(R)-sotalol | 30236-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-sotalol
• 英文别名: (-)-Sotalol；R(-)-sotalol；l-sotalol(0)；D-sotalol；N-[4-[(1R)-1-hydroxy-2-(propan-2-ylamino)ethyl]phenyl]methanesulfonamide
• CAS: 30236-31-8
• 化学式: C₁₂H₂₀N₂O₃S
• mdl: MFCD00242936
• 分子量: 272.368
• InChiKey: ZBMZVLHSJCTVON-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.8
• 氢给体数：
  3
• 氢受体数：
  5

制备方法与用途

索他洛尔是一种非选择性的、竞争性的β-肾上腺素能受体阻滞剂，同时具备III类抗心律失常作用。

反应信息

• 作为产物：
  描述：

  索他洛尔 在 glutathione and methylate β-CD-functionalized covalent organic framework 作用下， 以 aq. phosphate buffer 、 异丙醇 为溶剂， 生成 右索他洛尔 、 (R)-sotalol
  参考文献：
  名称：

  用于对映选择性识别和分离的协同多手性共价有机框架

  摘要：

  在对映体识别和分离中，迫切需要一种具有普遍适用性的高度对映选择性方法，但很难实现，特别是在手性分子的情况下。为了解决对映选择性和通用性之间的权衡，设计并合成了一种具有多孔性和丰富的手性表面的谷胱甘肽（GSH）和甲基化环糊精（MCD）功能化的共价有机框架（GSH-MCD COF），用于识别和分离各种对映体。正如预期的那样，GSH-MCD COF 可用作分离各种对映体的手性固定相，包括芳香醇、芳香酸、酰胺、氨基酸和有机酸，其性能和多功能性甚至优于一些广泛使用的商业手性固定相色谱柱。此外，合成的 GSH-MCD COF 在与拉曼光谱耦合时表现出高对映选择性，可快速识别和鉴定对映体和手性代谢物。分子模拟表明，COF 为环糊精和肽提供了一个有限的微环境，决定了分离和识别能力。这项工作提供了一种合成协同多手性COF并实现复杂样品中对映体分离和识别的策略。

  DOI：

  10.1021/acs.analchem.3c05227

文献信息

• Effect of Basic and Acidic Additives on the Separation of Some Basic Drug Enantiomers on Polysaccharide-Based Chiral Columns With Acetonitrile as Mobile Phase
  作者：Khatuna Gogaladze、Lali Chankvetadze、Maia Tsintsadze、Tivadar Farkas、Bezhan Chankvetadze

  DOI：10.1002/chir.22417

  日期：2015.12

  The separation of enantiomers of 16 basic drugs was studied using polysaccharide‐based chiral selectors and acetonitrile as mobile phase with emphasis on the role of basic and acidic additives on the separation and elution order of enantiomers. Out of the studied chiral selectors, amylose phenylcarbamate‐based ones more often showed a chiral recognition ability compared to cellulose phenylcarbamate

  使用基于多糖的手性选择剂和乙腈作为流动相，研究了16种基本药物的对映异构体的分离，重点研究了碱性和酸性添加剂对对映异构体的分离和洗脱顺序的作用。在研究的手性选择剂中，与纤维素苯基氨基甲酸酯衍生物相比，基于直链苯基氨基甲酸酯的选择剂更经常显示出手性识别能力。观察到甲酸作为添加剂对某些基本药物的对映体拆分和对映体洗脱顺序的有趣影响。因此，例如，几种β-阻滞剂（阿替洛尔，索他洛尔，甲苯酚）的对映异构体分离不仅可以通过在流动相中添加更常规的碱性添加剂来实现，而且可以通过添加酸性添加剂来实现。而且，手性27：228–234，2015年。©2015 Wiley Periodicals，Inc.
• Preparation and evaluation of a triazole‐bridged <i>bis</i> (β‐cyclodextrin)–bonded chiral stationary phase for HPLC
  作者：Yazhou Shuang、Yuqin Liao、Hui Wang、Yuanxing Wang、Laisheng Li

  DOI：10.1002/chir.23147

  日期：2020.2

  spectroscopy, mass spectrometry, elemental analysis, and thermogravimetric analysis. The chiral performance of TBCDP was evaluated by using chiral pesticides and drugs as probes including triazoles, flavanones, dansyl amino acids and β‐blockers. Some effects of the composition in mobile phase and pH value on the enantioseparations were investigated in different modes. The nine triazoles, eight flavanones, and

  通过6-叠氮基-β-环糊精和6-丙炔基氨基-β-环糊精之间的高产率Click化学反应合成了三唑桥联的双（β-环糊精），然后将其键合到有序硅胶SBA-15上获得新颖的三唑桥双（β-环糊精）-键合手性固定相（TBCDP）。通过红外光谱，质谱，元素分析和热重分析对桥联的环糊精和TBCDP的结构进行了表征。通过使用手性农药和药物（包括三唑，黄烷酮，丹酰氨基酸和β受体阻滞剂）作为探针，评估了TBCDP的手性性能。以不同方式研究了流动相中的组成和pH值对对映体的影响。在反相色谱下成功分离了9种三唑，8种黄烷酮和8种丹磺酰基氨基酸，其分辨率为六康唑，2'-羟基黄酮和dansyl- DL酪氨酸，在30分钟内分别为2.49、5.40和3.25。十种β受体阻滞剂在极性有机模式下也被分离，阿替洛尔的分辨率达到1.71。初步讨论了一些相关的分离机制。与天然环糊精固定相（CDSP）相比，TBCDP具有更高的对映选择
• Chiral Separations Using a Polypeptide and Polymeric Dipeptide Surfactant Polyelectrolyte Multilayer Coating in Open-Tubular Capillary Electrochromatography
  作者：Mary W. Kamande、Xiaofeng Zhu、Constantina Kapnissi-Christodoulou、Isiah M. Warner

  DOI：10.1021/ac049313t

  日期：2004.11.1

  A polyelectrolyte multilayer (PEM) coating consisting of the polypeptide, poly(l-lysine) hydrobromide, poly(l-lysine) and the polymeric dipeptide surfactant, poly(sodium undecanoyl-l-leucyl-alaninate), poly(l-SULA), is investigated as a new medium for the separation of chiral analytes in open-tubular capillary electrochromatography (OT-CEC). In this approach, a stable PEM is constructed in situ by alternative rinses of the cationic polymer poly(l-lysine) and the anionic polymer poly(l-SULA). In previous studies, the PEM coating has been constructed by use of the cationic polyelectrolyte poly (diallydimethylammonium chloride), PDADMAC. In this study, we investigate the use of a biopolymer as the cationic polyelectrolyte. The results reported here indicate an increase in selectivity and resolution when poly(l-lysine) is used as the cationic polymer in place of PDADMAC. To evaluate the chromatographic performance of the PEM coating as a chiral stationary phase, the separation of the β-blockers, labetalol and sotalol, and the binaphthyl derivatives, 1,1‘-bi-2-naphthyl-2,2‘-dihydrogen phosphate, 1,1‘-bi-2-naphthol, and 1,1-binaphthyl-2,2‘-diamine, are investigated. In addition, the effect of varying the amino acid order of the polymeric dipeptide surfactant on resolution is investigated. The number of bilayers also significantly influences the separation efficiency and resolution of enantiomers. The run-to-run and capillary-to-capillary reproducibilities are evaluated by calculating the relative standard deviations (RSDs) of the electroosmotic flow. These RSD values were found to be less than 1%. The coating is also stable and allows more than 290 runs to be performed in the same capillary. In addition, coupling of this chiral OT-CEC column with mass spectrometry is investigated.

  conducted.
• Chemoenzymatic synthesis of (S) and (R)-propranolol and sotalol employing one-pot lipase resolution protocol
  作者：Ahmed Kamal、Mahendra Sandbhor、Ahmad Ali Shaik

  DOI：10.1016/j.bmcl.2004.05.084

  日期：2004.9

  Synthesis of both enantiomers of biologically active propranolol and sotalol has been achieved in high optical purity by one-pot reduction of 3 and 7 followed by in situ lipase resolution of the respective chlorohydrins. Pseudomonas cepacia lipase immobilized on ceramic particles (PS-C) provided the chlorohydrin and acetate, which on nucleophilic substitution with isopropyl amine afforded the target amino alcohols in high enantio selectivity under mild reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.
• Hancu, Gabriel; Smrghian, Claudia; Rusu, Aura, Journal of the Chilean Chemical Society, 2014, vol. 59, # 3, p. 2559 - 2563
  作者：Hancu, Gabriel、Smrghian, Claudia、Rusu, Aura、Mircia, Eleonora

  DOI：——

  日期：——