1-acetyl-3-methyl-thiourea | 72886-35-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-acetyl-3-methyl-thiourea
• 英文别名: N-acetyl-N'-methyl-thiourea；N-Acetyl-N'-methyl-thioharnstoff；N-Acetyl-N'-methyl-thioharnstoff；N-Methyl-N'-acetylthiourea；N-(methylcarbamothioyl)acetamide
• CAS: 72886-35-2
• 化学式: C₄H₈N₂OS
• mdl: MFCD01677025
• 分子量: 132.186
• InChiKey: VVXPTPQAHRALFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-acetyl-3-methyl-thiourea 、 2-溴苯乙酮 生成 N-((Z)-3-methyl-4-phenyl-3H-thiazol-2-ylidene)-acetamide
  参考文献：
  名称：

  S---S and S---O interactions in some 4-thiazoline derivatives

  摘要：

  DOI：

  10.1016/s0040-4020(01)93745-7
• 作为产物：
  描述：

  N-甲硫脲 、 乙酰氯 在 甲苯 作用下， 生成 1-acetyl-3-methyl-thiourea
  参考文献：
  名称：

  Moore; Crossley, Journal of the American Chemical Society, 1940, vol. 62, p. 3274

  摘要：

  DOI：

文献信息

• 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��
• Brown,B.T.; Phillips,J.N., Australian Journal of Chemistry, 1970, vol. 23, p. 553 - 559
  作者：Brown,B.T.、Phillips,J.N.

  DOI：——

  日期：——
• Kavalek, Jaromir; Jirman, Josef; Machacek, Vladimir, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 8, p. 1992 - 1998
  作者：Kavalek, Jaromir、Jirman, Josef、Machacek, Vladimir、Sterba, Vojeslav

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  DOI：——

  日期：——
• JIRMAN, JOSEF;KAVALEK, JAROMIR;MACHACEK, VLADIMIR, SB. VED. PR. VSCHT. PARDUBICE, 50A,(1987) 101-110
  作者：JIRMAN, JOSEF、KAVALEK, JAROMIR、MACHACEK, VLADIMIR

  DOI：——

  日期：——