potassium-2-(4-nitrobenzoyl) hydrazinecarbodithioate | 84459-83-6

• 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: potassium-2-(4-nitrobenzoyl) hydrazinecarbodithioate
• 英文别名: potassium;N-[(4-nitrobenzoyl)amino]carbamodithioate
• CAS: 84459-83-6
• 化学式: C₈H₆N₃O₃S₂*K
• 分子量: 295.384
• InChiKey: UVPPLLPWGZITML-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.33
• 重原子数：
  17
• 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：
  120
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  potassium-2-(4-nitrobenzoyl) hydrazinecarbodithioate 以 乙醇 为溶剂， 反应 20.08h， 生成 2-(对硝基苯基)-5-(甲硫基)-1,3,4-恶二唑
  参考文献：
  名称：

  A novel synthesis of peptides based on the photochemistry of 5-azido-1,3,4-oxadiazoles

  摘要：

  DOI：

  10.1021/ja00342a044
• 作为产物：
  描述：

  4-硝基苯甲酰氯 在 一水合肼 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 potassium-2-(4-nitrobenzoyl) hydrazinecarbodithioate
  参考文献：
  名称：

  Synthesis and evaluation of novel azoles as potent antifungal agents

  摘要：

  Using a rational approach to the design of antifungal agents, a series of azole agents with 1,3,4-oxadiazole side chains were designed and synthesized. The results of preliminary in vitro antifungal tests with eight human pathogenic compounds showed that all of the title compounds exhibited excellent activities against all of the tested fungi except Aspergillus fumigatus. Compounds 11e and 11f were found to be the most effective, with a minimum inhibitory concentration of 0.0039 mu g/mL, followed by voriconazole, which has a MIC of 0.0625 mu g/mL. The 1,3,4-oxadiazole side chain is not the major contributor but plays a role in eliciting the observed antifungal activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.037

文献信息

• Synthesis and in-vitro antimicrobial activity of new 1,2,4-triazoles
  作者：A R Bhat、G Varadaraj Bhat、G Gautham Shenoy

  DOI：10.1211/0022357011775307

  日期：2010.2.18

  described the synthesis of new 1,2,4-triazoles and have evaluated their antimicrobial profile. Antitubercular activity was determined in triplicate using the Lowenstein-Jensen medium. A loopful of Mycobacterium tuberculosis suspension was inoculated on the surface of each Lowenstein-Jensen media containing the test compounds (100, 10 or 1 microg mL(-1)). To evaluate in-vitro antibacterial activity, compounds

  我们已经描述了新的1,2,4-三唑的合成，并评估了它们的抗菌特性。使用Lowenstein-Jensen培养基一式三份确定抗结核活性。在含有测试化合物（100、10或1微克mL（-1））的每种Lowenstein-Jensen培养基的表面上接种一圈结核分枝杆菌悬液。为了评估体外抗菌活性，通过圆盘扩散法对枯草芽孢杆菌，大肠杆菌，铜绿假单胞菌，金黄色葡萄球菌和伤寒葡萄球菌评估了化合物（50、5或0.5微克）。为了评估抗真菌活性，使用了Sabourauds葡萄糖琼脂培养基。筛选了某些化合物（5、0.5或0.05微克mL（-1））的抗黑曲霉88和黑曲霉90的活性，而其他化合物则抗T的活性。使用杯板法将红花TR1，红花R.R6，红花R7和薄荷茶T. 我们的结果表明，与在分子4位具有吡嗪部分的三唑相比，在3位具有吡嗪部分的三唑作为抗结核剂和抗真菌剂更具活性。
• Design, synthesis, antibacterial evaluation, and computational studies of hybrid oxothiazolidin–1,2,4‐triazole scaffolds
  作者：Prateek Pathak、Jurica Novak、Parjanya K. Shukla、Maria Grishina、Vladimir Potemkin、Amita Verma

  DOI：10.1002/ardp.202000473

  日期：2021.6

  Furthermore, the compounds were also tested for antibacterial activity against three Gram-positive (Bacillus subtilis [NCIM 2063], Bacillus cereus [NCIM 2156], Staphylococcus aureus [NCIM 2079]) and two Gram-negative (Escherichia coli [NCIM 2065], Proteus vulgaris [NCIM 2027]) bacteria. The derivatives showed a significant-to-moderate antibacterial activity with noticeable antibiofilm efficacy. Quantitative

  由于对目前使用的抗生素产生抗药性，细菌感染对人类健康构成严重威胁。随着新型抗生素的短缺，抗生素耐药性不断增长和广泛存在的问题只会变得更糟，这在治疗严重细菌感染方面造成了大量未满足的医疗需求。因此，在目前的工作中，我们报告了 18 种新型杂化噻唑烷-1,2,4-三唑衍生物作为 DNA 促旋酶抑制剂。衍生物通过多步有机合成法合成，并通过光谱方法（1 H 和13C 核磁共振和质谱）。对衍生物进行了 DNA 促旋酶抑制测试，结果强调合成的衍生物具有抑制 DNA 促旋酶功能的趋势。此外，还测试了这些化合物对三种革兰氏阳性菌（枯草芽孢杆菌[NCIM 2063]、蜡状芽孢杆菌[NCIM 2156]、金黄色葡萄球菌[NCIM 2079]）和两种革兰氏阴性菌（大肠杆菌[NCIM 2065]，变形杆菌[NCIM 2027]) 细菌。这些衍生物显示出显着至中等的抗菌活性，具有显着的抗生物膜功效。还进行了定量构效关系
• Efficient formation of C–S bond using heterocyclic thiones and arynes
  作者：Yu An、Gang Xu、Menglu Cai、Shihui Wang、Xiao zhong Wang、Yingqi Chen、Liyan Dai

  DOI：10.1016/j.tet.2020.131829

  日期：2021.1

  their diverse biological activities and medicinal prospects. Here, a facile method was reported. An arylation of 1,3,4-oxa(thia)diazol-2-thiones reacting with arynes to build C(aryl)-S bonds in the presence of CsF had good yields and excellent selectivity. The reaction was completed in short time without using expensive reagents and catalysts. Present reaction system is an efficient procedure to process

  苯硫基杂环化合物因其多样的生物学活性和医学前景而被广泛使用。在此，报道了一种简便的方法。在CsF存在下，与芳烃反应形成芳基-S键的1,3,4-氧杂噻唑并噻吩-2-硫酮的芳基化反应具有良好的收率和优异的选择性。反应在短时间内完成，无需使用昂贵的试剂和催化剂。目前的反应体系是一种处理苯硫基杂环化合物的有效方法，它揭示了一种可持续的方法，并在未来的有机合成中具有更好的应用前景。
• Synthesis of Triazole Based Novel Ionic Liquids and Salts
  作者：Geetika Bhasin、Richa Srivastava、Ram Singh

  DOI：10.1080/00304948.2017.1343037

  日期：2017.7.4

  on the development of nitrogen-rich heterocyclic energetic salts that should have low vapor pressure, higher density and better thermal stability. To extend the scope of triazolium based ILs, we have synthesized different aryl substituted, 4-amino1-ethyl-3-mercapto-5-phenyl-4H-[1,2,4]triazol-1-ium salts. The synthesis of ionic liquids and salts based on 4-amino-1,2,4-triazole has been done as shown

  离子液体 (IL) 或有机离子盐由有机阳离子和无机或有机阴离子组成。在 100°C 或低于 100°C 熔化的离子盐被称为离子液体。这些分子显示出特殊的特性，例如低蒸气压、宽温度范围内的流动性、高热稳定性、离子导电性、结构可设计性和溶解各种化学物质的能力。It is possible to form any specific IL's composition depending on one's needs, and the desired chemical and physical properties can be realized in a single salt, by proper selection of the component ions. 因此，离子液体的多功能性通过选择合适的离子组合而产生。IL 在化学和材料科学的几乎每个分支中都很普遍，包括催化、有机合成、分离和分析、
• New Heparanase-Inhibiting Triazolo-Thiadiazoles Attenuate Primary Tumor Growth and Metastasis
  作者：Uri Barash、Shobith Rangappa、Chakrabhavi Dhananjaya Mohan、Divakar Vishwanath、Ilanit Boyango、Basappa Basappa、Israel Vlodavsky、Kanchugarakoppal S. Rangappa

  DOI：10.3390/cancers13122959

  日期：——

  Compelling evidence ties heparanase, an endoglycosidase that cleaves heparan sulfate side (HS) chains of proteoglycans, with all steps of tumor development, including tumor initiation, angiogenesis, growth, metastasis, and chemoresistance. Moreover, heparanase levels correlate with shorter postoperative survival of cancer patients, encouraging the development of heparanase inhibitors as anti-cancer drugs. Heparanase-inhibiting heparin/heparan sulfate-mimicking compounds and neutralizing antibodies are highly effective in animal models of cancer progression, yet none of the compounds reached the stage of approval for clinical use. The present study focused on newly synthesized triazolo–thiadiazoles, of which compound 4-iodo-2-(3-(p-tolyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl)phenol (4-MMI) was identified as a potent inhibitor of heparanase enzymatic activity, cell invasion, experimental metastasis, and tumor growth in mouse models. To the best of our knowledge, this is the first report showing a marked decrease in primary tumor growth in mice treated with small molecules that inhibit heparanase enzymatic activity. This result encourages the optimization of 4-MMI for preclinical and clinical studies primarily in cancer but also other indications (i.e., colitis, pancreatitis, diabetic nephropathy, tissue fibrosis) involving heparanase, including viral infection and COVID-19.

  引人注目的证据将肝素酶与肿瘤发展的所有阶段联系起来，包括肿瘤的发生、血管生成、生长、转移和化疗抵抗。此外，肝素酶水平与癌症患者术后生存时间较短相关，鼓励开发肝素酶抑制剂作为抗癌药物。抑制肝素酶的肝素/肝素硫酸模拟化合物和中和抗体在癌症进展的动物模型中非常有效，但是这些化合物中没有一个达到了临床使用批准的阶段。本研究侧重于新合成的三唑-噻二唑类化合物，其中4-碘-2-(3-(对甲苯基)-[1,2,4]三唑[3,4-b][1,3,4]噻二唑-6-基)酚（4-MMI）被确定为对肝素酶酶活性、细胞侵袭、实验性转移和小鼠模型中肿瘤生长的有效抑制剂。据我们所知，这是第一份报告显示用抑制肝素酶酶活性的小分子治疗的小鼠原发肿瘤生长显著减少。这一结果鼓励优化4-MMI，主要用于癌症但也包括其他适应症（如结肠炎、胰腺炎、糖尿病肾病、组织纤维化）的临床前和临床研究，这些适应症涉及肝素酶，包括病毒感染和COVID-19。