4-amino-N-benzylbutyramide | 103621-64-3

• 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: 4-amino-N-benzylbutyramide
• 英文别名: 4-amino-N-benzylbutanamide
• CAS: 103621-64-3
• 化学式: C₁₁H₁₆N₂O
• 分子量: 192.261
• InChiKey: DCRRVDXYSHOJEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯-1-乙氧基乙胺 、 4-amino-N-benzylbutyramide 、 三氟乙酸 在 三乙胺 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Identification of Multiple Structurally Distinct, Nonpeptidic Small Molecule Inhibitors of Protein Arginine Deiminase 3 Using a Substrate-Based Fragment Method

  摘要：

  The protein arginine deiminases (PADs) are a family of enzymes that catalyze the post-translational hydrolytic deimination of arginine residues. Four different enzymologically active PAD subtypes have been characterized and exhibit tissue-specific expression and association with a number of different diseases. In this Article we describe the development of an approach for the reliable discovery of low molecular weight, nonpeptidic fragment substrates of the PADs that then can be optimized and converted to mechanism-based irreversible PAD inhibitors. The approach is demonstrated by the development of potent and selective inhibitors of PAD3, a PAD subtype implicated in the neurodegenerative response to spinal cord injury. Multiple structurally distinct inhibitors were identified with the most potent inhibitors having >10,000 min(-1) M-1 k(inact)/K-I values and >= 10-fold selectivity for PAD3 over PADs 1, 2, and 4.

  DOI：

  10.1021/jacs.5b00095
• 作为产物：
  描述：

  苄胺 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-amino-N-benzylbutyramide
  参考文献：
  名称：

  Identification of Multiple Structurally Distinct, Nonpeptidic Small Molecule Inhibitors of Protein Arginine Deiminase 3 Using a Substrate-Based Fragment Method

  摘要：

  The protein arginine deiminases (PADs) are a family of enzymes that catalyze the post-translational hydrolytic deimination of arginine residues. Four different enzymologically active PAD subtypes have been characterized and exhibit tissue-specific expression and association with a number of different diseases. In this Article we describe the development of an approach for the reliable discovery of low molecular weight, nonpeptidic fragment substrates of the PADs that then can be optimized and converted to mechanism-based irreversible PAD inhibitors. The approach is demonstrated by the development of potent and selective inhibitors of PAD3, a PAD subtype implicated in the neurodegenerative response to spinal cord injury. Multiple structurally distinct inhibitors were identified with the most potent inhibitors having >10,000 min(-1) M-1 k(inact)/K-I values and >= 10-fold selectivity for PAD3 over PADs 1, 2, and 4.

  DOI：

  10.1021/jacs.5b00095

文献信息

• Absence of stereoelectronic control in hydrolysis of cyclic amidines
  作者：Charles L. Perrin、Oswaldo. Nunez

  DOI：10.1021/ja00279a055

  日期：1986.9

  L'hydrolyse de trois amidines cycliques a 6 chainons donne essentiellement un aminoamide (produit de decyclisation) et seulement 3,9% de lactame (produit theorique). Par contre l'hydrolyse de trois amidines cycliques a 5 ou 7 chainons donne environ 50% de lactame

  L'hydrolyse de trois camides cycliques a 6 chainons donne essentiellement unaminoamide (produit de decyclisation) et seulement 3,9% de lactame (produit theorique)。Par contre l'hydrolyse de trois amidines cycliques a 5 ou 7 chainons donne environment 50% de内酰胺
• 2-Pyrrolidinone moiety is not critical for the cognition-enhancing activity of piracetam-like drugs
  作者：Serena Scapecchi、Cecilia Martelli、Carla Ghelardini、Luca Guandalini、Elisabetta Martini、Fulvio Gualtieri

  DOI：10.1016/s0014-827x(03)00111-3

  日期：2003.9

  Following the indications of previous work, 2-pyrrolidinone moiety of piracetam and piracetam-like compounds has been opened to the corresponding amide derivatives. As found previously in the case of 1,4-diazabicyclo[4.3.0]nonan-9-one compounds, the cognition-enhancing activity of 2-pyrrolidinone compounds is maintained in most cases, suggesting that this moiety is not crucial for activity.
• INHIBITOR COMPOUNDS OF 11-BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1
  申请人：Laboratorios SALVAT, S.A.

  公开号：EP2439202B1

  公开（公告）日：2016-04-20
• USE OF AMINES AND AMIDES FOR THE STABILIZATION OF ORGANIC MICRONIZED UV ABSORBERS
  申请人：BASF SE

  公开号：EP2120846A2

  公开（公告）日：2009-11-25
• US8524894B2
  申请人：——

  公开号：US8524894B2

  公开（公告）日：2013-09-03