5-(3-Aminopropyl)imidazolidine-2,4-dione | 69489-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-(3-Aminopropyl)imidazolidine-2,4-dione
• CAS: 69489-33-4
• 化学式: C₆H₁₁N₃O₂
• mdl: MFCD01851013
• 分子量: 157.172
• InChiKey: SSCQGFVQZYZZSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  84.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氯-1-乙氧基乙胺 、 5-(3-Aminopropyl)imidazolidine-2,4-dione 在 base 作用下， 以 甲醇 为溶剂， 反应 0.5h， 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：

  N^δ-benzyloxycarbonyl D,L-ornithine hydantoin 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 5-(3-Aminopropyl)imidazolidine-2,4-dione
  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

• Neue Mikroorganismen, deren Verwendung und Verfahren zur Herstellung von L-Alpha-Aminosäuren
  申请人：Degussa Aktiengesellschaft

  公开号：EP0625571A2

  公开（公告）日：1994-11-23

  2.1. N-5-monosubstituierte Hydantoine können fermentativ bzw. enzymatisch in die enantiomerenreine L-α-Aminosäure umgewandelt werden. Aufgabe sind neue Mikroorganismen, die einfach zu kultivieren sind und hohe L-α-Aminosäure-Ausbeuten aus verschiedenen Substraten ermöglichen. 2.2. Die Mikroorganismen DSM 7329 und 7330 sind geeignet zur Herstellung von L-α-Aminosäuren aus entsprechenden Hydantoinen oder Carbamoyl-α-Aminosäuren. Vorzugsweise erfolgt die Umsetzung mit ruhenden Mikroorganismen. 2.3. Herstellung von verschiedenen L-α-Aminosäuren.

  2.1 N-5-单取代海因可以通过发酵或酶法转化为对映体纯度高的 L-α-氨基酸。我们的任务是开发易于培养的新微生物，使各种底物都能产生高产率的 L-α-氨基酸。 2.2 微生物 DSM 7329 和 7330 适用于从相应的海因或氨基甲酰-α-氨基酸生产 L-α-氨基酸。反应最好使用休眠微生物进行。 2.3 制备各种 L-α-氨基酸。
• Neuer Mikroorganismus, dessen Verwendung und Verfahren zur Herstellung von L-Alpha-Aminosäuren
  申请人：Degussa-Hüls Aktiengesellschaft

  公开号：EP0745678B1

  公开（公告）日：2001-03-14
• US4691021A
  申请人：——

  公开号：US4691021A

  公开（公告）日：1987-09-01
• US5714355A
  申请人：——

  公开号：US5714355A

  公开（公告）日：1998-02-03
• Identification of Multiple Structurally Distinct, Nonpeptidic Small Molecule Inhibitors of Protein Arginine Deiminase 3 Using a Substrate-Based Fragment Method
  作者：Haya Jamali、Hasan A. Khan、Joseph R. Stringer、Somenath Chowdhury、Jonathan A. Ellman

  DOI：10.1021/jacs.5b00095

  日期：2015.3.18

  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.