Cyclopentyl (3-(2-Methoxy-4-((O-Tolylsulfonyl)Carbamoyl)Benzyl)-1-Methyl-1H-Indol-5-Yl)Carbamate (3-(2-甲氧基-4-((邻甲苯基磺酰基)氨基甲酰基)苄基)-1-甲基-1H-吲哚-5-基)氨基甲酸环戊酯
CAS 107753-78-6 MFCD00864775
化学结构图
SMILES: CC1C=CC=CC=1S(=O)(=O)NC(=O)C1C=C(OC)C(CC2=CN(C)C3C=CC(=CC2=3)NC(=O)OC2CCCC2)=CC=1
化学属性
| Mol. Formula | C31H33N3O6S |
|---|---|
| Mol. Weight | 576 |
| Appearance | 从甲醇得白色固体，熔点138～140℃。 |
| Melting Point | 139°C |
别名和识别编码
| Chemical Name | Cyclopentyl (3-(2-Methoxy-4-((O-Tolylsulfonyl)Carbamoyl)Benzyl)-1-Methyl-1H-Indol-5-Yl)Carbamate |
|---|---|
| CAS Number | 107753-78-6 |
| Synonym | 4-[5-(Cyclopentyloxycarbonylamino)-1-methyl-1H-indol-3-ylmethyl]-3-methoxy-N-(2-methylphenylsulfonyl)benzamide Carbamic acid, [3-[[2-methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-1-methyl-1H-indol-5-yl]-, cyclopentyl ester Cyclopentyl 3-[2-methoxy-4-[(o-tolylsulfonyl)carbamoyl]benzyl]-1-met Cyclopentyl N-[3-{[2-methoxy-4-[(2-methylphenyl) sulfonylcarbamoyl]phenyl]methyl}-1-methyl-indol-5-yl]carbam Cyclopentyl [3-[[2-methoxy-4-[(2-methylphenyl)sulfonylcarbamoyl]phenyl]methyl]-1-methyl-indol-5-yl]aminoformate IC-204219 ICI-2204219 N-[3-[[2-Methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-1-methyl-1H-indol-5-yl]carbamic acid cyclopentyl ester Vanticon ZAFIRLUKAST [3-[2-甲氧基-4-[(2-甲苯基)磺酰胺基甲酰基]苄基]-1-甲基-吲哚-5-基]氨基甲酸环戊酯 [3-[[2-Methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-1-methyl-1H-indol-5-y1]carbamic acid eyclopent [3-[[2-Methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-1-methyl-1H-indol-5-yl]carbamic Acid Cyclopentyl Ester [3-[[2-Methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-1-methyl-1H-indol-5-yl]carbamic Acid Cyclopentyl Ester, ICI-2204219, Accolate [3-[[2-Methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-1-methyl-1H-indol-5-yl]carbamic a cyclopentyl [3-[[2-methoxy-4-[(2-methylphenyl)sulfonylcarbamoyl]phenyl]methyl]-1-methyl-indol-5-yl]aminoformate cyclopentyl n-[3-{[2-methoxy-4-[(2-methylphenyl) sulfonylcarbamoyl]phenyl]methyl}-1-methyl-indol-5-yl]carbamate {} {Chemicalbook} 扎鲁司特 扎鲁斯特 |
| MDL Number | MFCD00864775 |
| Chemical Name Translation | (3-(2-甲氧基-4-((邻甲苯基磺酰基)氨基甲酰基)苄基)-1-甲基-1H-吲哚-5-基)氨基甲酸环戊酯 |
| PubChem Substance ID | 253661584 |
| Reaxys-RN | 3641829 |
| Merck Number | 10108 |
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分类
- {Chemicalbook} 药物: 呼吸系统用药: 平喘药
- Approved Therapeutics/Drug Candidates, Arachidonic Acid Cascade, AstraZeneca, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Leukotrienes, Lipids in Cell Signaling, Z
- {SNA} Approved Therapeutics/Drug Candidates, Arachidonic Acid Cascade, AstraZeneca, Bioactive Small Molecule Alphabetical Index, Diversification Ready Pharma-Developed Compounds, Leukotrienes, Lipids in Cell Signaling, Z, 生物活性小分子, 细胞信号转导和神经科学, 细胞生物学
- {SNA} Approved Therapeutics/Drug Candidates, Arachidonic Acid Cascade, AstraZeneca, Bioactive Small Molecules,
产品应用
- A potent, selective and orally active cysteinyl leukotriene type 1 receptor antagonist. Used as an antiasthmatic.
相关文献及参考
- [2]. Gunning WT, et al. Chemoprevention by lipoxygenase and leukotriene pathway inhibitors of vinyl carbamate-induced lung tumors in mice. Cancer Res. 2002 Aug 1;62(15):4199-201.
- [3]. Lei C, et al. Zafirlukast attenuates advanced glycation end-products (AGEs)-induced degradation of articular extracellular matrix (ECM). Int Immunopharmacol. 2019;68:68-73.
- Findlay, S.R., et al.: J. Allergy Clin. Immunol., 89, 1040 (1992),
- Krell, R.D., et al.: Am. Rev. Respir. Dis., 141, 978 (1990),
- Matassa, V.G., et al.: J. Med. Chem., 33, 1781 (1990),
- Merck 14 ,10108
- Schain, F., et al Int. J. Cancer 123 , 2285-2293, (2008)
- Scuderi, N., et al Int. J. Immunopharmacol. 20 , 577-584, (2007)
- Woszczek, G., et al J. Immunol. 184 , 2219-2225, (2010)
- [1]. Finnerty JP, et al. Role of leukotrienes in exercise-induced asthma. Inhibitory effect of ICI 204219, a potent leukotriene D 4 receptor antagonist. Am Rev Respir Dis. 1992 Apr;14
安全信息
- H413 Maycauselonglastingharmfuleffectstoaquaticlife 可能对水生生物造成长期持续有害影响。
其他信息
- MSDS 信息:Cyclopentyl [3-[[2-methoxy-4-[(2-methylphenyl)sulfonylcarbamoyl]phenyl]methyl]-1-methyl-indol-5-yl]aminoformate(107753-78-6).msds
- 上游原料:四氢呋喃 --> 氢化钠 --> 1,4-二氧六环 --> 碘甲烷 --> N-甲基吗啡啉 --> 5-硝基吲哚 --> 10%钯碳 --> 钯碳催化剂 --> 3-甲氧基苯甲酸甲酯
- 方法一:5-硝基吲哚(I，5.0g，30.8mmol)和4-(溴甲基)-3-甲氧基苯甲酸甲酯(Ⅱ，7.99g，30.8mmo1)溶于30ml二氧六环，在氮气保护和搅拌下加入氧化银(7.15g，30.8mmo1)，在60℃下加热20h。减压蒸出溶剂，加入50ml乙酸乙酯。过滤，滤液浓缩，再用层析分离，以3：7的乙酸乙酯-己烷洗脱。得到的黄色油状物再用二氯甲烷-己烷结晶，得4.6g化合物(Ⅲ)，收率45%，熔点153～155℃。 在氮气保护下，将化合物(Ⅲ)(0.44g，1.29mmo1)加到已游离的氢化钠(0.031g，1.29mmo1)在100ml干燥四氢呋喃的悬浮液中，在10min后再加入碘甲烷(0.18g，1.29mmo1)，反应30min。倾入30ml 1mol/L盐酸，用乙酸乙酯(2×50ml)提取。提取液用饱和盐水洗，干燥，浓缩。经层析分离，以50：45：5的己烷一二氯甲烷-乙酸乙酯洗脱，得到的黄色油状物经二氯甲烷和己烷的混合液结晶，得0.33g化合物(Ⅳ)，收率72%，熔点144～146℃。 化合物(Ⅳ)(0.56g，1.57mmol)溶于30ml四氢呋喃，加入0.1g10%钯-碳催化剂，在0.345MPa的氢压下加氢2h。过滤，滤液浓缩，再经层析提纯，以1：1的乙酸乙酯-己烷洗脱，得0.5g化合物(V)，收率98%。 化合物(V)(0.25g，0.77mmo1)和N-甲基吗啉(0.77mmo1)溶于3ml二氯甲烷，在氮气保护下加入氯甲酸环戊基酯(0.11g，0.77mmo1)，搅拌2h。倾入1mol/L盐酸，用乙酸乙酯提取。提取液用饱和盐水洗，干燥，浓缩。剩余黏稠油状物用层析提纯，以3：7的乙酸乙酯-己烷洗脱，得0.25g化合物(Ⅵ)，收率74%。 化合物(Ⅵ)用氢氧化锂在室温进行水解，得到化合物(Ⅶ)。(Ⅶ)和邻甲基苯磺酰胺，在1-[3-(二甲胺基)丙基]-3-乙基碳化二亚胺盐酸盐和4-(二甲胺基)吡啶存在下，在二氯甲烷中缩合，可得扎夫司特，收率69%，熔点138～140℃。
- MOL 文件:107753-78-6.mol
- 用途一:白三烯拮抗剂。用于治疗哮喘。
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