(2S,5'R)-Tricholomic acid | 24135-91-9

• 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: (2S,5'R)-Tricholomic acid
• 英文别名: (2S)-2-amino-2-[(5R)-3-oxo-1,2-oxazolidin-5-yl]acetic acid
• CAS: 24135-91-9
• 化学式: C₅H₈N₂O₄
• 分子量: 160.13
• InChiKey: NTHMUJMQOXQYBR-FONMRSAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,5'R)-Tricholomic acid
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization at Glutamate Receptors of the Four Enantiopure Isomers of Tricholomic Acid

  摘要：

  The two enantiomeric pairs of erythro- and threo-amino-(3'-hydroxy-4',5'-dihydro-isoxazol-5'-yl)-acetic acids were synthesized via the 1,3-dipolar cycloaddition of bromonitrile oxide to (R)- or (S)-3-(tert-butoxycarbonyl)2,2-dimethyl-4-vinyloxazolidine. The pharmacological profiles of the studied amino acids reflect the relationship between the activity/selectivity and the stereochemistry of the two stereogenic centers: while the (2S,5'S) stereoisomer is an agonist at the AMPA and KA receptors, its (2R,5'R) enantiomer interacts selectively with the NMDA receptors; the (2S,5'R) stereoisomer is the only one capable to activate the mGluRs.

  DOI：

  10.1021/jm701394a

文献信息

• Total synthesis of antitumor agent at-125, (αS,5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid
  作者：Jack E. Baldwin、Jin K. Cha、Lawrence I. Kruse

  DOI：10.1016/s0040-4020(01)96774-2

  日期：1985.1

  A short and efficient total synthesis of racemic AT-125 and its racemic threo isomer proceeds via an intramolecular Michael cyclization of a protected α,β-dehydroglutamic acid γ-hydroxamate. Separation of diastereomers and deprotection to racemic AT-125 followed by enzymatic resolution of the N-chloroacetamide with hog-kidney acylase provides the natural αS,5S isomer.

  外消旋AT-125及其外消旋苏式异构体的短而有效的全合成通过受保护的α，β-脱氢谷氨酸γ-异羟肟酸酯的分子内迈克尔环化进行。分离非对映异构体并将其脱保护为外消旋AT-125，然后用猪肾酰化酶酶促拆分N-氯乙酰胺，即可提供天然αS，5 S异构体。
• Synthesis and pharmacological characterization at glutamate receptors of erythro- and threo-tricholomic acid and homologues thereof
  作者：Paola Conti、Marco De Amici、Gabriella Roda、Andrea Pinto、Lucia Tamborini、Ulf Madsen、Birgitte Nielsen、Hans Bräuner-Osborne、Carlo De Micheli

  DOI：10.1016/j.tet.2006.12.066

  日期：2007.3

  The erythro- and threo-amino-(3′-hydroxy-4′,5′-dihydro-isoxazol-5′-yl)-acetic acids, stereoisomers of tricholomic acid, were synthesized along with the corresponding higher homologues erythro- and threo-amino-(3′-carboxy-4′,5′-dihydro-isoxazol-5′-yl)-acetic acids. The target compounds were prepared via the 1,3-dipolar cycloaddition of a suitable nitrile oxide to (±)-2-tert-butoxycarbonylamino-3-buten-1-ol

  所述赤-和苏式-氨基- （3'-羟基-4'，5'-二氢-异恶唑-5'-基） -乙酸，tricholomic酸的立体异构体，分别与相应的高级同系物沿着合成赤-和苏-氨基-（3'-羧基-4'，5'-二氢-异恶唑-5'-基）-乙酸。通过将合适的腈氧化物与（±）-2-叔丁基的1,3-偶极环加成制备目标化合物-丁氧基羰基氨基-3-丁烯-1-醇。这种策略允许以可比较的量合成两个立体异构氨基酸。通过对大鼠皮膜的受体结合试验，电生理试验和在CHO细胞中表达的克隆受体的第二信使试验，研究了这些化合物对离子型和代谢型谷氨酸受体（iGluR和mGluRs）的药理活性。将它们的药理学特征与1-谷氨酸盐和先前描述的选择性NMDA受体拮抗剂5-（2-氨基-2-羧乙基）-4,5-二氢异恶唑-3-羧酸的药理学特征进行了比较，以强调增加剂量的作用。减小代表两个药效团实体的氨基酸部分和远端酸基团之间的距离。
• Synthesis and Pharmacological Characterization at Glutamate Receptors of the Four Enantiopure Isomers of Tricholomic Acid
  作者：Andrea Pinto、Paola Conti、Marco De Amici、Lucia Tamborini、Ulf Madsen、Birgitte Nielsen、Thomas Christesen、Hans Bräuner-Osborne、Carlo De Micheli

  DOI：10.1021/jm701394a

  日期：2008.4.1

  The two enantiomeric pairs of erythro- and threo-amino-(3'-hydroxy-4',5'-dihydro-isoxazol-5'-yl)-acetic acids were synthesized via the 1,3-dipolar cycloaddition of bromonitrile oxide to (R)- or (S)-3-(tert-butoxycarbonyl)2,2-dimethyl-4-vinyloxazolidine. The pharmacological profiles of the studied amino acids reflect the relationship between the activity/selectivity and the stereochemistry of the two stereogenic centers: while the (2S,5'S) stereoisomer is an agonist at the AMPA and KA receptors, its (2R,5'R) enantiomer interacts selectively with the NMDA receptors; the (2S,5'R) stereoisomer is the only one capable to activate the mGluRs.