3-[1-((4-phenylthiazol-2-yl)hydrazono)ethyl]-2H-chromen-2-one | 1359132-58-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-[1-((4-phenylthiazol-2-yl)hydrazono)ethyl]-2H-chromen-2-one
• 英文别名: 3-(1-(2-(4-phenylthiazol-2-yl)hydrazono)ethyl)-2H-chromen-2-one；3-[C-methyl-N-[(4-phenyl-1,3-thiazol-2-yl)amino]carbonimidoyl]chromen-2-one
• CAS: 1359132-58-3
• 化学式: C₂₀H₁₅N₃O₂S
• 分子量: 361.424
• InChiKey: ZIKBIKSNUOYYBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  67.49
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-[1-((4-phenylthiazol-2-yl)hydrazono)ethyl]-2H-chromen-2-one 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77 %的产率得到3-(2-oxo-2H-chromen-3-yl)-1-(4-phenylthiazol-2-yl)-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  超声辅助从3-(2-氧代-2H-色烯-3-基)-1-(4-苯基噻唑-2-基)-1H-吡唑-4-甲醛合成新型席夫碱及其细胞毒性、细胞凋亡、细胞周期、分子对接和 ADMET 分析

  摘要：

  本研究的最终目标是发现新的抗癌药物，涉及设计和合成 15 种新型席夫碱 4a、b、5、6a–d、7a–e 和 8–10，其中含有 3-(2-oxo-2H) -铬...

  DOI：

  10.1080/00397911.2024.2347501
• 作为产物：
  描述：

  3-乙酰基香豆素 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.33h， 生成 3-[1-((4-phenylthiazol-2-yl)hydrazono)ethyl]-2H-chromen-2-one
  参考文献：
  名称：

  一种方便的超声促进合成一些带有香豆素核的新型噻唑衍生物及其细胞毒活性。

  摘要：

  成功实施超声辐照以快速合成一系列新型 3-[1-(4-取代-5-(芳基二烯基)噻唑-2-基)肼基)乙基]-2H-chromen-2-ones 5a-h通过 2-(1-(2-oxo-2H-chromen-3-yl)ethylidene) 氨基硫脲 (2) 和腙酰卤 3(4) 的反应，证明了这一点。此外，由反应合成了一系列新的 5-arylidene-2-(2-(1-(2-oxo-2H-chromen-3-yl)ethylidene)hydrazinyl)thiazol-4(5H)-ones 10a-d 2 与氯乙酸和不同的醛。此外，2-氰基-N'-(1-(2-氧代-2H-色烯-3-基)亚乙基)-乙酰肼(12)与取代的苯甲醛在所用条件下反应得到各自的亚芳基衍生物13a-c。基于元素分析和光谱数据指定合成化合物的结构。还，评估了噻唑衍生物 5a 对 HaCaT 细胞（人角质形成细胞）的细胞毒活性。发现化合物5a具有有效的细胞毒活性。

  DOI：

  10.3390/molecules17089335

文献信息

• A facile one-pot, three-component synthesis of a new series of thiazolyl pyrazole carbaldehydes: In vitro anticancer evaluation, in silico ADME/T, and molecular docking studies
  作者：Srikanth Mamidala、R Kowshik Aravilli、Gondru Ramesh、Shaik Khajavali、Raju Chedupaka、Vijjulatha Manga、Rajeswar Rao Vedula

  DOI：10.1016/j.molstruc.2021.130356

  日期：2021.7

  A series of thiazolyl pyrazole carbaldehydes (4a-n) were synthesized by conventional method using thiosemicarbazide, substituted phenacyl bromides, substituted 3-acetylcoumarins, and Vilsmeyer-Hack reagent. Structures of all the synthesized compounds were confirmed by spectral (1H & 13C NMR, FTIR, Mass) and analytical data. The target compounds were screened for their in vitro anticancer activity.

  使用硫代氨基脲，取代的苯甲酰溴，取代的3-乙酰香豆素和Vilsmeyer-Hack试剂，通过常规方法合成了一系列噻唑基吡唑甲醛（4a-n）。通过光谱（1 H和13 C NMR，FTIR，Mass）和分析数据确认所有合成化合物的结构。筛选目标化合物的体外抗癌活性。从结果可知，化合物4m已经显示出对所有测试的细胞系显着的抗增殖活性。此外，还进行了计算机模拟ADME / T，以为未来的抗癌药物发现计划设定有效的潜在候选人。针对秋水仙碱对β-微管蛋白的结合位点进行了分子对接研究，其结果与体外抗癌数据一致。
• New thiazol-hydrazono-coumarin hybrids targeting human cervical cancer cells: Synthesis, CDK2 inhibition, QSAR and molecular docking studies
  作者：Somaia S. Abd El-Karim、Yasmin M. Syam、Ahmed M. El Kerdawy、Tamer M. Abdelghany

  DOI：10.1016/j.bioorg.2019.01.026

  日期：2019.5

  Motivated by the potential anticancer activity of both coumarin and 2-aminothiazole nuclei, a new set of thiazol-2-yl hydrazono-chromen-2-one analogs were efficiently synthesized aiming to obtain novel hybrids with potential cytotoxic activity. MTT assay investigated the significant potency of all the target compounds against the human cervical cancer cell lines (HeLa cells). Cell cycle analysis showed that the representative compound 8a led to cell cycle cessation at G0/G1 phase indicating that CDK2/E1complex could be the plausible biological target for these newly synthesized compounds. Thus, the most active compounds (7c and 8a-c) were tested for their CDK2 inhibitory activity. The biological results revealed their significant CDK2 inhibitory activity with IC50 range of 0.022-1.629 nM. Moreover, RT-PCR gene expression assay showed that compound 8a increased the levels of the nuclear CDK2 regulators P21 and P27 by 2.30 and 5.7 folds, respectively. ELISA tequnique showed also that compound 8a led to remarkable activation of caspases-9 and -3 inducing cell apoptosis. QSAR study showed that the charge distribution and molecular hydrophobicity are the structural features affecting cytotoxic activity in this series. Molecular docking study for the most potent cytotoxic compounds (7c and 8a-c) rationalized their superior CDK2 inhibitory activity through their hydrogen bonding and hydrophobic interactions with the key amino acids in the CDK2 binding site. Pharmacokinetic properties prediction of the most potent compounds showed that the newly synthesized compounds are not only with promising antitumor activity but also possess promising pharmacokinetic properties.