5'-(bis(2-hydroxyethyl)amino)-1',3'-dihydrospiro[imidazolidine-4,2'-indene]-2,5-dione | 1240303-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5'-(bis(2-hydroxyethyl)amino)-1',3'-dihydrospiro[imidazolidine-4,2'-indene]-2,5-dione
• CAS: 1240303-17-6
• 化学式: C₁₅H₁₉N₃O₄
• 分子量: 305.334
• InChiKey: XZPAOHRMTHQMDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.85
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  101.9
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5'-(bis(2-hydroxyethyl)amino)-1',3'-dihydrospiro[imidazolidine-4,2'-indene]-2,5-dione 在 三氯氧磷 作用下， 生成
  参考文献：
  名称：

  Regiospecific and conformationally restrained analogs of melphalan and dl-2-NAM-7 and their affinities for the large neutral amino acid transporter (system LAT1) of the blood–brain barrier

  摘要：

  Regiospecific and conformationally restrained analogs of melphalan and DL-2-NAM-7 have been synthesized and their affinities for the large neutral amino acid transporter (LAT1) of the blood-brain barrier have been determined to assess their potential for accessing the CNS via facilitated transport. Several analogs had K-i values in the range 2.1-8.5 mu M with greater affinities than that of either L-phenylalanine (K-i = 11 mu M) or melphalan (K-i = 55 mu M), but lower than DL-2-NAM-7 (K-i = 0.08 mu M). The results indicate that regiospecific positioning of the mustard moiety on the aromatic ring in these analogs is very important for optimal affinity for the large neutral amino acid transporter, and that conformational restriction of the DL-2-NAM-7 molecule in benzonorbornane and indane analogs leads to 25- to 60-fold loss, respectively, in affinity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.086
• 作为产物：
  描述：

  环氧乙烷 、 1',3'-二氢螺[咪唑烷-4,2'-茚]-2,5-二酮 在 硝酸 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 生成 5'-(bis(2-hydroxyethyl)amino)-1',3'-dihydrospiro[imidazolidine-4,2'-indene]-2,5-dione 、
  参考文献：
  名称：

  Regiospecific and conformationally restrained analogs of melphalan and dl-2-NAM-7 and their affinities for the large neutral amino acid transporter (system LAT1) of the blood–brain barrier

  摘要：

  Regiospecific and conformationally restrained analogs of melphalan and DL-2-NAM-7 have been synthesized and their affinities for the large neutral amino acid transporter (LAT1) of the blood-brain barrier have been determined to assess their potential for accessing the CNS via facilitated transport. Several analogs had K-i values in the range 2.1-8.5 mu M with greater affinities than that of either L-phenylalanine (K-i = 11 mu M) or melphalan (K-i = 55 mu M), but lower than DL-2-NAM-7 (K-i = 0.08 mu M). The results indicate that regiospecific positioning of the mustard moiety on the aromatic ring in these analogs is very important for optimal affinity for the large neutral amino acid transporter, and that conformational restriction of the DL-2-NAM-7 molecule in benzonorbornane and indane analogs leads to 25- to 60-fold loss, respectively, in affinity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.086