5-acetyl-2-mercapto-4-methyl-1-phenylimidazole | 340008-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-acetyl-2-mercapto-4-methyl-1-phenylimidazole
• 英文别名: 5-acetyl-2-mercapto-4-methyl-1-phenyl-1H-imidazole；1-(5-methyl-3-phenyl-2-sulfanylidene-1H-imidazol-4-yl)ethanone
• CAS: 340008-24-4
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: UMBOJAOVCXFNFB-UHFFFAOYSA-N

物化性质

• 沸点：
  362.5±52.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-acetyl-2-mercapto-4-methyl-1-phenylimidazole 在 phenyltrimethylammonium tribromide 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-(7-ethoxy-4H-1,4-benzothiazin-3-yl)-5-methyl-3-phenyl-1H-imidazol-3-ium-2-thiol;bromide
  参考文献：
  名称：

  Bhingolikar; Ingle; Dengle, Journal of the Indian Chemical Society, 2002, vol. 79, # 8, p. 703 - 704

  摘要：

  DOI：
• 作为产物：
  描述：

  苯胺 、 硫氰酸铵 、 3-氯-2,4-戊二酮 以 乙醇 为溶剂， 反应 14.0h， 生成 5-acetyl-2-mercapto-4-methyl-1-phenylimidazole
  参考文献：
  名称：

  (E)-2-(1-[2-mercapto-4-methyl-1-phenyl-1H-imidazol-5-yl]ethyleneidene)hydrazinecarbothioamide 衍生物作为抗菌剂的设计、合成和生物学评价

  摘要：

  近年来，开发作为抗菌剂的新药是克服耐药病原体的重要解决方案。咪唑衍生物采用微波辐射法合成，并使用质子核磁共振、质量和傅里叶变换红外光谱等光谱分析技术进行表征。所有类似物的体外抗菌活性和计算机都进行了评估；针对超广谱β-内酰胺酶、耐万古霉素肠球菌和耐甲氧西林金黄色葡萄球菌评估了一些缀合物的最小抑制浓度值来自临床样本的菌株。所有类似物都被用作分子对接和吸附、分布、代谢和排泄的配体，以对抗saDHPS。此外，还检查了化合物的体外抗结核和抗疟疾活性。

  DOI：

  10.1002/jhet.4378

文献信息

• Structure based design, synthesis, and biological evaluation of imidazole derivatives targeting dihydropteroate synthase enzyme
  作者：Drashti G. Daraji、Dhanji P. Rajani、Smita D. Rajani、Edwin A. Pithawala、Sivaraman Jayanthi、Hitesh D. Patel

  DOI：10.1016/j.bmcl.2021.127819

  日期：2021.3

  )-4-methyl-1H-imidazol-2-yl)thio)-N-(4-((benzyl)oxy)phenyl) acetamide derivatives. Antimicrobial activities of all the imidazole derivatives have been examined against Gram-positive and Gram-negative bacteria and results showed that the conjugates have appreciable antibacterial activity. Besides, several analogous were evaluated for their in vitro antiresistant bacterial strains such as Extended-spectrum

  在本研究中，我们设计并合成了 2-((5-acetyl-1-(phenyl)-4-methyl-1 H -imidazol-2-yl)thio) -N- (4-((benzyl)oxy)苯基）乙酰胺衍生物。已经检测了所有咪唑衍生物对革兰氏阳性和革兰氏阴性细菌的抗菌活性，结果表明缀合物具有可观的抗菌活性。此外，还评估了几种类似物的体外抗耐药菌株，如超广谱β-内酰胺酶（ESBL）、耐万古霉素肠球菌（VRE）和耐甲氧西林金黄色葡萄球菌(MRSA)。SAR 显示 12l 化合物具有抗所有细菌菌株以及 ESBL、VRE 和 MRSA 菌株的效力。对含有金黄色葡萄球菌二氢蝶酸合酶 (SADHPS) 蛋白（PDB ID：6CLV）的所有合成化合物进行了 Lipinski 的五法则和 ADME 研究，并发现了缀合物的标准药物相似特性。此外，配体与蛋白质研究的结合模式已经通过分子对接进行了检查，结果非常有希
• Synthesis and biological evaluation of new pyridines containing imidazole moiety as antimicrobial and anticancer agents
  作者：Ikhlass ABBAS、Sobhi GOMHA、Mahmoud ELAASSER、Mohammed BAUOMI

  DOI：10.3906/kim-1410-25

  日期：——

  The synthesis of a novel series of pyridine and bipyridine derivatives is described via one-pot multicomponent reaction of 5-acetylimidazole, malonitrile (or ethylcyanoacetate or diethylmalonate), substituted benzaldehyde (or terephthaldehyde), and ammonium acetate in good yields. The structures of all the new compounds were elucidated on the basis of elemental analysis and spectral data. The antimicrobial activities of the synthesized compounds were screened and the results showed that most of such compounds exhibit considerable activities. Furthermore, some of the newly synthesized compounds were screened for their anticancer activity against human breast cell line (MCF-7) and liver carcinoma cell line (HEPG2) in comparison to doxorubicin. Most of the tested compounds exhibited promising activity.

  描述了一系列新型吡啶和二吡啶衍生物的合成，采用5-乙酰咪唑、马来腈（或乙基氰乙酸酯或二乙基马来酸酯）、取代苯甲醛（或对苯二甲醛）和醋酸铵进行一锅多组分反应，产率良好。所有新化合物的结构通过元素分析和光谱数据进行了阐明。合成化合物的抗菌活性进行了筛选，结果显示大多数化合物表现出相当的活性。此外，一些新合成的化合物还被筛选用于与多柔比星比较的抗癌活性实验，针对人乳腺癌细胞系（MCF-7）和肝癌细胞系（HEPG2）。大多数测试化合物显示出良好的活性。
• Dhawas, Amol K.; Thakare, Suresh S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 5, p. 642 - 646
  作者：Dhawas, Amol K.、Thakare, Suresh S.

  DOI：——

  日期：——
• Ingle; Sawale; Ingle, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 2, p. 124 - 128
  作者：Ingle、Sawale、Ingle、Mane

  DOI：——

  日期：——
• Synthetic Utility of Ethylidenethiosemicarbazide: Synthesis and Anticancer Activity of 1,3-Thiazines and Thiazoles with Imidazole Moiety
  作者：Sayed M. Riyadh、Sobhi M. Gomha、Ikhlass M. Abbas、Mohammed A. Bauomi

  DOI：10.3987/com-12-12625

  日期：——

  Reactions of ethylidenethiosemicarbazide 3 with DMAD 4 or substituted methylenemalononitriles 8 gave thiazolidin-4-one 6 or 1,3-thiazine derivatives (10, 11), respectively. Also, treatment of 3 with hydrazonoyl halides 12a-i, alpha-haloketones 15a-d, and chloroacetic acid 18 afforded the corresponding arylazothiazoles 14a-i, thiazoles 17a-d, and thiazolin-4-one derivative 20, respectively. The structures of the synthesized products were confirmed by IR, H-1 NMR, C-13 NMR and mass spectral techniques. The anticancer activity of the selected products against the colon carcinoma cell line (HCT-116) was determined and the results revealed promising activity of compound 6.