γ-azido-MTX | 1286737-12-9

• 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: γ-azido-MTX
• 英文别名: (2S)-5-(3-azidopropylamino)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]-5-oxopentanoic acid
• CAS: 1286737-12-9
• 化学式: C₂₃H₂₈N₁₂O₄
• 分子量: 536.553
• InChiKey: JIKWXDJWZAZURD-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  217
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  4-[N-(2,4-二氨基-6-蝶啶甲基)-N-甲氨基]苯甲酸半盐酸盐n水 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 生成 γ-azido-MTX
  参考文献：
  名称：

  通过无铜点击化学轻松合成多功能 PAMAM 树枝状大分子缀合物

  摘要：

  通过无铜点击化学，将三种叠氮基修饰功能（即治疗药物（甲氨蝶呤）、靶向部分（叶酸）和显像剂（荧光素））与表面具有环辛炔分子的 G5 PAMAM 树枝状聚合物支架轻松缀合被报道。单、二和三官能的 PAMAM 树枝状聚合物缀合物可以通过同时或顺序地与树枝状聚合物平台组合混合不同的叠氮基修饰官能团来获得。初步流式细胞术结果表明叶酸靶向纳米颗粒与 KB 细胞有效结合。

  DOI：

  10.1016/j.bmcl.2012.03.052

文献信息

• Multifunctional small molecules
  申请人：The Regents of the University of Michigan

  公开号：US09402911B2

  公开（公告）日：2016-08-02

  The present invention relates to dendrimer synthesis. Specifically, the present invention relates to dendrimer compositions (e.g., scaffolds) capable of copper-free click conjugation for use in the synthesis of functionalized dendrimers, and methods of use of the same.

  本发明涉及树枝状聚合物的合成。具体而言，本发明涉及能够进行无铜点击共轭的树枝状聚合物组成物（例如支架），用于合成功能化树枝状聚合物，以及其使用方法。
• The facile synthesis of multifunctional PAMAM dendrimer conjugates through copper-free click chemistry
  作者：Baohua Huang、Jolanta F. Kukowska-Latallo、Shengzhuang Tang、Hong Zong、Kali B. Johnson、Ankur Desai、Chris L. Gordon、Pascale R. Leroueil、James R. Baker

  DOI：10.1016/j.bmcl.2012.03.052

  日期：2012.5

  The facile conjugation of three azido modified functionalities, namely a therapeutic drug (methotrexate), a targeting moiety (folic acid), and an imaging agent (fluorescein) with a G5 PAMAM dendrimer scaffold with cyclooctyne molecules at the surface through copper-free click chemistry is reported. Mono-, di-, and tri-functional PAMAM dendrimer conjugates can be obtained via combinatorial mixing of

  通过无铜点击化学，将三种叠氮基修饰功能（即治疗药物（甲氨蝶呤）、靶向部分（叶酸）和显像剂（荧光素））与表面具有环辛炔分子的 G5 PAMAM 树枝状聚合物支架轻松缀合被报道。单、二和三官能的 PAMAM 树枝状聚合物缀合物可以通过同时或顺序地与树枝状聚合物平台组合混合不同的叠氮基修饰官能团来获得。初步流式细胞术结果表明叶酸靶向纳米颗粒与 KB 细胞有效结合。
• [EN] MULTIFUNCTIONAL SMALL MOLECULES<br/>[FR] PETITES MOLÉCULES MULTIFONCTIONNELLES
  申请人：UNIV MICHIGAN

  公开号：WO2013085718A1

  公开（公告）日：2013-06-13

  The present invention relates to dendrimer synthesis. Specifically, the present invention relates to dendrimer compositions (e.g., scaffolds) capable of copper-free click conjugation for use in the synthesis of functionalized dendrimers, and methods of use of the same.

  本发明涉及树状聚合物的合成。具体而言，本发明涉及可用于合成功能化树状聚合物的铜无需点击偶联的树状聚合物组成物（例如支架），以及其使用方法。
• Copper-free click conjugation of methotrexate to a PAMAM dendrimer platform
  作者：Baohua Huang、Ankur Desai、Hong Zong、Shengzhuang Tang、Pascale Leroueil、James R. Baker

  DOI：10.1016/j.tetlet.2010.12.025

  日期：2011.3

  The synthesis of a generation 5 (G5) poly(amidoamine) (PAMAM) dendrimer platform having cyclooctyne ligands that were subsequently be used for a copper-free Huisgen 1,3-dipolar cycloaddition (click reaction) with azido modified methotrexate is described. The G5 PAMAM dendrimer was first partially (70%) acetylated and then coupled with 20 cyclooctyne ligands through amide bonds. The remaining primary amine groups on the dendrimer surface were neutralized by acetylation. The platform was then 'clicked' with different numbers (5, 10, and 17) of gamma-azido functionalized methotrexate. The copper-free click reactions were stoichiornetric with excellent yields. (c) 2010 Elsevier Ltd. All rights reserved.
• MULTIFUNCTIONAL SMALL MOLECULES
  申请人：BAKER, JR. James R.

  公开号：US20140294733A1

  公开（公告）日：2014-10-02

  The present invention relates to dendrimer synthesis. Specifically, the present invention relates to dendrimer compositions (e.g., scaffolds) capable of copper-free click conjugation for use in the synthesis of functionalized dendrimers, and methods of use of the same.