N-acetyl-N’-(4-methoxyphenyl)thiourea | 21258-19-5

• 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: N-acetyl-N’-(4-methoxyphenyl)thiourea
• 英文别名: N-(4-methoxyphenyl)-N'-acetylthiourea；1-acetyl-3-(4-methoxyphenyl)thiourea；N-(4-anisyl)-N'-acetylthiourea；N-(4-Methoxy-phenyl)-N'-acetyl-thioharnstoff；N-((4-Methoxyphenyl)carbamothioyl)acetamide；N-[(4-methoxyphenyl)carbamothioyl]acetamide
• CAS: 21258-19-5
• 化学式: C₁₀H₁₂N₂O₂S
• mdl: MFCD02969020
• 分子量: 224.283
• InChiKey: FFEKDJKWVBTBPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  199 °C
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-acetyl-N’-(4-methoxyphenyl)thiourea 在 copper(l) iodide 、 caesium carbonate 、 L-脯氨酸 、 palladium dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以98%的产率得到N-(6-甲氧基-2-苯并噻唑基)-乙酰胺
  参考文献：
  名称：

  Pd催化的C（sp 2）H官能团的合成N-苯并噻唑-2-基酰胺

  摘要：

  摘要在钯催化剂存在下，通过C（sp2）H官能化/ CS键的形成，由1-酰基-3-（苯基）硫脲催化合成了N-苯并噻唑-2-基酰胺。这种合成方法可以高收率生产具有良好官能团耐受性的各种N-苯并噻唑-2-基-酰胺。

  DOI：

  10.1016/j.cclet.2015.08.001
• 作为产物：
  描述：

  甲氧苯胺 、 异硫氰酸乙酰酯 以 丙酮 为溶剂， 生成 N-acetyl-N’-(4-methoxyphenyl)thiourea
  参考文献：
  名称：

  新型1-乙酰基-3-芳基硫脲衍生物作为有效胆碱酯酶抑制剂的合成，计算研究和生物学评估

  摘要：

  通过使乙酰基异硫氰酸酯与各种适当取代的芳族苯胺反应，合成了一系列新的1-乙酰基-3-芳基硫脲（3f1 – 15）。通过使相应的酰氯与硫氰酸钾反应新鲜制备乙酰基异硫氰酸酯。所有化合物的结构确认均通过光谱技术进行，对于3a，则通过X射线衍射研究进行确认。对新制备的化合物进行了计算研究，并评估了其对胆碱酯酶（乙酰胆碱酯酶和丁酰胆碱酯酶）的抑制作用。除3f9和3f15外，所有衍生物均被发现是乙酰胆碱酯酶的选择性抑制剂。复合发现3f2（IC 50  ±SEM = 1.99±0.11 µM）是最有效的乙酰胆碱酯酶抑制剂，其抑制潜能是参考抑制剂新斯的明（IC 50  ±SEM = 22.2±3.2 µM）约11倍。已发现化合物3f9是最有效的丁酰胆碱酯酶抑制剂（IC 50  ±SEM = 1.33±0.11 µM），对丁酰胆碱酯酶的选择性是乙酰胆碱酯酶的约四倍。进行了分子对接研究以确定这些有效抑制剂与胆

  DOI：

  10.1007/s00044-017-1829-6

文献信息

• Synthesis, inhibition studies against AChE and BChE, drug-like profiling, kinetic analysis and molecular docking studies of N-(4-phenyl-3-aroyl-2(3H)-ylidene) substituted acetamides
  作者：Fayaz Ali Larik、Aamer Saeed、Muhammad Faisal、Salma Hamdani、Farukh Jabeen、Pervaiz Ali Channar、Amara Mumtaz、Imtiaz Khan、Mahar Ali Kazi、Qamar Abbas、Mubashir Hassan、Jan Korabecny、Sung-Yum Seo

  DOI：10.1016/j.molstruc.2019.127459

  日期：2020.3

  by 1H NMR and 13C NMR spectroscopy and were screened against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzyme inhibition activities. Molecular docking studies, drug-like profiling and kinetic analysis were performed to further investigate the inhibition mechanism of the compounds. This study provided useful insights into the design and development of novel dual inhibitors, in addition

  摘要 通过相应的乙酰硫脲与苯甲酰溴的碱催化环化反应制备了卤代和非卤代N-(4-苯基-3-芳酰基-2(3H)-亚基)取代的乙酰胺。合成的化合物通过 1H NMR 和 13C NMR 光谱进行结构表征，并针对乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BChE) 酶抑制活性进行筛选。进行了分子对接研究、类药物分析和动力学分析，以进一步研究化合物的抑制机制。除了了解此类药物与靶标相互作用并发挥其生化作用的机制外，这项研究还为新型双重抑制剂的设计和开发提供了有用的见解。与分别对 AChE 和 BChE 具有亚微摩尔和微摩尔 IC50 值的标准品相比，所有化合物都显示出优异的抑制特性。对接模拟表明，化合物 6g 在 AChE 和 BChE 的活性位点峡谷内表现出强结合。获得了极好的一致性，因为最佳对接姿势显示出重要的结合特征，主要基于化合物的芳族部分和氧原子的相互作用。阳离子-π/π-π 相互作用
• Formal [3+2] Annulation Involving Allylic Bromides and Thioureas. Synthesis of 2-Iminothiazolidines through a Base-Catalyzed Intramolecular<i>anti</i>-Michael Addition
  作者：Misael Ferreira、Marcus M. Sá

  DOI：10.1002/adsc.201401026

  日期：2015.3.9

  A simple and efficient protocol was developed for the synthesis of 2‐iminothiazolidines through a base‐mediated [3+2] annulation involving substituted thioureas and allylic bromides bearing electron‐withdrawing groups. This domino process consists of nucleophilic displacement, followed by intramolecular anti‐Michael addition of the preformed allylic isothiourea under mild conditions to give the thiazolidine

  开发了一种简单有效的方案，用于通过碱介导的[3 + 2]环合反应合成2-亚氨基并噻唑烷，该环合反应涉及取代的硫脲和带有吸电子基团的烯丙基溴。该多米诺过程包括亲核取代，然后在温和条件下将预先形成的烯丙基异硫脲进行分子内抗迈克尔加成，得到噻唑烷核心。
• The anti-inflammatory activity of 2-iminothiazolidines: evidence for macrophage repolarization
  作者：Eduarda Talita Bramorski Mohr、Tainá Larissa Lubschinski、Julia Salvan da Rosa、Guilherme Nicácio Vieira、Mariano Felisberto、Robson Ruan Romualdo、Misael Ferreira、Marcus Mandolesi Sá、Eduardo Monguilhott Dalmarco

  DOI：10.1007/s10787-022-01084-x

  日期：2022.12

  Nowadays, macrophages are recognized as key cells involved in chronic inflammatory conditions, and play central roles in all inflammatory diseases and cancer. Due to their extensive involvement in the pathogenesis of inflammatory diseases, they are now considered a relevant therapeutic target in the development of new therapeutic strategies. 2-Iminothiazolidines are associated with important anti-inflammatory activity and represent a rich source for the development of new drugs and treatments. Our research focuses on evaluating the anti-inflammatory capacity of these compounds and their relationship with M1/M2 macrophage polarization. The results demonstrate that 2-iminothiazolidines have the capacity to decrease the levels of anti-inflammatory biomarkers, such as cytokines (IL-1β, TNF-α, and IL-6), nitric oxide synthase (with impact on NOx production), and COX-2, following a significant decline in NF-kB activation. We also observed an increase in levels of anti-inflammatory cytokines (IL-4 and IL-13) in the in vitro model of RAW 264.7 macrophages induced by LPS. Moreover, this is the first report, suggesting that the anti-inflammatory activity of 2-iminothiazolidines is associated with the ability to enhance phagocytosis, increase Arginase-1 and CD206 expression, and increase the secretion of IL-10. Furthermore, an in vivo study using the acute lung injury model induced by LPS proved the anti-inflammatory activity of a selected 2-iminothiazolidine, named methyl 2-(benzoylimino)-3-methyl-4-(4-nitrobenzyl)-1,3-thiazolidine-4-carboxylate. All these results, taken together, lead us to hypothesize that the mechanism of anti-inflammatory effect observed with this compound is closely related to the ability of this compound to produce macrophage repolarization, from the M1 to the M2 phenotype.

  如今，巨噬细胞被认为是慢性炎症的关键细胞，在所有炎症性疾病和癌症中发挥着核心作用。由于它们广泛参与炎症性疾病的发病机制，因此现在被认为是开发新疗法的重要治疗靶点。2-亚氨基噻唑啉具有重要的抗炎活性，是开发新药和治疗方法的重要来源。我们的研究重点是评估这些化合物的抗炎能力及其与M1/M2巨噬细胞极化的关系。结果表明，2-亚氨基噻唑啉能够降低抗炎生物标志物的水平，例如细胞因子（IL-1β、TNF-α和IL-6）、一氧化氮合酶（影响NOx的产生）和COX-2，同时显著降低NF-kB的激活。我们还观察到，在LPS诱导的RAW 264.7巨噬细胞体外模型中，抗炎细胞因子（IL-4和IL-13）的水平增加。此外，这是第一份报告，表明2-亚氨基噻唑啉的抗炎活性与增强吞噬作用、增加Arginase-1和CD206的表达以及增加IL-10的分泌有关。此外，使用LPS诱导的急性肺损伤模型进行的体内研究证实了所选2-亚氨基噻唑啉（甲基2-(苯甲酰亚氨基)-3-甲基-4-(4-硝基��
• Pandeya; Yadav, Meena K.; Mishra, Vaishali, Asian Journal of Chemistry, 2011, vol. 23, # 7, p. 3003 - 3007
  作者：Pandeya、Yadav, Meena K.、Mishra, Vaishali、Srivastava, Shobhit、Singh, Bal Krishna

  DOI：——

  日期：——
• Iron Trichloride and Air Mediated Guanylation of Acylthioureas. An Ecological Route to Acylguanidines: Scope and Mechanistic Insights
  作者：Simon Pape、Pablo Wessig、Heiko Brunner

  DOI：10.1021/acs.joc.6b00600

  日期：2016.6.3

  Recently we introduced iron trichloride as an environmentally benign and cost-efficient reagent for the synthesis of N-benzoylguanidines. This highly attractive synthetic approach grants access to a broad spectrum of N-benzoylguanidines under mild conditions in short reaction times. In this work we present an extended scope of Our methodology along with the results obtained from mechanistic studies via in situ IR spectroscopy in combination with LC (liquid chromatography)-MS analyses. On the basis of these new mechanistic insights we were able to optimize the synthetic protocol and to develop an alternative mechanistic proposal. In this context the symbiotic roles of iron trithloride and oxygen in the guanylation process are highlighted.