2-Pivaloyl-6-formyl-5-deazapterin | 120040-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 2-Pivaloyl-6-formyl-5-deazapterin
• 英文别名: 2-Pivaloylamino-4-hydroxy-6-formylpyrido[2,3-d]pyrimidine；N-(6-formyl-4-oxo-3H-pyrido[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide
• CAS: 120040-44-0
• 化学式: C₁₃H₁₄N₄O₃
• 分子量: 274.279
• InChiKey: UXVKWTDUPVJDII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Pivaloyl-6-formyl-5-deazapterin 在 platinum(IV) oxide sodium hydroxide 、 三乙胺-硼烷 、 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 92.5h， 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
• 作为产物：
  描述：

  2-氨基-6-溴吡啶并[2,3-d]嘧啶-4(3H)-酮 在 吡啶 、 copper(l) iodide 、 palladium diacetate 、 臭氧 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 30.0h， 生成 2-Pivaloyl-6-formyl-5-deazapterin
  参考文献：
  名称：

  Taylor, Edward C.; Yoon, Cheol-min, Synthetic Communications, 1988, vol. 18, # 11, p. 1187 - 1192

  摘要：

  DOI：

文献信息

• Synthesis of <i>p</i>-Aminophenyl Aryl H-Phosphinic Acids and Esters via Cross-Coupling Reactions:  Elaboration to Phosphinic Acid Pseudopeptide Analogues of Pteroyl Glutamic Acid and Related Antifolates
  作者：Yonghong Yang、James K. Coward

  DOI：10.1021/jo0707840

  日期：2007.7.1

  addition of either a PIII species or phosphorus anion, generated in situ from either the free H-phosphinic acid or ester, to a 2-methylene glutaric acid ester provided the aryl phosphinic acid analogue of p-aminobenzoyl glutamic acid. Alkylation of these suitably protected p-aminophenyl phosphinic acid esters with a 6-(bromomethyl)pteridine or the corresponding (bromomethyl)pyridopyrmidine, followed by hydrolytic

  由相应的对位取代的芳基卤化物合成适当保护的对氨基苯基H-次膦酸和酯，是通过在不存在或存在正硅酸四烷基酯的情况下，通过次磷酸苯磺酸亚磷鎓的钯催化交叉偶联反应完成的。分别提供游离的H-次膦酸或相应的酯。随后将由游离的H-次膦酸或酯原位产生的P III物种或磷阴离子共轭加成至2-亚甲基戊二酸酯，提供了对氨基苯甲酰基谷氨酸的芳基次膦酸类似物。这些适当保护的p的烷基化与6-（溴甲基）蝶啶或相应的（溴甲基）吡啶吡啶-甲基-氨基苯基次膦酸酯，然后水解除去保护基，提供了叶酸和相关抗叶酸的目标芳基次膦酸类似物。或者，为合成稍大规模的叶酸或5-脱氮叶酸类似物，可以用任一N 2进行还原胺化-乙酰基或N 2优选-新戊酰基-6-甲酰基蝶呤或相应的甲酰基吡啶并吡啶和相同的适当保护的对-氨基苯基次膦酸酯，然后除去保护基。在该研究过程中，观察到与未取代的对应物相比，苯胺氮和衍生自对氨基苯次膦酸衍生物的各种P III物质的亲核性均显着降低。
• N-[N-(tetrahydropyrido[2,3-D]pyrimidinylmethyl)-aminomethylbenzo
  申请人：The Trustees of Princeton University

  公开号：US04871746A1

  公开（公告）日：1989-10-03

  N-[N-(Tetrahydropyrido[2,3-d]pyrimidinylmethyl) aminomethylbenzoyl]glutamic acid derivatives are antineoplastic agents with an effect on one or more enzymes which utilize metabolic derivatives of folic acid. The compounds can be prepared by allowing a protected aminomethylbenzoylglutamic acid derivative to react with 2-amino-4-hydroxy-6-formylpyrido[2,3-d]pyrimidine, reducing the intermediate Schiff base, and subjecting the intermediate to catalytic hydrogenation. A typical embodiment is (S,S) N-[N-(2-amino-4-hydroxy-5,6,7,8- tetrahydropyrido-[2,3-d]pyrimidin-6-ylmethyl)-4-aminomethylbenzoyl]-glutam ic acid.

  N-[N-(四氢吡啶[2,3-d]嘧啶基甲基)氨甲基苯甲酰基]谷氨酸衍生物是一种抗肿瘤药物，对利用叶酸代谢产物的一个或多个酶具有作用。该化合物可通过将受保护的氨甲基苯甲酰谷氨酸衍生物与2-氨基-4-羟基-6-甲酰基吡啶[2,3-d]嘧啶反应，还原中间产物席夫碱，并将中间产物经催化氢化处理而制备得到。一个典型的实施例是(S,S)N-[N-(2-氨基-4-羟基-5,6,7,8-四氢吡啶[2,3-d]嘧啶-6-基甲基)-4-氨甲基苯甲酰基]-谷氨酸。
• N-(N-(tetrahydropyrido(2,3-d)pyrimidinylmethyl)-aminomethylbenzoyl)glutamic acid derivatives
  申请人：THE TRUSTEES OF PRINCETON UNIVERSITY

  公开号：EP0344922A2

  公开（公告）日：1989-12-06

  N-[N-(Tetrahydropyrido[2,3-d]pyrimidinylmethyl)aminomethylbenzoyl]glutamic acid derivatives of formula are anti-neoplastic agents with an effect on one or more enzymes which utilize metabolic derivatives of folic acid. The compounds can be prepared by allowing a protected aminomethylbenzoylglutamic acid derivative to react with 2-amino-4-hydroxy-6-formylpyrido[2,3-d]pyrimidine, reducing the intermediate Schiff base, and subjecting the intermediate to catalytic hydrogenation. A typical embodiment is (S,S) N-[N-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido-[2,3-d]pyrimidin-6-ylmethyl)-4-aminomethylbenzoyl]-glutamic acid.

  N-[N-(四氢吡啶并[2,3-d]嘧啶甲基)氨甲基苯甲酰基]谷氨酸衍生物的式 是一种抗肿瘤药，对一种或多种利用叶酸代谢衍生物的酶有影响。这些化合物可以通过使受保护的氨甲基苯甲酰基谷氨酸衍生物与 2-氨基-4-羟基-6-甲酰基吡啶并[2,3-d]嘧啶反应，还原中间体席夫碱，并使中间体进行催化氢化反应来制备。一个典型的实施方案是 (S,S) N-[N-(2-氨基-4-羟基-5,6,7,8-四氢吡啶并[2,3-d]嘧啶-6-基甲基)-4-氨基甲基苯甲酰基]-谷氨酸。
• Inhibitors of Glycinamide Ribonucleotide Formyltransferase as Potential Cytotoxic Agents. Synthesis of 5-Deaza-5,6,7,8-tetrahydrohomofolic Acid, 5-Deaza-5,6,7,8-tetrahydroisohomofolic Acid, and 10-Formyl-5-deaza-5,6,7,8-tetrahydroisohomofolic Acid
  作者：Edward C. Taylor、Cheol-min Yoon、James M. Hamby

  DOI：10.1021/jo00102a039

  日期：1994.11

  Syntheses of three new analogs of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF, Lometrexol)-5-deaza-5,6,7,8-tetrahydrohomofolic acid (11), 5-deaza-5,6,7,8-tetrahydroisohomofolic acid (16a), and 10-formyl-5-deaza-5,6,7,8-tetrahydroisohomofolic acid (16b)-are described.
• TAYLOR, EDWARD C.;HAMBY, JAMES M.;SHIH, CHUAN;GRINDEY, GERALD B.;RINZEL, +, J. MED. CHEM., 32,(1989) N, C. 1517-1522
  作者：TAYLOR, EDWARD C.、HAMBY, JAMES M.、SHIH, CHUAN、GRINDEY, GERALD B.、RINZEL, +

  DOI：——

  日期：——