1-[(9H-芴-9-基甲氧基)羰基]-3-吡咯烷羧酸 | 193693-66-2

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 1-[(9H-芴-9-基甲氧基)羰基]-3-吡咯烷羧酸
• 中文别名: 芴甲氧羰基-L-β-脯氨酸；2(1H)-吡嗪酮,3,4-二氢-5-巯基-3-硫代-；FMOC-(3S)-1-吡咯烷-3-羧酸
• 英文名称: Fmoc-β-ProOH
• 英文别名: Fmoc-(3S)-1-pyrrolidine-3-carboxylic acid；(3S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-3-carboxylic acid
• CAS: 193693-66-2
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: GUAMYYOQAAUXLR-ZDUSSCGKSA-N

物化性质

• 沸点：
  548.6±43.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  H-Asp(Ot-Bu)-OBn 、 1-[(9H-芴-9-基甲氧基)羰基]-3-吡咯烷羧酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以85%的产率得到
  参考文献：
  名称：

  逆转录α4β1整合素靶向基序的合成与分析

  摘要：

  近年来，几个研究小组基于经典整合素结合基序RGD的反向序列，提出了整合素αvβ3，α5β1，αIIbβ3，αvβ6，αvβ5等的新型拟肽拮抗剂。对于未结合RGD的α4β1整联蛋白，逆向策略仍然被很大程度上忽略。本文我们提出复古序列的第一实施例用于靶向整合此，Asp或组成异天冬氨酸配备有在芳香族帽Ñ -末端，（小号） -吡咯烷-3-羧酸（β 2-Pro）作为受约束的核心，以及众所周知的靶向α4的二苯基脲MPUPA的氨基变体（AMPUMP）。我们讨论了α4β1受体亲和力（SPA），细胞粘附测定，小鼠血清中的稳定性以及构象分析。对于他们的显著能力抑制细胞粘附和显着的稳定性，该逆向肽模拟物BNCO-ASP-β-PRO-AMPUMP（3）和BnCO-异天冬氨酸-β-PRO-AMPUMP（4）表示用于设计小分子希望的候选作为潜在的抗炎药。

  DOI：

  10.1016/j.ejmech.2013.12.009
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 (R)-3-羧基吡咯烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-[(9H-芴-9-基甲氧基)羰基]-3-吡咯烷羧酸
  参考文献：
  名称：

  Constrained β-alanine based GpIIb/IIIa antagonists

  摘要：

  The concepts of centrally constrained and peptide based fibrinogen receptor antagonists have been successfully combined into a single series of analogs which have been demonstrated to be potent inhibitors of platelet aggregation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00311-9

文献信息

• DS-70, a novel and potent α₄ integrin antagonist, is an effective treatment for experimental allergic conjunctivitis in guinea pigs
  作者：Samantha Deianira Dattoli、Monica Baiula、Rossella De Marco、Andrea Bedini、Michele Anselmi、Luca Gentilucci、Santi Spampinato

  DOI：10.1111/bph.14458

  日期：2018.10

  Background and PurposeAllergic conjunctivitis is an eye inflammation that involves the infiltration of immune cells into the conjunctiva via cell surface‐adhesion receptors, such as integrin α4β1. These receptors interact with adhesion molecules expressed on the conjunctival endothelium and may be a target to treat this disease. We synthesized DS‐70, a novel α/β‐peptidomimetic α4 integrin antagonist, to prevent the conjunctival infiltration of immune cells and clinical symptoms in a model of allergic conjunctivitis.Experimental ApproachIn vitro, DS‐70 was pharmacologically characterized using a scintillation proximity procedure to measure its affinity for α4β1 integrin, and its effect on cell adhesion mediated by different integrins was also evaluated. The effects of DS‐70 on vascular cell adhesion molecule‐1 (VCAM‐1)‐mediated degranulation of a human mast cell line and an eosinophilic cell line, which both express α4β1, and on VCAM‐1‐mediated phosphorylation of ERK 1/2 in Jurkat E6.1 cells were investigated. Effects of DS‐70 administered in the conjunctival fornix of ovalbumin‐sensitized guinea pigs were evaluated.Key ResultsDS‐70 bound to integrin α4β1 with nanomolar affinity, prevented the adhesion of α4 integrin‐expressing cells, antagonized VCAM‐1‐mediated degranulation of mast cells and eosinophils and ERK 1/2 phosphorylation. Only 20% was degraded after an 8 h incubation with serum. DS‐70 dose‐dependently reduced the clinical symptoms of allergic conjunctivitis, conjunctival α4 integrin expression and conjunctival levels of chemokines and cytokines in ovalbumin‐sensitized guinea pigs.Conclusions and ImplicationsThese findings highlight the role of α4 integrin in allergic conjunctivitis and suggest that DS‐70 is a potential treatment for this condition.
• EP2694095A1
  申请人：——

  公开号：EP2694095A1

  公开（公告）日：2014-02-12
• PEPTIDES COMPRISING NON-NATURAL AMINO ACIDS AND METHODS OF MAKING AND USING THE SAME
  申请人：Longevity Biotech, Inc.

  公开号：EP2968469A2

  公开（公告）日：2016-01-20
• Methods for synthesis of encoded libraries
  申请人：Morgan Barry

  公开号：US20070042401A1

  公开（公告）日：2007-02-22

  The present invention provides a method of synthesizing libraries of molecules which include an encoding oligonucleotide tag.
• Methods for identifying compounds of interest using encoded libraries
  申请人：Morgan Barry

  公开号：US20070224607A1

  公开（公告）日：2007-09-27

  The present invention provides a method for identifying a compound of interest by screening libraries of molecules which include an encoding oligonucleotide tag.