N-(4-carbethoxyphenyl)-β-alanine | 6959-76-8

• 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: N-(4-carbethoxyphenyl)-β-alanine
• 英文别名: 3-((4-(ethoxycarbonyl)phenyl)amino)propanoic acid；N-(4-ethoxycarbonyl-phenyl)-β-alanine；N-(4-Aethoxycarbonyl-phenyl)-β-alanin；3-(4-Ethoxycarbonylanilino)propanoic acid
• CAS: 6959-76-8
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: BRZXYYOOKCQWKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-carbethoxyphenyl)-β-alanine 在 platinum(IV) oxide 氯化亚砜 、 sodium azide 、 氢溴酸 、 氢气 作用下， 以 甲醇 、 乙醚 、 水 、 溶剂黄146 、 苯 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 41.5h， 生成 1-azido-4-butane-2-one
  参考文献：
  名称：

  Folate analogs. 20. Synthesis and antifolate activity of 1',2',3',4',5',6'-hexahydrohomofolic acid

  摘要：

  The synthesis of 1',2',3',4',5',6'-hexahydrohomofolic acid (3), a close analogue of homofolic acid (2), has been carried out by replacement of the benzene ring of 2 with a cyclohexane ring. The synthetic methods employed here were based on the Boon-Leigh strategy to obtain products with unambiguous structures. Based on a number of chemical and spectral observations, a tentative cis stereochemistry was assigned to the 1,4-substituents of the cyclohexane ring of both the homopteroate analogue 13 and the target compound 3. We investigated hexahydrohomopteroic acid (13), hexahydrohomofolic acid (3), and their 7,8-dihydro and d,l-5,6,7,8-tetrahydro derivatives for antifolate activity employing several biological test systems. The dihydro and tetrahydro derivatives of both 13 and 3 were active against Streptococcus faecium, whereas they were inactive against Lactobacillus casei. These compounds were neither substrates nor inhibitors of L. casei dihydrofolate reductase or thymidylate synthase.

  DOI：

  10.1021/jm00356a004
• 作为产物：
  描述：

  β-丙内酯 、 苯佐卡因 以 丙酮 为溶剂， 反应 4.0h， 以52%的产率得到N-(4-carbethoxyphenyl)-β-alanine
  参考文献：
  名称：

  设计，合成和生物学评价新型吡咯并[2,3-d]嘧啶作为肿瘤靶向剂，对还原性叶酸载体具有高亲和力的叶酸受体选择性吸收肿瘤。

  摘要：

  在2碳桥上，通过杂原子N（4），O（5）或S取代邻位（C11）碳，在4碳桥上等位修饰基于肿瘤的6取代吡咯并[2,3- d ]嘧啶苯甲酰基化合物。（6），或具有N-取代的甲酰基（7），三氟乙酰基（8）或乙酰基（9）。用硫替代（6）提供了最有效的KB肿瘤细胞抑制剂，比亲代2好约6倍。另外6通过叶酸受体（FR）α和-β在普遍存在的还原性叶酸载体（RFC）上保留了肿瘤的转运选择性。FRα介导的6细胞抑制作用通常相当于2，而FRβ介导的活性是2的16倍。N（4）和O（5）替代提供了与2类似的肿瘤细胞抑制作用，相对RFC对FRα和-β具有选择性。所述Ñ取代类似物7 - 9为FRα还保存运输选择性和-β在RFC。对于表达FRα的CHO细胞，效价为8  >  7  >  9。而8和9在表达FRβ的CHO细胞中显示出相似的结果，而7的活性是2的16倍。通过核苷挽救实验，所有化合物均可能在嘌呤酰胺核糖核苷酸甲

  DOI：

  10.1016/j.bmc.2020.115544

文献信息

• Cyclopenta[d]pyrimidines And Substituted Cyclopenta[d]pyrimidines As Antitubulin and Microtubule Targeting Agents, Monocyclic Pyrimidines As Tubulin Inhibitors, And Pyrrolopyrimidines As Targeted Antifolates And Tubulin and Multiple Receptor Tyrosine Kinase Inhibition And Antitumor Agents
  申请人：Duquesne University of the Holy Spirit

  公开号：US20160304525A1

  公开（公告）日：2016-10-20

  The present invention provides a compound of Formula I, and salts thereof, and a pharmaceutical composition comprising a compound of Formula I: wherein R 1 is selected from the group consisting of and R 2 is an alkyl group having from one to ten carbon atoms, or wherein R 2 is selected from the group consisting of R 1 is an alkyl group having from one to ten carbon atoms; and R is H, or an alkyl group having from one to ten carbon atoms, and R 3 is H, an alkyl group having from one to ten carbon atoms, or a halogen. Preferably the compound of Formula V includes wherein R 3 is a halogen, and most preferably wherein the halogen is chlorine. Methods of treating a patient with cancer with these compounds are also provided.

  本发明提供了一种化合物I的盐，以及包括化合物I的药物组合物：其中R1选自以下组成的群体，R2是具有一到十个碳原子的烷基基团，或者R2选自以下组成的群体，R1是具有一到十个碳原子的烷基基团；R是H，或者具有一到十个碳原子的烷基基团，R3是H，具有一到十个碳原子的烷基基团，或者卤素。优选化合物V包括其中R3是卤素，最优选其中卤素是氯。还提供了使用这些化合物治疗癌症患者的方法。
• Cyclopenta[d]pyrimidines and substituted cyclopenta[d]pyrimidines as antitubulin and microtubule targeting agents, monocyclic pyrimidines as tubulin inhibitors, and pyrrolopyrimidines as targeted antifolates and tubulin and multiple receptor tyrosine kinase inhibition and antitumor agents
  申请人：Duquesne University of the Holy Spirit

  公开号：US10239880B2

  公开（公告）日：2019-03-26

  The present invention provides a compound of Formula I, and salts thereof, and a pharmaceutical composition comprising a compound of Formula I: wherein R1 is selected from the group consisting of and R2 is an alkyl group having from one to ten carbon atoms, or wherein R2 is selected from the group consisting of R1 is an alkyl group having from one to ten carbon atoms; and R is H, or an alkyl group having from one to ten carbon atoms, and R3 is H, an alkyl group having from one to ten carbon atoms, or a halogen. Preferably the compound of Formula V includes wherein R3 is a halogen, and most preferably wherein the halogen is chlorine. Methods of treating a patient with cancer with these compounds are also provided.

  本发明提供了一种式 I 的化合物及其盐类，以及一种包含式 I 化合物的药物组合物： 其中 R1 选自以下组成的组 和 R2 是具有 1 至 10 个碳原子的烷基，或 其中 R2 选自以下组成的组 R1 是具有一至十个碳原子的烷基；R 是 H 或具有一至十个碳原子的烷基，R3 是 H、具有一至十个碳原子的烷基或卤素。其中 R3 是卤素，最优选的是卤素是氯。还提供了用这些化合物治疗癌症患者的方法。
• Cyclopenta[d]pyrimidines and substituted cyclopenta[d]pyrimidines as antitubulin and microtubule targeting agents, monocyclic pyrimidines as tubulin inhibitors, and pyrrolopyrimidines as targeted antifolates and tubulin and multiple receptor tyrosine kinase inhibitor and antitumor agents
  申请人：Duquesne University of the Holy Spirit

  公开号：US11124520B2

  公开（公告）日：2021-09-21

  The present invention provides a compound of Formula III, and salts thereof, and a pharmaceutical composition comprising a compound of Formula III: wherein R1 is selected from the group consisting of: wherein R2 is H or an alkyl group having from one to ten carbon atoms; R3 is H or an alkyl group having from one to ten carbon atoms; and R4 is H or an alkyl group having from one to ten carbon atoms. Methods of treating a patient with cancer with these compounds are also provided.

  本发明提供了一种式 III 的化合物及其盐类，以及一种包含式 III 化合物的药物组合物： 其中 R1 选自以下组成的组 在其中 R2 是 H 或具有一至十个碳原子的烷基； R3 是 H 或具有一至十个碳原子的烷基；以及 R4 是 H 或具有一至十个碳原子的烷基。还提供了用这些化合物治疗癌症患者的方法。
• Reaction of Propiolactone with Aniline Derivatives
  作者：Charles D. Hurd、Shin Hayao

  DOI：10.1021/ja01143a019

  日期：1952.12
• [EN] CYCLOPENTA[D]PYRIMIDINES AND SUBSTITUTED CYCLOPENTA[D]PYRIMIDINES AS ANTITUBULIN AND MICROTUBULE TARGETING AGENTS, MONOCYCLIC PYRIMIDINES AS TUBULIN INHIBITORS, AND PYRROLOPYRIMIDINES AS TARGETED ANTIFOLATES AND TUBULIN AND MULTIPLE RECEPTOR TYROSINE KINASE INHIBITION AND ANTITUMOR AGENTS<br/>[FR] CYCLOPENTA[D]PYRIMIDINES ET CYCLOPENTA[D]PYRIMIDINES SUBSTITUÉES UTILISÉES EN TANT QU'AGENTS ANTITUBULINE ET DE CIBLAGE DE MICROTUBULES, PYRIMIDINES MONOCYCLIQUES UTILISÉES EN TANT QU'INHIBITEURS DE TUBULINE, ET PYRROLOPYRIMIDINES UTILISÉES EN TANT QU'ANTIFOLATES CIBLÉS ET AGENTS ANTITUMORAUX ET D'INHIBITION DE TUBULINE ET DE TYROSINE KINASE À RÉCEPTEURS MULTIPLES
  申请人：UNIV HOLY GHOST DUQUESNE

  公开号：WO2016168637A2

  公开（公告）日：2016-10-20

  The present invention provides a pyrimidine compound and salts thereof, and substituted pyrimidine compounds and salts thereof, and a pharmaceutical composition comprising these compounds. Methods of treating a patient with cancer with these compounds are also provided.