(S)-2-(4-isobutylphenyl)-N-phenylpropanamide | 114529-45-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-2-(4-isobutylphenyl)-N-phenylpropanamide
• 英文别名: (2S)-2-[4-(2-methylpropyl)phenyl]-N-phenylpropanamide
• CAS: 114529-45-2
• 化学式: C₁₉H₂₃NO
• 分子量: 281.398
• InChiKey: UHKIXOMKDZNTLI-HNNXBMFYSA-N

物化性质

• 沸点：
  460.6±24.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-isobutylphenyl)-N-phenylpropanamide 在 硫酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 8.0h， 以93%的产率得到(S)-(+)-布洛芬
  参考文献：
  名称：

  钯-单齿亚磷酰胺催化烯烃的不对称马尔可夫尼科夫氢氨基羰基化

  摘要：

  已经开发了钯催化的烯烃与苯胺的不对称马尔科夫尼科夫氢氨基羰基化反应，用于原子经济合成带有 α-立体中心的 2-取代丙酰胺。发现了一种新的亚磷酰胺配体 L16，它在反应中表现出非常高的反应性和选择性。这种不对称 Markovnikov 氢氨基羰基化使用容易获得的起始材料并耐受范围广泛的官能团，从而为在环境条件下区域选择性和对映选择性合成 2-取代丙酰胺提供了一种简便而直接的方法。机理研究表明，该反应通过钯氢化物途径进行。

  DOI：

  10.1021/jacs.0c11249
• 作为产物：
  描述：

  (S)-(+)-布洛芬 在 氯化亚砜 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 (S)-2-(4-isobutylphenyl)-N-phenylpropanamide
  参考文献：
  名称：

  Synthesis of Ibuprofen Derivatives with Improved Antibacterial Activity

  摘要：

  一系列新的布洛芬衍生物，即(S)-布洛芬酰胺、(S)-4-(2-(4-异丁基苯基)丙酰胺)苯甲酸、(S)-3-(4-异丁基苯基)丁-2-酮与吗啉的化合物、(S)-2-(4-异丁基苯基)-N-(4-硝基苯基)丙酰胺和(S)-3-羟基-5-(2-(4-异丁基苯基)丙基氨基苯甲酸，已通过将市售的2-(4-异丁基苯基)丙酸(布洛芬)与亚硫酰氯反应得到2-(4-异丁基苯基)丙酰氯来合成。酸氯化物进一步与不同的胺反应得到布洛芬酰胺。所有这些化合物的结构都是基于它们的分析和光谱数据确认的。进行了FTIR和元素分析以表征合成的化合物。化学稳定性研究表明，酰胺衍生物在pH 1.2-6.8下是化学稳定的。使用扩散盘法和微量稀释法评估合成的布洛芬衍生物对革兰氏阳性菌，即枯草芽孢杆菌和革兰氏阴性菌，即大肠杆菌的抗菌潜力。布洛芬酰胺衍生物对测试细菌的抑制作用比酯衍生物更强。所有衍生物的MIC值在2-20 mg/mL范围内。结果表明，布洛芬酰胺衍生物具有更多的抗菌潜力，可能用于对抗感染性疾病。

  DOI：

  10.14233/ajchem.2015.18498

文献信息

• Clickable coupling of carboxylic acids and amines at room temperature mediated by SO₂F₂: a significant breakthrough for the construction of amides and peptide linkages
  作者：Shi-Meng Wang、Chuang Zhao、Xu Zhang、Hua-Li Qin

  DOI：10.1039/c9ob00699k

  日期：——

  carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in

  酰胺键和肽键的构建是所有生命过程和有机合成中最基本的转变之一。结构无处不在的酰胺基序的合成对于许多重要分子（如肽，蛋白质，生物碱，药剂，聚合物，配体和农用化学品）的组装至关重要。开发了一种SO2F2介导的羧酸与胺的直接可点击偶合方法，以简单，温和，高效，稳健和实用的方式合成各种酰胺（> 110例，大多数情况下> 90％的收率） ）。
• Amides, useful in the inhibition of il-8-induced chemotaxis of neutrophils
  申请人：——

  公开号：US20040181073A1

  公开（公告）日：2004-09-16

  N-(2-aryl-propionyl)-amides of formula (I) are described. 1 The process for their preparation and pharmaceutical preparations thereof are also described. The amides of the invention are useful in the prevention and treatment of tissue damage due to the exacerbate recruitment of polymorphonuclear neutrophils (leukocytes PMN) at the inflammatory sites. In particular, the invention relates to the R enantiomers of N-(2-aryl-propionyl)amides of formula (I) for use in the ihibition of the chemotaxis of neutrophils induced by IL-8. The compounds of the invention are used in the treatment of psoriasis, ulcerative cholitis, glomerular nephritis, acute respiratory insufficiency, idiopathic fibrosis, and rheumatoid arthritis.

  公式（I）的N-（2-芳基丙酰基）酰胺已被描述。还描述了它们的制备过程和药物制剂。本发明的酰胺在预防和治疗由于在炎症部位加重多形核中性粒细胞（白细胞PMN）的招募而导致的组织损伤方面是有用的。具体而言，本发明涉及用于抑制IL-8诱导的中性粒细胞趋化作用的N-（2-芳基丙酰基）酰胺的R对映体。本发明的化合物用于治疗牛皮癣、溃疡性结肠炎、肾小球肾炎、急性呼吸功能不全、特发性纤维化和类风湿关节炎。
• [EN] NEW CHIRAL STATIONARY PHASES FOR CHROMATOGRAPHY BASED ON AROMATIC ALLYL AMINES<br/>[FR] NOUVELLES PHASES STATIONNAIRES CHIRALES POUR CHROMATOGRAPHIE À BASE D'AMINES D'ALLYLE AROMATIQUES
  申请人：RUDJER BOSKOVIC INST

  公开号：WO2009109792A1

  公开（公告）日：2009-09-11

  New chiral stationary phases (CSPs) based on chiral selectors covalently bound on a solid support were prepared. Chiral selectors were obtained from enantiomerically pure aromatic amines and 3,5-dinitrobenzoic acid and then linked to the support surface through the allylic double bond. Such obtained materials allow enantioseparation of racemates or enantiomerically enriched compounds. These chiral stationary phases can be used as fillings in chromatographic columns for enantiomer separation of naproxen type drugs and other similar non-steroidal anti-inflammatory drugs (NSAID) by means of high performance liquid chromatography on both the analytical and preparative scale.

  基于手性选择剂共价结合在固体支持上的新手性固定相（CSPs）已经制备。手性选择剂是从对映异构纯芳香胺和3,5-二硝基苯甲酸中获得的，然后通过烯丙基双键连接到支持表面。这样获得的材料可以用于拆分混合物或对映富集化合物的手性分离。这些手性固定相可以作为色谱柱中的填料，通过高效液相色谱在分析和制备尺度上对萘普生类药物和其他类似的非甾体类抗炎药物（NSAID）进行对映异构体分离。
• Visible Light Induced Copper‐Catalyzed Enantioselective Deaminative Arylation of Amino Acid Derivatives Assisted by Phenol
  作者：Yue Jia、Zhihan Zhang、Guo‐Ming Yu、Xuan Jiang、Liang‐Qiu Lu、Wen‐Jing Xiao

  DOI：10.1002/anie.202312102

  日期：2023.12.18

  A visible light induced enantioselective deaminative arylation of amino acid derivatives by bifunctional copper catalysis is disclosed. A variety of α-aryl-N-phenylamides are prepared with good efficiency and high enantioselectivity. A possible reaction mechanism and an asymmetric induction mode have been proposed based on experimental and computational evidence.

  公开了通过双功能铜催化的可见光诱导的氨基酸衍生物的对映选择性脱氨芳基化。多种α-芳基-N-苯基酰胺的制备具有良好的效率和高对映选择性。基于实验和计算证据，提出了一种可能的反应机制和不对称诱导模式。
• &lt;p&gt;Dexibuprofen amide derivatives as potential anticancer agents: synthesis, in silico docking, bioevaluation, and molecular dynamic simulation&lt;/p&gt;
  作者：Zaman Ashraf、Tariq Mahmood、Mubashir Hassan、Samina Afzal、Hummera Rafique、Khurram Afzal、Jalifah Latip

  DOI：10.2147/dddt.s178595

  日期：——

  Background: The amide derivatives of nonsteroidal anti-inflammatory drugs have been reported to possess antitumor activity. The present work describes the synthesis of dexibuprofen amide analogues (4a-j) as potential anticancer agents.Methods: The title amides (4a-j) were obtained by simple nucleophilic substitution reaction of dexibuprofen acid chloride with substituted amines in good yield and chemical structures were confirmed by FTIR, H-1 NMR, C-13 NMR and mass spectral data.Results: The brine shrimp lethality assay results showed that all of the synthesized compounds are non-toxic to shrimp larvae. The inhibitory effects on tumor growth were evaluated and it was observed that N-(2,5-dichlorophenyl)-2-(4-isobutylphenyl) propionamide (4e) and N-(2-chlorophenyl)-2-(4-isobutylphenyl) propionamide (4g) exhibited excellent antitumor activity compared to all other derivatives. The compound 4e bearing 2,5-dichloro substituted phenyl ring and 4g possesses 2-chioro substituted phenyl ring exhibited 100% inhibition of the tumor growth. The anticancer activity was evaluated against breast carcinoma cell line (MCF-7) and it was observed that derivative 4e exhibited excellent growth inhibition of cancer cells with IC50, value of 0.01 +/- 0.002 mu m, which is better than the standard drugs. The docking studies against breast cancer type 1 susceptibility protein BRCA1 (PDBID 3K0H) exhibited good binding affinities, which are in good agreement with the wet lab results. The compounds 4e and 4g showed the binding energy values of -6.39 and -6.34 Kcal/mol, respectively. The molecular dynamic (MD) simulation was also carried out to evaluate the residual flexibility of the best docking complexes of compounds 4e and 4g. The MD simulation analysis assured that the 4e formed a more stable complex with the target protein than the 4g. The synthesized amide derivatives exhibited were devoid of gastrointestinal side effects and no cytotoxic effects against human normal epithelial breast cell line (MCF-12A) were found.Conclusion: Based upon our wet lab and dry lab findings we propose that dexibuprofen analogue 4e may serve as a lead structure for the design of more potent anticancer drugs.