2-pivaloylamino-4-hydroxy-6-(4-carboxyphenylethynyl)pyrido[2,3-d]pyrimidine

• 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-pivaloylamino-4-hydroxy-6-(4-carboxyphenylethynyl)pyrido[2,3-d]pyrimidine
• 英文别名: 2-Pivaloylamino-4-hydroxy-6-(4-carboxyphenylethynyl)pyrido[2,3-d]pyrimidine；4-[2-[2-(2,2-dimethylpropanoylamino)-4-oxo-3H-pyrido[2,3-d]pyrimidin-6-yl]ethynyl]benzoic acid
• 化学式: C₂₁H₁₈N₄O₄
• 分子量: 390.398
• InChiKey: WWZVCZYGJDPXMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-pivaloylamino-4-hydroxy-6-(4-carboxyphenylethynyl)pyrido[2,3-d]pyrimidine 在 palladium on activated charcoal N-甲基吗啉 、 N-甲基吡咯烷酮 、 氢气 、 N-苯基磷氨基氯化苯 作用下， 以 三氟乙酸 为溶剂， 25.0 ℃ 、365.42 kPa 条件下， 反应 48.83h， 生成 diethyl N-<4-<<2-(pivaloylamino)-4-hydroxy-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl>ethyl>benzoyl>-L-glutamate
  参考文献：
  名称：

  Convergent and efficient palladium-effected synthesis of 5, 10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF)

  摘要：

  DOI：

  10.1021/jo00276a023
• 作为产物：
  描述：

  2-(pivaloylamino)-4-hydroxy-6-<<4-(tert-butoxycarbonyl)phenyl>ethynyl>pyrido<2,3-d>pyrimidine 在 盐酸 作用下， 以 硝基甲烷 为溶剂， 反应 1.0h， 以93%的产率得到2-pivaloylamino-4-hydroxy-6-(4-carboxyphenylethynyl)pyrido[2,3-d]pyrimidine
  参考文献：
  名称：

  Convergent and efficient palladium-effected synthesis of 5, 10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF)

  摘要：

  DOI：

  10.1021/jo00276a023

文献信息

• N-(5,6,7,8-tetrahydropyrido(2,3-D)pyrimidin-6-yl-alkanoyl)-glutamic acid derivatives
  申请人：THE TRUSTEES OF PRINCETON UNIVERSITY

  公开号：EP0343801A2

  公开（公告）日：1989-11-29

  A compound selected from the group consisting of a glutamic acid derivative of the formula: in which: R¹ is -OH or -NH₂; R² is hydrogen or a carboxy protecting group; R³ is a carbon-carbon bond, alkylene of 1 to 4 car­bon atoms, cyclohexylene, or R⁴ is hydrogen or an amino protecting group; Q is -S- or -O-; R⁵ is hydrogen, chloro or fluoro; and the configuration about the carbon atom designated * is S; and the pharmaceutically acceptable salts thereof. Also disclosed is a method of combatting neoplastic growth in a mammal and a pharmaceutical composition for combatting neoplastic growth in a mammal making use of the above compound.

  本发明涉及一种从以下组合中选择的化合物：其中：R¹为-OH或-NH₂；R²为氢或羧基保护基；R³为碳-碳键，1到4个碳原子的烷基，环己烷基，或R⁴为氢或氨基保护基；Q为-S-或-O-；R⁵为氢，氯或氟；并且指定的碳原子*的构型为S；以及其药学上可接受的盐。本发明还公开了一种在哺乳动物中对抗肿瘤生长的方法和一种制备上述化合物的药物组合物，用于对抗哺乳动物中的肿瘤生长。
• 6-alkenyl and ethynyl derivatives of
  申请人：The Trustees of Princeton University

  公开号：US04902796A1

  公开（公告）日：1990-02-20

  2-Amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-en-1-yl]pyrido[2,3,-d]pyrimid ines and 2-amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-yn-1-yl]pyrido[2,3-d]pyrimid ines are prepared through the reaction of a halo-aromatic compound and an unsaturated compound in the prosence of a palladium catalyst. The products are chemical intermediates for the preparation of antineo-plastic agents. A typical embodiment is the reaction of a protected 2-amino-4-hydroxy-6-ethynylpyrido[2,3-d]pyrimidine and an ester of 4-iodobenzoic acid.

  2-氨基-4-羟基-6-[2-(4-羧基苯基)烯基]吡啶[2,3-d]嘧啶和2-氨基-4-羟基-6-[2-(4-羧基苯基)炔基]吡啶[2,3-d]嘧啶是通过在钯催化剂的存在下，卤素芳香化合物和不饱和化合物的反应制备而成。这些产物是制备抗肿瘤药物的化学中间体。一个典型的实施例是保护的2-氨基-4-羟基-6-乙炔基吡啶[2,3-d]嘧啶和4-碘苯甲酸酯的反应。
• Process for the preparation of fused pyridine compounds
  申请人：The Trustees of Princeton University

  公开号：US04988813A1

  公开（公告）日：1991-01-29

  2-Amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-en-1-yl]pyrido[2,3,-d]pyrimid ines and 2-amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-yn-1-yl]pyrido[2,3-d]pyrimid ines are prepared through through the reaction of a haloaromatic compound and an unsaturated compound in the presence of a palladium catalyst. The products are chemical intermediates for the preparation of antineoplastic agents. A typical embodiment is the reaction of a protected 2-amino-4-hydroxy-6-ethynylpyrido[2,3-d]pyrimidine and an ester of 4-iodobenzoic acid.

  2-氨基-4-羟基-6-[2-(4-羧基苯基)烯丙基]吡啶[2,3-d]嘧啶和2-氨基-4-羟基-6-[2-(4-羧基苯基)炔基]吡啶[2,3-d]嘧啶是通过在钯催化剂的存在下，卤代芳香化合物和不饱和化合物反应制备而成。这些产物是制备抗肿瘤药物的化学中间体。一个典型的实施例是保护的2-氨基-4-羟基-6-乙炔基吡啶[2,3-d]嘧啶和4-碘苯甲酸酯的反应。
• N-(5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl-alkanoyl)-glutamic acid
  申请人：The Trustess of Princeton University

  公开号：US04882333A1

  公开（公告）日：1989-11-21

  N-alkanoylglutamic acid derivatives in which the alkanoyl group is substituted with the 2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-yl or 2,4-diamino-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl group are antineoplastic agents. Typical embodiments are N-[6-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)hexa noyl]-L-glutamic acid and N-[4--(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl ethyl}cyclohex-1-yl]-L-glutamic acid.

  N-烷酰谷氨酸衍生物，其中烷酰基被2-氨基-4-羟基-5,6,7,8-四氢吡咯[2,3-d]嘧啶-6-基或2,4-二氨基-5,6,7,8-四氢吡咯[2,3-d]嘧啶-6-基取代，是抗肿瘤剂。典型的实施例包括N-[6-(2-氨基-4-羟基-5,6,7,8-四氢吡咯[2,3-d]嘧啶-6-基)己酰基]-L-谷氨酸和N-[4--(2-氨基-4-羟基-5,6,7,8-四氢吡咯[2,3-d]嘧啶-6-基乙基}环己-1-基]-L-谷氨酸。
• TAYLOR, EDWARD C.;WONG, GEORGE S. K.
  作者：TAYLOR, EDWARD C.、WONG, GEORGE S. K.

  DOI：——

  日期：——