the exposure of test compounds. Out of all the compounds evaluated, two right-handed conjugates MI-7b and MI-8b and two left-handed conjugates MI-4b, MI-6b displayed significant cytotoxic potential and exhibited an IC50 range from 1.3 to 3.5 mu M against HeLa Cell line..
• Discovery of a Locally and Orally Active CXCL12 Neutraligand (LIT-927) with Anti-inflammatory Effect in a Murine Model of Allergic Airway Hypereosinophilia
  作者：Pierre Regenass、Dayana Abboud、François Daubeuf、Christine Lehalle、Patrick Gizzi、Stéphanie Riché、Muriel Hachet-Haas、François Rohmer、Vincent Gasparik、Damien Boeglin、Jacques Haiech、Tim Knehans、Didier Rognan、Denis Heissler、Claire Marsol、Pascal Villa、Jean-Luc Galzi、Marcel Hibert、Nelly Frossard、Dominique Bonnet

  DOI：10.1021/acs.jmedchem.8b00657

  日期：2018.9.13

  We previously reported Chalcone-4 (1) that binds the chemokine CXCL12, not its cognate receptors CXCR4 or CXCR7, and neutralizes its biological activity. However, this neutraligand suffers from limitations such as poor chemical stability, solubility, and oral activity. Herein, we report on the discovery of pyrimidinone 57 (LIT-927), a novel neutraligand of CXCL12 which displays a higher solubility than 1 and is no longer a Michael acceptor. While both 1 and 57 reduce eosinophil recruitment in a murine model of allergic airway hypereosinophilia, 57 is the only one to display inhibitory activity following oral administration. Thereby, we here describe 57 as the first orally active CXCL12 neutraligand with anti-inflammatory properties. Combined with a high binding selectivity for CXCL12 over other chemokines, 57 represents a powerful pharmacological tool to investigate CXCL12 physiology in vivo and to explore the activity of chemokine neutralization in inflammatory and related diseases.
• Synthesis of 1,2,3-triazole tethered bifunctional hybrids by click chemistry and their cytotoxic studies
  作者：Jagjeet Singh、Sahil Sharma、A. K. Saxena、Kunal Nepali、Preet Mohinder Singh Bedi

  DOI：10.1007/s00044-012-0312-7

  日期：2013.7

  for cytotoxic studies against three human cancer cell lines (THP, COLO-205, A-549). The results of the preliminary investigation exhibited marked dependence of the cytotoxic activity on the electronic factors. Placement of naphthyl (JGPT-11) and trimethoxy phenyl ring (JGPT-6) as ring A proved to be extremely beneficial in enhancing the cytotoxic potential. Thus we herein report the synthesis and cytotoxic

  考虑到目前使用的大多数抗癌药物的耐药性，已合成了吡唑基查耳酮和由三唑环束缚的对硝基苄基官能团的分子杂合物，并评估了其对三种人类癌细胞系（THP，COLO-205）的细胞毒性研究，A-549）。初步研究的结果显示出细胞毒性活性对电子因子的显着依赖性。萘基（JGPT-11）和三甲氧基苯基环（JGPT-6）作为环A的放置被证明对增强细胞毒性潜力极为有利。因此，我们在本文中报道了新型分子杂合体的合成和细胞毒性研究。对JGPT-11和6的生物学机理的详细研究正在进行中。