4-(4-chlorophenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-thiosemicarbazide | 16434-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(4-chlorophenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-thiosemicarbazide
• 英文别名: 1-(3-hydroxy-4-methoxybenzylidene)-4-(4-chlorophenyl)thiosemicarbazide；α-<4-(4-Chlor-phenyl)-thiosemicarbazono>-4-hydroxy-3-methoxy-toluol；4-Hydroxy-3-methoxy-ω-<4-(4-Chlor-phenyl)-thiosemicarbazono>-toluol；4-Hydroxy-3-methoxy-ω-[4-(4-Chlor-phenyl)-thiosemicarbazono]-toluol
• CAS: 16434-24-5
• 化学式: C₁₅H₁₄ClN₃O₂S
• 分子量: 335.814
• InChiKey: JXEGNNMAFSIRBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  65.88
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(4-chlorophenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-thiosemicarbazide 在 ammonium iron(III) sulfate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-(3-methoxy-4-hydroxyphenyl)-5-(4-chloro-phenylamino)-1,3,4-thiadiazole
  参考文献：
  名称：

  One-pot synthesis and anticancer studies of 2-arylamino-5-aryl-1,3,4-thiadiazoles

  摘要：

  A series of 2-arylamino-5-aryl-1,3,4-thiadiazoles 1a-j were synthesized and screened for their anticancer activity against various human cancer cell lines. The novel one-pot synthesis of 1,3,4-thiadiazoles was achieved by refluxing aryl aldehydes, hydrazine hydrate, and aryl isothiocyanates in methanol followed by oxidative cyclization with ferric ammonium sulfate. The compounds 1g-j with trimethoxyphenyl at the C-5 position displayed extremely potent anticancer activity with at least twofold selectivity (IC(50): 4.3-9.2 mu M). The nature of substituent on the C-2 arylamino ring may be critical in opting for the selectivity towards a particular cancer cell. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.083
• 作为产物：
  描述：

  4-氯异硫氰酸苯酯 、 香草醛 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4-(4-chlorophenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-thiosemicarbazide
  参考文献：
  名称：

  One-pot synthesis and anticancer studies of 2-arylamino-5-aryl-1,3,4-thiadiazoles

  摘要：

  A series of 2-arylamino-5-aryl-1,3,4-thiadiazoles 1a-j were synthesized and screened for their anticancer activity against various human cancer cell lines. The novel one-pot synthesis of 1,3,4-thiadiazoles was achieved by refluxing aryl aldehydes, hydrazine hydrate, and aryl isothiocyanates in methanol followed by oxidative cyclization with ferric ammonium sulfate. The compounds 1g-j with trimethoxyphenyl at the C-5 position displayed extremely potent anticancer activity with at least twofold selectivity (IC(50): 4.3-9.2 mu M). The nature of substituent on the C-2 arylamino ring may be critical in opting for the selectivity towards a particular cancer cell. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.083

文献信息

• Synthesis and In Vitro Anti-Toxoplasma gondii Activity of Novel Thiazolidin-4-one Derivatives
  作者：Nazar Trotsko、Adrian Bekier、Agata Paneth、Monika Wujec、Katarzyna Dzitko

  DOI：10.3390/molecules24173029

  日期：——

  parasites prompted us to look for new agents. We designed and synthesized a series of new thiazolidin-4-one derivatives through a two-step reaction between 4-substituted thiosemicarbazides with hydroxybenzaldehydes followed by the treatment with ethyl bromoacetate; maleic anhydride and dimethyl acetylenedicarboxylate afforded target compounds. The thiazolidin-4-one derivatives were used to assess the

  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
• 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.