N_α-formyl-L-tryptophan amide | 497140-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N_α-formyl-L-tryptophan amide
• 英文别名: (2S)-2-formamido-3-(1H-indol-3-yl)propanamide
• CAS: 497140-74-6
• 化学式: C₁₂H₁₃N₃O₂
• 分子量: 231.254
• InChiKey: KISNLDBLSNUORB-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-叔丁氧羰基-N'-醛基-L-色氨酸 在 吡啶 、 二碳酸二叔丁酯 、 碳酸氢铵 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 356.0h， 生成 N_α-formyl-L-tryptophan amide 、 N_α-formyl-L-tryptophan amide
  参考文献：
  名称：

  在Boc-SPPS过程中，通过从Trp（For）残基到Nα的序列特异性甲酰基转移，形成截短的肽副产物。

  摘要：

  色氨酸的（N In）‐甲酰基保护基已被引入为对碱基/亲核试剂敏感的保护基。长期以来，人们一直知道该肽的游离Nα-氨基可以用作亲核试剂：当最后对具有游离Nα的脱保护的肽进行甲酰化反应时，始终观察到不可逆的甲酰基N In  →NH 2转移氨基 显然，只要游离氨基暴露于Trp（For），就应预期会发生这种特殊的副反应，但据我们所知，在Boc-SPPS过程中从未有过报道。在本通讯中，我们描述了一组经过适当设计的模型实验，可以检测溶液和固相反应中的标题副反应。我们观察到了模型化合物Trp（For）-NH 2的分子间甲酰基转移。重要的是，我们还观察到了在固相支持物上的迁移，其迁移率粗略估计高达每分钟残留物的1％。我们还观察到甲酰基转移反应以序列依赖性方式发生，并被原位抑制到不可检测的水平。中和技术。由于这种副反应是序列依赖性的，有可能是情况下，当n的形成速率α -甲酰基终止副产物是显著。在其他情况下，将N

  DOI：

  10.1002/psc.2547

文献信息

• Biologically active lysine containing octapeptides
  申请人：The Administrators of The Tulane University Educational Fund

  公开号：EP0203031A2

  公开（公告）日：1986-11-26

  Novel compositions of the formula wherein A represents an L, D or DL amino-acid selected from the group consisting of Ala, Val, Phe, p-CI-Phe, Trp, Pro, Ser, Thr, Glu, Gly, Beta Ala, Abu, N-Me Ala, 5-F-Trp, 5-Br-Trp, 5-Cl-Trp, their acetylated derivatives or a pharmaceutically acceptable acid addition salt thereof; B represents an L, D or DL amino acid amide selected from the group consisting of Thr NH2, Val NH,, Pro NH2, HO-Pro NH2, Ser NH2, Tyr NH2, Trp NH2, 5-F-Trp NH,, For-Trp NH., Ala NH2, Gly NH2, Me Ala NH2; X represents L-Phe or L-Tyr, Y represents L-Thr or L-Val; Z is L, D or DL-5-F-Trp, 5-Br-Trp, 5-C1-Trp, 5-I-Trp or D-Trp; and C" and C' represent L or D Cys, Abu, Asp or Lys; provided that where C' is Cys, C" is also Cys and where C' or C" are other than Cys, C" is different from C' and is other than Cys and the pharmaceutically acceptable acid addition salts thereof; are useful as agents for inhibiting the release of growth hormone, for the treatment of gastrointestinal disorders and for therapy of certain cancers and the management of diabetes. These biologically active octapeptides all possess a terminal amino acid amide at position 8 and are prepared by solid phase methods.

  式中的新型组合物 式中 A 代表选自以下组别的 L、D 或 DL 氨基酸：Ala、Val、Phe、p-CI-Phe、Trp、Pro、Ser、Thr、Glu、Gly、Beta Ala、Abu、N-Me Ala、5-F-Trp、5-Br-Trp、5-Cl-Trp、它们的乙酰化衍生物或其药学上可接受的酸加成盐； B 代表选自 Thr NH2、Val NH、Pro NH2、HO-Pro NH2、Ser NH2、Tyr NH2、Trp NH2、5-F-Trp NH、For-Trp NH、Ala NH2、Gly NH2、Me Ala NH2 所组成的组的 L、D 或 DL 氨基酸酰胺； X 代表 L-Phe或 L-Tyr、 Y 代表 L-Thr 或 L-Val Z 是 L、D 或 DL-5-F-Trp、5-Br-Trp、5-C1-Trp、5-I-Trp 或 D-Trp；以及 C "和 C'代表 L 或 D Cys、Abu、Asp 或 Lys；条件是当 C' 是 Cys 时，C "也是 Cys，当 C' 或 C "不是 Cys 时，C "不同于 C'，也不是 Cys 及其药学上可接受的酸加成盐；可用作抑制生长激素释放、治疗胃肠道疾病、治疗某些癌症和糖尿病的药物。这些具有生物活性的八肽都在第 8 位具有一个末端氨基酸酰胺，并通过固相方法制备。
• N-METHYL-D-ASPARTATE RECEPTOR MODULATORS AND METHODS OF MAKING AND USING SAME
  申请人：Naurex, Inc.

  公开号：EP3916003A1

  公开（公告）日：2021-12-01

  Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of diseases and disorders, such as learning, cognitive activities, and analgesia, particularly in alleviating and/or reducing neuropathic pain. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

  所公开的化合物在调节 NMDA 受体活性方面具有更强的效力。这些化合物可用于治疗疾病和失调，如学习、认知活动和镇痛，特别是减轻和/或减少神经性疼痛。还公开了这些化合物的口服制剂和其他药学上可接受的给药形式，包括静脉注射制剂。
• Targeted conjugates and particles and formulations thereof
  申请人：TARVEDA THERAPEUTICS, INC.

  公开号：US10322191B2

  公开（公告）日：2019-06-18

  Nanoparticles and microparticles, and pharmaceutical formulations thereof, containing conjugates of an active agent such as a therapeutic, prophylactic, or diagnostic agent attached to a targeting moiety, such as a somatostatin receptor binding moiety, via a linker have been designed. Such nanoparticles and microparticles can provide improved temporospatial delivery of the active agent and/or improved biodistribution. Methods of making the conjugates, the particles, and the formulations thereof are provided. Methods of administering the formulations to a subject in need thereof are provided, for example, to treat or prevent cancer or infectious diseases.

  现已设计出纳米颗粒和微颗粒及其药物制剂，其中含有通过连接体连接到靶向分子（如体生长抑素受体结合分子）的活性剂（如治疗剂、预防剂或诊断剂）的共轭物。这种纳米颗粒和微颗粒可改善活性剂的时间空间递送和/或生物分布。本文提供了共轭物、颗粒及其制剂的制造方法。还提供了向有需要的受试者施用制剂的方法，例如治疗或预防癌症或传染性疾病。
• SSTR-targeted conjugates and particles and formulations thereof
  申请人：TARVEDA THERAPEUTICS, INC.

  公开号：US11160871B2

  公开（公告）日：2021-11-02

  Conjugates of an active agent such as DM1 attached to a targeting moiety, such as a somatostatin receptor binding moiety, via a linker, and particles comprising such conjugates have been designed. Such conjugates and particles can provide improved temporospatial delivery of the active agent, improved biodistribution and penetration in tumor, and/or decreased toxicity. Methods of making the conjugates, the particles, and the formulations thereof are provided. Methods of administering the formulations to a subject in need thereof are provided, for example, to treat or prevent cancer.

  目前已设计出通过连接体将 DM1 等活性剂与体泌素受体结合分子等靶向分子连接的共轭物，以及包含这种共轭物的微粒。这种共轭物和微粒可以改善活性剂的时间空间递送，改善生物分布和在肿瘤中的渗透，和/或降低毒性。本文提供了共轭物、颗粒及其制剂的制造方法。还提供了向有需要的受试者施用制剂的方法，例如治疗或预防癌症。
• TARGETED CONJUGATES AND PARTICLES AND FORMULATIONS THEREOF
  申请人：Tarveda Therapeutics, Inc.

  公开号：US20170095569A1

  公开（公告）日：2017-04-06

  Nanoparticles and microparticles, and pharmaceutical formulations thereof, containing conjugates of an active agent such as a therapeutic, prophylactic, or diagnostic agent attached to a targeting moiety, such as a somatostatin receptor binding moiety, via a linker have been designed. Such nanoparticles and microparticles can provide improved temporospatial delivery of the active agent and/or improved biodistribution. Methods of making the conjugates, the particles, and the formulations thereof are provided. Methods of administering the formulations to a subject in need thereof are provided, for example, to treat or prevent cancer or infectious diseases.