盐酸普奈洛尔 | 4199-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 盐酸普奈洛尔
• 中文别名: (S)-盐酸普萘洛尔；S(-)-盐酸心得安；(s)-(-)-丙醇盐酸盐；(S)-1-异丙基氨基-3-(1-萘氧基)-2-丙醇盐酸盐
• 英文名称: (S)-(-)-propanolol hydrochloride
• 英文别名: (S)-(-)-propranolol hydrochloride；(-)-Propranolol hydrochloride；(S)-1-(isopropylamino)-3-(1-naphthyloxy)-2-propanol hydrochloride；propranolol；[(2S)-2-hydroxy-3-naphthalen-1-yloxypropyl]-propan-2-ylazanium;chloride
• CAS: 4199-10-4
• 化学式: C₁₆H₂₁NO₂*ClH
• mdl: MFCD00064547
• 分子量: 295.809
• InChiKey: ZMRUPTIKESYGQW-UQKRIMTDSA-N

物化性质

• 熔点：
  193-195 °C(lit.)
• 溶解度：
  乙醇：10 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  41.5
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 安全说明：
  S36
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2906199090
• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22
• 储存条件：
  2-8°C

制备方法与用途

生物活性

(S)-(-)-普萘洛尔盐酸盐是一种肾上腺素能受体（β-adrenergic receptor）拮抗剂，针对 β1、β2 和 β3 的 log Kd 值分别为 -8.16、-9.08 和 -6.93。该化合物可用于高血压、嗜铬细胞瘤、心肌梗塞、心律不齐、心绞痛和肥厚型心肌病的相关研究。

靶点

• β1-腺能受体: log Kd: -8.16
• β2-腺能受体: log Kd: -9.08
• β3-腺能受体: log Kd: -6.93

用途

普萘洛尔的 S 对映体（P831800）是一种 β 阻滞剂，具有抗高血压、抗心绞痛和抗心律失常（II 类）的作用。

反应信息

• 作为反应物：
  描述：

  盐酸普奈洛尔 在 sodium nitrite 作用下， 以 盐酸 、 水 为溶剂， 反应 2.0h， 以4.78%的产率得到N-nitrosopropranolol
  参考文献：
  名称：

  Effects of mono-, di- and tri-hydroxybenzoic acids on the nitrosation of propranolol: structure-activity relationship

  摘要：

  Nitrosation of propranolol under standard conditions recommended by the World Health Organization (10 mM propranolol hydrochloridre, 40 mM sodium nitrite, pH 3.5) was performed in the absence and in the presence of benzoic acid and of twelve mono-, di- and tri-hydroxybenzoic acids, added to the nitrosation mixture in concentrations ranging from 2 to 40 mM. in order to examine their effect on the nitrosation reaction. The yield of N-nitrosopropranol (NOP) was reduced by benzoic acid and, with potency decreasing in the following order, by 2,3,4-tri-hydroxybenzoic acid greater than or equal to 3,4-tri-hydroxybenzoic acid > 2,5-di-hydroxybenzoic acid > 2,3-di-hydroxybenzoic acid > 3-hydroxybenzoic acid > 2-hydroxybenzoic acid > 3,4,5 -tri-hydroxybenzoic acid, 4-hydroxybenzoic acid; their inhibiting effect was concentration-dependent. In contrast, 2,4-di-hydroxybenzoic acid, 2,6-di-hydroxybenzoic acid and 2,3,6-tri-hydroxybenzoic acid caused an increase in the yield of NOP that was inversely related to their concentration. 3,5-Di-hydroxybenzoic acid was substantially inactive. These findings indicate that, depending on the positions of carboxyl group and hydroxyl groups on the benzene ring, mono-, di- and tri-hydroxybenzoic acids may inhibit or hasten nitrosation reactions. As compared with benzenediols and benzenetriols [Mutat. Res. 398 (1998) 75], hydroxybenzoic acids inhibit the nitrosation of propranolol to a greater extent and have the advantage of being nonmutagenic and less toxic. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1383-5718(00)00155-8
• 作为产物：
  描述：

  1-萘酚钠 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 46.0h， 生成 盐酸普奈洛尔
  参考文献：
  名称：

  摘要：

  Nonracemic beta -blockers, viz., (S)-propranolol and (S)-timolol, were prepared from (S)-glycidol in three steps consisting in the reaction with SOCl2 followed by the reaction of the resulting (4S)-4-chloromethyl-2-oxo-1,3,2-dioxathiolanes with the corresponding phenol and the final cleavage of (4R)-aryloxymethyl sulfites under the action of amines in DMF.

  DOI：

  10.1023/a:1011300921771

文献信息

• 1,5-Substituted indol-2-yl amide derivatives
  申请人：Nettekoven Matthias

  公开号：US20070123515A1

  公开（公告）日：2007-05-31

  The present invention relates to compounds of formula I wherein R 1 to R 4 and G are as defined in the description and claims and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prevention of diseases which are associated with the modulation of H3 receptors.

  本发明涉及式I的化合物，其中R1至R4和G如描述和索赔中定义的，并且其药学上可接受的盐。这些化合物可用于治疗和/或预防与H3受体调节相关的疾病。
• INDOL-2-YL-PIPERAZIN-1-YL-METHANONE DERIVATIVES
  申请人：Nettekoven Matthias

  公开号：US20080188484A1

  公开（公告）日：2008-08-07

  The present invention relates to compounds of formula I wherein A and R 1 to R 4 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prevention of diseases which are associated with the modulation of H3 receptors.

  本发明涉及公式I的化合物，其中A和R1至R4如描述和声明中所定义，并且其药学上可接受的盐。这些化合物可用于治疗和/或预防与H3受体调节相关的疾病。
• BENZOFURAN AND BENZOTHIOPHENE-2-CARBOXYLIC ACID AMIDE DERIVATIVES
  申请人：Mohr Peter

  公开号：US20090029976A1

  公开（公告）日：2009-01-29

  The present invention relates to compounds of formula I wherein X, A and R 1 to R 4 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prevention of diseases which are associated with the modulation of H3 receptors.

  本发明涉及公式I的化合物，其中X，A和R1至R4如描述和索赔中所定义，并且其药学上可接受的盐。这些化合物可用于治疗和/或预防与H3受体调节相关的疾病。
• [EN] NITROGEN RING CONTAINING COMPOUNDS FOR TREATMENT OF INFLAMMATORY DISORDERS<br/>[FR] COMPOSÉS CONTENANT UN CYCLE AZOTÉ POUR LE TRAITEMENT DE TROUBLES INFLAMMATOIRES
  申请人：WEINGARTEN M DAVID

  公开号：WO2012135669A1

  公开（公告）日：2012-10-04

  The invention provides compounds, pharmaceutical compositions and methods of treatment of inflammatory disorders including a compound of Formula I, or its pharmaceutically acceptable salt, ester, pharmaceutically acceptable derivative or prodrug wherein R1, R2, R3, R4, X, Y, W, Z and Q are as defined herein.

  这项发明提供了化合物、药物组合物和治疗炎症性疾病的方法，包括式I的化合物，或其药用可接受的盐、酯、药用可接受的衍生物或前药，其中R1、R2、R3、R4、X、Y、W、Z和Q如本文所定义。
• Dibenzylamine compound and medicinal use thereof
  申请人：Maeda Kimiya

  公开号：US20050059810A1

  公开（公告）日：2005-03-17

  A dibenzylamine compound represented by the formula (1) wherein R 1 and R 2 are each a C 1-6 alkyl group optionally substituted by halogen atoms and the like; R 3 , R 4 and R 5 are each a hydrogen atom, a halogen atom and the like, or R 3 and R 4 may form, together with carbon atoms bonded thereto, a homocyclic or heterocyclic ring optionally having substituent(s); A is —N(R 7 ) (R 8 ) and the like; ring B is an aryl group or a heterocyclic residue; R 6 is a hydrogen atom, a halogen atom, a nitro group, a C 1-6 alkyl group and the like; n is an integer of 1 to 3, a prodrug thereof and a pharmaceutically acceptable salt thereof show selective and potent CETP inhibitory activity, and therefore, they can be provided as therapeutic or prophylactic agents for hyperlipidemia or arteriosclerosis and the like.

  一种二苄胺化合物，其化学式如下： 其中，R1和R2分别是C1-6烷基基团，可选择性地被卤原子等取代；R3、R4和R5分别是氢原子、卤原子等，或者R3和R4可以与与之相结合的碳原子一起形成一个具有取代基的同环或异环环；A是-N(R7)(R8)等；环B是芳基或杂环残基；R6是氢原子、卤原子、硝基、C1-6烷基基团等；n是1到3的整数，其前体和药学上可接受的盐表现出选择性和强效的CETP抑制活性，因此，它们可以作为治疗或预防高脂血症或动脉硬化等疾病的药物。