5-[(2-甲氧基苯基)甲基]-3-苯基-1H-哒嗪-6-酮 | 121137-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-[(2-甲氧基苯基)甲基]-3-苯基-1H-哒嗪-6-酮
• 中文别名: 3(2H)-哒嗪酮,4-[(2-甲氧苯基)甲基]-6-苯基-
• 英文名称: 5-[(2-methoxyphenyl)methyl]-3-phenyl-1H-pyridazin-6-one
• 英文别名: 4-(2-Methoxy-benzyl)-6-phenyl-pyridazin-3-ol
• CAS: 121137-72-2
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.3
• InChiKey: GXNMRGXXAVELSO-UHFFFAOYSA-N

物化性质

• 熔点：
  171-173 °C(Solv: benzene (71-43-2))
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

文献信息

• Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides
  作者：Yi-Ling Tsai、Siang-en Syu、Shu-Mei Yang、Utpal Das、Yu-Shiou Fan、Chia-Jui Lee、Wenwei Lin

  DOI：10.1016/j.tet.2014.06.015

  日期：2014.8

  A Bu3P-mediated mild and efficient synthesis of multi-functional alkenes has been described starting from substituted acrylate with aldehydes. In situ generated zwitterionic intermediates underwent proton-exchange to afford ylide intermediates, which were trapped by corresponding aldehydes providing the products in up to 92% yield with complete E-stereoselectivity. Further derivatization of the products

  已经描述了Bu 3 P介导的温和而有效的多功能烯烃的合成，该合成是从用醛取代的丙烯酸酯开始的。原位生成的两性离子中间体进行质子交换，以提供叶立德中间体，该中间体被相应的醛捕获，从而以最高92％的收率提供具有完全E-立体选择性的产物。进行产物的进一步衍生化以提供功能性哒嗪酮。
• Reactivity of pyridazin-3(2H) thiones
  作者：N. G. Kandile、H. T. Zaky、M. I. Mohamed、Abdel-Sattar S. Hamad Elgazwy

  DOI：10.1002/hc.10157

  日期：——

  4,6-Disubstituted pyridazin-3(2H) thiones 3a–f were prepared by thiation of 4,6-disubstituted pyridazin-3(2H)-one 1a–f either with thiourea or phosphorus pentasulphide. The reactivity of 3a-f towards nucleophilic and electrophilic species under different conditions was studied successively. The structure of the products was confirmed by NMR and mass spectral data. Mechanisms for their formation are

  4,6-二取代哒嗪-3(2H) 硫酮 3a-f 是通过 4,6-二取代哒嗪-3(2H)-one 1a-f 与硫脲或五硫化二磷硫合制备的。先后研究了 3a-f 在不同条件下对亲核和亲电物种的反应性。产物的结构由NMR和质谱数据证实。还提出了它们的形成机制。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:334–341, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10157
• Optimization of 4‐amino‐pyridazin‐3(2<i>H</i>)‐one as a valid <i>core</i> scaffold for FABP4 inhibitors
  作者：Giuseppe Floresta、Letizia Crocetti、Renan Rodrigues de Oliveira Silva、Vincenzo Patamia、Francesca Mazzacuva、Yu Chee Sonia Chen、Claudia Vergelli、Agostino Cilibrizzi

  DOI：10.1002/ardp.202300314

  日期：2023.10

  Current clinical research suggests that fatty acid‐binding protein 4 inhibitors (FABP4is), which are of biological and therapeutic interest, may show potential in treating cancer and other illnesses. We sought to uncover new structures through the optimization of the previously reported 4‐amino and 4‐ureido pyridazinone‐based series of FABP4is as part of a larger research effort to create more potent FABP4 inhibitors. This led to the identification of 14e as the most potent analog with IC₅₀ = 1.57 μM, which is lower than the IC₅₀ of the positive control. Advanced modeling investigations and in silico absorption, distribution, metabolism, and excretion ‐ toxicity calculations suggested that 14e represents a potential candidate for in vivo studies such as FABP4i.

  摘要目前的临床研究表明，脂肪酸结合蛋白 4 抑制剂（FABP4is）具有生物学和治疗学意义，可能在治疗癌症和其他疾病方面显示出潜力。我们试图通过优化以前报道过的基于 4-氨基和 4-脲基哒嗪酮的 FABP4is 系列来发现新的结构，作为创造更有效的 FABP4 抑制剂的更大研究努力的一部分。结果发现 14e 是最有效的类似物，其 IC50 = 1.57 μM，低于阳性对照的 IC50。先进的建模研究和硅学吸收、分布、代谢和排泄-毒性计算表明，14e 是 FABP4i 等体内研究的潜在候选药物。
• Kandile, N. G.; Soliman, A. A.; El Sawi, E. A., Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1989, vol. 19, p. 779 - 786
  作者：Kandile, N. G.、Soliman, A. A.、El Sawi, E. A.

  DOI：——

  日期：——
• Antiproliferative effects of metal complexes of new isatin hydrazones against HCT116, MCF7 and HELA tumour cell lines
  作者：Nadia G. Kandile、Mansoura I. Mohamed、Hind M. Ismaeel

  DOI：10.3109/14756366.2011.588950

  日期：2012.6.1

  New hydrazone ligands (HL) derived from 5-substituted isatins and 1-(4-(2-methoxybenzyl)-6-arylpyridazin-3-yl) hydrazines and its complexes with Co(II) and Cu(II) were synthesized. The new hydrazones and their complexes were characterized by means of elemental, spectral analyses and magnetic studies. Primary cytotoxicity evaluation of HL 5a and the new complexes showed that these complexes could act as anticancer agents since they reduced the growth of samples of human tumour cell lines (HCT116((Colon)), MCF7((Breast)) and HELA((Cervix))) to <= 18.5 mu g/mL for the new complexes.