N-(cyanoacetyl)-L-phenylalanine | 135406-57-4

• 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-(cyanoacetyl)-L-phenylalanine
• 英文别名: N-cyanoacetyl-l-phenylalanine；(2S)-2-[(2-cyanoacetyl)amino]-3-phenylpropanoic acid
• CAS: 135406-57-4
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: VNVDSCNQCLNEOR-JTQLQIEISA-N

物化性质

• 沸点：
  535.8±50.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  90.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(cyanoacetyl)-L-phenylalanine 在 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 N--L-phenylalanine
  参考文献：
  名称：

  The first mechanism-based inactivators for angiotensin-converting enzyme

  摘要：

  The first example of mechanism-based inactivation of angiotensin-converting enzyme (ACE) is described for N-[N-(cyanoacetyl)-L-phenylalanyl]-L-phenylalanine (compound 1). It is proposed that an ACE-mediated deprotonation of 1 unmasks a ketenimine intermediate, which traps an active-site nucleophile, and hence irreversibly modifies the enzyme. In competition with the inactivation reaction, ACE also hydrolyzes 1 with a partition ratio of 8300 (i.e., k(cat)/k(inact)). Since the corresponding keto analogue, N-[(R)-2-benzyl-5-cyano-4-oxopentanoyl]-L-phenylalanine (compound 4), does not inactivate the enzyme, it is suggested that the NH in compound 1 is critical for the proper active-site anchoring of the inhibitor for the inactivation process to take place.

  DOI：

  10.1021/jm00100a024

文献信息

• [EN] INHIBITORS OF FARNESYL PROTEIN TRANSFERASE<br/>[FR] INHIBITEURS DE LA FARNESYL-TRANSFERASE
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：WO1997030992A1

  公开（公告）日：1997-08-28

  (EN) This invention relates to compounds that inhibit farnesyl-protein transferase and ras protein farnesylation, thereby making them useful as anti-cancer agents. The compounds are also useful in the treatment of diseases, other than cancer, associated with signal transduction pathways operating through ras and those associated with proteins other than ras that are also post-translationally modified by the enzyme farnesyl protein transferase. The compounds may also act as inhibitors of other prenyl transferases, and thus be effective in the treatment of diseases associated with other prenyl modifications of proteins.(FR) La présente invention concerne des composés inhibant la farnésyl-transférase et la farnésylation de la protéine Ras, ce qui en fait d'utiles agents anticancéreux. Ces composés conviennent également particulièrement au traitement de maladies autres que le cancer, associées aux canaux de transduction de signaux par la protéine Ras, et de maladies associées à des protéines autres que les protéines Ras qui subissent une modification post-translationnelle sous l'effet de la farnésyl-transférase. Ces composés se comportent également comme inhibiteurs d'autres prényl-transférases, et peuvent de ce fait convenir au traitement d'affections associées à d'autres modifications prényl des protéines.

  （中文翻译）本发明涉及抑制法尼醇-蛋白质转移酶和ras蛋白质法尼醇化的化合物，因此使它们成为有用的抗癌剂。这些化合物还适用于治疗与ras信号转导途径以及其他被酶法尼醇蛋白质转移酶后翻译修饰的蛋白质相关的疾病，除了癌症。这些化合物还可以作为其他异戊二烯基转移酶的抑制剂，因此在治疗与其他蛋白质的异戊二烯基修饰相关的疾病方面也很有效。
• Inhibitors of farnesyl protein transferase
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP1481975A1

  公开（公告）日：2004-12-01

  This invention relates to compounds that inhibit farnesyl-protein transferase and ras protein farnesylation, thereby making them useful as anti-cancer agents. The compounds are also useful in the treatment of diseases, other than cancer, associated with signal transduction pathways operating through ras and those associated with proteins other than ras that are also post-translationally modified by the enzyme farnesyl protein transferase. The compounds may also act as inhibitors of other prenyl transferases, and thus be effective in the treatment of diseases associated with other prenyl modifications of proteins.

  本发明涉及抑制法尼基蛋白转移酶和 ras 蛋白法尼基化，从而使其可用作抗癌剂的化合物。除癌症外，这些化合物还可用于治疗与通过 ras 运作的信号转导通路有关的疾病，以及与同样经法尼基蛋白转移酶翻译后修饰的 ras 以外的蛋白质有关的疾病。这些化合物还可以作为其他前炔基转移酶的抑制剂，从而有效治疗与蛋白质的其他前炔基化修饰有关的疾病。
• Methods and compositions for treating disorders
  申请人：Epeius Biotechnologies Corporation

  公开号：EP2353389A1

  公开（公告）日：2011-08-10

  Methods and compositions for producing targeted delivery vectors are provided. Such vectors are useful for treating neoplastic disorders. Also provided are protocols for administering targeted vectors in a clinical setting such that a therapeutic effect is achieved.

  本文提供了生产靶向递送载体的方法和组合物。 这些载体可用于治疗肿瘤性疾病。还提供了在临床环境中施用靶向载体以达到治疗效果的方案。
• Thymidine kinase gene
  申请人：GenVivo, Inc.

  公开号：US10610603B2

  公开（公告）日：2020-04-07

  Nucleic acid sequences encoding improved Herpes Simplex Virus Thymidine Kinases are provided, including their use in diagnostic and therapeutic applications. The thymidine kinases may be mutated using conservative mutations, non-conservative mutations, or both. Also provided are gene therapeutic systems, including viral and retroviral particles.

  提供了编码改良的单纯疱疹病毒胸苷激酶的核酸序列，包括它们在诊断和治疗中的应用。胸苷激酶可通过保守突变、非保守突变或两者兼而有之的方式进行突变。还提供了基因治疗系统，包括病毒和逆转录病毒颗粒。
• Compositions and methods for subcutaneous administration of cancer immunotherapy
  申请人：Alkermes Pharma Ireland Limited

  公开号：US11246906B2

  公开（公告）日：2022-02-15

  The invention provides compositions, methods and treatment regimens for treating cancer comprising periodic subcutaneous administration of the fusion protein of SEQ ID NO:1 to a cancer patient resulting in enhanced activation of CD8+ T-cells with minimal effects on regulatory T cell (Treg) expansion and providing enhanced anti-tumor efficacy while also mitigating T cell inactivation/exhaustion.

  本发明提供了治疗癌症的组合物、方法和治疗方案，包括对癌症患者定期皮下注射SEQ ID NO:1的融合蛋白，从而增强CD8+ T细胞的活化，对调节性T细胞（Treg）的扩增影响最小，并提供增强的抗肿瘤疗效，同时还能减轻T细胞失活/衰竭。