[(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester | 1058148-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester
• 英文别名: Fmoc-L-Ser(OBn)-F；9H-fluoren-9-ylmethyl N-[(2S)-1-fluoro-1-oxo-3-phenylmethoxypropan-2-yl]carbamate
• CAS: 1058148-80-3
• 化学式: C₂₅H₂₂FNO₄
• 分子量: 419.452
• InChiKey: GZGJSVCNVVDYAT-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester 、 (1R,3r)-1,2,3,4-四氢-1-(3,4-亚甲基二氧基苯基)-9h-吡啶并[3,4-b]吲哚-3-羧酸甲酯 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 生成
  参考文献：
  名称：

  Drug to Genome to Drug: Discovery of New Antiplasmodial Compounds

  摘要：

  The dominant strategy for discovery of new antimalarial drugs relies on cell-free assays on specific biochemical pathways of Plasmodium falciparum . However, it appears that screening directly on the parasite is a more rewarding approach. The "drug to genome to drug" approach consists of testing a small set of structural analogues of a drug acting on human proteins that have plasmodial orthologues. Both man and plasmodium possess cyclic nucleotide phosphodiesterases (PDEs) that are key players of cell homeostasis. We synthesized and tested 40 analogues of tadalafil, a human PDE5 inhibitor, on P. falciparum in culture and obtained potent inhibitors of parasite growth. We discuss the structure-activity relationships, which support the hypothesis that our compounds kill the parasite via inhibition of plasmodial PDE activity. We also prove that antiplasmodial derivatives inhibit the hydrolysis of cyclic nucleotides of the parasite, validating the cAMP/cGMP pathways as therapeutic targets against Plasmodium falciparum .

  DOI：

  10.1021/jm1014617
• 作为产物：
  描述：

  Fmoc-O-苄基-L-丝氨酸 在 吡啶 、 三聚氟氰 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以100%的产率得到[(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester
  参考文献：
  名称：

  5,5-Dimethylproline dipeptides: an acid-stable class of pseudoproline

  摘要：

  Commercially available Fmoc-protected L-amino acids were employed and coupled to L-allylglycine. Cross metathesis with 2-methyl-2-butene using second generation Grubbs' catalyst gave L-prenylglycine-containing dipeptides. Treatment with trifluoromethanesulfonic acid resulted in cyclisation and subsequent formation of acid-stable 5,5-dimethyl-L-proline dipeptides for direct insertion into linear peptide sequences. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.068

文献信息

• Synthesis of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics
  作者：Vommina V. Sureshbabu、Hosahalli P. Hemantha、Shankar A. Naik

  DOI：10.1016/j.tetlet.2008.06.091

  日期：2008.8

  The synthesis of a new class of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics is described. The protocol employs a reaction between an N-protected amino acyl fluoride and an amino acid-derived amidoxime. All the three commonly employed urethanes have been used in this protocol for N-protection. The course of the reaction was found to be high yielding and all new compounds were well characterized by NMR and mass spectroscopy. The C-acyl amidoxime intermediate has also been isolated as a stable solid. (C) 2008 Elsevier Ltd. All rights reserved.