2-hydroxy-2-phenyl-valeric acid amide | 2019-67-2

• 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: 2-hydroxy-2-phenyl-valeric acid amide
• 英文别名: (+/-)-2-Hydroxy-2-phenyl-valeramid；2-Hydroxy-2-phenyl-valeriansaeure-amid；2-Hydroxy-2-phenylpentanamide
• CAS: 2019-67-2
• 化学式: C₁₁H₁₅NO₂
• mdl: MFCD00068936
• 分子量: 193.246
• InChiKey: MTTTVCAELXLXCX-UHFFFAOYSA-N

物化性质

• 熔点：
  98.5-100.0 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  368.9±35.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2-phenyl-valeric acid amide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以71%的产率得到2-hydroxy-2-phenyl-valeric acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship Studies for Hydantoins and Analogues as Voltage-Gated Sodium Channel Ligands

  摘要：

  We previously developed a preliminary 3-D QSAR model for the binding of 14 hydantoins to the neuronal voltage-gated sodium channel; this model was successful in designing,an effective non-hydantoin ligand. To further understand structural features that result in optimum binding. here we synthesized a variety of compound classes and evaluated their binding affinities to the neuronal voltage-gated sodium channel using the [H-3]-batrachotoxinin A 20-a-benzoate ([H-3]BTX-B) binding assay. In order to understand the importance of the hydantoin ring for good sodium channel binding, related non-hydantoins such as hydroxy amides, oxazolidinediones, hydroxy acids, and amino acids were included. Two major conclusions were drawn: (1) The hydantoin ring is not critical for compounds with long alkyl side chains, but it is important for compounds with shorter side chains. (2) Relative to Khodorov's pharmacophore. which contains two hydrophobic regions, a third hydrophobic region may enhance binding to provide nanomolar inhibitors.

  DOI：

  10.1021/jm040077o
• 作为产物：
  描述：

  苯丁酮 在 哌啶 、 氢氰酸 作用下， 生成 2-hydroxy-2-phenyl-valeric acid amide
  参考文献：
  名称：

  5,5-Dialkyl-2,4-oxazolidinediones^1,2

  摘要：

  DOI：

  10.1021/ja01854a019

文献信息

• [EN] 1,2,3-BENZOTRIAZOLE DERIVATIVES AS ROR GAMMA T MODULATORS<br/>[FR] DÉRIVÉS DE 1,2,3-BENZOTRIAZOLE EN TANT QUE MODULATEURS DE ROR GAMMA T
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2018042342A1

  公开（公告）日：2018-03-08

  The present disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein ring A, G, L, R1, Rx, Ry, X1, X2, X3, X4, n, p, q and t are as defined herein, which are active as modulators of retinoid-related orphan receptor gamma t (RORyt). These compounds prevent, inhibit, or suppress the action of RORyt and are therefore useful in the treatment of RORyt mediated diseases, disorders, syndromes or conditions such as, e.g., pain, inflammation, COPD, asthma, rheumatoid arthritis, colitis, multiple sclerosis, psoriasis, neurodegenerative diseases and cancer (I).

  本公开涉及式(I)的化合物及其药用可接受的盐，其中环A、G、L、R1、Rx、Ry、X1、X2、X3、X4、n、p、q和t如本文所定义，这些化合物作为视黄醇相关孤儿受体γt（RORγt）的调节剂具有活性。这些化合物可以预防、抑制或抑制RORγt的作用，因此在治疗RORγt介导的疾病、紊乱、综合症或症状方面具有用处，例如疼痛、炎症、慢性阻塞性肺病（COPD）、哮喘、类风湿性关节炎、结肠炎、多发性硬化症、牛皮癣、神经退行性疾病和癌症。
• Compounds as ROR gamma modulators
  申请人：Glenmark Pharmaceuticals S.A.

  公开号：US10344024B2

  公开（公告）日：2019-07-09

  The present disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein ring A, ring B, L, R1, R2, R3, R4, R5, Ra, Rb, n, m, p and q are as defined herein, which are active as modulators of retinoid-related orphan receptor gamma t (RORγt). These compounds prevent, inhibit, or suppress the action of RORγt and are therefore useful in the treatment of RORγt mediated diseases, disorders, syndromes or conditions such as, e.g., pain, inflammation, COPD, asthma, rheumatoid arthritis, colitis, multiple sclerosis, psoriasis, neurodegenerative diseases and cancer.

  本公开涉及式（I）化合物及其药学上可接受的盐类，其中环 A、环 B、L、R1、R2、R3、R4、R5、Ra、Rb、n、m、p 和 q 如本文所定义，它们作为视黄醇相关孤儿受体 gamma t（RORγt）的调节剂具有活性。这些化合物可防止、抑制或抑制 RORγt 的作用，因此可用于治疗 RORγt 介导的疾病、失调、综合症或病症，如疼痛、炎症、慢性阻塞性肺病、哮喘、类风湿性关节炎、结肠炎、多发性硬化症、银屑病、神经退行性疾病和癌症。
• MASHEVSKAYA M. S.; VAXRIN M. I., IZV. VUZOV. XIMIYA I XIM. TEXNOL., 1979, 22, HO 11, 1323-1326
  作者：MASHEVSKAYA M. S.、 VAXRIN M. I.

  DOI：——

  日期：——
• MASHEVSKAYA M. S.; PETYUNIN P. A., IZV. VYSSH. UCHEB. ZAVEDENIJ, XIMIYA I XIM. TEXNOL., 1977, 20, HO 2, 174-+
  作者：MASHEVSKAYA M. S.、 PETYUNIN P. A.

  DOI：——

  日期：——
• NOVEL COMPOUNDS AS ROR GAMMA MODULATORS
  申请人：Glenmark Pharmaceuticals S.A.

  公开号：US20170233380A1

  公开（公告）日：2017-08-17

  The present disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein ring A, ring B, L, R 1 , R 2 , R 3 , R 4 , R 5 , R a , R b , n, m, p and q are as defined herein, which are active as modulators of retinoid-related orphan receptor gamma t (RORγt). These compounds prevent, inhibit, or suppress the action of RORγt and are therefore useful in the treatment of RORγt mediated diseases, disorders, syndromes or conditions such as, e.g., pain, inflammation, COPD, asthma, rheumatoid arthritis, colitis, multiple sclerosis, psoriasis, neurodegenerative diseases and cancer.