877636-42-5

基本信息
CS-2842
ML 221
ML-221
ML221 >=98% (HPLC)
ML221
ML 221
ML-221
5-[(4-Nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-4H-pyran-4-one
4H-Pyran-4-one, 5-[(4-nitrobenzoyl)oxy]-2-[(2-pyrimidinylthio)methyl]-
物理化学性质
制备方法
![5-hydroxy-2-[(pyrimidin-2-ylsulfanyl)methyl]-4H-pyran-4-one](/CAS/20180529/GIF/941868-82-2.gif)
941868-82-2

122-04-3

877636-42-5
以5-羟基-2-(羟甲基)-4H-吡喃-4-酮(曲酸)(0.55g,3.87mmol)为起始原料,将其溶于亚硫酰氯(5mL,68.5mmol)中,于室温下搅拌3小时。反应完成后,通过减压蒸馏除去过量的亚硫酰氯,得到2-(氯甲基)-5-羟基-4H-吡喃-4-酮(0.61g,收率98%),产物为灰白色固体。1H NMR(500MHz,DMSO-d6)δ:8.13(s,1H),6.57(s,1H),4.66(s,2H)。 步骤2:将嘧啶-2-硫醇(161mg,1.433mmol)溶于2mL甲醇中,加入甲醇钠溶液(310mg,1.433mmol),搅拌至完全溶解。随后加入乙腈(10mL)和2-(氯甲基)-5-羟基-4H-吡喃-4-酮(230mg,1.433mmol),室温下搅拌3小时。通过LC/MS分析确认反应完成。减压除去溶剂,得到粗产物5-羟基-2-((嘧啶-2-基硫代)甲基)-4H-吡喃-4-酮(406mg,收率96%)及等摩尔量的氯化钠,产物为黄色固体,无需进一步纯化即可用于下一步反应。1H NMR(500MHz,CDCl3)δ:8.52(d,2H,J=4.9Hz),7.80(s,1H),7.02(t,1H,J=4.8Hz),6.63(s,1H),4.23(s,2H)。 步骤3:将5-羟基-2-((嘧啶-2-基硫代)甲基)-4H-吡喃-4-酮(200mg,0.847mmol)、碳酸铯(276mg,0.847mmol)和4-硝基苯甲酰氯(220mg,1.185mmol)溶于乙腈(8mL)中,室温下搅拌过夜。反应完成后,减压除去溶剂,得到浅黄色固体。将该固体用约20mL 1:1的乙酸乙酯和水进行分配。目标产物4-氧代-6-((嘧啶-2-基硫基)甲基)-4H-吡喃-3-基4-硝基苯甲酸酯在两相中均不溶,通过过滤收集。将固体真空干燥,得到目标产物(202mg,收率62%),为褐色固体。1H NMR(500MHz,DMSO-d6)δ:8.69(d,2H,J=4.8Hz),8.68(s,1H),8.40(d,2H,J=8.8Hz),8.29(d,2H,J=8.8Hz),7.29(t,1H,J=4.9Hz),6.65(s,1H),4.45(s,2H)。13C NMR(125MHz,DMSO-d6)δ:171.2,168.8,165.9,161.7,158.1,150.8,149.9,140.3,133.0,131.4,124.2,118.0,114.6,31.2。
参考文献:
[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6656 - 6660,5
[2] Patent: US2014/5181, 2014, A1. Location in patent: Paragraph 0155
报价日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
2025/05/22 | HY-103254 | ML221 ML221 | 877636-42-5 | 5mg | 580元 |
2025/05/22 | HY-103254 | ML221 ML221 | 877636-42-5 | 10mM * 1mLin DMSO | 638元 |
2025/05/22 | HY-103254 | ML221 ML221 | 877636-42-5 | 10mg | 870元 |
常见问题列表
IC50: 1.75 μM (APJ, cell-based)
ML221 is a potent apelin/APJ functional antagonist, inhibiting apelin-13-mediated activation of APJ, with IC 50 s of 0.70 μM in the cAMP assay, and 1.75 μM in the β-arrestin assay, and EC 80 of 10 nM in both assays. ML221 is >37-fold selective over the closely related angiotensin II type 1 (AT1) receptor (IC 50 , >79 μM) in cells. ML221 displays limited cross reactivity against a range of GPCRs except the κ-opioid and benzodiazepinone receptors (<50/<70%I at 10 μM).