(+)-(S)-2-[(1R,5S)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-4-(methylthio)butanoic acid

• 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: (+)-(S)-2-[(1R,5S)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-4-(methylthio)butanoic acid
• 英文别名: (+)-2-[(1R,5S)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-2(S)-4-methylthiobutanoic acid；2-[(1R,5S)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-2(R)-4-methylthiobutanoic acid；(2S)-2-[(3aR,6aS)-2,5-dioxo-3,3a,6,6a-tetrahydro-1H-imidazo[4,5-d]imidazol-4-yl]-4-methylsulfanylbutanoic acid
• 化学式: C₉H₁₄N₄O₄S
• 分子量: 274.301
• InChiKey: ZIJZHICDZSWHSK-HCWXCVPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,5-二羟基四氢-2H-咪唑-2-酮 、 (S)-N-carbamoylmethionine 在 盐酸 作用下， 以 水 为溶剂， 以37%的产率得到(+)-(S)-2-[(1R,5S)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-4-(methylthio)butanoic acid
  参考文献：
  名称：

  Neuroprotective Activity of (+)-(S)-2-[(1S,5R)-(3,7-Dioxo-2,4,6,8-Tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid

  摘要：

  A study of the neurotropic, neuroprotective, and antioxidant action of the enantiomers and racemate of 2-[(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid synthesized in a stereoselective reaction of (R)-, (S)-, or (R,S)-N-carbamoylmethionine with 4,5-dihydroxyimidazolidine-2-one showed that only (+)-(S)-2-[(1S,5R)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid had neuroprotective properties. X-ray structure analysis showed that the predominating racemate of glycolurils is crystallized from aqueous solutions as a conglomerate. Antioxidant activity was not detected.

  DOI：

  10.1134/s106816201205007x

文献信息

• Synthesis of 1S,5R- and 1R,5S-glycoluriles by diastereospecific α-ureidoalkylation of (S)/(R)-N-carbamoyl-α-amino acids with 4,5-dihydroxyimidazolidin-2-one
  作者：Il’ya E. Chikunov、Angelina N. Kravchenko、Pavel A. Belyakov、Konstantin A. Lyssenko、Vladimir V. Baranov、Oleg V. Lebedev、Nina N. Makhova

  DOI：10.1070/mc2004v014n06abeh002050

  日期：2004.1

  A diastereospecific method for the synthesis of individual enantiomers of 1S,5R- and 1R,5S-glycoluriles has been developed based on the α-ureidoalkylation of (S)/(R)-N-carbamoyl-α-amino acids with 4,5-dihydroxyimidazolidin-2-one.

  基于（S）/（R）-N-氨基甲酰基-α-氨基酸与4,5的α-脲基烷基化反应，开发了一种非对映体特异性的方法，用于合成1S，5R-和1R，5S-糖醇的单个对映体-二羟基咪唑烷基-2-酮。
• Highly diastereoselective synthesis of 2-monosubstituted 1R,5S(1S,5R)-glycoluriles on the basis of S- and R-N-carbamoyl-α-amino acids
  作者：Angelina N. Kravchenko、Konstantin Yu. Chegaev、Il’ya E. Chikunov、Pavel A. Belyakov、Elena Yu. Maksareva、Konstantin A. Lyssenko、Oleg V. Lebedev、Nina N. Makhova

  DOI：10.1070/mc2003v013n06abeh001802

  日期：2003.1

  The reactions of 4,5-dihydroxyimidazolidin-2-one with chiral S- and R-N-carbamoyl-alpha-amino acids occur diastereoselectively with the formation of corresponding 1R,5S(1S,5R)-glycoluriles as predominant diastereomers; the absolute configuration is determined for three stereoisomers by X-ray diffraction analysis.
• Neuroprotective Activity of (+)-(S)-2-[(1S,5R)-(3,7-Dioxo-2,4,6,8-Tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid
  作者：A. N. Kravchenko、V. V. Baranov、L. V. Anikina、Yu. B. Vikharev、I. S. Bushmarinov、Yu. V. Nelyubina

  DOI：10.1134/s106816201205007x

  日期：2012.9

  A study of the neurotropic, neuroprotective, and antioxidant action of the enantiomers and racemate of 2-[(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid synthesized in a stereoselective reaction of (R)-, (S)-, or (R,S)-N-carbamoylmethionine with 4,5-dihydroxyimidazolidine-2-one showed that only (+)-(S)-2-[(1S,5R)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid had neuroprotective properties. X-ray structure analysis showed that the predominating racemate of glycolurils is crystallized from aqueous solutions as a conglomerate. Antioxidant activity was not detected.