4-aminomethylbenzoyl-L-glutamic acid diethyl ester | 39271-60-8

• 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: 4-aminomethylbenzoyl-L-glutamic acid diethyl ester
• 英文别名: Diethyl N-[4-(aminomethyl)benzoyl]-L-glutamate；diethyl N-(4-aminomethylbenzoyl)-L-glutamate；diethyl (2S)-2-[[4-(aminomethyl)benzoyl]amino]pentanedioate
• CAS: 39271-60-8
• 化学式: C₁₇H₂₄N₂O₅
• 分子量: 336.388
• InChiKey: TYQIWOBAZGHGGP-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-aminomethylbenzoyl-L-glutamic acid diethyl ester 在 sodium hydroxide 、 caesium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 (S)-2-{4-[(3-Carboxy-6,7-difluoro-quinoxalin-2-ylamino)-methyl]-benzoylamino}-pentanedioic acid
  参考文献：
  名称：

  Quinoxaline chemistry. Part 13: 3-carboxy-2-benzylamino-substituted quinoxalines and N-[4-[(3-carboxyquinoxalin-2-yl) aminomethyl]benzoyl]-l-glutamates: synthesis and evaluation of in vitro anticancer activity

  摘要：

  Among a new series of 28 3-carboxy or carbethoxy quinoxalines bearing a substituted benzylamino or N-[4-(aminomethyl)benzoyl]glutamate group on position 2 of the ring and various substituents at C-6, 7 positions, 21 were selected at the National Cancer Institute for evaluation of their in vitro anticancer activity. The results obtained seem to confirm that the carboxy or carbethoxy group on position 3 is not helpful, with a few exceptions, for the anticancer activity. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00119-6
• 作为产物：
  描述：

  三氟乙酸 、 diethyl N-<4-<methyl>benzoyl>-L-glutamate 在 甲醇 、 氯仿 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以to yield about 0.68 g of Compound 35的产率得到4-aminomethylbenzoyl-L-glutamic acid diethyl ester
  参考文献：
  名称：

  Pyrimidine derivatives and methods of making and using these derivatives

  摘要：

  本发明揭示了化合物及其药学上可接受的盐，用于治疗或预防患有疾病的患者。这些疾病包括癌症，以及免疫功能受损患者中由肺孢子菌和弓形虫引起的继发感染。本发明还揭示了这些化合物本身，制备这些化合物的方法以及使用这些化合物的方法。

  公开号：

  US20030144509A1

文献信息

• Synthesis of Classical and a Nonclassical 2-Amino-4-oxo-6-methyl-5-substituted Pyrrolo[2,3-<i>d</i>]pyrimidine Antifolate Inhibitors of Thymidylate Synthase
  作者：Aleem Gangjee、Farahnaz Mavandadi、Roy L. Kisliuk、Sherry F. Queener

  DOI：10.1021/jm980586o

  日期：1999.6.1

  Compounds 2-5 were designed as potential antifolate nonpolyglutamatable inhibitors of thymidylate synthase (TS). These analogues are structurally related to 2-amino-4-oxo-5-substituted quinazolines and 2-amino-4-oxo-5-substituted pyrrolo[2, 3-d]pyrimidines which have shown excellent inhibition of TS and, for the quinazoline, significant promise as clinically useful antitumor agents. Compounds 2-4 were

  将化合物2-5设计为潜在的胸苷酸合酶（TS）的抗叶酸非多聚谷氨酸抑制剂。这些类似物在结构上与2-氨基-4-氧代-5-取代的喹唑啉和2-氨基-4-氧代5-取代的吡咯并[2,3-d]嘧啶有关，它们对TS表现出优异的抑制作用，并且对于喹唑啉作为临床上有用的抗肿瘤药物具有重大前景。通过在新戊酰基保护的5-二甲基氨基甲基取代的6-甲基吡咯并[2,3-d]嘧啶7上的适当的胺交换反应，合成了化合物2-4，而后者又是从吡咯烷基化的6-甲基吡咯并[3]的曼尼希反应中获得的。 2，2，3-d]嘧啶6.在胺交换反应缓慢的情况下，用甲基碘将曼尼希碱季铵化，从而提供了更快的交换反应，并提高了收率。对于化合物5 4-巯基吡啶用作亲核试剂并与7反应。类似物2-4抑制干酪乳杆菌（lc）TS和重组人（h）TS，IC50在10（-4）至10（-5）M范围内。化合物5在26和25 microM分别抑制lcTS和hTS 20％。
• Novel pyrimidine derivatives and methods of making and using these derivatives
  申请人：——

  公开号：US20020052384A1

  公开（公告）日：2002-05-02

  This invention discloses pyrimidine derivatives, and pharmaceutically acceptable salts and prodrugs thereof, useful in therapeutically and/or prophylactically treating patients with an illness. Such illnesses include cancer, and secondary infections caused by Pneumocystis carinii and Toxoplasmosis gondii in immunocompromised patients. The compounds themselves, methods of making these compounds, and methods of using these compounds are all disclosed.

  本发明披露了嘧啶衍生物及其药学上可接受的盐和前药，用于治疗患有疾病的患者的治疗和/或预防。这种疾病包括癌症和免疫功能受损的患者因肺孢子菌和弓形虫感染而引起的继发感染。本发明披露了这些化合物本身，制备这些化合物的方法以及使用这些化合物的方法。
• Pyrimidine derivatives and method of making and using derivatives
  申请人：Duquesne University of the Holy Ghost

  公开号：US06420370B1

  公开（公告）日：2002-07-16

  This invention discloses compounds, and pharmaceutically acceptable salts thereof, useful in therapeutically and/or prophylactically treating patients with an illness. Such illnesses include cancer, and secondary infections caused by Pneumocystis carinii and Toxoplasmosis gondii in immunocompromised patients. The compounds themselves, methods of making these compounds, and methods of using these compounds are all disclosed.

  该发明揭示了化合物及其药学上可接受的盐，可用于治疗或预防患有疾病的患者。这些疾病包括癌症，以及免疫受损患者中由肺孢子虫和弓形虫引起的继发性感染。该发明还揭示了这些化合物本身、制备这些化合物的方法以及使用这些化合物的方法。
• Furopyrimidines and methods of making and using the same derivatives
  申请人：Duquesne University of the Holy Ghost

  公开号：US06096750A1

  公开（公告）日：2000-08-01

  This invention discloses compounds, and pharmaceutically acceptable salts thereof, useful in therapeutically and/or prophylactically treating patients with an illness. Such illnesses include cancer, and secondary infections caused by Pneumocystis carinii and Toxoplasmosis gondii in immunocompromised patients. The compounds themselves, methods of making these compounds, and methods of using these compounds are all disclosed. More specifically, furo[2,3-d[pyrimidines are disclosed.

  本发明揭示了化合物及其药学上可接受的盐，用于治疗和/或预防患有疾病的患者。这些疾病包括癌症以及由免疫系统受损引起的Pneumocystis carinii和Toxoplasmosis gondii的继发感染。该发明揭示了这些化合物本身、制备这些化合物的方法以及使用这些化合物的方法。更具体地，揭示了furo[2,3-d[pyrimidines。
• Furo-pyrimidine derivatives and methods of making and using these
  申请人：Duquesne University of the Holy Ghost

  公开号：US05863920A1

  公开（公告）日：1999-01-26

  This invention discloses furo-pyrimidine compounds, and pharmaceutically acceptable salts thereof, useful in therapeutically and/or prophylactically treating patients with an illness. Such illnesses include cancer, and secondary infections caused by Pneumocystis carinii and Toxoplasmosis gondii in immunocompromised patients. The furo-pyrimidine compounds themselves, methods of making these compounds, and methods of using these furo-pyrimidine compounds are all disclosed.

  该发明揭示了呋喃嘧啶化合物及其药学上可接受的盐，可用于治疗和/或预防患有疾病的患者。这些疾病包括癌症以及免疫功能受损患者由肺孢子虫和弓形虫引起的继发感染。本发明还揭示了呋喃嘧啶化合物本身、制备这些化合物的方法以及使用这些呋喃嘧啶化合物的方法。