Thioxalsaeure-nitril-<4-iod-anilid> | 89898-66-8

• 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: Thioxalsaeure-nitril-<4-iod-anilid>
• 英文别名: (4-iodophenyl)carbamothioyl cyanide；p-iodocyanothioformanilide；1-cyano-N-(4-iodophenyl)methanethioamide
• CAS: 89898-66-8
• 化学式: C₈H₅IN₂S
• 分子量: 288.112
• InChiKey: UUILDWMUCJOQCC-UHFFFAOYSA-N

物化性质

• 熔点：
  151 °C
• 沸点：
  326.3±44.0 °C(Predicted)
• 密度：
  1.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 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：
  67.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Thioxalsaeure-nitril-<4-iod-anilid> 在 碘 、 二甲基亚砜 作用下， 反应 19.0h， 以74%的产率得到(4-iodophenyl)carbamoyl cyanide
  参考文献：
  名称：

  碘-DMSO 介导 N-芳基氰基硫代甲酰胺向 N-芳基氰基甲酰胺的转化和 2-氰基苯并噻唑的意外形成

  摘要：

  氰基甲酰胺作为组装关键中间体和生物活性分子的有用成分无处不在。开发一种有效且简单的方法来处理这个主题是一个挑战。在此，我们证明了 I 2 -DMSO 氧化系统在从N制备N-芳基氰基甲酰胺中的有效性。-芳基氰基硫代甲酰胺。该合成方法具有条件温和、底物范围广、反应效率高等特点。此外，这种方法提供了一个很好的入口，可以专门提供 2-氰基苯并噻唑，它们是获得新荧光素类似物的有用底物。所有新产品的结构均通过多核核磁共振光谱和高精度质谱分析进行了阐明。用单晶X射线衍射对(4-溴苯基)氨基甲酰氰、5,6-二甲氧基苯并[ d ]噻唑-2-甲腈、5-(苄氧基)苯并[ d ]恶唑进行晶体结构测定-2-甲腈，4,7-二甲氧基苯并[ d]噻唑-2-甲腈和(5-碘-2,4-二甲氧基苯基)氨基甲酰氰，一种具有机理意义的关键中间体。

  DOI：

  10.1039/d2ra00049k

文献信息

• Synthesis, characterization, and derivatization of some novel types of fluorinated mono- and bis-imidazolidineiminothiones with antitumor, antiviral, antibacterial, and antifungal activities
  作者：Marwa A.M.Sh. El-Sharief、Ziad Moussa、Ahmed M.Sh. El-Sharief

  DOI：10.1016/j.jfluchem.2011.06.015

  日期：2011.9

  Aspergillus niger, and Aspergillus flavus). Whereas compound 6a exhibited the highest antibacterial activity against Gram positive and Gram negative bacteria, 13b displayed the strongest antifungal activity against all fungal strains, reaching as high as 30 mm. Finally, 15a,b,d were subjected to in vitro testing of antiviral activity against hepatitis A virus (HAV), human herpes simplex virus 1 (HSV1), and Coxsackie

  一系列38种新型咪唑烷亚氨基硫酮（6a – g，10a – h，13a，b，15a – d和16a），5-硫代氧杂咪唑烷-2,4-二酮（7a – d，11a – e，14a，b，和16B），和双- imidazolidineiminothiones（17 - 20），在各种氟化芳族取代基ñ - （1）和ñ-（3）的制备产率为75-85％。由氟化的N-芳基氰基硫代甲酰苯胺和取代的芳族异氰酸酯，以及氟化的芳族异氰酸酯与氟化的和非氟化的芳族N-芳基氰基硫代甲酰苯胺反应，合成咪唑烷亚氨基硫酮。所选产物的随后水解产生了相应的5-硫代氧杂咪唑烷-2，4-二酮。初步筛选了几种针对Ehrlich腹水癌细胞（EAC）的化合物，结果表明6f和16a的活性最高（分别为90％和80％抑制）。进一步评估针对其他肿瘤细胞系的细胞毒性，得出IC 50值为0.67至3.83μg/ mL，其中化合物15a和16a对所有细胞
• Synthesis, characterization and derivatization of some novel types of mono- and bis-imidazolidineiminothiones and imidazolidineiminodithiones with antitumor, antiviral, antibacterial and antifungal activities – part I
  作者：Ahmed M. Sh. El-Sharief、Ziad Moussa

  DOI：10.1016/j.ejmech.2009.07.019

  日期：2009.11

  Halogenated and alkylated N-arylcyanothioformanilides were reacted with the nucleophilic reagents triethylamine, hydrazine and diphenyldiazomethane to produce N-arylcyanothioformanilide ammonium salts, a thiosemicarbazide and a 2-(arylamino)-3,3-diphenylacrylonitrile, respectively. They also underwent several types of electrophilic reactions with aryl-, arylbisisocyanates and arylisothiocyanates to

  使卤代和烷基化的N-芳基氰基硫代甲酰苯胺与亲核试剂三乙胺，肼和二苯基重氮甲烷反应，分别生成N-芳基氰基硫代甲酰苯胺铵盐，硫代氨基脲和2-（芳基氨基）-3,3-二苯基丙烯腈。他们还与芳基-，芳基双异氰酸酯和芳基异硫氰酸酯进行了几种亲电反应，以生成单-和双-咪唑烷亚氨基硫酮和咪唑烷亚氨基二硫酮。硫化氢，取代邻位处理咪唑烷亚氨基硫酮-苯二胺和硫代碳酰肼得到相应的硫代乙内酰脲，喹喔啉和咪唑三嗪衍生物。对几种合成产物进行了针对抗肿瘤，抗病毒，抗微生物和抗真菌菌株的体外生物学评估。大多数测试的化合物显示出显着的活性。
• Synthesis and Evaluation of 5-imino-4-thioxoimidazolidin-2-one Derivatives as Antibacterial and Antifungal Agents
  作者：Samir Y. Abbas、Marwa A.M. Sh. El-Sharief、Reem A.K. Al-Harbi、Eman W. El-Gammal、Ahmed M.S. El-Sharief

  DOI：10.2174/1573406416666191227112648

  日期：2021.7

  purity. The activities of imidazolidines as antibacterial and antifungal agents were studied. Some of the imidazolidine derivatives displayed significant antibacterial and antifungal activities. Conclusion: 5-Imino-4-thioxoimidazolidin-2-ones were obtained in 77-90% yields with excellent purity. The antibacterial and antifungal activities suggest that some of the imidazole derivatives possess significant

  目的：合成一些在 N-(1) 和 N-(3) 处具有不同卤化和烷基化芳族取代基的新型 5-imino-4-thioxoimidazolidin-2-one 衍生物并评估其预期的抗菌和抗真菌活性是很有趣的。 方法：通过不同卤化和烷基化的N-芳基氰基硫代甲酰胺与卤化和烷基化的异氰酸芳基酯反应，合成了新的5-imino-4-thioxoimidazolidin-2-one衍生物。 结果： 5-Imino-4-thioxoimidazolidin-2-ones 以高收率和优异的纯度获得。研究了咪唑烷作为抗菌剂和抗真菌剂的活性。一些咪唑烷衍生物显示出显着的抗菌和抗真菌活性。 结论： 5-Imino-4-thioxoimidazolidin-2-ones 以 77-90% 的产率获得，纯度极佳。抗菌和抗真菌活性表明，某些咪唑衍生物对枯草芽孢杆菌、肺炎克雷伯菌和白色念珠菌具有显着的抗菌活性，对金黄色葡萄球菌具有中等活性。
• Synthesis and Biological Evaluation of Bis-Imidazolidineiminothiones: A Comparative Study
  作者：Marwa A. M. Sh. El-Sharief、Ziad Moussa、Ahmed M. Sh. El-Sharief

  DOI：10.1002/ardp.201300097

  日期：2013.7

  the matching effect of properly positioned substituents on N‐(1) and the appropriate N‐(3)‐N‐(3) linker. Likewise, all heterocyles were tested against microbial organisms (Pseudomonas aeruginosa, Sarcina lutea, Bacillus pumilus, and Micrococcus luteus) and fungal strains (Candida albicans and Penicilium chrysogenum). Most compounds showed significant antibacterial and antifungal activities, reaching in

  一系列 15 种新型对称和非对称双咪唑烷亚胺硫酮（6a-g、7a-e、8a、b 和 9）在 N-(1) 处具有各种取代基（对甲苯基、对甲氧基苯基、对乙氧基苯基） 、对氯苯基、对溴苯基、对碘苯基和 3,5-二氯苯基）以及 N-(3) 原子之间的不同连接体 [4,4'-氧双 (4,1-亚苯基), 2,2' -二甲氧基联苯和（1,3,3-三甲基环己基）甲基）]由取代的 N-芳基氰基硫代甲酰苯胺和各种双异氰酸酯以 65-75% 的产率制备。筛选对 HEPG2、HEP2、MCF7 和 HCT116 肿瘤细胞系的细胞毒性的 IC50 值范围为 6.3 至 84.6 µM，其中化合物 6b、d、e、g 和 7a 对至少一种细胞系具有显着活性，强调了匹配适当位置的取代基对 N-(1) 和适当的 N-(3)-N-(3) 接头的影响。同样地，所有杂环均针对微生物（铜绿假单胞菌、黄八叠球菌、短小芽孢杆菌和藤黄微
• Synthesis and characterization of new types of halogenated and alkylated imidazolidineiminothiones and a comparative study of their antitumor, antibacterial, and antifungal activities
  作者：Ziad Moussa、Marwa A.M.Sh. El-Sharief、Ahmed M.Sh. El-Sharief

  DOI：10.1016/j.ejmech.2011.03.009

  日期：2011.6

  A series of twenty novel imidazolidineiminothiones (4-8) with various substituents at N-(1) and N-(3) were synthesized by various permutations of halogenated and alkylated N-arylcyanothioformanilides (1) with aromatic isocyanates (2). Preliminary screening of all compounds against Ehrlich ascites carcinoma cells (EAC) indicated that 5d, and 8a c were the most active compounds as they displayed the highest percent inhibition of cell viability (80%, 70%, 80%, and 70%, respectively). Thus, they were further subjected to in vitro biological evaluation against other tumor cancer cell lines (HEPG2, HEP2, MCF7, HELA, and HCT116). The IC50 values ranged from 3.12 to 12.1 mu g/mL where compound 8b (N-(1): 2,4-dimethoxyphenyl: N-(3): 4-methoxyphenyl) was markedly active against all cell lines and consistently produced low IC50 values in all cases (ranging from 3.12 to 4.34 mu g/mL). This underscored the synergistic effect of the suitably positioned methoxy groups on the aromatic rings of N-(1) and N-(3) of the imidazolidineiminothiones. All compounds were also tested against microbial organisms (Escherichia coli, Sarcina lutea, Bacillus subtilis, and Staphylococcus aureus), and fungal strains (Candida albicans and Aspergillus flavus). Most tested compounds showed significant activities which could be optimized with the appropriate selection of matching aromatic substituents on N-(1) and N-(3). (C) 2011 Elsevier Masson SAS. All rights reserved.