CAS: 118457-16-2; Nebivolol

该化合物是一种选择性的乙型-1肾上腺受体阻塞器,主要用于治疗高血压和心脏衰竭,其特点是独特的行动机制,不仅包括封锁乙型-1受体,而且还通过释放硝基氧化物促进血管变异,使其有别于其他乙型阻塞体.这种双重行动有助于其有利的副作用,包括降低支气管受限和代谢干扰的发生率.该化合物是手性,其(-)抗生素是其治疗效果的积极形式.其药用植物动力包括口服生物利用率高,以及相对长的半衰期,允许每日服用一次.此外,(-)-Nebivool醇的脂溶性很高,这可能影响其分布和消化.

英文名称Nebivolol
中文名称(1S)-1-[(2S)-6-氟色满-2-基]-2-[[(2S)-2-[(2S)-6-氟色满-2-基]-2-羟基乙基]氨基]乙醇
IUPAC名称(S)-1-((R)-6-fluorochroman-2-yl)-2-(((S)-2-((S)-6-fluorochroman-2-yl)-2-hydroxyethyl)amino)ethan-1-ol
其它别名2H-1-Benzopyran-2-methanol,a,a'-[iminobis(methylene)]bis[6-fluoro-3,4-dihydro-,[2S-[2R*[R*[R*(S*)]]]]-; (-)-Nebivolol; Levonebivolol; l-Nebivolol
CAS编号118457-16-2
MFCD编号:MFCD00887480
分子式:C22H25F2NO4分子量:405.43
产品CID: 236332
产品分类分析化学 → 标准品 → 药典标准品和杂质标准品

相似结构搜索
InChIKey: KOHIRBRYDXPAMZ-YHDSQAASSA-N
1S/C22H25F2NO4/c23-15-3-7-19-13(9-15)1-5-21(28-19)17(26)11-25-12-18(27)22-6-2-14-10-16(24)4-8-20(14)29-22/h3-4,7-10,17-18,21-22,25-27H,1-2,5-6,11-12H2/t17-,18-,21-,22+/m0
计算化学: 氢键受体数7.0氢键供体数3.0可旋转键数6.0

物理性质

熔点135-137°C
沸点600.5±55.0 °C(预测)
闪点316.9 °C
密度1.309±0.06 g/cm3(预测)
pKa:14.29±0.20(预测)
PSA:70.95
LogP:2.7545
折射率1.58
蒸汽压2.88E-15 mmHg at 25 °C
溶解性Chloroform (Slightly), Methanol (Slightly)
外观形态白色至类白色固体
储存条件-20°C 冷藏
产品应用该化合物用于抗血压.

MSDS等安全信息

上下游产品

nebivolol N-[(S,S)-1-hydroxy-2-(6-fluoro-chroman-4-one-2-yl)]-N-[(R,S)-1-hydroxy-2-(6-fiuoro-chroman-4-one-2-yl)]-amine (2S)-6-fluoro-2-[(2S)-oxiran-2-yl]-3,4-dihydro-2H-chromene 2-amino-1-[6-fluoro-(2R)-3H,4H-2-chromenyl]-(1S)-ethan-1-ol nebivolol hydr°Chloride

合成工艺路线路线简述

📜N-[(S,S)-1-Hydroxy-2-(6-Fluoro-Chroman-4-One-2-yl)]-N-[(R,S)-1-Hydroxy-2-(6-Fiuoro-Chroman-4-One-2-yl)]-Amine置于palladium 10% On Activated Carbon 盐酸,氢气,碳酸氢钠体系中,用乙醇,水用作溶剂,50.0~55.0 °C,300.01 Kpa 条件下,反应 16.0H,以62%的收率获得(1S)-1-[(2S)-6-氟色满-2-基]-2-[[(2S)-2-[(2S)-6-氟色满-2-基]-2-羟基乙基]氨基]乙醇
参考文献: New Process For The Preparation Of Racemic ([2S[2R*[r[r*]]]] And ([2R[2S*[s[s*]]]]-(+/-)-Alpha,Alpha'-[imino-Bis(Methylene)]Bis[6-Fluorochroman-2-Methanol] And Its Pure [2S[2R*[r[r*]&[fr] Nouveau Procede De Preparation De ([2S[2R*[r[r*]]]] Et ([2R[2S*[s[s*]]]]-(+/-)-20040521Us4654362Avan Lommen Guy R E [be],Et Al198703311528Da1Daj. Hendrickx Et Al.: "Location Of The Oh Functions In Hydroxylated Metabolites Of Nebivolol",Journal Of Chromatography A,Vol. 729,No. 1+2,1996,Gb,Pages 341-354,Xp002270638J. Hendrickx Et Al.Location Of The Oh Functions In Hydroxylated Metabolites Of Nebivololjournal Of Chromatography Agb19967291+2341354353Va1,54,55A
标题: New Process For The Preparation Of Racemic ([2S[2R*[r[r*]]]] And ([2R[2S*[s[s*]]]]-(+/-)-Alpha,Alpha'-[imino-Bis(Methylene)]Bis[6-Fluorochroman-2-Methanol] And Its Pure [2S[2R*[r[r*]&[fr] Nouveau Procede De Preparation De ([2S[2R*[r[r*]]]] Et ([2R[2S*[s[s*]]]]-(+/-)-20040521Us4654362Avan Lommen Guy R E [be],Et Al198703311528Da1Daj. Hendrickx Et Al.: "Location Of The Oh Functions In Hydroxylated Metabolites Of Nebivolol",Journal Of Chromatography A,Vol. 729,No. 1+2,1996,Gb,Pages 341-354,Xp002270638J. Hendrickx Et Al.Location Of The Oh Functions In Hydroxylated Metabolites Of Nebivololjournal Of Chromatography Agb19967291+2341354353Va1,54,55A
摘要:用于制备化合物(i)的混合对映体([2S[2R*[r[r*]]]]-和([2R[2S*[s[s*]]]]-(+/-)-α,α'-[亚胺-双(亚甲基)]双[6-氟基-色苷-2-甲醇]的过程及其纯度([2S[2R*[r[r*]]]]-和([2R[2S*[s[s*]]]]-对映体化合物的特征在于所述产物是从4-氟苯酚或4-氟苯甲醚经过结晶的,具有光学活性的中间体制备而成.