N-hydroxymethyl-N'-phenyl hydantoin | 33584-02-0

• 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: N-hydroxymethyl-N'-phenyl hydantoin
• 英文别名: 3-hydroxymethyl-1-phenylhydantoin；3-hydroxymethyl-1-phenyl-imidazolidine-2,4-dione；3-(Hydroxymethyl)-1-phenylimidazolidine-2,4-dione
• CAS: 33584-02-0
• 化学式: C₁₀H₁₀N₂O₃
• 分子量: 206.201
• InChiKey: CPCOYQZHKVRIJM-UHFFFAOYSA-N

物化性质

• 沸点：
  343.7±44.0 °C(Predicted)
• 密度：
  1.406±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-hydroxymethyl-N'-phenyl hydantoin 在 三溴化磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 以86%的产率得到3-bromomethyl-1-phenyl-imidazolidine-2,4-dione
  参考文献：
  名称：

  Substituted 3-(Phenylsulfonyl)-1-phenylimidazolidine-2,4-dione Derivatives as Novel Nonpeptide Inhibitors of Human Heart Chymase

  摘要：

  A series of 3-(phenylsulfonyl)-1-phenylimidazolidine-2,4-dione derivatives have been synthesized and evaluated for their ability to selectively inhibit human heart chymase. The structure-activity relationship studies on these compounds gave the following results. The 1-phenyl moiety participates in a hydrophobic interaction where an optimum size is required. At this position, 3,4-dimethylphenyl is the best moiety for inhibiting chymase and showed high selectivity compared with chymotrypsin and cathepsin G. A 3-phenylsulfonyl moiety substituted with hydrogen-bond accepters such as nitrile and methoxycarbonyl enhances its activity. Molecular-modeling studies on the interaction of 3-[(4-chlorophenyl)sulfonyl]-1-(4-chlorophenyl)imidazolidine-2,4-dione (29) with the active site of human heart chymase suggested that the 1-phenyl moiety interacts with the hydrophobic P-1 pocket, the 3-phenylsulfonyl moiety resides in the S-1'-S-2' subsites, and the 4-carbonyl of the imidazolidine ring and sulfonyl group interact with the oxyanion hole and the His-45 side chain of chymase, respectively. The complex model is consistent with the structure-activity relationships.

  DOI：

  10.1021/jm960793t
• 作为产物：
  描述：

  聚合甲醛 、 1-苯基咪唑烷-2,4-二酮 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到N-hydroxymethyl-N'-phenyl hydantoin
  参考文献：
  名称：

  Substituted 3-(Phenylsulfonyl)-1-phenylimidazolidine-2,4-dione Derivatives as Novel Nonpeptide Inhibitors of Human Heart Chymase

  摘要：

  A series of 3-(phenylsulfonyl)-1-phenylimidazolidine-2,4-dione derivatives have been synthesized and evaluated for their ability to selectively inhibit human heart chymase. The structure-activity relationship studies on these compounds gave the following results. The 1-phenyl moiety participates in a hydrophobic interaction where an optimum size is required. At this position, 3,4-dimethylphenyl is the best moiety for inhibiting chymase and showed high selectivity compared with chymotrypsin and cathepsin G. A 3-phenylsulfonyl moiety substituted with hydrogen-bond accepters such as nitrile and methoxycarbonyl enhances its activity. Molecular-modeling studies on the interaction of 3-[(4-chlorophenyl)sulfonyl]-1-(4-chlorophenyl)imidazolidine-2,4-dione (29) with the active site of human heart chymase suggested that the 1-phenyl moiety interacts with the hydrophobic P-1 pocket, the 3-phenylsulfonyl moiety resides in the S-1'-S-2' subsites, and the 4-carbonyl of the imidazolidine ring and sulfonyl group interact with the oxyanion hole and the His-45 side chain of chymase, respectively. The complex model is consistent with the structure-activity relationships.

  DOI：

  10.1021/jm960793t

文献信息

• [EN] METHOD FOR THE SYNTHESIS OF AMINOALKYLENEPHOSPHONIC ACID<br/>[FR] PROCÉDÉ DE SYNTHÈSE D'ACIDE AMINOALKYLÈNEPHOSPHONIQUE
  申请人：STRAITMARK HOLDING AG

  公开号：WO2014012987A1

  公开（公告）日：2014-01-23

  The present invention is related to a method for the synthesis of an aminoalkylenephosphonic acid or its phosphonate esters comprising the following steps: a) forming, in the presence of an aldehyde or ketone and an acid catalyst, a reaction mixture by mixing a compound comprising at least one HNR1R2 moiety or a salt thereof, with a compound having one or more P-O-P anhydride moieties, said moieties comprising one P atom at the oxidation state (+III) and one P atom at the oxidation state (+III) or (+V), wherein the ratio of moles of aldehyde or ketone to N-H moieties is 1 or more and wherein the ratio of N-H moieties to P-O-P anhydride moieties is 0.3 or more and, b) recovering the resulting aminoalkylenephosphonic acid comprising compound or its phosphonate esters.

  本发明涉及一种合成氨基烯膦酸或其膦酸酯的方法，包括以下步骤：a) 在醛或酮和酸催化剂的存在下，通过将至少含有一个HNR1R2基团或其盐的化合物与至少含有一个或多个P-O-P酸酐基团的化合物混合形成反应混合物，所述基团包括一个氧化态为(+III)的P原子和一个氧化态为(+III)或(+V)的P原子，其中醛或酮的摩尔比与N-H基团的比值为1或更多，N-H基团与P-O-P酸酐基团的比值为0.3或更多；b) 回收所得的氨基烯膦酸化合物或其膦酸酯。