N-allyl-N’-(4-methylbenzoyl)thiourea | 431076-17-4

• 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-allyl-N’-(4-methylbenzoyl)thiourea
• 英文别名: 4-methyl-N-(prop-2-enylcarbamothioyl)benzamide
• CAS: 431076-17-4
• 化学式: C₁₂H₁₄N₂OS
• 分子量: 234.322
• InChiKey: FYGVEXLVGIVQSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-allyl-N’-(4-methylbenzoyl)thiourea 在 sodium tetrahydroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 生成 3-allyl-4-hydroxymethyl-2-(4-methylbenzoylimino)-4-(4-nitrobenzyl)-1,3-thiazolidine
  参考文献：
  名称：

  The anti-inflammatory activity of 2-iminothiazolidines: evidence for macrophage repolarization

  摘要：

  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��

  DOI：

  10.1007/s10787-022-01084-x

文献信息

• A Facile Synthesis of New 4-Amino-2-iminothiazoles from Unsymmetrical Thioureas
  作者：Yellajyosula Lakshmi Narasimha Murthy、Rama Mohana Rao Saviri、Parimi Atchuta Ramaiah、Saranapu Nareesh

  DOI：10.1246/cl.2012.535

  日期：2012.5.5

  An efficient methodology for the synthesis of 4-amino-2-iminothiazole derivatives has been developed. The synthesis involves the cyclization of unsymmetrical 1-aroyl-3-arylthioureas with a variety ...

  已开发出一种合成 4-氨基-2-亚氨基噻唑衍生物的有效方法。该合成涉及不对称的 1-芳酰基-3-芳基硫脲与多种...
• 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��