2-[(4-hydroxy-3-methoxyphenyl)methylidene]-N-phenylhydrazine-1-carbothioamide | 20158-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-N-phenylhydrazine-1-carbothioamide
• 英文别名: 1-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-phenyl-3-thiosemicarbazide；2-(4-hydroxy-3-methoxybenzylidene)-N-phenylhydrazine-1-carbothioamide；4-hydroxy-3-methoxy-benzaldehyde 4-phenyl-thiosemicarbazone；vanillin-(4-phenyl thiosemicarbazone)；Vanillin-(4-phenyl-thiosemicarbazon)；4-Hydroxy-3-methoxy-benzaldehyd-<4-phenyl-thiosemicarbazon>；1-[(4-Hydroxy-3-methoxyphenyl)methylideneamino]-3-phenylthiourea
• CAS: 20158-15-0
• 化学式: C₁₅H₁₅N₃O₂S
• 分子量: 301.369
• InChiKey: JWLFZGSWRRLBAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  98
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(4-hydroxy-3-methoxyphenyl)methylidene]-N-phenylhydrazine-1-carbothioamide 在 碘 作用下， 以 乙醇 为溶剂， 生成 2-Phenylimino-5-(4-hydroxy-3-methoxy-phenyl)-2,3-dihydro-1,3,4-thiadiazol
  参考文献：
  名称：

  Sen,A.B.; Gupta,S.K., Journal of the Indian Chemical Society, 1962, vol. 39, p. 628 - 634

  摘要：

  DOI：
• 作为产物：
  描述：

  香草醛 、 4-苯基-3-硫代氨基脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以80%的产率得到2-[(4-hydroxy-3-methoxyphenyl)methylidene]-N-phenylhydrazine-1-carbothioamide
  参考文献：
  名称：

  新型 Thiazolidin-4-one 衍生物的合成及体外抗弓形虫活性

  摘要：

  近期关于噻唑烷-4-酮生物活性的发现，并考虑到治疗弓形体病的有效药物缺乏、副作用众多，以及寄生虫耐药性问题促使我们寻找新的药物. 我们通过4-取代氨基脲与羟基苯甲醛之间的两步反应，然后用溴乙酸乙酯处理，设计并合成了一系列新的噻唑啉-4-one衍生物；马来酸酐和乙炔二羧酸二甲酯得到目标化合物。thiazolidin-4-one 衍生物用于评估体外弓形虫生长的抑制作用。所有活性 thiazolidine-4-one 衍生物（12 种化合物）均抑制 T. 体外弓形虫增殖比使用的参考药物磺胺嘧啶以及磺胺嘧啶+甲氧苄啶（重量比5：1）的协同作用要好得多。其中最活跃的衍生物 94 和 95 显示出比磺胺嘧啶更好约 392 倍和比磺胺嘧啶和甲氧苄啶更好 18 倍的增殖抑制作用。所有针对弓形虫的活性化合物（82-88 和 91-95）代表的值从 1.75 到 15.86 (CC30/IC50) 低于无细胞毒性值

  DOI：

  10.3390/molecules24173029

文献信息

• Discovery of Novel Bromophenol–Thiosemicarbazone Hybrids as Potent Selective Inhibitors of Poly(ADP-ribose) Polymerase-1 (PARP-1) for Use in Cancer
  作者：Chuanlong Guo、Lijun Wang、Xiuxue Li、Shuaiyu Wang、Xuemin Yu、Kuo Xu、Yue Zhao、Jiao Luo、Xiangqian Li、Bo Jiang、Dayong Shi

  DOI：10.1021/acs.jmedchem.8b01946

  日期：2019.3.28

  Poly(ADP-ribose) polymerase-1 (PARP-1) is a new potential target for anticancer drug discovery. A series of bromophenol-thiosemicarbazone hybrids as PARP-1 inhibitors were designed, synthesized, and evaluated for their antitumor activities. Among them, the most promising compound, 11, showed excellent selective PARP-1 inhibitory activity (IC50 = 29.5 nM) over PARP-2 (IC50 > 1000 nM) and potent anticancer

  聚（ADP-核糖）聚合酶-1（PARP-1）是抗癌药物发现的新潜在目标。设计，合成并评估了一系列作为PARP-1抑制剂的溴酚-硫代半碳杂zone杂化物的抗肿瘤活性。其中，最有前途的化合物11对PARP-2（IC50> 1000 nM）表现出优异的选择性PARP-1抑制活性（IC50 = 29.5 nM），并对SK-OV-3，Bel-7402和在体内SK-OV-3细胞异种移植模型中，HepG2癌细胞系（IC50 = 2.39、5.45和4.60μM）以及肿瘤生长的抑制作用。进一步的研究表明，化合物11通过多种抗癌机制发挥了抗肿瘤作用，包括诱导凋亡和细胞周期停滞，DNA双链断裂的细胞蓄积，DNA修复改变，抑制H2O2触发的PARylation，通过产生细胞毒性活性氧而产生的抗增殖作用以及自噬。另外，化合物11显示出良好的药代动力学特性和良好的安全性。这些观察表明，化合物11可以用作发现新的抗癌药物的先导化合物。
• Design and Synthesis of Novel Thiosemicarbazones as Potent Anti-breast Cancer Agents
  作者：Mashooq Ahmad Bhat、M. Al-Tahhan、Mohamed A. Al-Omar、Ahmed M. Naglah、Abdullah Al-Dhfyan

  DOI：10.2174/1570180815666181008100944

  日期：2019.3.8

  Thiosemicarbazones and its derivatives received a great pharmaceutical importance due to their prominent biological activities. Methods: A series of disubstituted thiosemicarbazone derivatives (1-12) were designed and synthesized as pure compounds in good yield. All the synthesized compounds were analyzed by spectral data. The anticancer activity of all the compounds was performed against breast cancer MCF-7

  背景：硫代氨基咔唑及其衍生物因其突出的生物活性而在制药上具有重要意义。 方法：设计并合成了一系列双取代的硫代半碳酰胺衍生物（1-12），其收率为纯净。通过光谱数据分析所有合成的化合物。所有化合物的抗癌活性均针对乳腺癌MCF-7和MDA-MB-231细胞系进行。 结果：大多数化合物显示出对乳腺癌MCF-7和MDA-MB-231细胞系的活性，分别为（IC50 = 12.25 µM ‒ 185.35 µM）和（IC50 = 12.97 µM ‒ 107.33 µM）。化合物9分别针对MCF-7和MDA-MB-231细胞系（IC50 = 12.76 µM和12.97 µM）。 结论：发现化合物9具有显着的抗乳腺癌活性。进一步评估该化合物在5和10 µM浓度下对乳腺癌细胞MCF-7的侧群抑制百分比测定。与参考药物维拉帕米相比，在5μM浓度下，它显示出对阻止侧群的优势超过80％。
• Synthesis and biological evaluation of novel benzoquinones as potential antimicrobial agents
  作者：Ibrahim Chaaban、El Sayeda M. El Khawass、Mona A. Mahran、Heba A. Abd El Razik、Nehad S. El Salamouni、Abeer E. Abdel Wahab

  DOI：10.1007/s00044-012-0076-0

  日期：2013.2

  New series of 2,5-dihydroxyphenyl-1,3-thiazoles 4a-l was synthesized by reacting 2,5-dihydroxyphenacyl bromide with various 4-aryl thiosemicarbazones 3a-l that on oxidation with ferric chloride yielded the corresponding N (1)-substituted benzylidene-N (2)-[3-aryl-4-(1,4-benzoquinon-2-yl)-1,3-thiazol-2-ylidene]hydrazines 5a-l. They were evaluated for antibacterial activity against Staphylococcus aureus and Bacillus subtilis as Gram-positive bacteria, Escherichia coli and Pseudomonas aeruginosa as Gram-negative bacteria. They were also evaluated for their in vitro antifungal potential against Candida albicans. Almost all tested compounds were found to possess variable degrees of antimicrobial activity. The obtained data revealed that compounds 4b-h and 5e, 5f and 5l exhibited promising antimicrobial activity against the tested organisms of which compound 4b proved to be the most active.
• Synthesis and Ribonucleotide reductase inhibitory activity of thiosemicarbazones
  作者：Kesavan Krishnan、Kumari Prathiba、Venkatesan Jayaprakash、Arijit Basu、Nibha Mishra、Bingsen Zhou、Shuya Hu、Yun Yen

  DOI：10.1016/j.bmcl.2008.09.097

  日期：2008.12

  Ribonucleotide reductase (RR) is an important therapeutic target for anticancer drugs. The structure of human RR features a 1: 1 complex of two homodimeric subunits, hRRM1 and hRRM2. Prokaryotically expressed and highly purified recombinant human RR subunits, hRRM1 and hRRM2, were used for holoenzyme-based [(3)H] CDP reduction in vitro assay. Ten new thiosemicarbazones (7-16) were synthesized and screened for their RR inhibitory activity. Two thiosemicarbazones derived from p-hydroxy benzaldehyde (9 and 10) were found to be active but less potent than the standard, Hydroxyurea (HU). Guided by the activity of compounds 9 and 10, 11 new thiosemicarbazones (17-27) derived from p-hydroxy benzaldehyde were prepared and screened for their RR inhibitory activity. All the 11 compounds were more potent than HU. (C) 2008 Elsevier Ltd. All rights reserved.
• Shah,I.D.; Trivedi,J.P., Journal of the Indian Chemical Society, 1963, vol. 40, p. 889 - 893
  作者：Shah,I.D.、Trivedi,J.P.

  DOI：——

  日期：——