1-(2-甲基苯基)-3-(吡啶-4-羰基氨基)硫脲 | 74270-70-5

• 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
• 中文名称: 1-(2-甲基苯基)-3-(吡啶-4-羰基氨基)硫脲
• 中文别名: 甲基2-硫烷基-1,3-苯并噁唑-6-羧酸酯
• 英文名称: 4-(2-methylphenyl)-1-(4-pyridoyl) thiosemicarbazide
• 英文别名: 1-isonicotinoyl-4-o-tolyl-thiosemicarbazide；1-Isonicotinoyl-4-(2-methyl-phenyl)-thiosemicarbazid；1-Isonicotinoyl-4-(2-tolyl)thiosemicarbazide；1-(2-methylphenyl)-3-(pyridine-4-carbonylamino)thiourea
• CAS: 74270-70-5
• 化学式: C₁₄H₁₄N₄OS
• 分子量: 286.357
• InChiKey: DUCBLVDTLSAVMM-UHFFFAOYSA-N

物化性质

• 溶解度：
  >43 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  98.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-甲基苯基)-3-(吡啶-4-羰基氨基)硫脲 在 硫酸 作用下， 以 水 为溶剂， 以80%的产率得到2-(2-methylphenyl)amino-5-(4-pyridyl)-1,3,4-thiadiazole
  参考文献：
  名称：

  Yar, Mohammad Shahar; Akhter, Mohammad Wasim, Acta poloniae pharmaceutica, 2009, vol. 66, # 4, p. 393 - 397

  摘要：

  DOI：
• 作为产物：
  描述：

  异烟肼 、 邻甲苯异硫氰酸酯 以 乙醇 为溶剂， 以70%的产率得到1-(2-甲基苯基)-3-(吡啶-4-羰基氨基)硫脲
  参考文献：
  名称：

  5-(4-吡啶基)-4-芳基-4H-1,2,4-三唑-3-硫醇新S-核苷的合成及分子结构

  摘要：

  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。

  DOI：

  10.1002/jccs.200800124

文献信息

• The Microwave-Assisted Dehydrative Cyclization of Thiosemicarbazides Forming Substituted 1,2,4-Triazoles
  作者：Khosrow Zamani、Shirindokht Bagheri

  DOI：10.1080/10426500500543859

  日期：2006.8.1

  irradiation as well as by a classical method. The beneficial effect of microwave irradiation on the dehydrative cyclization of thiosemicarbazides in different reaction media is described. Our results show that the effect of microwave irradiation on the reaction studied was the shortening of reaction times (from 2–9 h to 2–4 min) and a minor decrease (1–4%) in yields. The structure of the new compounds was

  不同类型的 4,5-二取代 1,2,4-三唑-3-硫酮是通过微波辐射和经典方法制备的。描述了微波辐射对氨基硫脲在不同反应介质中脱水环化的有益影响。我们的结果表明，微波辐射对所研究反应的影响是反应时间的缩短（从 2-9 小时到 2-4 分钟）和产率的轻微下降（1-4%）。通过FTIR、MS和1H NMR光谱数据确定了新化合物的结构。
• Design, Synthesis, and Herbicidal Activities of 3-Aryl-4-substituted-5-[3-(trifluoromethyl)phenoxy]-1,2,4-triazoles
  作者：Man-Yun Liu、De-Qing Shi

  DOI：10.1002/jhet.1920

  日期：2014.8

  oxidation of in the presence of H2O2 and Na2WO4, followed by the substitution with 3-(trifluoromethyl)phenol in moderate to good yields. Their structures were confirmed by IR, 1H NMR, EI–MS, and elemental analyses. The preliminary bioassay indicated that some of them displayed moderate to good selective herbicidal activity against Brassica campestris L at the concentration of 100 µg/mL. Compounds and possessed

  为了找到新型的漂白除草剂先导化合物，通过多步反应设计合成了一系列新型的3-芳基-4-取代的5- [3-（三氟甲基）苯氧基] -1，2，4-三唑。 。N-（芳基甲酰胺基）苯基硫脲在氢氧化钠的存在下发生闭环反应，生成3-芳基-4-取代的-4 H- [1,2,4]三唑-5-硫醇，其在K 2 CO 3存在下与硫酸甲酯反应，得到3-芳基-5-甲基硫烷基-4-取代的-4 H- [1,2,4]三唑。目标化合物 通过氧化的方式合成 在H 2 O 2和Na 2 WO 4存在下，然后用3-（三氟甲基）苯酚的产率中等至良好。通过IR，1 H NMR，EI-MS和元素分析证实了它们的结构。初步的生物测定表明，它们中的一些在100 µg / mL的浓度下对甘蓝型油菜表现出中等至良好的选择性除草活性。化合物 和 在100 µg / mL的浓度下对甘蓝型油菜具有75.0％和82.6％的抑制作用。但是，目标化合物在浓度为100和10
• Zamani, Khosrow; Faghihi, Khalil; Bagheri, Shirindokht, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 12, p. 2716 - 2718
  作者：Zamani, Khosrow、Faghihi, Khalil、Bagheri, Shirindokht、Kalhor, Mahdi

  DOI：——

  日期：——
• 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.