N-cinnamoyl phenylalanine | 49659-77-0

• 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: N-cinnamoyl phenylalanine
• 英文别名: N-(3t-phenyl-acryloyl)-phenylalanine；N-trans-cinnamoyl-DL-phenylalanine；N-trans-Cinnamoyl-DL-phenylalanin；opt.inakt. trans-Cinnamoyl-DL-phenylalanin；3-phenyl-2-[[(E)-3-phenylprop-2-enoyl]amino]propanoic acid
• CAS: 49659-77-0
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: YFHVCODMDZNZEA-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-cinnamoyl phenylalanine 在 碘苯二乙酸 、 碘 、 苯甲酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以55%的产率得到5-phenyl-2-[(E)-2-phenylethenyl]-1,3-oxazole
  参考文献：
  名称：

  氨基酸一锅转化为2,5-二取代的恶唑：不需要金属

  摘要：

  Abstract2,5‐Disubstituted oxazoles with a variety of alkyl and aryl groups are efficiently formed from N‐acylamino acids, by a one‐pot radical decarboxylation–oxidation–enolization and iodine‐promoted cyclization process. Remarkably, the reaction takes place under mild conditions, and no metal catalysis is needed. The process can be useful for the direct modification of small peptides.magnified image

  DOI：

  10.1002/adsc.201400496
• 作为产物：
  描述：

  肉桂酸 在 sodium hydroxide 、 氯化亚砜 作用下， 以 水 、 丙酮 为溶剂， 反应 3.83h， 生成 N-cinnamoyl phenylalanine
  参考文献：
  名称：

  Phenylalanine derivatives enhancing intestinal absorption of insulin in mice.

  摘要：

  研究了N-酰基-L-和D-苯丙氨酸衍生物对正常小鼠胰岛素肠道吸收的辅助效应。根据小鼠口服胰岛素和辅料联合给药后的血糖浓度和胰岛素水平，推测了N-酰基部分的化学结构性质与促吸收活性之间的相关性。N-酰基-苯丙氨酸衍生物对胰岛素肠道吸收具有辅效应的化学结构性质如下：1. 芳环存在，与酰基羰基相隔两个原子。2. 图2中的X或Y之一为氧，或者X-Y是双键。3. N-酰基部分具有较小的疏水取代基，如F、Cl或Me在Rα、Rβ、Rη位置，并且整个分子具有适当的亲水-疏水平衡。利用这些制剂增强胰岛素吸收，为口服胰岛素治疗提供了新的途径。

  DOI：

  10.1248/cpb.36.4426

文献信息

• Synthesis of unsaturated azlactones from N-acylamino acids
  作者：James M. Riordan、Charles H. Stammer

  DOI：10.1021/jo00919a017

  日期：1974.3
• Direct Acylation of α-Amino Acids and Dipeptides
  作者：Edward Ronwin

  DOI：10.1021/jo50017a014

  日期：1953.11
• PHARMACEUTICAL COMPOSITIONS OF ACTIVE POLYPEPTIDES FOR ENHANCED PHARMACOLOGICAL ACTIVITY THROUGH ORAL AND PARENTERAL ADMINISTRATION
  申请人：Zimmer, Robert H.

  公开号：EP1372733B1

  公开（公告）日：2012-10-03
• TASTE-MODIFYING COMPOUNDS AND USES THEREOF
  申请人：Firmenich SA

  公开号：US20220304352A1

  公开（公告）日：2022-09-29

  The present disclosure generally relates to compounds useful as taste modifiers, particularly as compounds useful for enhancing umami taste, and their use in various comestible products, such as food and beverage products.
• [EN] PLATELET ADDITIVE SOLUTION HAVING A SELF-ASSEMBLING HYDROGEL-FORMING PEPTIDE<br/>[FR] SOLUTION ADDITIVE PLAQUETTAIRE AYANT UN PEPTIDE FORMANT UN HYDROGEL À AUTO-ASSEMBLAGE
  申请人：VELICO MEDICAL INC

  公开号：WO2014120886A1

  公开（公告）日：2014-08-07

  A platelet additive solution (PAS) has an amount of one or more self-assembling hydrogel- forming peptides with none, either, or both of an amount of one or more sialidase inhibitors and one or more β-galactosidase inhibitors; and optionally an amount of one or more glycan-modifying agents; and one or more of PAS components that include a salt, a citrate source, a carbon source, or any combination thereof. The PAS optionally has, as part of the same solution or as a separate solution, a second platelet additive solution having an amount of one or more cationic polymers with none, either, or both of an amount of one or more sialidase inhibitors and one or more β- galactosidase inhibitors; and optionally an amount of one or more glycan-modifying agents; and one or more of PAS components that include a salt, a citrate source, a carbon source, or any combination thereof.