N-Boc-L-serine tetradecyl amide | 362620-86-8

• 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-Boc-L-serine tetradecyl amide
• 英文别名: (S)-tert-butyl 3-hydroxy-1-oxo-1-(tetradecylamino)propan-2-ylcarbamate；tert-butyl N-[(2S)-3-hydroxy-1-oxo-1-(tetradecylamino)propan-2-yl]carbamate
• CAS: 362620-86-8
• 化学式: C₂₂H₄₄N₂O₄
• 分子量: 400.602
• InChiKey: IAKNHCVBQJFFAQ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Boc-L-serine tetradecyl amide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以65.7%的产率得到L-serine myristylamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of a Family of Novel Ceramide Analogues in Chemoresistant Breast Cancer Cells

  摘要：

  Resistance to chemotherapy and endocrine therapy is a major cause of breast cancer treatment failure. We have synthesized six novel analogues using C8-ceramide as the lead analogue and studied their effect on hormone therapy resistant (MDA-MB-231) and chemoresistant (MCF-7TN-R) breast cancer cells. Pharmacologic intervention using these ceramide analogues inhibited clonogenic survival and induced apoptosis, with one analogue being more effective than C8-ceramide. Our results show ceramide-based therapy has therapeutic potential in treating drug resistant breast cancer.

  DOI：

  10.1021/jm9009668
• 作为产物：
  描述：

  十四胺 在 4-二甲氨基吡啶 、 palladium on activated charcoal 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 N-Boc-L-serine tetradecyl amide
  参考文献：
  名称：

  IONIZABLE COMPOUNDS AND COMPOSITIONS AND USES THEREOF

  摘要：

  这项发明涉及可离子化的化合物，以及其组合物和使用方法。这些可离子化的化合物可用于制备纳米粒子组合物，用于生物制药和治疗。更具体地说，这项发明涉及提供纳米粒子以包裹活性剂，如核酸剂，并将活性剂传递和分发到细胞、组织、器官和受试者的化合物、组合物和方法。

  公开号：

  US20160376229A1

文献信息

• Glycosylated α-Azido Amino Acids: Versatile Intermediates in the Synthesis of Neoglycoconjugates
  作者：Trinidad Velasco-Torrijos、Róisín O’Flaherty

  DOI：10.1055/s-0036-1591902

  日期：2018.4

  biomolecules for drug discovery, and sensor development. The synthetically challenging 1,2-cis α-galactosylated species described herein were designed as building blocks in the synthesis of analogues of α-galactosyl ceramide, a potent immunomodulator. A benzyl-protected 1,2,3-triazolyl α-galactosyl- l -serine derivative was prepared using copper azide alkyne cycloaddition to showcase the potential of

  合成了一系列糖基化的 α-叠氮基氨基酸作为新糖缀合物的前体，这是一类用于药物发现和传感器开发的重要生物分子。本文所述的具有合成挑战性的 1,2-顺式 α-半乳糖基化物种被设计为合成 α-半乳糖基神经酰胺类似物的构件，该类似物是一种有效的免疫调节剂。使用叠氮化铜炔环加成反应制备了苄基保护的 1,2,3-三唑基 α-半乳糖基-1-丝氨酸衍生物，以展示糖基化 α-叠氮基氨基酸在新糖缀合物设计中的潜力。
• COMPOUNDS, THEIR SYNTHESES, COMPOSITIONS, AND METHODS TO TREAT CANCER
  申请人：Beckman Barbara S.

  公开号：US20120027844A1

  公开（公告）日：2012-02-02

  Compounds and their syntheses are disclosed herein. Compositions and pharmaceutical compositions comprising a compound are also described, and include compositions also comprising liposomes. Methods for the treatment of cancer in animals comprising administering a compound or a composition comprising a compound are also described.

  本文披露了化合物及其合成方法。还描述了包含化合物的组合物和药物组合物，其中包括还包含脂质体的组合物。还描述了用于治疗动物癌症的方法，包括给动物施用化合物或包含化合物的组合物。
• Ionizable compounds and compositions and uses thereof
  申请人：Nitto Denko Corporation

  公开号：US10167253B2

  公开（公告）日：2019-01-01

  This invention includes ionizable compounds, and compositions and methods of use thereof. The ionizable compounds can be used for making nanoparticle compositions for use in biopharmaceuticals and therapeutics. More particularly, this invention relates to compounds, compositions and methods for providing nanoparticles to encapsulate active agents, such as nucleic acid agents, and to deliver and distribute the active agents to cells, tissues, organs, and subjects.

  本发明包括可离子化化合物及其组合物和使用方法。可离子化化合物可用于制造纳米颗粒组合物，用于生物制药和治疗。更具体地说，本发明涉及提供纳米颗粒的化合物、组合物和方法，以封装活性剂，如核酸制剂，并将活性剂输送和分配到细胞、组织、器官和受试者。
• [EN] COMPOUNDS, THEIR SYNTHESES, COMPOSITIONS, AND METHODS TO TREAT CANCER<br/>[FR] COMPOSÉS, LEURS SYNTHÈSES, LEURS COMPOSITIONS ET MÉTHODES POUR TRAITER LE CANCER
  申请人：TULANE UNIVERSITY

  公开号：WO2010093615A3

  公开（公告）日：2010-11-25
• Synthesis and biological evaluation of novel cytotoxic phospholipids for prostate cancer
  作者：Veeresa Gududuru、Eunju Hurh、Gangadhar G. Durgam、Seoung Soo Hong、Vineet M. Sardar、Huiping Xu、James T. Dalton、Duane D. Miller

  DOI：10.1016/j.bmcl.2004.07.026

  日期：2004.10

  We describe herein synthesis, SAR, and biological evaluation of a novel series of cytotoxic serine amide phosphates (SAPs) for prostate cancer. These compounds were tested for their cytotoxicity in five human prostate cancer cell lines (DU-145, PC-3, LNCaP, PPC-1, and TSU), and in CHO and RH7777 cells (negative controls). Comparison of anticancer effects of these compounds with a standard chemotherapeutic agent 5-fluorouracil shows that they are very effective in killing prostate cancer cells with low micromolar cytotoxicity and provide us a new lead for the development of drugs for prostate cancer. (C) 2004 Elsevier Ltd. All rights reserved.