2-Amino-4-methoxy-6-methylthio-pyrimidin | 56922-40-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-Amino-4-methoxy-6-methylthio-pyrimidin
• 英文别名: 4-methoxy-6-methylsulfanyl-pyrimidin-2-ylamine；4-Methoxy-6-(methylsulfanyl)pyrimidin-2-amine；4-methoxy-6-methylsulfanylpyrimidin-2-amine
• CAS: 56922-40-8
• 化学式: C₆H₉N₃OS
• 分子量: 171.223
• InChiKey: FLIYNRYUKILIRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  、 2-Amino-4-methoxy-6-methylthio-pyrimidin 在 四丁基溴化铵 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 N-((4-methoxy-6-(methylthio)pyrimidin-2-yl)carbamothioyl)-5-methyl-3-(4-(trifluoromethyl)phenyl)isoxazole-4-carboxamide
  参考文献：
  名称：

  Ultrasound-assisted synthesis and preliminary bioactivity of novel 2H-1,2,4-thiadiazolo[2,3-a]pyrimidine derivatives containing fluorine

  摘要：

  Eight novel 5,7-disubstituted-2-{5-methyl-3-(4-trifluoromethylphenyl)isoxazol-4-ylcarbonylimin} -2H-1,2,4-thiadiazolo[2,3-a]pyrimidines were synthesized by multi-step reactions in yields 68-85%. Reactions were carried out either by ultrasound irradiation or conventional method, and found it was faster and more efficient under ultrasonic irradiation. Preliminary herbicidal activities against Echinochloa crus-galli, Digitaria sanguinalis and Chenopodium serotinum were also evaluated by flat-utensil method, and the results indicated that the target compounds exhibited significant activities, some were even higher than the control herbicide. (C) 2012 Lin Jiang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.03.005

文献信息

• Design, synthesis and biological evaluation of 5‑substituted sulfonylureas as novel antifungal agents targeting acetohydroxyacid synthase
  作者：Fanfei Meng、Pengcheng Mi、Zhenwu Yu、Wei Wei、Li Gao、Jinzhou Ren、Zhengming Li、Huanqin Dai

  DOI：10.1016/j.molstruc.2022.132756

  日期：2022.7

  mortality of fungal infections and the emergence of severe antifungal drug resistance. In this work, 36 target compounds were designed and synthesized and several 5-substituted sulfonylureas possess much better antifungal activities than those of Fluconazole (FCZ) and amphotericin B (AMB). The most potent of these were L10, L23 and L31 with inhibition constants (Ki) determined in the range of 5.6∼9.6 nM

  乙酰羟酸合酶（AHAS；EC2.2.1.6）仅存在于植物和微生物中，当磺酰脲类与AHAS催化亚基活性位点结合时，支链氨基酸（缬氨酸、亮氨酸和异亮氨酸）的生物合成受阻，导致无法进行合成这些蛋白质并最终导致植物和微生物的死亡。因此，AHAS 也是一个很有前途的抗真菌靶点。如今，迫切需要发现新的潜在靶点和化学结构，以防止真菌感染的发病率和死亡率不断增加，以及出现严重的抗真菌药物耐药性。在这项工作中，设计和合成了 36 种目标化合物，其中几种 5-取代磺酰脲类药物具有比氟康唑​​ (FCZ) 和两性霉素 B (AMB) 更好的抗真菌活性。L10、L23和L31对白色念珠菌AHAS 和 MICs 的抑制常数 ( K i ) 在 5.6∼9.6 nM 范围内（MIC 被确定为相对于相应药物抑制真菌生长 > 90% 的药物浓度- 无生长控制）<0.05∼0.78 µg/mL白色念珠菌SC 5314、17#