N-pyrimidin-6-yl)methyl>-4-aminobenzoyl>glutamic Acid | 115499-24-6

• 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: N-pyrimidin-6-yl)methyl>-4-aminobenzoyl>glutamic Acid
• 英文别名: (6R,6S)-5-deaza-tetrahydrofolate；(2S)-2-[[4-[(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pyrido[2,3-d]pyrimidin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
• CAS: 115499-24-6
• 化学式: C₂₀H₂₄N₆O₆
• 分子量: 444.447
• InChiKey: XQZVRAWIARJOCJ-SBNLOKMTSA-N

物化性质

• 熔点：
  198 °C (decomp)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  195
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲酸 、 N-pyrimidin-6-yl)methyl>-4-aminobenzoyl>glutamic Acid 以 乙酸酐 为溶剂， 反应 3.0h， 以47%的产率得到N-pyrimidin-6-yl)methyl>-N¹⁰-formyl-4-aminobenzoyl>glutamic Acid
  参考文献：
  名称：

  Synthesis and antitumor activity of 5-deaza-5,6,7,8-tetrahydrofolic acid and its N10-substituted analogs

  摘要：

  Syntheses of 5-deaza-5,6,7,8-tetrahydrofolic acid (7a) and its 10-formyl (7b), 10-acetyl (7c), and 10-methyl (7d) derivatives are described. These compounds, prepared as analogues of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF), the lead compound of a new class of folate antimetabolites, exhibit potent growth inhibition against leukemic cells in culture as well as substantial antitumor activity against transplantable murine solid tumors in vivo.

  DOI：

  10.1021/jm00127a019
• 作为产物：
  描述：

  Diethyl N-pyrimidin-6-yl>methyl>-4-aminobenzoyl>glutamate 在 platinum(IV) oxide sodium hydroxide 、 氢气 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 76.5h， 生成 N-pyrimidin-6-yl)methyl>-4-aminobenzoyl>glutamic Acid
  参考文献：
  名称：

  Synthesis and antitumor activity of 5-deaza-5,6,7,8-tetrahydrofolic acid and its N10-substituted analogs

  摘要：

  Syntheses of 5-deaza-5,6,7,8-tetrahydrofolic acid (7a) and its 10-formyl (7b), 10-acetyl (7c), and 10-methyl (7d) derivatives are described. These compounds, prepared as analogues of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF), the lead compound of a new class of folate antimetabolites, exhibit potent growth inhibition against leukemic cells in culture as well as substantial antitumor activity against transplantable murine solid tumors in vivo.

  DOI：

  10.1021/jm00127a019

文献信息

• TAYLOR, EDWARD C.;BEARDSLEY, GEORGE P.;HAMBY, JAMES M.
  作者：TAYLOR, EDWARD C.、BEARDSLEY, GEORGE P.、HAMBY, JAMES M.

  DOI：——

  日期：——
• 4(3H)-Oxo-5,6,7,8,-Tetrahydropyrido-(2,3-d)Pyrimidine derivatives
  申请人：THE TRUSTEES OF PRINCETON UNIVERSITY

  公开号：EP0255228B1

  公开（公告）日：1991-05-02
• US4831037A
  申请人：——

  公开号：US4831037A

  公开（公告）日：1989-05-16
• US4833145A
  申请人：——

  公开号：US4833145A

  公开（公告）日：1989-05-23
• Synthesis and antitumor activity of 5-deaza-5,6,7,8-tetrahydrofolic acid and its N10-substituted analogs
  作者：Edward C. Taylor、James M. Hamby、Chuan Shih、Gerald B. Grindey、Sharon M. Rinzel、G. Peter Beardsley、Richard G. Moran

  DOI：10.1021/jm00127a019

  日期：1989.7

  Syntheses of 5-deaza-5,6,7,8-tetrahydrofolic acid (7a) and its 10-formyl (7b), 10-acetyl (7c), and 10-methyl (7d) derivatives are described. These compounds, prepared as analogues of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF), the lead compound of a new class of folate antimetabolites, exhibit potent growth inhibition against leukemic cells in culture as well as substantial antitumor activity against transplantable murine solid tumors in vivo.