1-(3-bromobenzoyl)-3-thiosemicarbazide | 126651-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3-bromobenzoyl)-3-thiosemicarbazide
• 英文别名: 2-(3-bromobenzoyl)hydrazinecarbothioamide；N2-(3-bromobenzoyl)thiosemicarbazide；[(3-bromobenzoyl)amino]thiourea
• CAS: 126651-84-1
• 化学式: C₈H₈BrN₃OS
• 分子量: 274.141
• InChiKey: RGXFOKHIGCHXKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-bromobenzoyl)-3-thiosemicarbazide 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 5-(3-溴-苯基)-2,4-二氢-[1,2,4]噻唑-3-硫酮
  参考文献：
  名称：

  新型1-二茂铁基-2-（3-苯基-1 H -1,2,4-三唑-5-基硫基）乙酮衍生物的合成，X射线晶体结构和光学性质

  摘要：

  通过3-取代的-1 H -1,2,4的反应合成了一系列新型的1-二茂铁基-2-（3-苯基-1 H -1,2,4-三唑-5-基硫基）乙酮衍生物-三唑-5-硫醇和氯乙酰基二茂铁在氢化钠和碘化钾存在下回流。通过IR和1 H NMR光谱以及HRMS确定新化合物的结构。通过X射线晶体学确定化合物5c的结构。在乙醇和二氯甲烷中记录了紫外可见吸收和荧光光谱。结果表明，化合物5a–g显示出相似的吸收范围从300到500 nm，最大发射带约为566 nm。荧光强度和最大发射带取决于与三唑环键合的基团。

  DOI：

  10.1016/j.saa.2010.04.019
• 作为产物：
  描述：

  间溴苯甲酸 在 盐酸 、 一水合肼 作用下， 以 甲醇 、 水 为溶剂， 反应 17.0h， 生成 1-(3-bromobenzoyl)-3-thiosemicarbazide
  参考文献：
  名称：

  An Efficient Nonconventional Glycerol-Based Solid Acid Catalyzed Synthesis and Biological Evaluation of Phosphonate Conjugates of 1,2,4-triazole Thiones

  摘要：

  一系列二乙基（3-（（5-芳基-1H-1,2,4-三唑-3-基）硫代）丙基）膦酸酯（7a–t）通过使用由甘油衍生的高效、绿色且非传统的SO3H碳固体催化剂，将二乙基（3-溴丙基）膦酸酯与5-芳基-1H-1,2,4-三唑-3-硫酮耦合合成，产率极佳。此外，还报道了一种利用甘油基固体酸催化剂进行羧酸酯化的简便且绿色的方法。合成的化合物的结构通过IR、NMR和HRMS研究进行了表征。这些三唑衍生物通过标准的MTT（3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴）法对五种不同的人类癌细胞系（HeLa：宫颈，A549：肺，A375：皮肤，MDA-MB-231：乳腺和T98G：脑）进行了体外细胞毒性筛选。合成的化合物的抗菌活性对四种细菌菌株：枯草杆菌、金黄色葡萄球菌、大肠杆菌、铜绿假单胞菌和三种真菌菌株：黑曲霉、土曲霉、烟曲霉进行了研究。初步结果表明，化合物7f显示出最大的抗癌活性，而化合物7d、7e、7f、7m和7q表现出中等抗菌活性。化合物7g、7h、7o和7p显示出良好的抗真菌活性，抑制区直径相比标准药物较大。

  DOI：

  10.2174/1570180813666160125222334

文献信息

• An Efficient Nonconventional Glycerol-Based Solid Acid Catalyzed Synthesis and Biological Evaluation of Phosphonate Conjugates of 1,2,4-triazole Thiones
  作者：Madugula S. R. Murty、Mohana R. Katiki、Busam R. Rao、Sai S. Narayanan、Ruby J. Anto、Sudhreer K. Buddana、Reddy S. Prakasham、Bethala L. A. P. Devi、Rachapudi B. N. Prasad

  DOI：10.2174/1570180813666160125222334

  日期：2016.10.3

  A series of diethyl (3-((5-aryl-1H-1,2,4-triazol-3-yl)thio)propyl)phos-phonates (7a–t) has been synthesized in excellent yields by coupling diethyl (3-bromopropyl)phosphonate and 5-aryl-1H-1,2,4-triazol-3-thiones employing an efficient, green and nonconventional heterogeneous SO3Hcarbon catalyst derived from glycerol. In addition, a facile and green approach for the esterification of carboxylic acids by utilizing glycerol-based solid acid catalyst has been reported. Structures of the synthesized compounds were characterized by IR, NMR and HRMS studies. These triazole derivatives were screened for their in vitro cytotoxicity using the standard MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetra-zolium bromide) assay against a panel of five different human cancer cell lines (HeLa: Cervix, A549: Lung, A375: Skin, MDA-MB-231: Breast and T98G: Brain). The antimicrobial activities of the synthesized compounds were investigated against four bacterial strains: Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and three fungal strains: Aspergillus niger, Aspergillus terreus, Aspergillus fumigatus. Preliminary results indicate that the compound 7f displayed maximum anticancer activity and the compounds 7d, 7e, 7f, 7m and 7q exhibited moderate antibacterial activity. The compounds 7g, 7h, 7o and 7p showed good antifungal activity with high inhibition zone diameter compared to the standard drug.

  一系列二乙基（3-（（5-芳基-1H-1,2,4-三唑-3-基）硫代）丙基）膦酸酯（7a–t）通过使用由甘油衍生的高效、绿色且非传统的SO3H碳固体催化剂，将二乙基（3-溴丙基）膦酸酯与5-芳基-1H-1,2,4-三唑-3-硫酮耦合合成，产率极佳。此外，还报道了一种利用甘油基固体酸催化剂进行羧酸酯化的简便且绿色的方法。合成的化合物的结构通过IR、NMR和HRMS研究进行了表征。这些三唑衍生物通过标准的MTT（3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴）法对五种不同的人类癌细胞系（HeLa：宫颈，A549：肺，A375：皮肤，MDA-MB-231：乳腺和T98G：脑）进行了体外细胞毒性筛选。合成的化合物的抗菌活性对四种细菌菌株：枯草杆菌、金黄色葡萄球菌、大肠杆菌、铜绿假单胞菌和三种真菌菌株：黑曲霉、土曲霉、烟曲霉进行了研究。初步结果表明，化合物7f显示出最大的抗癌活性，而化合物7d、7e、7f、7m和7q表现出中等抗菌活性。化合物7g、7h、7o和7p显示出良好的抗真菌活性，抑制区直径相比标准药物较大。
• The synthesis, X-ray crystal structure and optical properties of novel 1-ferrocenyl-2-(3-phenyl-1H-1,2,4-triazol-5-ylthio)ethanone derivatives
  作者：Wei-Yong Liu、Yong-Sheng Xie、Bao-Xiang Zhao、Song Lian、Hong-Shui Lv、Zhong-Liang Gong、Dong-Soo Shin

  DOI：10.1016/j.saa.2010.04.019

  日期：2010.9

  1-ferrocenyl-2-(3-phenyl-1H-1,2,4-triazol-5-ylthio)ethanone derivatives was synthesized by the reaction of 3-substituted-1H-1,2,4-triazole-5-thiol and chloroacetyl ferrocene in the presence of sodium hydride and potassium iodide at reflux. The structures of the new compounds were determined by IR and 1H NMR spectroscopy and HRMS. The structure of compound 5c was established by X-ray crystallography. UV–vis

  通过3-取代的-1 H -1,2,4的反应合成了一系列新型的1-二茂铁基-2-（3-苯基-1 H -1,2,4-三唑-5-基硫基）乙酮衍生物-三唑-5-硫醇和氯乙酰基二茂铁在氢化钠和碘化钾存在下回流。通过IR和1 H NMR光谱以及HRMS确定新化合物的结构。通过X射线晶体学确定化合物5c的结构。在乙醇和二氯甲烷中记录了紫外可见吸收和荧光光谱。结果表明，化合物5a–g显示出相似的吸收范围从300到500 nm，最大发射带约为566 nm。荧光强度和最大发射带取决于与三唑环键合的基团。
• Inhibiting G Protein Coupled Receptor 6 Kinase Polypeptides
  申请人：Mayo Foundation for Medical Educational and Research

  公开号：US20140309185A1

  公开（公告）日：2014-10-16

  This document relates to inhibitors of G protein coupled receptor 6 kinase (GRK6) polypeptides as well as methods and materials for using such inhibitors to treat hematological malignancies, inflammation diseases, and autoimmune disorders.

  这份文件涉及G蛋白偶联受体6激酶（GRK6）多肽的抑制剂，以及利用这些抑制剂治疗血液恶性肿瘤、炎症性疾病和自身免疫性疾病的方法和材料。
• Inhibiting G protein coupled receptor 6 kinase polypeptides
  申请人：Mayo Foundation for Medical Education and Research

  公开号：US10252984B2

  公开（公告）日：2019-04-09

  This document relates to inhibitors of G protein coupled receptor 6 kinase (GRK6) polypeptides as well as methods and materials for using such inhibitors to treat hematological malignancies, inflammation diseases, and autoimmune disorders.

  本文件涉及 G 蛋白偶联受体 6 激酶（GRK6）多肽的抑制剂以及使用这种抑制剂治疗血液恶性肿瘤、炎症疾病和自身免疫性疾病的方法和材料。
• Discovery and Biophysical Characterization of 2-Amino-oxadiazoles as Novel Antagonists of PqsR, an Important Regulator of Pseudomonas aeruginosa Virulence
  作者：Michael Zender、Tobias Klein、Claudia Henn、Benjamin Kirsch、Christine K. Maurer、Dagmar Kail、Christiane Ritter、Olan Dolezal、Anke Steinbach、Rolf W. Hartmann

  DOI：10.1021/jm400830r

  日期：2013.9.12

  The human pathogen Pseudomonas aeruginosa employs alkyl quinolones for cell-to-cell communication. The Pseudomonas quinolone signal (PQS) regulates various virulence factors via interaction with the transcriptional regulator PqsR. Therefore, we consider the development of PqsR antagonists a novel strategy to limit the pathogenicity of P. aeruginosa. A fragment identification approach using surface plasmon resonance screening led to the discovery of chemically diverse PqsR ligands. The optimization of the most promising hit (5) resulted in the oxadiazole-2-amine 37 showing pure antagonistic activity in Escherichia coli (EC50 = 7.5 mu M) and P. aeruginosa (EC50 = 38.5 mu M) reporter gene assays. 37 was able to diminish the production of the PQS precursor HHQ in a PqsH-deficient P. aeruginosa mutant The level of the major virulence factor pyocyanin was significantly reduced in wild-type P. aeruginosa. In addition, site-directed mutagenesis in combination with isothermal titration calorimetry and NMR INPHARMA experiments revealed that the identified ligands bind to the same site of PqsR by adopting different binding modes. These findings will be utilized in a future fragment growing approach aiming at novel therapeutic options for the treatment of P. aeruginosa infections.