(R)-2-amino-3-(4-methylphenyl)propanamide | 1246351-09-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-amino-3-(4-methylphenyl)propanamide
• 英文别名: β-(p-tolyl)-D-alaninamide；(2R)-2-amino-3-(4-methylphenyl)propanamide
• CAS: 1246351-09-6
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: YWWCETNVBOLXJS-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (R)-2-amino-3-(4-methylphenyl)propanamide 以 甲醇 为溶剂， 以83%的产率得到N2-Boc-β-(p-tolyl)-D-alaninamide
  参考文献：
  名称：

  Enantiopure trans-3-Arylaziridine-2-carboxamides: Preparation by Bacterial Hydrolysis and Ring-Openings toward Enantiopure, Unnatural d-α-Amino Acids

  摘要：

  Several racemic trans-3-arylaziridine-2-carboxamides were prepared and then resolved by Rhodococcus rhodochrous IFO 15564-catalyzed hydrolysis. The resulting enantiopure (2R,3S)-3-arylaziridine-2-carboxamides are adequate substrates to undergo fully stereoselective nucleophilic ring-openings at the C-3 ring position to finally yield enantiopure, unnatural D-alpha-aminocarboxylic acids. Experimental evidence is provided that suggests the fate of the (2S,3R)-3-arylaziridine-2-carboxylic acids concomitantly formed during the resolution processes. In this context, the similar bacterial resolution of racemic 1-arylaziridine-2-carboxamides and -carbonitriles, previously investigated by our research group, has been partially re-examined.

  DOI：

  10.1021/jo101377j
• 作为产物：
  描述：

  (2R,3S)-3-(p-tolyl)aziridine-2-carboxamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以100%的产率得到(R)-2-amino-3-(4-methylphenyl)propanamide
  参考文献：
  名称：

  Enantiopure trans-3-Arylaziridine-2-carboxamides: Preparation by Bacterial Hydrolysis and Ring-Openings toward Enantiopure, Unnatural d-α-Amino Acids

  摘要：

  Several racemic trans-3-arylaziridine-2-carboxamides were prepared and then resolved by Rhodococcus rhodochrous IFO 15564-catalyzed hydrolysis. The resulting enantiopure (2R,3S)-3-arylaziridine-2-carboxamides are adequate substrates to undergo fully stereoselective nucleophilic ring-openings at the C-3 ring position to finally yield enantiopure, unnatural D-alpha-aminocarboxylic acids. Experimental evidence is provided that suggests the fate of the (2S,3R)-3-arylaziridine-2-carboxylic acids concomitantly formed during the resolution processes. In this context, the similar bacterial resolution of racemic 1-arylaziridine-2-carboxamides and -carbonitriles, previously investigated by our research group, has been partially re-examined.

  DOI：

  10.1021/jo101377j

文献信息

• NOVEL NICOTINAMIDE DERIVATIVE OR SALT THEREOF
  申请人：FUJIWARA Hideyasu

  公开号：US20130116430A1

  公开（公告）日：2013-05-09

  An object of the present invention is to provide to a compound and a pharmaceutical composition, which have excellent Syk-inhibitory activity. The present invention provides a nicotinamide derivative represented by the following formula (I) (wherein R 1 represents a halogen atom; R 2 represents a C 1-12 alkyl group, a C 2-12 alkenyl group, a C 2-12 alkynyl group, a C 3-8 cycloalkyl group, an aryl group, an ar-C 1-6 alkyl group or a heterocyclic group, each optionally having at least one substituent; R 3 represents an aryl group or a heterocyclic group each optionally having at least one substituent; and R 4 and R 5 each independently represent a hydrogen atom; and R 2 and R 4 may form a cyclic amino group optionally having at least one substituent together with the nitrogen atom to which they bind) or a salt thereof, and a pharmaceutical composition for use in the treatment of a Syk-related disease which comprises the nicotinamide derivative or a salt thereof.

  本发明的目的是提供一种具有优异的Syk抑制活性的化合物和制药组合物。本发明提供了一种由以下式(I)表示的烟酰胺衍生物（其中R1表示卤素原子；R2表示C1-12烷基、C2-12烯基、C2-12炔基、C3-8环烷基、芳基、芳基-C1-6烷基或杂环基，每种均可选地具有至少一个取代基；R3表示芳基或杂环基，每种均可选地具有至少一个取代基；R4和R5各自独立地表示氢原子；且R2和R4可以与它们结合的氮原子一起形成具有至少一个取代基的环状氨基团）或其盐，并且用于治疗Syk相关疾病的制药组合物包括该烟酰胺衍生物或其盐。
• US8772320B2
  申请人：——

  公开号：US8772320B2

  公开（公告）日：2014-07-08
• US8809371B2
  申请人：——

  公开号：US8809371B2

  公开（公告）日：2014-08-19
• US8895585B2
  申请人：——

  公开号：US8895585B2

  公开（公告）日：2014-11-25
• Enantiopure <i>trans</i>-3-Arylaziridine-2-carboxamides: Preparation by Bacterial Hydrolysis and Ring-Openings toward Enantiopure, Unnatural <scp>d</scp>-α-Amino Acids
  作者：Roberto Morán-Ramallal、Ramón Liz、Vicente Gotor

  DOI：10.1021/jo101377j

  日期：2010.10.1

  Several racemic trans-3-arylaziridine-2-carboxamides were prepared and then resolved by Rhodococcus rhodochrous IFO 15564-catalyzed hydrolysis. The resulting enantiopure (2R,3S)-3-arylaziridine-2-carboxamides are adequate substrates to undergo fully stereoselective nucleophilic ring-openings at the C-3 ring position to finally yield enantiopure, unnatural D-alpha-aminocarboxylic acids. Experimental evidence is provided that suggests the fate of the (2S,3R)-3-arylaziridine-2-carboxylic acids concomitantly formed during the resolution processes. In this context, the similar bacterial resolution of racemic 1-arylaziridine-2-carboxamides and -carbonitriles, previously investigated by our research group, has been partially re-examined.