1-(2-Methoxyphenyl)-3-(pyridine-4-carbonylamino)thiourea | 74270-73-8

• 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: 1-(2-Methoxyphenyl)-3-(pyridine-4-carbonylamino)thiourea
• CAS: 74270-73-8
• 化学式: C₁₄H₁₄N₄O₂S
• 分子量: 302.357
• InChiKey: FXLPMAOCVQDSLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-Methoxyphenyl)-3-(pyridine-4-carbonylamino)thiourea 在 mycobacterium tuberculosis H₃₇Rv strain 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.17h， 生成
  参考文献：
  名称：

  Synthesis and Molecular Docking Studies of Glucose-linked Isonicotinoyl- 1,3,4-Thiadiazolidines as Antitubercular Agents

  摘要：

  背景：最近出现了对异烟肼和利福平这两种主要有效药物具有耐药性的结核杆菌耐多药菌株，这促使我们尝试通过改变现有药物的结构来开发一类新的强效抗结核药物。为此，我们进行了葡萄糖连接异烟酰基-1,3,4-噻二唑烷的高效合成。 方法：通过 1-异烟酰基-4-芳基硫代氨基甲酸与 N-四-O-乙酰基-β-D-吡喃葡萄糖基异氰基二氯的环缩合反应合成了标题化合物。 通过红外光谱、1H NMR、13C NMR、质谱和元素分析验证了新合成化合物的结构。采用 Lowenstein-Jensen 方法评估了标题化合物对结核杆菌 H37Rv 株的体外抗结核效力。 结果：发现一些标题化合物与参比药物利福平的效力相当，而与参比药物异烟肼相比，效力适中。对这些化合物进行了分子对接研究，发现其结果与体外研究结果一致。 结论：我们报道了利用 N-四-O-乙酰基-β-D-吡喃葡萄糖基异氰基二氯化物作为糖基化的合适试剂，合成一系列具有生物活性的葡萄糖苷联异烟酰基-1,3,4-噻二唑烷的简单而有效的方法。这种方法是对快速发展的葡萄糖连接杂环领域的宝贵补充，可用于开发新的潜在药物。我们展示了在单一分子框架中引入异烟酰基和葡萄糖基的方法，这可能会被证明有利于开发新型抗结核药物。

  DOI：

  10.2174/1570178614666170608130326
• 作为产物：
  描述：

  异烟肼 、 异氰酸2-甲氧苯酯 以 乙醇 为溶剂， 反应 4.0h， 生成 1-(2-Methoxyphenyl)-3-(pyridine-4-carbonylamino)thiourea
  参考文献：
  名称：

  Synthesis and Molecular Docking Studies of Glucose-linked Isonicotinoyl- 1,3,4-Thiadiazolidines as Antitubercular Agents

  摘要：

  背景：最近出现了对异烟肼和利福平这两种主要有效药物具有耐药性的结核杆菌耐多药菌株，这促使我们尝试通过改变现有药物的结构来开发一类新的强效抗结核药物。为此，我们进行了葡萄糖连接异烟酰基-1,3,4-噻二唑烷的高效合成。 方法：通过 1-异烟酰基-4-芳基硫代氨基甲酸与 N-四-O-乙酰基-β-D-吡喃葡萄糖基异氰基二氯的环缩合反应合成了标题化合物。 通过红外光谱、1H NMR、13C NMR、质谱和元素分析验证了新合成化合物的结构。采用 Lowenstein-Jensen 方法评估了标题化合物对结核杆菌 H37Rv 株的体外抗结核效力。 结果：发现一些标题化合物与参比药物利福平的效力相当，而与参比药物异烟肼相比，效力适中。对这些化合物进行了分子对接研究，发现其结果与体外研究结果一致。 结论：我们报道了利用 N-四-O-乙酰基-β-D-吡喃葡萄糖基异氰基二氯化物作为糖基化的合适试剂，合成一系列具有生物活性的葡萄糖苷联异烟酰基-1,3,4-噻二唑烷的简单而有效的方法。这种方法是对快速发展的葡萄糖连接杂环领域的宝贵补充，可用于开发新的潜在药物。我们展示了在单一分子框架中引入异烟酰基和葡萄糖基的方法，这可能会被证明有利于开发新型抗结核药物。

  DOI：

  10.2174/1570178614666170608130326

文献信息

• Synthesis and Molecular Structure of New S-Nucleosides of 5-(4-Pyridyl)-4-Aryl-4<i>H</i>-1,2,4-Triazole-3-Thiols
  作者：Huan-Huan Zhang、Xiu-Qin Hu、Gui-Fang Fan、Peng-Fei Xu

  DOI：10.1002/jccs.200800124

  日期：2008.8

  The synthesis of some new S-nucleosides of 5-(4-pyridyl)-4-aryl-4H-1,2,4-triazole-3-thiols (4a-n) is described. Direct glycosylation of (4a-n) with tetra-O-acetyl-a-D-glucopyranosyl bromide in the presence of potassium hydroxide followed by deacetylation using dry ammonia in methanol gave the corresponding 3-S-(β-D-glucopyranosyl)-5-(4-pyridyl)-4-aryl-4H-1,2,4-triazoles (6a-n) in good yields. All the

  描述了 5-(4-pyridyl)-4-aryl-4H-1,2,4-triazole-3-thiols (4a-n) 的一些新的 S-核苷的合成。在氢氧化钾存在下，用四-O-乙酰基-aD-吡喃葡萄糖基溴将(4a-n)直接糖基化，然后用甲醇中的无水氨脱乙酰基，得到相应的3-S-(β-D-吡喃葡萄糖基)-5- (4-吡啶基)-4-芳基-4H-1,2,4-三唑(6a-n)，收率良好。通过 1 H NMR、 13 C NMR 光谱和元素分析对所有化合物进行了充分表征。为了帮助解释光谱数据，3-S-(2',3',4',6'-四-O-乙酰基-β-D-吡喃葡萄糖基)-5-(4-吡啶基)的晶体结构)-4-苯基-4H-1,2,4-三唑(5a)通过X射线衍射测定。
• 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.
• Yar, Mohammad Shahar; Akhter, Mohammad Wasim, Acta poloniae pharmaceutica, 2009, vol. 66, # 4, p. 393 - 397
  作者：Yar, Mohammad Shahar、Akhter, Mohammad Wasim

  DOI：——

  日期：——
• Electrochemically initiated oxidative cyclization: a versatile route for the synthesis of 5-substituted 2-amino-1,3,4-oxadiazoles
  作者：Sushma Singh、Laxmi Kant Sharma、Apoorv Saraswat、R. K. P. Singh

  DOI：10.1007/s00706-011-0711-3

  日期：2012.10

  A rapid, improved, and environmentally benign synthesis of 5-substituted 2-amino-1,3,4-oxadiazoles by one-pot electrocyclization of acylthiosemicarbazones is reported. Controlled potential electrolysis was performed at room temperature in acetonitrile as non-aqueous solvent and LiClO4 as supporting electrolyte. The reaction products were characterized by spectroscopic methods and a mechanism was deduced from voltammetric data. Better yields at room temperature, shortest reaction time, and easy work-up are attractive features of this green procedure.