2-(3-chlorobenzoyl)hydrazinecarbothioamide | 881-74-3

• 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: 2-(3-chlorobenzoyl)hydrazinecarbothioamide
• 英文别名: 1-(m-chlorobenzoyl)-3-thiosemicarbazide；N2-(3-chlorobenzoyl)thiosemicarbazide；m-chlorobenzoylthiosemicarbazide；1-(3-chloro-benzoyl)-thiosemicarbazide；1-<3-Chlorbenzoyl>-3-thiosemicarbazid；2-[(3-Chlorophenyl)carbonyl]hydrazinecarbothioamide；[(3-chlorobenzoyl)amino]thiourea
• CAS: 881-74-3
• 化学式: C₈H₈ClN₃OS
• 分子量: 229.69
• InChiKey: DRCDKPCXWJSZKU-UHFFFAOYSA-N

物化性质

• 溶解度：
  27.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 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：

  2-(3-chlorobenzoyl)hydrazinecarbothioamide 在 过氧化苯甲酰 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 2-(m-chlorophenyl)-6-(p-chlorophenyl)imidazo<2,1-b>-1,3,4-thiadiazole
  参考文献：
  名称：

  Mohan, Jag; Anjaneyulu, G. S. R.; Kiran, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 500 - 502

  摘要：

  DOI：
• 作为产物：
  描述：

  间氯苯甲酸甲酯 在 盐酸 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-(3-chlorobenzoyl)hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis of New S-alkylated-3-mercapto-1,2,4-triazole Derivatives Bearing Cyclic Amine Moiety as Potent Anticancer Agents

  摘要：

  一系列3-[3-[4-(取代)-1-环胺]丙基]硫-5-取代[1,2,4]三唑(8a-j)，从相应的羧酸出发，以良好的收率被合成。这些衍生物对五种不同的人类癌细胞系进行了细胞毒性研究。三种化合物显示出良好的抗癌活性。三唑衍生物，8i和8j，对U937和HL-60细胞尤其有效。化合物的细胞毒性效力在不同细胞系之间有所变化，这表明这些化合物的结构特性可能是其生物活性的可能决定因素。

  DOI：

  10.2174/157018012799129882

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。
• Synthesis of New S-alkylated-3-mercapto-1,2,4-triazole Derivatives Bearing Cyclic Amine Moiety as Potent Anticancer Agents
  作者：M. S.R. Murty、Kesur R. Ram、Rayudu Venkateswara Rao、J. S. Yadav、Janapala Venkateswara Rao、L. R. Velatooru

  DOI：10.2174/157018012799129882

  日期：2012.3.1

  A series of 3-[3-[4-(Substituted)-1-cyclicamine]propyl]thio-5-substituted[1,2,4]triazoles (8a-j) were synthesized with good yields starting from corresponding carboxylic acids. The cytotoxicity studies of these derivatives were studied against five different human cancer cell lines. Three compounds had shown good anticancer activity. The triazole derivatives, 8i and 8j were most potent particularly against U937 and HL-60 cells. The cytotoxic potency of the compounds varied between the cell lines suggesting that a structural property of these compounds as possible determinants of their biological activity.

  一系列3-[3-[4-(取代)-1-环胺]丙基]硫-5-取代[1,2,4]三唑(8a-j)，从相应的羧酸出发，以良好的收率被合成。这些衍生物对五种不同的人类癌细胞系进行了细胞毒性研究。三种化合物显示出良好的抗癌活性。三唑衍生物，8i和8j，对U937和HL-60细胞尤其有效。化合物的细胞毒性效力在不同细胞系之间有所变化，这表明这些化合物的结构特性可能是其生物活性的可能决定因素。
• Identification of 1,2,4-triazoles as new thymidine phosphorylase inhibitors: Future anti-tumor drugs
  作者：Sohail Anjum Shahzad、Muhammad Yar、Zulfiqar Ali Khan、Lubna Shahzadi、Syed Ali Raza Naqvi、Adeem Mahmood、Sami Ullah、Ahson Jabbar Shaikh、Tauqir Ali Sherazi、Adebayo Tajudeen Bale、Jędrzej Kukułowicz、Marek Bajda

  DOI：10.1016/j.bioorg.2019.01.005

  日期：2019.4

  Thymidine phosphorylase (TP) is over expressed in several solid tumors and its inhibition can offer unique target suitable for drug discovery in cancer. A series of 1,2,4-triazoles 3a-3l has been synthesized in good yields and subsequently inhibitory potential of synthesized triazoles 3a-3l against thymidine phosphorylase enzyme was evaluated. Out of these twelve analogs five analogues 3b, 3c, 3f,

  胸苷磷酸化酶（TP）在几种实体瘤中过度表达，其抑制作用可提供适用于癌症药物发现的独特靶标。已经以高产率合成了一系列1,2,4-三唑3a-3l，随后评估了合成的三唑3a-3l对胸苷磷酸化酶的抑制潜力。在这十二个类似物中，五个类似物3b，3c，3f，3l和3l对胸苷磷酸化酶表现出良好的抑制潜力。以IC50值表示的抑制潜力在61.98±0.43至273.43±0.96μM范围内，将7-地塞黄嘌呤用作标准抑制剂，IC50 = 38.68±4.42μM。这些结果的鼓励下，合成了更多的类似物1,2,4-三唑-3-巯基羧酸4a-4g，并评估了它们对胸苷磷酸化酶的抑制潜力。在该系列中，六个类似物4b-4g在43.86±1.11-163.43±2.03μM范围内表现出良好的抑制潜力。1,2,4-三唑酸4d的血管生成反应使用鸡绒毛膜尿囊膜（CAM）分析进行了评估。根据这些发现，讨论了选定的三唑的结构活性关系和
• A Convenient Synthesis of 5-substituted 2-amino-1,3,4-oxadiazoles from Corresponding Acylthiosemicarbazides Using iodine and Oxone®
  作者：Vikas N. Shinde、Bheemarao G. Ugarkar、Sandeep R. Ghorpade

  DOI：10.3184/174751912x13551638283701

  日期：2013.1

  A convenient methodology has been developed for the synthesis of substituted 2-amino-1,3,4-oxadiazoles from corresponding acylthiosemicarbazides using catalytic amount of iodine/KI in the presence of Oxone® as a bulk oxidant. This offers the advantage of short reaction times and substrate variability which is suitable for the rapid production of analogues required for lead optimisation programmes. The method could also be useful for large-scale synthesis because of the mild reaction conditions and the use commercially inexpensive and safe reagents.

  我们开发了一种简便的方法，在 Oxone® 作为大量氧化剂存在的情况下，使用催化量的碘/KI，从相应的酰基硫代氨基甲酰肼合成取代的 2-氨基-1,3,4-恶二唑。这种方法具有反应时间短、底物可变性强的优点，适合快速生产先导优化计划所需的类似物。由于反应条件温和，且使用的试剂在商业上既便宜又安全，因此该方法也可用于大规模合成。
• Synthesis and Antibacterial Activities of New S-glycosides Bearing 1,2,4-Triazole
  作者：Shu-Jun Chao、Ming-Jiang Geng、Ying-Ling Wang

  DOI：10.5012/jkcs.2010.54.6.731

  日期：2010.12.20

  Several new 5-aryl-3-(β-D-glucopyranosylthio)-1,2,4-triazoles have been synthesized. The structures of these new compounds were confirmed by 1 H NMR, 13 C NMR and elemental analyses.The antibacterial activities of the compounds were also evaluated.

  已经合成了几种新的5-芳基-3-（β-D-吡喃葡萄糖基硫基）-1，2，4-三唑。通过1 H NMR，13 C NMR和元素分析证实了这些新化合物的结构。还评估了这些化合物的抗菌活性。