Dimethyl N-(4-ethynylbenzoyl)-L-glutamate | 135352-72-6

• 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: Dimethyl N-(4-ethynylbenzoyl)-L-glutamate
• 英文别名: dimethyl 4-ethynylbenzoyl-L-glutamate；Dimethyl 4-ethynylbenzoylglutamate；dimethyl (2S)-2-[(4-ethynylbenzoyl)amino]pentanedioate
• CAS: 135352-72-6
• 化学式: C₁₆H₁₇NO₅
• 分子量: 303.315
• InChiKey: LLIOKEUXNHKVHC-ZDUSSCGKSA-N

物化性质

• 沸点：
  470.1±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Dimethyl N-(4-ethynylbenzoyl)-L-glutamate 在 palladium on activated charcoal copper(l) iodide 、 四(三苯基膦)钯 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0~60.0 ℃ 、344.73 kPa 条件下， 反应 52.0h， 生成 dimethyl N-<4-<2-(2-pivaloylamino-4(3H)-oxo-7H-pyrrolo<2,3-d>pyrimidin-6-yl)ethyl>benzoyl>-L-glutamate
  参考文献：
  名称：

  Taylor, Edward C.; Young, Wendy B.; Chaudhari, Rajendra, Heterocycles, 1993, vol. 36, # 8, p. 1897 - 1908

  摘要：

  DOI：

文献信息

• Pyrrolo(2,3-d)pyrimidines
  申请人：The Trustees of Princeton University

  公开号：US05248775A1

  公开（公告）日：1993-09-28

  3-Ethynylpyrrolo[2,3-d]pyrimidines are chemical intermediates for antineoplastic N-(acyl)glutamic acid derivatives. A typical embodiment is 3-ethynyl-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine.

  3-乙炔基吡咯并[2,3-d]嘧啶是抗肿瘤N-(酰基)谷氨酸衍生物的化学中间体。一个典型的实施例是3-乙炔基-4-羟基-6-异戊酰胺基吡咯并[2,3-d]嘧啶。
• N-(pyrrolo(2,3-d)pyrimidin-3-ylacyl)-glutamic acid derivatives
  申请人：Trustees of Princeton University

  公开号：US05344932A1

  公开（公告）日：1994-09-06

  N-(Acyl)glutamic acid derivatives in which the acyl group is substituted with 4-hydroxypyrrolo[2,3-d]-pyrimidin-3-yl group are antineoplastic agents. A typical embodiment is N-[4-(2-4-hydroxy-6-aminopyrrolo-[2,3-d]pyrimidin-3-yl}ethyl)benzoyl]-L-g lutamic acid.

  N-(酰基)谷氨酸衍生物中，酰基被4-羟基吡咯并[2,3-d]-嘧啶-3-基取代，具有抗肿瘤作用。典型的实施例是N-[4-(2-4-羟基-6-氨基吡咯并[2,3-d]嘧啶-3-基}乙基)苯甲酰]-L-谷氨酸。
• Process for the synthesis of 4-hydroxy-5-halopyrrolo 2,3-D pyrimidine intermediates
  申请人：ELI LILLY AND COMPANY

  公开号：EP0576211A2

  公开（公告）日：1993-12-29

  4-Hydroxypyrrolo[2,3-d]pyrimidines are regiospecifically halogenated at the C-5 position by silylation in the presence of an inert organic solvent and iodination, bromination or chlorination.

  4-羟基吡咯并[2,3-d]嘧啶是在惰性有机溶剂存在下，通过硅烷化、碘化、溴化或氯化反应，在 C-5 位进行特定的区域卤化。
• Synthesis of pyrazolo 3,4-pyrimidine analogues of the potent agent N-4-2-2-amino-4 3-oxo-7-pyrrolo 2,3-pyrimidin-5-yl ethylbenzoyl-L-glutamic acid (LY231514)
  作者：Edward C. Taylor、Hemantkumar H. Patel

  DOI：10.1016/s0040-4020(01)80479-8

  日期：1992.1

  Several pyrazolo[3,4-d]pyrimidine analogues of the potent antitumor agent N-4-12-(2-amino-4(3H)-oxo-7H-pyrrolo [2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid (LY231514, 5) have been prepared. A principal synthetic step proved to be a palladium-catalyzed C-C coupling of the 5-halo-substituted pyrazolo[3,4-d]pyrimidines 12-15 with dimethyl 4-ethynylbenzoyl-L-glutamate (16). An additional pyrazolo[3,4-d]pyrimidine analogue of 5 possessing an isofolic acid bridge unit (-NHCH2-) was prepared by reductive alkylation of diethyl 4-formylbenzoyl-L-glutamate (31) with 2-methyl-5-amino-4(3H)-oxo-7H-pyrazolo[3,4-d]pyrimidine (30). Only compound 26 proved to have in vitro cell growth inhibitory activity.
• Synthesis of <i>N</i>-{4-[2-(2-Amino-5,6-dihydro-4(3<i>H</i>)-oxo-7<i>H</i>-pyrrolo[2,3-<i>d</i>]pyrimidin-6-yl)- ethyl]benzoyl}-<scp>l</scp>-glutamic Acid:  A Ring-Contracted Analogue of 5,10-Dideaza-5,6,7,8-tetrahydrofolic Acid
  作者：Edward C. Taylor、Wendy B. Young、Carsten Spanka

  DOI：10.1021/jo951471k

  日期：1996.1.1

  This paper describes the synthesis of N-(4-[2-(2-amino-5,6-dihydro-4(3H)-oxo-7H-pyrrolo[2,3-d]-pyrimidin-6-yl)ethyl]benzoyl) -L-glutamic acid (4), which can be viewed as a ring-contracted analogue of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF, 1) in which the C-7 methylene group of the latter has been excised and C-6 joined to N-8. This compound exhibits significant activity as an inhibitor of the growth of human (CCRF-CEM) lymphoblastic leukemic cells in vitro and apparently acts by blocking de novo purine biosynthesis through inhibition of glycinamide ribonucleotide formyltransferase (GAR FTase).