3-amino-4-[5-[bis(2-chloroethyl)amino]-2-methyl-phenyl]butanoic acid

• 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: 3-amino-4-[5-[bis(2-chloroethyl)amino]-2-methyl-phenyl]butanoic acid
• 英文别名: 3-Amino-4-[5-[bis(2-chloroethyl)amino]-2-methylphenyl]butanoic acid；3-amino-4-[5-[bis(2-chloroethyl)amino]-2-methylphenyl]butanoic acid
• 化学式: C₁₅H₂₂Cl₂N₂O₂
• 分子量: 333.258
• InChiKey: CWYYHMPCMCTGFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 3-benzyloxycarbonylamino-4-[5-[bis(2-chloroethyl)amino]-2-methyl-phenyl]butanoate 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以722 mg的产率得到3-amino-4-[5-[bis(2-chloroethyl)amino]-2-methyl-phenyl]butanoic acid
  参考文献：
  名称：

  BETA-SUBSTITUTED BETA-AMINO ACIDS AND ANALOGS AS CHEMOTHERAPEUTIC AGENTS

  摘要：

  β-取代β-氨基酸，β-取代β-氨基酸衍生物，β-取代β-氨基酸类似物和（生物）同位素及其作为化疗药物的用途被披露。β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物和（生物）同位素是选择性LAT1/4F2hc底物，并在表达LAT1/4F2hc转运蛋白的肿瘤中表现出快速摄取和保留。还披露了合成β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物的方法以及使用这些化合物治疗癌症的方法。β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物在表达LAT1/4F2hc转运蛋白的肿瘤细胞中表现出选择性摄取，并在体内给予受试者后在癌细胞中积累。β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物和（生物）同位素对几种肿瘤类型表现出细胞毒性。

  公开号：

  US20150218086A1

文献信息

• [EN] BETA-SUBSTITUTED BETA-AMINO ACIDS AND ANALOGS AS CHEMOTHERAPEUTIC AGENTS AND USES THEREOF<br/>[FR] ACIDES BÊTA-AMINÉS SUBSTITUÉS EN BÊTA ET ANALOGUES À UTILISER EN TANT QU'AGENTS DE CHIMIOTHÉRAPIE ET LEURS UTILISATIONS
  申请人：QUADRIGA BIOSCIENCES INC

  公开号：WO2017024009A1

  公开（公告）日：2017-02-09

  β-Substituted β-amino acids, β-substituted β-amino acid derivatives, and β-substituted β-amino acid analogs and (bio)isosteres and their use as chemotherapeutic agents are disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres are selective LAT1/4F2hc substrates and exhibit rapid uptake and retention in tumors expressing the LAT1/4F2hc transporter. Methods of synthesizing the β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and methods of using the compounds for treating cancer are also disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs exhibit selective uptake in tumor cells expressing the LAT1/4F2hc transporter and accumulate in cancerous cells when administered to a subject in vivo. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres exhibit cytotoxicity toward several tumor types.

  β-取代β-氨基酸，β-取代β-氨基酸衍生物，β-取代β-氨基酸类似物和（生物）同位素以及它们作为化疗药物的用途被披露。β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物和（生物）同位素是选择性LAT1/4F2hc底物，并在表达LAT1/4F2hc转运蛋白的肿瘤中表现出快速摄取和保留。还披露了合成β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物的方法以及使用这些化合物治疗癌症的方法。β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物在表达LAT1/4F2hc转运蛋白的肿瘤细胞中表现出选择性摄取，并在体内给予受试者后在癌细胞中积累。β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物和（生物）同位素对几种肿瘤类型表现出细胞毒性。
• Beta-substituted beta-amino acids and analogs as chemotherapeutic agents
  申请人：QUADRIGA BIOSCIENCES, INC.

  公开号：US10034847B2

  公开（公告）日：2018-07-31

  β-Substituted β-amino acids, β-substituted β-amino acid derivatives, and β-substituted β-amino acid analogs and (bio)isosteres and their use as chemotherapeutic agents are disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres are selective LAT1/4F2hc substrates and exhibit rapid uptake and retention in tumors expressing the LAT1/4F2hc transporter. Methods of synthesizing the β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and methods of using the compounds for treating cancer are also disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs exhibit selective uptake in tumor cells expressing the LAT1/4F2hc transporter and accumulate in cancerous cells when administered to a subject in vivo. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres exhibit cytotoxicity toward several tumor types.

  本研究公开了 β-取代的 β-氨基酸、β-取代的 β-氨基酸衍生物和 β-取代的 β-氨基酸类似物和（生物）异构体及其作为化疗药物的用途。β-取代的β-氨基酸衍生物和β-取代的β-氨基酸类似物和（生物）异甾烷是选择性的 LAT1/4F2hc 底物，在表达 LAT1/4F2hc 转运体的肿瘤中表现出快速吸收和滞留。此外，还公开了β-取代的β-氨基酸衍生物和β-取代的β-氨基酸类似物的合成方法以及使用这些化合物治疗癌症的方法。β-取代的β-氨基酸衍生物和β-取代的β-氨基酸类似物在表达LAT1/4F2hc转运体的肿瘤细胞中表现出选择性吸收，并且在体内给受试者用药时会在癌细胞中蓄积。β-取代的 β-氨基酸衍生物和 β-取代的 β-氨基酸类似物及（生物）异构体对多种肿瘤类型具有细胞毒性。
• β-substituted β-amino acids and analogs as chemotherapeutic agents and uses thereof
  申请人：Quadriga Biosciences, Inc.

  公开号：US10017459B2

  公开（公告）日：2018-07-10

  β-Substituted β-amino acids, β-substituted β-amino acid derivatives, and β-substituted β-amino acid analogs and (bio)isosteres and their use as chemotherapeutic agents are disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres are selective LAT1/4F2hc substrates and exhibit rapid uptake and retention in tumors expressing the LAT1/4F2hc transporter. Methods of synthesizing the β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and methods of using the compounds for treating cancer are also disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs exhibit selective uptake in tumor cells expressing the LAT1/4F2hc transporter and accumulate in cancerous cells when administered to a subject in vivo. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres exhibit cytotoxicity toward several tumor types.

  本研究公开了 β-取代的 β-氨基酸、β-取代的 β-氨基酸衍生物和 β-取代的 β-氨基酸类似物和（生物）异构体及其作为化疗药物的用途。β-取代的β-氨基酸衍生物和β-取代的β-氨基酸类似物和（生物）异甾烷是选择性的 LAT1/4F2hc 底物，在表达 LAT1/4F2hc 转运体的肿瘤中表现出快速吸收和滞留。此外，还公开了β-取代的β-氨基酸衍生物和β-取代的β-氨基酸类似物的合成方法以及使用这些化合物治疗癌症的方法。β-取代的β-氨基酸衍生物和β-取代的β-氨基酸类似物在表达LAT1/4F2hc转运体的肿瘤细胞中表现出选择性吸收，并且在体内给受试者用药时会在癌细胞中蓄积。β-取代的 β-氨基酸衍生物和 β-取代的 β-氨基酸类似物及（生物）异构体对多种肿瘤类型具有细胞毒性。
• β-substituted β-amino acids and analogs as chemotherapeutic agents
  申请人：QUADRIGA BIOSCIENCES, INC.

  公开号：US10245246B2

  公开（公告）日：2019-04-02

  β-Substituted β-amino acids, β-substituted β-amino acid derivatives, and β-substituted β-amino acid analogs and (bio)isosteres and their use as chemotherapeutic agents are disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres are selective LAT1/4F2hc substrates and exhibit rapid uptake and retention in tumors expressing the LAT1/4F2hc transporter. Methods of synthesizing the β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and methods of using the compounds for treating cancer are also disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs exhibit selective uptake in tumor cells expressing the LAT1/4F2hc transporter and accumulate in cancerous cells when administered to a subject in vivo. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres exhibit cytotoxicity toward several tumor types.

  本研究公开了 β-取代的 β-氨基酸、β-取代的 β-氨基酸衍生物和 β-取代的 β-氨基酸类似物和（生物）异构体及其作为化疗药物的用途。β-取代的β-氨基酸衍生物和β-取代的β-氨基酸类似物和（生物）异甾烷是选择性的 LAT1/4F2hc 底物，在表达 LAT1/4F2hc 转运体的肿瘤中表现出快速吸收和滞留。此外，还公开了β-取代的β-氨基酸衍生物和β-取代的β-氨基酸类似物的合成方法以及使用这些化合物治疗癌症的方法。β-取代的β-氨基酸衍生物和β-取代的β-氨基酸类似物在表达LAT1/4F2hc转运体的肿瘤细胞中表现出选择性吸收，并且在体内给受试者用药时会在癌细胞中蓄积。β-取代的 β-氨基酸衍生物和 β-取代的 β-氨基酸类似物及（生物）异构体对多种肿瘤类型具有细胞毒性。
• Beta-substituted beta-amino acids and analogs as chemotherapeutic agents and uses thereof
  申请人：Quadriga Biosciences, Inc.

  公开号：US10246406B2

  公开（公告）日：2019-04-02

  β-Substituted β-amino acids, β-substituted β-amino acid derivatives, and β-substituted β-amino acid analogs and (bio)isosteres and their use as chemotherapeutic agents are disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres are selective LAT1/4F2hc substrates and exhibit rapid uptake and retention in tumors expressing the LAT1/4F2hc transporter. Methods of synthesizing the β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and methods of using the compounds for treating cancer are also disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs exhibit selective uptake in tumor cells expressing the LAT1/4F2hc transporter and accumulate in cancerous cells when administered to a subject in vivo. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres exhibit cytotoxicity toward several tumor types.

  本研究公开了 β-取代的 β-氨基酸、β-取代的 β-氨基酸衍生物和 β-取代的 β-氨基酸类似物和（生物）异构体及其作为化疗药物的用途。β-取代的β-氨基酸衍生物和β-取代的β-氨基酸类似物和（生物）异甾烷是选择性的 LAT1/4F2hc 底物，在表达 LAT1/4F2hc 转运体的肿瘤中表现出快速吸收和滞留。此外，还公开了β-取代的β-氨基酸衍生物和β-取代的β-氨基酸类似物的合成方法以及使用这些化合物治疗癌症的方法。β-取代的β-氨基酸衍生物和β-取代的β-氨基酸类似物在表达LAT1/4F2hc转运体的肿瘤细胞中表现出选择性吸收，并且在体内给受试者用药时会在癌细胞中蓄积。β-取代的 β-氨基酸衍生物和 β-取代的 β-氨基酸类似物及（生物）异构体对多种肿瘤类型具有细胞毒性。