4-(3-chlorophenyl)-1-(isonicotinoyl)thiosemicarbazide | 13094-44-5

• 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
• 英文名称: 4-(3-chlorophenyl)-1-(isonicotinoyl)thiosemicarbazide
• 英文别名: 4-(3-chloro-phenyl)-1-isonicotinoyl-thiosemicarbazide；4-(3-Chlor-phenyl)-1-isonicotinoyl-thiosemicarbazid；1-(3-Chlorophenyl)-3-(pyridine-4-carbonylamino)thiourea
• CAS: 13094-44-5
• 化学式: C₁₃H₁₁ClN₄OS
• 分子量: 306.776
• InChiKey: FFHIKXXAROVKKM-UHFFFAOYSA-N

物化性质

• 密度：
  1.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-(3-chlorophenyl)-1-(isonicotinoyl)thiosemicarbazide 在 sodium hydroxide 作用下， 生成 4-(3-chlorophenyl)-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  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
• 作为产物：
  描述：

  异烟肼 、 3-氯异硫氰酸苯酯 以 乙醇 为溶剂， 以77%的产率得到4-(3-chlorophenyl)-1-(isonicotinoyl)thiosemicarbazide
  参考文献：
  名称：

  合成烟碱/烟碱型硫代氨基脲：体外脲酶抑制活性和分子对接研究

  摘要：

  烟酸和异烟酸氨基硫脲或肼carbothioamides 3 - 27合成的和合成的化合物的结构是由不同的光谱技术如EI-MS，阐明1 H-和13 C NMR。对合成衍生物的脲酶抑制活性进行了评估，结果表明，与标准硫脲相比，所有衍生物几乎没有表现出对IC 50值在1.21–51.42μM范围内的出色抑制作用（IC 50  = 21.25± 0.13μM ）。间的25合成的衍生物19 1 - 5，7，8，10，12，14 - 18，20 - 22，24 - 27被认为是更具活性表示IC 50个1.13 19.74和之间的值表示μM比标准更高的活性。有限的结构活性关系表明，吡啶环中取代基的位置以及氮的位置对于此类化合物的抑制活性非常重要。为了验证这些解释，还进行了计算机模拟研究。在活性化合物的生物学评估和对接研究之间获得了良好的相关性。

  DOI：

  10.1016/j.bioorg.2018.04.004

文献信息

• 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.
• Pyridine-Based 1,2,4-Triazolo-Tethered Indole Conjugates Potentially Affecting TNKS and PI3K in Colorectal Cancer
  作者：Prasanna A. Yakkala、Samir R. Panda、Vegi G. M. Naidu、Syed Shafi、Ahmed Kamal

  DOI：10.1021/acsmedchemlett.2c00475

  日期：2023.3.9
• Synthetic nicotinic/isonicotinic thiosemicarbazides: In vitro urease inhibitory activities and molecular docking studies
  作者：Basharat Ali、Khalid Mohammed Khan、Arshia、Kanwal、Shafqat Hussain、Safdar Hussain、Muhammad Ashraf、Muhammad Riaz、Abdul Wadood、Shahnaz Perveen

  DOI：10.1016/j.bioorg.2018.04.004

  日期：2018.9

  Nicotinic and isonicotinic thiosemicarbazide or hydrazine carbothioamides 3–27 were synthesized and the structures of synthetic compounds were elucidated by various spectroscopic techniques such as EI-MS, 1H-, and 13C NMR. Synthetic derivatives were evaluated for their urease inhibitory activity which revealed that except few all derivatives demonstrated excellent inhibition in the range of IC50 values

  烟酸和异烟酸氨基硫脲或肼carbothioamides 3 - 27合成的和合成的化合物的结构是由不同的光谱技术如EI-MS，阐明1 H-和13 C NMR。对合成衍生物的脲酶抑制活性进行了评估，结果表明，与标准硫脲相比，所有衍生物几乎没有表现出对IC 50值在1.21–51.42μM范围内的出色抑制作用（IC 50  = 21.25± 0.13μM ）。间的25合成的衍生物19 1 - 5，7，8，10，12，14 - 18，20 - 22，24 - 27被认为是更具活性表示IC 50个1.13 19.74和之间的值表示μM比标准更高的活性。有限的结构活性关系表明，吡啶环中取代基的位置以及氮的位置对于此类化合物的抑制活性非常重要。为了验证这些解释，还进行了计算机模拟研究。在活性化合物的生物学评估和对接研究之间获得了良好的相关性。
• 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。