8-(benzyloxy)carbostyril-5-carboxaldehyde | 66546-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-(benzyloxy)carbostyril-5-carboxaldehyde
• 英文别名: 5-formyl-8-benzyloxycarbostyril；8-benzyloxy-2-oxo-1,2-dihydro-quinoline-5-carbaldehyde；8-(benzyloxy)carbostyril-5-carboxyaldehyde；8-Benzyloxy-5-formylcarbostyril；8-(Benzyloxy)-2-oxo-1,2-dihydroquinoline-5-carbaldehyde；2-oxo-8-phenylmethoxy-1H-quinoline-5-carbaldehyde
• CAS: 66546-38-1
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: NTYPNYLLLDBZMO-UHFFFAOYSA-N

物化性质

• 熔点：
  150-151 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  552.0±50.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(benzyloxy)carbostyril-5-carboxaldehyde 在 sodium hydride 、 二甲基亚砜 作用下， 以 正丁醇 为溶剂， 反应 24.5h， 生成 5-[1-hydroxy-2-[[1-(4-iodophenyl)-2-methylpropan-2-yl]amino]ethyl]-8-phenylmethoxy-1H-quinolin-2-one
  参考文献：
  名称：

  Carbostyril derivatives having potent .beta.-adrenergic agonist properties

  摘要：

  Derivatives carrying a substituent in the para position of the phenyl group of 8-hydroxy-5-[2-[(1-phenyl-2-methylprop-2-yl)amino]-1-hydroxyethyl] carbostyril (10) were prepared and their effects on beta-adrenoceptors evaluated in vitro. Unsubstituted compound 10, iodo 11, amino 12, and bromoacetamido 13 derivatives (all racemic) bound to the receptor with 15-100-fold lower dissociation constants than that of (-)-isoproterenol. All the above compounds stimulated adenylate cyclase more potently than (-)-isoproterenol. The intrinsic activities of compounds 10 and 12 were equal to that of (-)-isoproterenol. The intrinsic activities of compounds 11 and 13 were 1.3 and 1.2 times that of (-)-isoproterenol, respectively. Treatment of membrane preparations with bromoacetamido derivative 13 resulted in an irreversible loss of binding sites, and thus, 13 seems to be an alkylating affinity label for beta-adrenoceptors.

  DOI：

  10.1021/jm00392a006
• 作为产物：
  描述：

  (8-苯基甲氧基喹啉-5-基)甲醇 在 乙酸酐 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 7.5h， 生成 8-(benzyloxy)carbostyril-5-carboxaldehyde
  参考文献：
  名称：

  Carbostyril derivatives having potent .beta.-adrenergic agonist properties

  摘要：

  Derivatives carrying a substituent in the para position of the phenyl group of 8-hydroxy-5-[2-[(1-phenyl-2-methylprop-2-yl)amino]-1-hydroxyethyl] carbostyril (10) were prepared and their effects on beta-adrenoceptors evaluated in vitro. Unsubstituted compound 10, iodo 11, amino 12, and bromoacetamido 13 derivatives (all racemic) bound to the receptor with 15-100-fold lower dissociation constants than that of (-)-isoproterenol. All the above compounds stimulated adenylate cyclase more potently than (-)-isoproterenol. The intrinsic activities of compounds 10 and 12 were equal to that of (-)-isoproterenol. The intrinsic activities of compounds 11 and 13 were 1.3 and 1.2 times that of (-)-isoproterenol, respectively. Treatment of membrane preparations with bromoacetamido derivative 13 resulted in an irreversible loss of binding sites, and thus, 13 seems to be an alkylating affinity label for beta-adrenoceptors.

  DOI：

  10.1021/jm00392a006

文献信息

• 一种盐酸丙卡特罗杂质的制备方法
  申请人：深圳海王医药科技研究院有限公司

  公开号：CN112645875A

  公开（公告）日：2021-04-13

  本发明公开了一种盐酸丙卡特罗杂质的制备方法，包括以下步骤：步骤1，在碱性条件下，在有机溶剂中加入盐酸丙卡特罗，然后再加入适量的卤化苄，加热回流至反应完全，经后处理后得到中间体1；步骤2，将中间体1加入反应瓶中，然后加入有机溶剂，升高温度，加入氧化剂水溶液，加热反应完全后，倒入冰水中，析出固体，得到中间体2；步骤3，将中间体2加入反应瓶中，然后加入有机溶剂，降至低温，缓慢加入三氯化硼，保持低温至反应完全后，倒入冰水中，析出固体，过滤，得到丙卡特罗杂质。以易于获得的盐酸丙卡特罗为起始原料来制备盐酸丙卡特罗杂质，降低了盐酸丙卡特罗杂质的合成成本，而且简化了盐酸丙卡特罗杂质的制备步骤，提高了选择性，从而节省了制备时间，提高了制备效率。本发明反应的总收率50‑70％。
• Synthesis of procaterol derivative having a piperidylmethanol group and its .BETA.-adrenoceptor stimulant activities.
  作者：Shiro YOSHIZAKI、Shigeharu TAMADA、Masanao UMEZATO、Youichi YABUUCHI

  DOI：10.1248/cpb.37.3403

  日期：——

  A procaterol derivative (6) having a piperidylmethanol group was synthesized by the nucleophilic reaction of a 5-formylcarbostyril derivative with pyridyllithium, followed by selective catalytic reductions to afford the erythro-isomer. Compound 6 showed non-selective beta-adrenoceptor agonist activities like those of l-isoproterenol in an in vivo assay using anesthetized dogs.

  通过5-甲酰基羰基乙炔基衍生物与吡啶基锂的亲核反应，然后选择性催化还原，得到赤型异构体，来合成具有哌啶基甲醇基的儿茶酚衍生物（6）。在使用麻醉的狗的体内测定中，化合物6显示出非选择性的β-肾上腺素受体激动剂活性，如1-异丙肾上腺素。
• [EN] A PROCESS FOR PREPARING ABEDITEROL AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ABÉDITÉROL ET DE SES INTERMÉDIAIRES
  申请人：GBR LABORATORIES PRIVATE LTD

  公开号：WO2022172292A1

  公开（公告）日：2022-08-18

  The present invention relates to a process for preparation of Abediterol of the Formula (I) or its pharmaceutically acceptable salts, and intermediate compounds including the compound of the Formula (VII) by chiral sulfide mediated epoxidation. The process involves preparation of the intermediate compounds followed by preparation of Abediterol from the intermediate compounds. The compound Abediterol having the formula I is synthesized by various routes from the intermediate compound of Formula (VII). The process is cost effective and gives higher yield and better purity. The process of the present invention uses simple raw materials and reagents; and does not use hypertoxic materials.

  本发明涉及一种通过手性硫化物介导的环氧化反应制备公布的公式（I）或其药学上可接受的盐的阿贝地特罗的方法，以及包括公式（VII）化合物在内的中间体化合物。该方法涉及制备中间体化合物，然后从中间体化合物制备阿贝地特罗。具有公式I的化合物阿贝地特罗通过从公式（VII）的中间体化合物的不同途径合成。该方法成本效益高，产率更高，纯度更好。本发明方法使用简单的原材料和试剂，并且不使用高毒性材料。
• [EN] A PROCESS FOR PREPARING NAVAFENTEROL AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DE NAVAFENTÉROL ET DE SES INTERMÉDIAIRES
  申请人：GBR LABORATORIES PRIVATE LTD

  公开号：WO2022172296A1

  公开（公告）日：2022-08-18

  The present invention relates to a process for preparation of Navafenterol of Formula (I) and intermediate compounds of Formula (VII) and Formula (XIII) by chiral sulfide mediated epoxidation. The process involves preparation of the intermediate compounds of Formula (VII) and Formula (XIII) followed by preparation of Navafenterol from the compound of Formula (XIII) either by condensation with the compound of Formula (XVI); or via intermediates of the compound of Formula (XVIII) and compound of Formula (XV); or via intermediates of the compound of Formula (XI-a) and compound of Formula (XVI). The process uses simple raw materials and reagents. Further, the process is cost effective and gives higher yield and better purity.

  本发明涉及一种通过手性硫化物介导的环氧化反应制备Navafenterol（式（I））及其中间化合物（式（VII）和式（XIII））的方法。该方法包括制备式（VII）和式（XIII）的中间体，然后通过与式（XVI）的缩合或通过式（XVIII）的中间体和式（XV）的化合物，或通过式（XI-a）和式（XVI）的中间体来制备Navafenterol。该方法使用简单的原材料和试剂。此外，该方法成本效益高，产量高，纯度更好。
• [EN] A PROCESS FOR PREPARING BATEFENTEROL AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DE BATÉFENTÉROL ET DE SES INTERMÉDIAIRES
  申请人：GBR LABORATORIES PRIVATE LTD

  公开号：WO2022175982A1

  公开（公告）日：2022-08-25

  The present invention discloses a process for preparation of Batefenterol of Formula (I) or pharmaceutically acceptable salts thereof, and its intermediates by epoxidation. The process involves preparation of the intermediate compound of Formula (VII), followed by preparation of Batefenterol from the intermediate compound of Formula (VII) via intermediate compounds of Formulae (X) and (XI); or via intermediate compounds of Formulae (IX) and (XI); or via intermediate compounds of Formulae (VII) and (XI); or via intermediate compounds of the Formulae (XV) and (XVI); or via intermediate compounds of the Formulae (XIX) and (XVI). The process is cost effective and gives higher yield and better purity. The process does not use hypertoxic materials and yields compound (I) that is highly efficient and possess excellent powdery nature.

  本发明揭示了一种制备式（I）的Batefenterol或其药学上可接受的盐的过程，以及通过环氧化反应制备其中间体。该过程涉及制备式（VII）的中间化合物，然后通过式（X）和（XI）的中间化合物从式（VII）的中间化合物制备Batefenterol；或通过式（IX）和（XI）的中间化合物从式（VII）的中间化合物制备Batefenterol；或通过式（VII）和（XI）的中间化合物从式（VII）的中间化合物制备Batefenterol；或通过式（XV）和（XVI）的中间化合物从式（VII）的中间化合物制备Batefenterol；或通过式（XIX）和（XVI）的中间化合物从式（VII）的中间化合物制备Batefenterol。该过程成本效益高，产量更高，纯度更好。该过程不使用高毒性材料，并产生高效且具有优异粉末性质的化合物（I）。