CAS: 870153-29-0; N-((S)-1-(((S)-4-Hydroxy-3-Oxo-1-((S)-2-Oxopyrrolidin-3-yl)Butan-2-yl)Amino)-4-Methyl-1-Oxopentan-2-yl)-4-Methoxy-1H-Indole-2-Carboxamide

该化合物是一个复杂的有机化合物,其特性是其内核结构,以其存在于各种生物活性分子中而闻名.这种化合物具有多种功能组,包括一个碳箱胺和甲基氧组,有助于其潜在的生物活动.[1S(3S)和(3S)的命名表明原子的具体空间安排,能够显著影响化合物与生物目标的相互作用.其分子结构结构结构表明,特别是在药品研制中的潜在应用.阳性激素环和氢氧化物组的存在可能增强其溶性和生物可承受性.这一化合物在使用药物时,其结构,复杂性和生物分子的发现中具有重要性.

英文名称N-((S)-1-(((S)-4-Hydroxy-3-Oxo-1-((S)-2-Oxopyrrolidin-3-yl)Butan-2-yl)Amino)-4-Methyl-1-Oxopentan-2-yl)-4-Methoxy-1H-Indole-2-Carboxamide
中文名称N-((S)-1-(((S)-4-羟基-3-氧代-1-((S)-2-氧代吡咯烷-3-基)丁-2-基)氨基)-4-甲基-1-基-2-基)-4-甲氧基-1H-吲哚-2-甲酰胺
IUPAC名称N-((S)-1-(((S)-4-hydroxy-3-oxo-1-((S)-2-oxopyrrolidin-3-yl)butan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)-4-methoxy-1H-indole-2-carboxamide
CAS编号870153-29-0
MFCD编号:MFCD33029312
FDA UNII编号:B5R5IQ1D64
分子式:C24H32N4O6分子量:472.54
产品CID: 1874624
同类组份化合物CAS870153-29-070153-89-2 (racemic)870153-90-5870153-91-6
产品分类Inhibitors/Agonists → Anti-infection → HIV Protease | Inhibitors/Agonists → Anti-infection → SARS-CoV | Inhibitors/Agonists → Anti-infection → HCV | Inhibitors/Agonists → Anti-infection → HIV

相似结构搜索
InChIKey: QDIMHKWNHMVDJB-WBAXXEDZSA-N
InChI=1S/C24H32N4O6/c1-13(2)9-18(23(32)27-17(20(30)12-29)10-14-7-8-25-22(14)31)28-24(33)19-11-15-16(26-19)5-4-6-21(15)34-3/h4-6,11,13-14,17-18,26,29H,7-10,12H2,1-3H3,(H,2
计算化学: 氢键受体数6.0氢键供体数5.0可旋转键数11.0

物理性质

沸点865.8±65.0 °C(预测)
密度1.264±0.06 g/cm3(预测)
pKa:12.76±0.10(预测)
LogP:1.6
溶解性DMSO: 250 mg/mL (529.07 Mm; Need Ultrasonic)
外观形态白色至类白色固体
储存条件储存在 -20°C
产品应用该化合物用于研究反SAS-CO V-2/COVID-19的PF-008352331. PH-00835231可以抑制细胞感染,也可以抑制动物模型中的感染.

合成工艺路线路线简述

103260-65-7 + 870153-94-9 = 870153-29-0
反应条件:1.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane; 2 H,Rt1.2 Reagents: 4-Methylmorpholine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dimethylformamide; 30 Min,0 °C1.3 Reagents: Sodium Bicarbonate Solvents: Water; 0 °C2.1 Reagents: Phenylglyoxylic Acid,Cesium Fluoride Solvents: Dimethylformamide; 4 H,Rt -> 65 °C; 65 °C -> Rt2.2 Reagents: Potassium Carbonate Solvents: Methanol; 1 H,< 30 °C
标题:Discovery Of Ketone-Based Covalent Inhibitors Of Coronavirus 3Cl Proteases For The Potential Therapeutic Treatment Of Covid-19
作者:Hoffman,Robert L.; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2020 卷标:63(21) 页码:12725-12747]

103260-65-7 + 870153-95-0 = 870153-29-0
反应条件:1.1 Reagents: 4-Methylmorpholine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dimethylformamide; 30 Min,0 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water; 0 °C2.1 Reagents: Phenylglyoxylic Acid,Cesium Fluoride Solvents: Dimethylformamide; 4 H,Rt -> 65 °C; 65 °C -> Rt2.2 Reagents: Potassium Carbonate Solvents: Methanol; 1 H,< 30 °C
标题:Discovery Of Ketone-Based Covalent Inhibitors Of Coronavirus 3Cl Proteases For The Potential Therapeutic Treatment Of Covid-19
作者:Hoffman,Robert L.; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2020 卷标:63(21) 页码:12725-12747]

870153-94-9 = 870153-29-0
反应条件:1.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane; 2 H,Rt2.1 Reagents: 4-Methylmorpholine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dimethylformamide; 30 Min,0 °C2.2 Reagents: Sodium Bicarbonate Solvents: Water; 0 °C3.1 Reagents: Phenylglyoxylic Acid,Cesium Fluoride Solvents: Dimethylformamide; 4 H,65 °C3.2 Catalysts: Potassium Carbonate Solvents: Methanol; 1 H,Rt
标题:The Discovery Of Ketone-Based Covalent Inhibitors Of Coronavirus 3Cl Proteases For The Potential Therapeutic Treatment Of Covid-19
作者:Hoffman,Robert L.; Et Al
参考文献:Chemrxiv 日期:2020 卷标:1 页码:1-106]

13139-15-6 + 870153-93-8 = 870153-29-0
反应条件:1.1 Reagents: 4-Methylmorpholine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dimethylformamide; 1 H,0 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water; 0 °C2.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane; 2 H,Rt3.1 Reagents: 4-Methylmorpholine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dimethylformamide; 30 Min,0 °C3.2 Reagents: Sodium Bicarbonate Solvents: Water; 0 °C4.1 Reagents: Phenylglyoxylic Acid,Cesium Fluoride Solvents: Dimethylformamide; 4 H,65 °C4.2 Catalysts: Potassium Carbonate Solvents: Methanol; 1 H,Rt
标题:The Discovery Of Ketone-Based Covalent Inhibitors Of Coronavirus 3Cl Proteases For The Potential Therapeutic Treatment Of Covid-19
作者:Hoffman,Robert L.; Et Al
参考文献:Chemrxiv 日期:2020 卷标:1 页码:1-106]

870153-28-9 = 870153-29-0
反应条件:1.1 Reagents: Phenylglyoxylic Acid,Cesium Fluoride Solvents: Dimethylformamide; 4 H,Rt -> 65 °C; 65 °C -> Rt1.2 Reagents: Potassium Carbonate Solvents: Methanol; 1 H,< 30 °C
标题:Discovery Of Ketone-Based Covalent Inhibitors Of Coronavirus 3Cl Proteases For The Potential Therapeutic Treatment Of Covid-19
作者:Hoffman,Robert L.; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2020 卷标:63(21) 页码:12725-12747]

870153-28-9 = 870153-29-0
反应条件:1.1 Reagents: Phenylglyoxylic Acid,Cesium Fluoride Solvents: Dimethylformamide; 4 H,65 °C1.2 Catalysts: Potassium Carbonate Solvents: Methanol; 1 H,Rt
标题:The Discovery Of Ketone-Based Covalent Inhibitors Of Coronavirus 3Cl Proteases For The Potential Therapeutic Treatment Of Covid-19
作者:Hoffman,Robert L.; Et Al
参考文献:Chemrxiv 日期:2020 卷标:1 页码:1-106]

870234-61-0 + 103260-65-7 = 870153-29-0
反应条件:1.1 Reagents: 4-Methylmorpholine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dimethylformamide; 30 Min,0 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water; 0 °C2.1 Reagents: Phenylglyoxylic Acid,Cesium Fluoride Solvents: Dimethylformamide; 4 H,65 °C2.2 Catalysts: Potassium Carbonate Solvents: Methanol; 1 H,Rt
标题:The Discovery Of Ketone-Based Covalent Inhibitors Of Coronavirus 3Cl Proteases For The Potential Therapeutic Treatment Of Covid-19
作者:Hoffman,Robert L.; Et Al
参考文献:Chemrxiv 日期:2020 卷标:1 页码:1-106]

13139-15-6 + 870234-60-9 = 870153-29-0
反应条件:1.1 Reagents: 4-Methylmorpholine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dimethylformamide; 0 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water2.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane; 2 H,Rt2.2 Reagents: 4-Methylmorpholine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dimethylformamide; 30 Min,0 °C2.3 Reagents: Sodium Bicarbonate Solvents: Water; 0 °C3.1 Reagents: Phenylglyoxylic Acid,Cesium Fluoride Solvents: Dimethylformamide; 4 H,Rt -> 65 °C; 65 °C -> Rt3.2 Reagents: Potassium Carbonate Solvents: Methanol; 1 H,< 30 °C
标题:Discovery Of Ketone-Based Covalent Inhibitors Of Coronavirus 3Cl Proteases For The Potential Therapeutic Treatment Of Covid-19
作者:Hoffman,Robert L.; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2020 卷标:63(21) 页码:12725-12747]

870153-94-9 = 870153-29-0
反应条件:1.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane; 2 H,Rt2.1 Reagents: 4-Methylmorpholine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dimethylformamide; 30 Min,0 °C2.2 Reagents: Sodium Bicarbonate Solvents: Water; 0 °C3.1 Reagents: Phenylglyoxylic Acid,Cesium Fluoride Solvents: Dimethylformamide; 4 H,Rt -> 65 °C; 65 °C -> Rt3.2 Reagents: Potassium Carbonate Solvents: Methanol; 1 H,< 30 °C
标题:Discovery Of Ketone-Based Covalent Inhibitors Of Coronavirus 3Cl Proteases For The Potential Therapeutic Treatment Of Covid-19
作者:Hoffman,Robert L.; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2020 卷标:63(21) 页码:12725-12747]

= 870153-29-0
反应条件:1.1 Solvents: Diethyl Ether; 0 °C; 0 °C -> Rt; 16 H,Rt2.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane; 0 °C; 1 H,0 °C -> Rt3.1 Reagents: 4-Methylmorpholine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dimethylformamide; 0 °C3.2 Reagents: Sodium Bicarbonate Solvents: Water4.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane; 2 H,Rt4.2 Reagents: 4-Methylmorpholine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dimethylformamide; 30 Min,0 °C4.3 Reagents: Sodium Bicarbonate Solvents: Water; 0 °C5.1 Reagents: Phenylglyoxylic Acid,Cesium Fluoride Solvents: Dimethylformamide; 4 H,Rt -> 65 °C; 65 °C -> Rt5.2 Reagents: Potassium Carbonate Solvents: Methanol; 1 H,< 30 °C
标题:Discovery Of Ketone-Based Covalent Inhibitors Of Coronavirus 3Cl Proteases For The Potential Therapeutic Treatment Of Covid-19
作者:Hoffman,Robert L.; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2020 卷标:63(21) 页码:12725-12747]

741267-75-4 = 870153-29-0
反应条件:1.1 Reagents: Triethylamine,Isobutyl Chloroformate Solvents: Tetrahydrofuran; 1 H,-23 °C1.2 Solvents: Diethyl Ether; 0 °C; 16 H,0 °C -> Rt2.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane; 0 °C; 1 H,0 °C -> Rt3.1 Reagents: 4-Methylmorpholine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dimethylformamide; 0 °C3.2 Reagents: Sodium Bicarbonate Solvents: Water4.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane; 2 H,Rt4.2 Reagents: 4-Methylmorpholine,O-(7-Azabenzotriazol-1-Yl)-N,N,N′,N′-Tetramethyluronium Hexafluorophosphate Solvents: Dimethylformamide; 30 Min,0 °C4.3 Reagents: Sodium Bicarbonate Solvents: Water; 0 °C5.1 Reagents: Phenylglyoxylic Acid,Cesium Fluoride Solvents: Dimethylformamide; 4 H,Rt -> 65 °C; 65 °C -> Rt5.2 Reagents: Potassium Carbonate Solvents: Methanol; 1 H,< 30 °C
标题:Discovery Of Ketone-Based Covalent Inhibitors Of Coronavirus 3Cl Proteases For The Potential Therapeutic Treatment Of Covid-19
作者:Hoffman,Robert L.; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2020 卷标:63(21) 页码:12725-12747

海关参考信息

2905121000-正丙醇
2905130000-正丁醇
2912110000-甲醛
2912120000-乙醛
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专利信息

专利号:WO-2005113580-A1
优先权日:2004-05-21
标题 :Anticoronviral compounds and compositions, their pharmaceutical uses and materials for their synthesis
发明人：HOFFMAN ROBERT LOUIS; KANIA ROBERT STEVEN; NIEMAN JAMES ANDREW; PLANKEN SIMON PAUL; SMITH GEORGE JOSEPH III
权利人:PFIZER; HOFFMAN ROBERT LOUIS; KANIA ROBERT STEVEN; NIEMAN JAMES ANDREW; PLANKEN SIMON PAUL; SMITH GEORGE JOSEPH III
摘要:The invention relates to methods of inhibiting SARS-related coronavirus viral replication activity comprising contacting a SARS-related coronavirus protease with a therapeutically effective amount of a SARS 3C like protease inhibitor of formula (I), and compositions comprising the same.

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主要参考文献

1: Zhou X, Lu X, Lin C, Zou X, Li W, Zeng X, Wang J, Zeng P, Wang W, Zhang J, Jiang H, Li J. Structural basis for the inhibition of coronaviral main proteases by PF-00835231. Acta Biochim Biophys Sin (Shanghai). 2024 Jul 29. doi: 10.3724/abbs.2024122. Epub ahead of print.
490:117030. doi: 10.1016/j.taap.2024.117030. Epub 2024 Jul 7. 10(8):ofad355. doi: 10.1093/ofid/ofad355.
4: Cheruvu N, van Duijn E, Spigt PA, Barbu IM, Toussi SS, Schildknegt K, Jones RM, Obach RS. The Metabolism of Lufotrelvir, a Prodrug Investigated for the Treatment of SARS-COV2 in Humans Following Intravenous Administration. Drug Metab Dispos. 2023 Oct;51(10):1419-1427. doi: 10.1124/dmd.123.001416. Epub 2023 Jul 10. 12(1):2211688. doi: 10.1080/22221751.2023.2211688.

合成参考文献

参考文献:10.1021/acs.jmedchem.0c01063
摘要:Hoffman RL, Kania RS, Brothers MA, Davies JF, Ferre RA, Gajiwala KS, He M, Hogan RJ, Kozminski K, Li LY, Lockner JW, Lou J, Marra MT, Mitchell LJ, Murray BW, Nieman JA, Noell S, Planken SP, Rowe T, Ryan K, Smith GJ, Solowiej JE, Steppan CM, Taggart B. Discovery of Ketone-Based Covalent Inhibitors of Coronavirus 3CL Proteases for the Potential Therapeutic Treatment of COVID-19. J Med Chem. 2020 Nov 12;63(21):12725–47. doi: 10.1021/acs.jmedchem.0c01063.
参考文献:10.1021/acs.jmedchem.0c01140
摘要:Cannalire R, Cerchia C, Beccari AR, Di Leva FS, Summa V. Targeting SARS-CoV-2 Proteases and Polymerase for COVID-19 Treatment: State of the Art and Future Opportunities. J. Med. Chem. 2020 Nov 13;65(4):2716–46. doi: 10.1021/acs.jmedchem.0c01140.