4-(4-nitrophenyl)-1-(pyridin-4-yl)carbonylthiosemicarbazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(4-nitrophenyl)-1-(pyridin-4-yl)carbonylthiosemicarbazide
• 英文别名: 2-isonicotinoyl-N-(4-nitrophenyl)-1-hydrazinecarbothioamide；1-(4-nitrophenyl)-3-(pyridine-4-carbonylamino)thiourea
• 化学式: C₁₃H₁₁N₅O₃S
• 分子量: 317.328
• InChiKey: VBCDRHBVTYSPEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-nitrophenyl)-1-(pyridin-4-yl)carbonylthiosemicarbazide 在 sodium hydroxide 作用下， 以85%的产率得到4-(4-nitrophenyl)-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Synthesis and Antimicrobial Activity of Some New 1,2,4-Trizoles

  摘要：

  采用适当的合成路线合成了一系列 1,2,4-三唑衍生物，并通过红外光谱、1H NMR 和元素分析确认了其结构。对所有合成的化合物（6a-6h 和 7a-7h）进行了抗菌活性评估，确定了它们对革兰氏阳性、革兰氏阴性细菌和真菌的最低抑菌浓度（MICs）。大多数化合物对革兰氏阳性菌（金黄色葡萄球菌、枯草杆菌）、革兰氏阴性菌（大肠杆菌、绿脓杆菌）和真菌（白僵菌、黑僵菌）具有明显的抗菌活性。与革兰氏阴性菌相比，一些化合物对革兰氏阳性菌显示出更好的抗菌活性。与参照物诺氟沙星相比，化合物 7g、6g 和 6a 对革兰氏阳性菌的 MIC 值较高，而 7f 对革兰氏阴性菌的 MIC 值较高。化合物 7f 和 7d 的 MIC 值与参考药物酮康唑相当。

  DOI：

  10.14233/ajchem.2017.20481
• 作为产物：
  描述：

  异烟酸乙酯 在 肼 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 4-(4-nitrophenyl)-1-(pyridin-4-yl)carbonylthiosemicarbazide
  参考文献：
  名称：

  新的硫代氨基脲衍生物作为抗结核药的合成，体外筛选和对接研究。

  摘要：

  通过羧酸酰肼与异硫氰酸酯的反应，设计合成了一系列硫代氨基脲衍生物。通过光谱分析证实了所研究的硫代氨基脲的分子结构。使用X射线分析表征了羰基硫代氨基脲分子的构象偏爱以及结晶状态下的分子内和分子间相互作用。在体外测试了目标化合物对四种分枝杆菌菌株的抗结核活性：M. H37Ra，M. phlei，M. smegmatis，M. timereck。活性最高的化合物是带有2-吡啶环的化合物。与其他异构体相比，它们的最低抑菌浓度（MIC）值较低，为7.81±31.25μg/ mL。化合物5在浓度为7时具有抗耻垢分枝杆菌的活性。81μg/ mL，而化合物2在15.625μg/ mL的浓度下对所有测试菌株均具有活性。使用结核分枝杆菌谷氨酰胺合成酶MtGS作为其分子靶标，对所研究的化合物进行了分子对接研究。

  DOI：

  10.3390/molecules24020251

文献信息

• Novel thiosemicarbazide derivatives with 4-nitrophenyl group as multi-target drugs: α-glucosidase inhibitors with antibacterial and antiproliferative activity
  作者：Maciej Wos、Małgorzata Miazga-Karska、Agnieszka A. Kaczor、Katarzyna Klimek、Zbigniew Karczmarzyk、Dorota Kowalczuk、Waldemar Wysocki、Grazyna Ginalska、Zofia Urbanczyk-Lipkowska、Maja Morawiak、Monika Pitucha

  DOI：10.1016/j.biopha.2017.07.049

  日期：2017.9

  A series of thiosemicarbazides with 4-nitrophenyl group was obtained in the reaction of carboxylic acid hydrazides with isothiocyanates. All compounds were checked for their antibacterial and antiproliferative activity. Our results have shown that derivatives possessed antibacterial activity against , , and , moderate cytotoxicity and good therapeutic safety . Additionally, compounds and significantly

  羧酸酰肼与异硫氰酸酯反应得到一系列带有4-硝基苯基的氨基硫脲。检查所有化合物的抗菌和抗增殖活性。我们的结果表明，衍生物具有抗菌活性，具有中等的细胞毒性和良好的治疗安全性。此外，化合物还显着抑制 A549、HepG2 和 MCF-7 细胞分裂。此外，PASS软件表明新获得的化合物是潜在的α-葡萄糖苷酶抑制剂。这已被研究证实。为了研究与分子目标化合物的相互作用模式，将化合物对接至酶的葡萄糖结合位点，并表现出与葡萄糖相似的结合模式。
• 1,3,4-Thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure−Antituberculosis Activity Relationship Investigation
  作者：Elçin E. Oruç、Sevim Rollas、Fatma Kandemirli、Nathaly Shvets、Anatholy S. Dimoglo

  DOI：10.1021/jm0495632

  日期：2004.12.1

  A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized, the compounds structures were elucidated and screened for the antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the tested compounds, 2-phenylamino-5-(4-fluorophenyl)-1,3,4-thiadiazole 22 showed the highest inhibitory activity. The relationships between the structures of compounds and their antituberculosis activity were investigated by the Electronic-Topological Method (ETM) and feed forward neural networks (FFNNs) trained with the back-propagation algorithm. As a result of the approach, a system of pharmacophores and anti-pharmacophores has been found that effectively separates compounds of the examination set into groups of active and inactive compounds. The system can be applied to the screening and design of new active compounds possessing skeletons similar to those used in the present study.
• Synthesis and antitumor activity of 4-cyclohexyl/aryl-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones
  作者：Mashooq Ahmad Bhat、Mohamed A. Al-Omar、Ahmed M. Naglah、Mohamed M. Abdulla、Hoong-Kun Fun

  DOI：10.1007/s00044-014-1216-5

  日期：2015.4

  The reaction of 2-isonicotinoyl-N-cyclohexyl/arylhydrazinecarbothioamide (2a-r) with sodium hydroxide, in each case, a single product was obtained. The structures of the compounds were confirmed on the basis of their elemental analysis and spectral data. The single crystal X-ray analysis confirmed the structure of these products as N-4-cyclohexyl/aryl-5-(pyridine-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones (3a-r). The in vitro antitumor activity of compounds was screened against three cell lines; BEL-7402, HUH-7 and HepG2 human hepatoma using MTT assay. Sorafenib (50 A mu M) was used as a positive control. The results of the MTT-dye reduction assay indicated that most of the compounds exert potent cytotoxic/antiproliferative effect in a time and dose-dependent manner via induced apoptosis of HepG2 cells. Results also showed that the tested compounds could significantly enhance the activity of caspase-3 which plays a very important role as the central effecter during apoptosis. The effect of different substitutions on the aromatic portion on the activity was found to be in the following order CH3 > OCH3 > I > SO2NH2 > OC2H5 > C2H5 > NO2 > Cl > CH3CONH.
• Synthesis and anti-Candidal activity of N-(4-aryl/cyclohexyl)-2-(pyridine-4-yl carbonyl) hydrazinecarbothioamide
  作者：Mashooq Ahmad Bhat、Abdul Arif Khan、Shahanavaj Khan、Mohamed A. Al-Omar、Mohammad Khalid Parvez、Mohammed Salem Al-Dosari、Abdullah Al-Dhfyan

  DOI：10.1016/j.bmcl.2014.01.060

  日期：2014.3

  Eighteen N-(4-aryl/cyclohexyl)-2-(pyridine-4-yl carbonyl) hydrazinecarbothioamide derivatives were synthesized, evaluated against ten clinical isolates of Candida spp. and compared with itraconazole. Introduction of p-chloro (2c), p-iodo (2q), m-chloro (2l) and o-nitro (2r) substitution at phenyl ring of thiosemicarbazide enhanced the anti-Candida activity. Compound (2c) bearing p-cholorophenyl ring was found to be the most effective against Candida albicans ATCC 66027, Candida spp. 12810 (blood) and Candida spp. 178 (HVS) with MIC value of 0.09-0.78 mu g/mL, whereas itraconazole exhibits the inhibitory activity with MIC value of 0.04-1.56 mu g/mL against all tested strains. There is a correlation between anti-Candidal activity and p-chloro substitution at phenyl ring of thiosemicarbazide. All synthesized compounds were investigated for their potential cytotoxicity against non cancer cell line MCF-10A. The active compounds 2c, 2r and 2a were further investigated for their cytotoxic effects on three cancer cell lines; HT1080 (skin), HepG2 (liver) and A549 (lung). The active compounds showed minimal cytotoxic activity against non cancer cell line and all three cancer cell lines. Moreover, compound 2c displaying better activity against C. albicans ATCC66027 and Candida spp. [blood] compared to reference drug (itraconazole), represents a good lead for the development of newer, potent and broad spectrum anti-Candidal agents. (C) 2014 Elsevier Ltd. All rights reserved.
• ZHANG, ZIYI;YANG, KEXIN;ZENG, FULI, CHEM. J. CHIN. UNIV., 9,(1988) N 3, 239-245
  作者：ZHANG, ZIYI、YANG, KEXIN、ZENG, FULI

  DOI：——

  日期：——