O-butyryl-L-serine | 63321-66-4

• 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: O-butyryl-L-serine
• 英文别名: O-butanoyl-L-serine；(2S)-2-amino-3-butanoyloxypropanoic acid
• CAS: 63321-66-4
• 化学式: C₇H₁₃NO₄
• 分子量: 175.185
• InChiKey: HTDGDRZVMBNEMO-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-丝氨酸 、 丁酰氯 在 三氟乙酸 作用下， 以79 %的产率得到O-butyryl-L-serine
  参考文献：
  名称：

  WO2022/226482

  摘要：

  公开号：

文献信息

• Prodrugs of Short-Chain Fatty Acids and Treatment Methods
  申请人：Ganapathy Vadivel

  公开号：US20090123388A1

  公开（公告）日：2009-05-14

  Prodrugs made up of biologically-active short-chain fatty acids or derivatives thereof conjugated to neutral or cationic amino acids capable of intracellular transport by ATB 0 , + are provided. The short-chain fatty acid or derivative thereof can be attached to the amino acid through a hydroxyl group of the amino acid to form a fatty acid ester of the amino acid, or it can be attached through the amino group of the amino acid to form a fatty-acid amide of the amino acid. Serine butyrate (O-butyryl serine) is a preferred prodrug. These prodrugs are useful for treatment of colon cancer, inflammatory bowel disease, ulcerative colitis, Crohn's disease, lung cancer, cervical cancer, and cancers resulting from metastases from primary colon cancer sites. Methods of delivering biologically-active short-chain fatty acids or derivatives thereof to cells in need of these molecules and methods of treating diseases using the prodrugs of this invention are also provided.

  本发明提供了由生物活性短链脂肪酸或其衍生物与中性或带正电氨基酸共轭而成的前药。这些氨基酸能够通过ATB0,+进行细胞内转运。短链脂肪酸或其衍生物可通过氨基酸的羟基与氨基酸结合形成氨基酸脂肪酸酯，或可通过氨基酸的氨基与氨基酸结合形成脂肪酸酰胺。丝氨酸丁酸酯（O-丁酰丝氨酸）是首选的前药。这些前药对于治疗结肠癌、炎性肠病、溃疡性结肠炎、克罗恩病、肺癌、宫颈癌以及由原发性结肠癌部位转移引起的癌症都有用处。本发明还提供了将生物活性短链脂肪酸或其衍生物传递到需要这些分子的细胞的方法，以及使用本发明的前药治疗疾病的方法。
• PRODRUGS OF SHORT-CHAIN FATTY ACIDS AND TREATMENT METHODS
  申请人：GANAPATHY VADIVEL

  公开号：US20110245339A1

  公开（公告）日：2011-10-06

  Prodrugs made up of biologically-active short-chain fatty acids or derivatives thereof conjugated to neutral or cationic amino acids capable of intracellular transport by ATB 0 , + are provided. The short-chain fatty acid or derivative thereof can be attached to the amino acid through a hydroxyl group of the amino acid to form a fatty acid ester of the amino acid, or it can be attached through the amino group of the amino acid to form a fatty-acid amide of the amino acid. Serine butyrate (O-butyryl serine) is a preferred prodrug. These prodrugs are useful for treatment of colon cancer, inflammatory bowel disease, ulcerative colitis, Crohn's disease, lung cancer, cervical cancer, and cancers resulting from metastases from primary colon cancer sites. Methods of delivering biologically-active short-chain fatty acids or derivatives thereof to cells in need of these molecules and methods of treating diseases using the prodrugs of this invention are also provided.

  本发明提供了由生物活性短链脂肪酸或其衍生物与能够通过ATB0,+进行细胞内转运的中性或阳离子氨基酸结合而成的前药。短链脂肪酸或其衍生物可以通过氨基酸的羟基与氨基酸结合形成氨基酸脂肪酸酯，也可以通过氨基酸的氨基与氨基酸结合形成脂肪酸酰胺。丝氨酸丁酸酯（O-丁酰丝氨酸）是一种优选的前药。这些前药可用于治疗结肠癌、炎症性肠病、溃疡性结肠炎、克罗恩病、肺癌、宫颈癌以及由原发性结肠癌部位转移引起的癌症。本发明还提供了将生物活性短链脂肪酸或其衍生物输送到需要这些分子的细胞的方法以及使用本发明的前药治疗疾病的方法。
• Prodrugs of short-chain fatty acids and treatment methods
  申请人：Ganapathy Vadivel

  公开号：US08518989B2

  公开（公告）日：2013-08-27

  Prodrugs made up of biologically-active short-chain fatty acids or derivatives thereof conjugated to neutral or cationic amino acids capable of intracellular transport by ATB0,+ are provided. The short-chain fatty acid or derivative thereof can be attached to the amino acid through a hydroxyl group of the amino acid to form a fatty acid ester of the amino acid, or it can be attached through the amino group of the amino acid to form a fatty-acid amide of the amino acid. Serine butyrate (O-butyryl serine) is a preferred prodrug. These prodrugs are useful for treatment of colon cancer, inflammatory bowel disease, ulcerative colitis, Crohn's disease, lung cancer, cervical cancer, and cancers resulting from metastases from primary colon cancer sites. Methods of delivering biologically-active short-chain fatty acids or derivatives thereof to cells in need of these molecules and methods of treating diseases using the prodrugs of this invention are also provided.

  本发明提供了由生物活性短链脂肪酸或其衍生物与能够通过ATB0，+进行细胞内转运的中性或阳离子氨基酸结合而成的前药。短链脂肪酸或其衍生物可以通过氨基酸的羟基与氨基酸结合形成氨基酸的脂肪酸酯，也可以通过氨基酸的氨基与氨基酸结合形成脂肪酰胺。丝氨酸丁酸酯（O-丁酰丝氨酸）是一种首选的前药。这些前药对于治疗结肠癌、炎症性肠病、溃疡性结肠炎、克罗恩病、肺癌、宫颈癌以及由原发性结肠癌部位的转移引起的癌症非常有用。本发明还提供了将生物活性短链脂肪酸或其衍生物传递到需要这些分子的细胞以及使用本发明的前药治疗疾病的方法。
• US8518989B2
  申请人：——

  公开号：US8518989B2

  公开（公告）日：2013-08-27
• [EN] PRODRUGS OF SHORT-CHAIN FATTY ACIDS AND TREATMENT METHODS<br/>[FR] PROMEDICAMENTS D'ACIDES GRAS A CHAINE COURTE ET PROCEDES DE TRAITEMENT
  申请人：MED COLLEGE GEORGIA RES INST

  公开号：WO2006076734A3

  公开（公告）日：2007-02-15

  [EN] Prodrugs made up of biologically-active short-chain fatty acids or derivatives thereof conjugated to neutral or cationic amino acids capable of intracellular transport by ATB⁰,⁺ are provided. The short-chain fatty acid or derivative thereof can be attached to the amino acid through a hydroxyl group of the amino acid to form a fatty acid ester of the amino acid, or it can be attached through the amino group of the amino acid to form a fatty-acid amide of the amino acid. Serine butyrate (O-butyryl serine) is a preferred prodrug. These prodrugs are useful for treatment of colon cancer, inflammatory bowel disease, ulcerative colitis, Crohn's disease, lung cancer, cervical cancer, and cancers resulting from metastases from primary colon cancer sites. Methods of delivering biologically-active short-chain fatty acids or derivatives thereof to cells in need of these molecules and methods of treating diseases using the prodrugs of this invention are also provided.
  [FR] L'invention concerne des promédicaments obtenus à partir d'acides gras à chaîne courte actifs sur le plan biologique ou de dérivés de ceux-ci conjugués à des acides aminés neutres ou cationiques pouvant assurer un transport intracellulaire par ATB^0,+. L'acide gras à chaîne courte ou le dérivé de celui-ci peut être relié à l'acide aminé au moyen d'un groupe hydroxyle de l'acide aminé afin que soit formé un ester d'acide gras de l'acide aminé, ou peut être relié au moyen du groupe amino de l'acide aminé afin que soit formé un amide d'acide gras de l'acide aminé. A titre de promédicament préféré, on peut citer le butyrate de sérine (O-butyryl sérine). Ces promédicaments sont utiles pour le traitement des maladies suivantes : cancer du côlon, maladies intestinales inflammatoires, recto-colite hémorragique, maladie de Crohn, cancer du poumon, cancer du col de l'utérus, et cancers provoqués par des métastases issues de sites du cancer du côlon. L'invention concerne également des procédés d'administration d'acides gras à chaîne courte actifs sur le plan biologique ou de dérivés de ceux-ci à des cellules nécessitant de telles molécules et des procédés de traitement de maladies faisant intervenir lesdits promédicaments.