tert-butyl 4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-azidopentanoate | 869735-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: tert-butyl 4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-azidopentanoate
• 英文别名: tert-butyl (4S)-5-azido-4-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoate
• CAS: 869735-62-6
• 化学式: C₂₄H₂₈N₄O₄
• 分子量: 436.511
• InChiKey: KEVCFYXYMGZMCU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-azidopentanoate 在 氯仿 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 生成 tert-butyl (4S)-5-amino-4-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoate;hydrochloride
  参考文献：
  名称：

  N-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides

  摘要：

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).

  DOI：

  10.1021/jo900675s
• 作为产物：
  描述：

  在 咪唑 、 sodium tetrahydroborate 、 sodium azide 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl 4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-azidopentanoate
  参考文献：
  名称：

  作为PD-L1抑制剂的杂环类化合物

  摘要：

  本发明属于医药化学领域，涉及一类作为PD‑L1抑制剂的杂环类化合物及其应用，具体地，本发明涉及式A所示的化合物或其异构体、药学上可接受的盐、溶剂化物或前药，它们的制备方法以及含有这些化合物的药物组合物和这些化合物或组合物用于治疗癌症或者感染类疾病的用途。

  公开号：

  CN108863963B

文献信息

• Mild and Efficient Synthesis of Fmoc-Protected Amino Azides from Fmoc-Protected Amino Alcohols
  作者：Erkang Fan、Somnath Mondal

  DOI：10.1055/s-2005-923589

  日期：——

  Fmoc-protected amino azides - key intermediates for monomers of oligomeric urea and guanidine - can be efficiently prepared from the corresponding amino alcohol through iodination followed by substitution with sodium azide. This synthetic route avoids the preparation, storage, and handling of the highly toxic azidic acid that is used in an alternative method.

  Fmoc保护的氨基叠氮化物 - 聚氨基脲和胍的单体关键中间体 - 可以通过碘化和随后用叠氮化钠取代的方法，从相应的氨基醇高效制备。该合成路线避免了在另一种方法中制备、储存和处理高度毒性的叠氮酸。
• Structure−Affinity Relationships of Glutamine Mimics Incorporated into Phosphopeptides Targeted to the SH2 Domain of Signal Transducer and Activator of Transcription 3
  作者：Pijus K. Mandal、Zhiyong Ren、Xiaomin Chen、Chiyi Xiong、John S. McMurray

  DOI：10.1021/jm901105k

  日期：2009.10.8

  In cancer cells, signal transducer and activator of transcription 3 (Stat3) participates in aberrant growth, survival, angiogenesis, and invasion signals and is a validated target for anticancer drug design. We are targeting its SH2 domain to prevent docking to cytokine and growth factor receptors and subsequent signaling. One of the important elements of the recognition sequence, pTyr-Xxx-Xxx-Gln, is glutamine. We incorporated novel Gin mimics into a lead peptide, pCinn-Leu-Pro-Gln-NHBn, and found that a linear, unconstrained side chain and carboxamide are necessary for high affinity, and the benzamide can be eliminated. Replacement of Gln-NHBn with (R)-4-aminopentanamide or 2-aminoethylurea produced inhibitors with equal or greater potency than that of the lead, as judged by fluorescence polarization (IC50 values were 110 and 130 nM, respectively). When Pro was replaced with cis-3,4-methanoproline, the glutamine mimic, (4R,5S)-4-amino-5-benzyloxyhexanamide resulted in an IC50 of 69 nM, the highest affinity Stat3 inhibitor reported to date.
• Solid-Phase and Solution-Phase Syntheses of Oligomeric Guanidines Bearing Peptide Side Chains
  作者：Zhongsheng Zhang、Erkang Fan

  DOI：10.1021/jo051226t

  日期：2005.10.1

  Synthetic strategies for preparing N,N'-bridged oligomeric guanidines bearing peptide side chains both on solid support and in solution are presented. Monomers are prepared from common a-amino acids and therefore contain conventionally protected peptide side chains. The side chains include alkyl, aromatic, hydroxyl, amino, carboxylic acid, and amide functional groups. Oligomer elongation utilizes acid-sensitive sulfonyl activated thiourea through the formation of carbodiimide intermediate. With proper preparation of monomers, synthesis of oligomer can be performed in two directions (equivalent to N to C terminal or C to N terminal in a peptide sequence) with excellent efficiency.
• <i>N</i>-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides
  作者：Vommina V. Sureshbabu、Shankar A. Naik、H. P. Hemantha、N. Narendra、Ushati Das、Tayur N. Guru Row

  DOI：10.1021/jo900675s

  日期：2009.8.7

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).
• 作为PD-L1抑制剂的杂环类化合物
  申请人：南京圣和药物研发有限公司

  公开号：CN108863963B

  公开（公告）日：2022-05-27

  本发明属于医药化学领域，涉及一类作为PD‑L1抑制剂的杂环类化合物及其应用，具体地，本发明涉及式A所示的化合物或其异构体、药学上可接受的盐、溶剂化物或前药，它们的制备方法以及含有这些化合物的药物组合物和这些化合物或组合物用于治疗癌症或者感染类疾病的用途。