potassium (4-methoxyphenyl)carbamodithioate | 1142816-82-7

• 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 (4-methoxyphenyl)carbamodithioate
• CAS: 1142816-82-7
• 化学式: C₈H₈NOS₂*K
• 分子量: 237.388
• InChiKey: IFEIPRWHUKDNQX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.06
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  21.26
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  potassium (4-methoxyphenyl)carbamodithioate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 4-(4-甲氧基苯基)-3-硫代氨基甲酰肼
  参考文献：
  名称：

  5-Nitrofuran-2-yl derivatives: Synthesis and inhibitory activities against growing and dormant mycobacterium species

  摘要：

  Eighteen 5-nitrofuran-2-yl derivatives were prepared by reacting 5-nitro-2-furfural with various (sub)phenyl/pyridyl thiosemicarbazide using microwave irradiation. The compounds were tested for their in vitro activity against tubercular and various non-tubercular mycobacterium species in log-phase and 6-week-starved cultures. Compound N-(3,5-dibromopyridin-2-yl)-2-((5-nitrofuran-2-yl) methylene) hydrazinecarbothioamide (4r) was found to be the most potent compound (MIC: 0.22 mu M) and was 3 times more active than standard isoniazid (INH) and equally active as rifampicin (RIF) in log-phase culture of Mycobacterium tuberculosis H37Rv. In starved M. tuberculosis H37Rv, 4r inhibited with MIC of 13.9 mu M and was found to be 50 times more active than INH and slightly more active than RIF. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.088
• 作为产物：
  描述：

  二硫化碳 、 甲氧苯胺 在 potassium carbonate 作用下， 以 水 为溶剂， 生成 potassium (4-methoxyphenyl)carbamodithioate
  参考文献：
  名称：

  Na 2 S 2 O 8介导的水中伯胺高效合成异硫氰酸酯

  摘要：

  我们已经开发了两种绿色，实用且有效的方法，包括一锅法，可通过胺和二硫化碳通过胺合成异硫氰酸酯。用过硫酸钠脱硫。使用水作为溶剂。为了使异硫氰酸酯具有良好的化学选择性，必须具备碱性条件。通过两种方法，结构令人满意的直链和支链烷基胺和芳基胺很容易以令人满意的产率转化为异硫氰酸酯。卤素，苄基CH键，甲硫基，硝基，酯，烯基，富电子或不足的（杂）芳基，乙炔基，甚至酚和醇羟基均被很好地耐受。在水中一锅法也可用于从手性胺制备手性异硫氰酸酯，以及用游离氨基修饰生物活性结构。在大规模制备中，开发了独立于柱色谱法的简单实用的纯化方法。

  DOI：

  10.1039/c8gc02261e

文献信息

• An efficient one-pot strategy for the synthesis of 4- methylene-2-thiazolidinethiones in water
  作者：Chang-Long Hou、Mei-Hong Wei、Li-Li Chen、Xiao-Ling Liu、Shou-Ri Sheng

  DOI：10.1080/00397911.2020.1746972

  日期：2020.5.18

  Abstract A simple and efficient, one-pot strategy for the preparation of 4-methylene-2-thiazolidinethiones has been developed. This protocol involved condensation of primary amines with carbon disulfide in water to generate the dithiocarbamate salts in situ, which coupled with 2,3-dibromopropene, followed by intramolecular cyclization to the corresponding heterocycles in moderate to good yields. Graphical

  摘要 开发了一种简单高效的一锅法制备 4-亚甲基-2-噻唑烷硫酮。该方案涉及伯胺与二硫化碳在水中的缩合，以原位生成二硫代氨基甲酸盐，其与 2,3-二溴丙烯结合，然后以中等至良好的产率进行分子内环化成相应的杂环。图形概要
• Structure–activity studies of 4-phenyl-substituted 2′-benzoylpyridine thiosemicarbazones with potent and selective anti-tumour activity
  作者：Adeline Y. Lukmantara、Danuta S. Kalinowski、Naresh Kumar、Des R. Richardson

  DOI：10.1039/c3ob41109e

  日期：——

  2′-Benzoylpyridine thiosemicarbazones (BpT) are effective iron chelators and display potent anti-proliferative activity against tumour cells. In order to gain greater insight into the structure–activity relationships of the BpT chelators, ten new analogues containing phenyl substituents at the N4-position of the BpT structure were synthesised. Importantly, aromatic substitution at the latter position of the BpT scaffold has not been previously explored and these studies represent the first attempt to investigate their structure–activity relationships. These compounds demonstrated significantly enhanced anti-proliferative activity compared to the clinically used iron chelator, desferrioxamine (DFO). Furthermore, the compounds showed appreciable therapeutic indices against cancer cells over normal cells in vitro. Structure–activity analysis revealed that electron-donating substituents such as –CH3 and –OCH3 resulted in greater anti-proliferative activity than electron-withdrawing groups such as –Br and –Cl. These findings help to elucidate the effect of a variety of 4-phenyl substituents on the biological activity of BpT series of chelators and facilitate the future development of thiosemicarbazones with improved anti-tumour activity.

  2⁢'-苯甲酰吡啶缩氨基硫脲（BpT）是一种有效的铁螯合剂，并显示出对肿瘤细胞具有强大的抗增殖活性。为了更深入地了解BpT螯合剂的构效关系，合成了10种新的含有N4-苯基取代基的BpT类似物。重要的是，先前未曾探索过在BpT骨架的该位置进行芳香族取代，这些研究代表了首次尝试调查其构效关系。这些化合物相对于临床使用的铁螯合剂去铁胺（DFO）显示了显著增强的抗增殖活性。此外，这些化合物在体外对癌细胞相对于正常细胞显示出可观的疗效指数。构效关系分析表明，供电子取代基如-CH3和-O 导致的抗增殖活性大于吸电子基团如-Br和-Cl。这些发现有助于阐明各种4-苯基取代基对BpT系列螯合剂生物活性的影响，并有助于未来开发具有改善抗肿瘤活性的缩氨基硫脲。
• Synthesis of new methylthiourea-thiophene, -thiazole, and -pyrazole conjugates: Molecular modelling and docking studies as antimicrobial agents
  作者：Arwa Alharbi、Alaa M. Alqahtani、Mariam Mojally、Ahmad Fawzi Qarah、Ali H. Alessa、Omar M. Alatawi、Roba M.S. Attar、Nashwa M. El-Metwaly

  DOI：10.1016/j.molstruc.2024.137833

  日期：2024.6

  new functionalized thiophene, thiazole, and pyrazole conjugates with methylthiourea was synthesized by cyclization of 1-(4-(2-bromoacetyl)phenyl)-3-methylthiourea () with different thioacetanilides, aryl carbamodithioates, and hydrazonoyl cyanide reagents, respectively. The DFT/B3LYP method showed that the thiazole derivatives had lower HOMO-LUMO energies and ΔE than the thiophenes and the pyrazoles

  通过 1-(4-(2-溴乙酰基)苯基)-3-甲基硫脲 () 分别与不同的硫代乙酰苯胺、芳基二硫代氨基甲酸酯和亚肼基氰试剂环化，合成了一系列新型功能化噻吩、噻唑和吡唑与甲基硫脲的缀合物。DFT/B3LYP方法表明，噻唑衍生物比噻吩和吡唑具有更低的HOMO-LUMO能量和ΔE。对合成的缀合物进行了检查，以研究其作为抗菌剂的潜力。通过严格的生物筛选，发现类似物对革兰氏阳性菌极其有效，而类似物 和 被发现对革兰氏阴性菌有效。抗真菌测试表明，类似物 和 非常有效。细菌蛋白 PDB ID 1AJ6 的分子对接研究表明，类似物 和 结合最强。这表明它们通过氢键和 π 相互作用具有重要的相互作用，使配体-受体复合物保持在一起。有趣的是，类似物不仅表现出最高的结合亲和力，而且与蛋白质靶点具有出色的结构相容性，使其成为进一步研究的先导分子。尽管它们的药理学品质很有前途，但所有类似物都面临着药代动力学挑战，例如
• Enantioselective synthesis of 3,5-disubstituted thiohydantoins and hydantoins
  作者：Yu Chen、Li Su、Xinying Yang、Wenyan Pan、Hao Fang

  DOI：10.1016/j.tet.2015.10.041

  日期：2015.12

  A mild method to convert optically pure amino acid thiourea and urea derivatives to thiohydantoins and hydantoins, respectively, is described. It provides an efficient way to realize enantioselective synthesis of thiohydantoins and hydantoins with good to high isolated yields and enantiomeric purities. We found that the enantiomeric purities were highly dependent on the reaction conditions including bases, solvents, and temperature. (C) 2015 Elsevier Ltd. All rights reserved.