4-[(2R)-1-amino-1-oxopropan-2-yl]phenyl trifluoromethanesulfonate | 849776-06-3

• 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: 4-[(2R)-1-amino-1-oxopropan-2-yl]phenyl trifluoromethanesulfonate
• 英文别名: 4-[(1R)-2-amino-1-methyl-2-oxoethyl]phenyltrifluoromethane sulfonate；(R)-2-[(4’-trifluoromethanesulfonyloxy)phenyl]propionamide；DF 2162；R(-)-2-[(4'-trifluoromethanesulfonyloxy)phenyl]propionamide；[4-[(2R)-1-amino-1-oxopropan-2-yl]phenyl] trifluoromethanesulfonate
• CAS: 849776-06-3
• 化学式: C₁₀H₁₀F₃NO₄S
• 分子量: 297.255
• InChiKey: UVKSSLZRUNYLIM-ZCFIWIBFSA-N

物化性质

• 熔点：
  67-69 °C
• 沸点：
  414.0±45.0 °C(Predicted)
• 密度：
  1.473±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  94.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[(2R)-1-amino-1-oxopropan-2-yl]phenyl trifluoromethanesulfonate 在 三乙胺 、 三氯乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 4-[(1R)-1-cyanoethyl]phenyl trifluoromethanesulfonate
  参考文献：
  名称：

  Retention of stereochemistry in the microwave assisted synthesis of 1H-tetrazole bioisosteric moiety from chiral phenyl-acetic acid derivatives

  摘要：

  Chiral substituted phenylethyl-1H-tetrazoles were built-up from the corresponding carboxylic acid derivatives by a useful three-step synthesis. The procedure, that preserves the chiral center from racemization, was successfully applied to a selection of several hit compounds by conversion of the carboxylic acid moiety to the nitrile derivatives and subsequent reaction with trimethylstannyl azide, under microwave conditions. A useful application to the corresponding tetrazole analogue has been found also in the conversion of the aminoacidic moiety like (R)-N-Cbz-phenylglycine showing a wide potential synthetic application. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.022
• 作为产物：
  描述：

  (R)-2-(4-hydroxyphenyl)propionic acid methyl ester 在 盐酸 、 氯化亚砜 、 氨 、 溶剂黄146 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 4-[(2R)-1-amino-1-oxopropan-2-yl]phenyl trifluoromethanesulfonate
  参考文献：
  名称：

  Predicting Human Serum Albumin Affinity of Interleukin-8 (CXCL8) Inhibitors by 3D-QSPR Approach

  摘要：

  A novel class of 2-(R)-phenylpropionamides has been recently reported to inhibit in vitro and in vivo interleukin-8 (CXCL8)-induced biological activities, These CXCL8 inhibitors are derivatives of phenylpropionic nonsteroidal antiinflammatory drugs (NSAIDs), high-affinity ligands for site II of human serum albumin (HSA). Up to date, only a limited number of in silico models for the prediction of albumin protein binding are available. A three-dimensional quantitative structure-property relationship (3D-QSPR) approach was used to model the experimental affinity constant (K-i) to plasma proteins of 37 structurally related molecules, using physicochemical. and 3D-pharmacophoric descriptors. Molecular docking studies highlighted that training set molecules preferentially bind site II of HSA. The obtained model shows satisfactory statistical parameters both in fitting and predicting validation. External validation confirmed the statistical significance of the chemometric model, which is a powerful tool for the prediction of HSA binding in virtual libraries of structurally related compounds.

  DOI：

  10.1021/jm049227l

文献信息

• 2-ARYL-2-FLUOROPROPANOIC ACIDS AND DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Allegretti Marcello

  公开号：US20100076034A1

  公开（公告）日：2010-03-25

  The present invention relates to (R,S) 2-aryl-2-fluoropropanoic acids, their single enantiomers (R) and (S), their derivatives amides and acylsulfonamides and to pharmaceutical compositions containing them, which are used in the prevention and treatment of tissue damage due to the exacerbated recruitment of polymorphonucleated neutrophils (PMN leukocytes) at inflammation sites. The present invention provides compounds for use in the treatment of psoriasis, ulcerative colitis, melanoma, chronic obstructive pulmonary disease (COPD), bullous pemphigo, rheumatoid arthritis, idiopathic fibrosis, glomerulonephritis and in the treatment of damages caused by ischemia and reperfusion.

  本发明涉及(R,S) 2-芳基-2-氟丙酸、它们的单对映体(R)和(S)、它们的衍生物酰胺和酰基磺酰胺以及含有它们的制药组合物，用于预防和治疗由于在炎症部位过度招募多形核中性粒细胞(PMN白细胞)引起的组织损伤。本发明提供了用于治疗银屑病、溃疡性结肠炎、黑色素瘤、慢性阻塞性肺疾病(COPD)、大疱性天疱疮、类风湿性关节炎、特发性纤维化、肾小球肾炎以及缺血再灌注引起的损伤的化合物。
• 2-ARYL-PROPIONAMIDE DERIVATIVES USEFUL AS BRADYKININ RECEPTOR ANTAGONISTS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Beccari Andrea

  公开号：US20120316169A1

  公开（公告）日：2012-12-13

  (R,S) 2-aryl-propionamide derivatives, or their single enantiomers (R) and (S) are disclosed useful in the treatment or prevention of symptoms and disorders such as pain and inflammation associated with the bradykinin B1 pathway.

  本文披露了(R,S) 2-芳基丙酰胺衍生物，或其单一对映体(R)和(S)，适用于治疗或预防与布雷金肽B1途径相关的疼痛和炎症等症状和疾病。
• IL-8 INHIBITORS FOR USE IN THE TREATMENT AND/OR PREVENTION OF BACTERIAL SECONDARY INFECTIONS
  申请人：Dompé farmaceutici s.p.a.

  公开号：EP3409277A1

  公开（公告）日：2018-12-05

  The present invention relates to IL-8 inhibitor compounds, preferably dual CXCR1/CXCR2 receptor inhibitors, useful in the treatment and/or prevention of secondary bacterial infections, preferably secondary respiratory infections.

  本发明涉及IL-8抑制剂化合物，最好是CXCR1/CXCR2双重受体抑制剂，可用于治疗和/或预防继发性细菌感染，最好是继发性呼吸道感染。
• Cellular factors involved in the cytotoxicity of Staphylococcus aureus leukocidins: novel therapeutic targets
  申请人：New York University

  公开号：US10301378B2

  公开（公告）日：2019-05-28

  The present invention relates to methods for treating and preventing Staphylococcus aureus infection and/or a condition resulting from a S. aureus infection in a subject that involves administering compositions that inhibit S. aureus interaction with CXCR1/CXCR2 and DARC cellular receptors. The present invention further relates to novel compositions for carrying out these and other methods.

  本发明涉及治疗和预防受试者金黄色葡萄球菌感染和/或由金黄色葡萄球菌感染引起的病症的方法，该方法涉及施用抑制金黄色葡萄球菌与CXCR1/CXCR2和DARC细胞受体相互作用的组合物。本发明进一步涉及用于实施这些方法和其他方法的新型组合物。
• Method for treating cancer using dual antagonists of CXCR1 and CXCR2
  申请人：Syntrix Biosystems, Inc.

  公开号：US10561676B2

  公开（公告）日：2020-02-18

  What is described is a method for treating cancer in a patient in need of such treatment through the use of a dual CXCR1/2 antagonist by administering a therapeutically effective amount of a dual CXCR1/2 antagonist, or pharmaceutical compositions thereof, either alone as monotherapy, or in combination with at least one other anticancer therapy.

  所描述的是一种通过使用双重CXCR1/2拮抗剂治疗需要这种治疗的患者癌症的方法，其方法是施用治疗有效量的双重CXCR1/2拮抗剂或其药物组合物，既可以单独作为单一疗法，也可以与至少一种其他抗癌疗法联合使用。