(S)-ketoprofen chloride | 109718-56-1

• 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: (S)-ketoprofen chloride
• 英文别名: (2S)-2-(3-benzoylphenyl)propanoyl chloride
• CAS: 109718-56-1
• 化学式: C₁₆H₁₃ClO₂
• 分子量: 272.731
• InChiKey: IZCCWISLNJGJIZ-NSHDSACASA-N

物化性质

• 沸点：
  401.2±38.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-ketoprofen chloride 在 N,N'-羰基二咪唑 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 ethyl (2R)-2-((2S)-1-((2S)-2-(3-benzoylphenyl)propanoyl)pyrrolidine-2-carboxamido)-3-mercaptopropanoate
  参考文献：
  名称：

  Compounds against inflammation and oxidative insult as potential agents for neurodegenerative disorders

  摘要：

  Amides of proline, a feature encountered in nootropics, via the carboxylic group of ibuprofen, indomethacin, ketoprofen and naproxen were prepared. Proline carboxylic group was amidated or esterified with potential antioxidant or neuroprotective compounds. Proline was replaced by 4-hydroxyproline, 2-pipecolic acid or omitted, for investigating the contribution of structure to activity. Anti-inflammatory activity was determined, and selected compounds were examined for anti-dyslipidemic action, protection against brain ischaemia/reperfusion and brain penetration.Amides of proline and related structures with NSAIDs were synthesized. They were amidated or esterified with antioxidant or neuroprotective compounds. Activity against lipid peroxidation, inflammation and brain ischaemia was evaluated.

  DOI：

  10.1007/s00044-011-9726-x
• 作为产物：
  描述：

  右旋酮洛芬 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S)-ketoprofen chloride
  参考文献：
  名称：

  一组右酮洛芬氨丁三醇新杂质及其制备方法

  摘要：

  本发明涉及了一组右酮洛芬氨丁三醇新杂质，即(S)‑2‑(3‑苯甲酰苯基)‑N‑(1,3‑二羟基‑2‑(羟甲基)丙‑2‑基)丙酰胺；(S)‑2‑((S)‑2‑(3‑苯甲酰苯基)丙酰胺基)‑3‑羟基‑2‑(羟甲基)丙基‑2‑(3‑苯甲酰苯基)丙酸甲酯以及他们的制备方法。改组新杂质的制备方法由右酮洛芬氨丁三醇高温降解并经纯化得到高纯度的产品。该组杂质结构新颖，本发明为首次报道，对右酮洛芬氨丁三醇原料药及注射液的质量控制有着重大意义，同时本制备方法具有方法简单，操作方便，产品纯度高等特点，可应用于右酮洛芬氨丁三醇的杂质对照品研究。

  公开号：

  CN113461561A

文献信息

• Stereoselective intramolecular hydrogen abstraction by a chiral benzophenone derivative
  作者：Miguel A. Miranda、Luis A. Martínez、Abdelouahid Samadi、Francisco Boscá、Isabel M. Morera

  DOI：10.1039/b108858k

  日期：2002.1.30

  An unprecedented stereoselective photoreduction of a chiral BZP is observed in steady state as well as in time-resolved studies.

  在稳态以及时间分辨研究中都观察到了手性BZP前所未有的立体选择性光还原。
• Efficient and Selective Photogeneration of Cholesterol-Derived Radicals by Intramolecular Hydrogen Abstraction in Model Dyads
  作者：Inmaculada Andreu、Francisco Boscá、Laura Sanchez、Isabel M. Morera、Pelayo Camps、Miguel A. Miranda

  DOI：10.1021/ol061854c

  日期：2006.9.1

  [GRAPHICS]Three model dyads have been synthesized by esterification of beta- and alpha-cholesterol (Ch) with (S)- and/or (R)-ketoprofen (Kp). The alpha-dyads are efficient photogenerators of the 7-allyl Ch radicals by intramolecular H abstraction. Subsequent cyclization via C-C coupling occurs in a stereoselective way.
• [EN] USE OF (R) AND (S)-2-ARYL-PROPIONIC ACID DERIVATIVES AS ANTISEPTIC AGENTS<br/>[FR] UTILISATION DE DÉRIVÉS ACIDES -2-ARYL-PROPIONIQUES (R) ET (S) EN TANT QU'AGENTS ANTISEPTIQUES;
  申请人：DOMPE PHA R MA SPA RES & MFG

  公开号：WO2008110351A2

  公开（公告）日：2008-09-18

  [EN] The present invention relates to the use of amides of (R) and (S)-2-aryl- propionic acids as antiseptic agents. The present invention also provides a pharmaceutical preparation including compounds of formula (I), having antiseptic properties for the treatment of gastrointestinal, muco-epidermal and epidermal infections. The present invention is related to pharmaceutical compositions containing an antiseptic agent carried in a suitable vehicle to provide mouthwashes, tablets, solutions, gels, creams and others. The formulations are applied topically to sites of gastrointestinal, muco-epidermal or epidermal infections. Compounds of present invention can be useful in the treatment of nausea, vomiting, bloating, diarrhea, constipation and oropharyngeal, esophageal, vaginal, rectal, nasal and other mucosal infections.
  [FR] L'invention porte: sur l'utilisation d'amides acides -2-aryl-propioniques (R) et (S) en tant qu'agents antiseptiques; sur une préparation pharmaceutique de composés de formule (I), aux propriétés antiseptiques pour le traitement d'infections gastrointestinales, muco-épidermiques et épidermiques, sur des compositions pharmaceutiques contenant un agent antiseptique dans des véhicules appropriés pouvant donner des rince-bouche, des comprimés, des solutions, des gels, des crèmes et autres. Lesdits composés sont utiles pour le traitement de la nausée, des vomissements, des flatulences, de la diarrhée, de la constipation et des infections des muqueuses bucopharyngiennes, oesophagiennes, vaginales, rectales, nasales, etc.
• Compounds against inflammation and oxidative insult as potential agents for neurodegenerative disorders
  作者：Christos M. Doulgkeris、Ioanna C. Siskou、Nikoletta Xanthopoulou、Vassiliki Lagouri、Constantina Kravaritou、Phaedra Eleftheriou、Panos N. Kourounakis、Eleni A. Rekka

  DOI：10.1007/s00044-011-9726-x

  日期：2012.9

  Amides of proline, a feature encountered in nootropics, via the carboxylic group of ibuprofen, indomethacin, ketoprofen and naproxen were prepared. Proline carboxylic group was amidated or esterified with potential antioxidant or neuroprotective compounds. Proline was replaced by 4-hydroxyproline, 2-pipecolic acid or omitted, for investigating the contribution of structure to activity. Anti-inflammatory activity was determined, and selected compounds were examined for anti-dyslipidemic action, protection against brain ischaemia/reperfusion and brain penetration.Amides of proline and related structures with NSAIDs were synthesized. They were amidated or esterified with antioxidant or neuroprotective compounds. Activity against lipid peroxidation, inflammation and brain ischaemia was evaluated.
• 一组右酮洛芬氨丁三醇新杂质及其制备方法
  申请人：南京恒正药物研究院有限公司

  公开号：CN113461561A

  公开（公告）日：2021-10-01

  本发明涉及了一组右酮洛芬氨丁三醇新杂质，即(S)‑2‑(3‑苯甲酰苯基)‑N‑(1,3‑二羟基‑2‑(羟甲基)丙‑2‑基)丙酰胺；(S)‑2‑((S)‑2‑(3‑苯甲酰苯基)丙酰胺基)‑3‑羟基‑2‑(羟甲基)丙基‑2‑(3‑苯甲酰苯基)丙酸甲酯以及他们的制备方法。改组新杂质的制备方法由右酮洛芬氨丁三醇高温降解并经纯化得到高纯度的产品。该组杂质结构新颖，本发明为首次报道，对右酮洛芬氨丁三醇原料药及注射液的质量控制有着重大意义，同时本制备方法具有方法简单，操作方便，产品纯度高等特点，可应用于右酮洛芬氨丁三醇的杂质对照品研究。