2-(chlorocarbonyl)-1-Fmoc-methylhydrazine | 250280-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-(chlorocarbonyl)-1-Fmoc-methylhydrazine
• 英文别名: 9H-fluoren-9-ylmethyl N-(carbonochloridoylamino)-N-methylcarbamate
• CAS: 250280-33-2
• 化学式: C₁₇H₁₅ClN₂O₃
• 分子量: 330.771
• InChiKey: TUWQLJHHOFPATO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  光气 、 (9H-fluoren-9-yl)methyl1-methylhydrazinecarboxylate 以 1,4-二氧六环 为溶剂， 以100%的产率得到2-(chlorocarbonyl)-1-Fmoc-methylhydrazine
  参考文献：
  名称：

  Novel Solid-Phase Synthesis of Azapeptides and Azapeptoides via Fmoc-Strategy and Its Application in the Synthesis of RGD-Mimetics

  摘要：

  The cell adhesion motif Arg-Gly-Asp (RGD) has been used as a starting point for the development of several antagonists for the alpha IIb beta 3 and alpha v beta 3 integrins, which are implicated in various pathological processes. In this paper, an efficient method for the solid-phase synthesis and biological evaluation of linear RGD-mimetics containing an azaamino acid instead of glycine are described. Activation of the Fmoc-protected hydrazines 1, 4, and 6 with a solution of phosgene in toluene provided Fmoc-protected activated azaglycine (2), azasarcosine (5), and azaalanine (7) in high yields. Six aza-RGD-mimetics have been synthesized on solid support using Fmoc peptide synthesis and individually optimized reaction conditions for the incorporation of activated azabuilding blocks. Due to orthogonal anchoring and side-chain protection, our strategy yielded TentaGel-bound RGD-mimetics, which meet all requirements of the one-bead-one-compound concept. We observed differing activity and selectivity in bioassays for the alpha IIb beta 3- and alpha v beta 3-integrin receptor depending on the substitution pattern of the azabuilding blocks. Our biological data suggest that azapeptides and azapeptoides can be employed as selectivity- and activity-inducing templates in pseudobio-oligomers.

  DOI：

  10.1021/jo9906173

文献信息

• Novel Solid-Phase Synthesis of Azapeptides and Azapeptoides via Fmoc-Strategy and Its Application in the Synthesis of RGD-Mimetics
  作者：Christoph Gibson、Simon L. Goodman、Diane Hahn、Günter Hölzemann、Horst Kessler

  DOI：10.1021/jo9906173

  日期：1999.10.1

  The cell adhesion motif Arg-Gly-Asp (RGD) has been used as a starting point for the development of several antagonists for the alpha IIb beta 3 and alpha v beta 3 integrins, which are implicated in various pathological processes. In this paper, an efficient method for the solid-phase synthesis and biological evaluation of linear RGD-mimetics containing an azaamino acid instead of glycine are described. Activation of the Fmoc-protected hydrazines 1, 4, and 6 with a solution of phosgene in toluene provided Fmoc-protected activated azaglycine (2), azasarcosine (5), and azaalanine (7) in high yields. Six aza-RGD-mimetics have been synthesized on solid support using Fmoc peptide synthesis and individually optimized reaction conditions for the incorporation of activated azabuilding blocks. Due to orthogonal anchoring and side-chain protection, our strategy yielded TentaGel-bound RGD-mimetics, which meet all requirements of the one-bead-one-compound concept. We observed differing activity and selectivity in bioassays for the alpha IIb beta 3- and alpha v beta 3-integrin receptor depending on the substitution pattern of the azabuilding blocks. Our biological data suggest that azapeptides and azapeptoides can be employed as selectivity- and activity-inducing templates in pseudobio-oligomers.