3-(8-环戊基-2,6-二氧代-1-丙基-7H-嘌呤-3-基)丙基4-氟磺酰基苯甲酸酯 | 156547-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 3-(8-环戊基-2,6-二氧代-1-丙基-7H-嘌呤-3-基)丙基4-氟磺酰基苯甲酸酯
• 英文名称: 8-cyclopentyl-3-(3-((4-fluorosulfonylbenzoyl)oxy)propyl)-1-propylxanthine
• 英文别名: 8-cyclopentyl-N³-[3-(4-(fluorosulfonyl)benzoyloxy)propyl]- N¹-propylxanthine；FSCPX；3-(8-cyclopentyl-2,6-dioxo-1-propyl-7H-purin-3-yl)propyl 4-fluorosulfonylbenzoate
• CAS: 156547-56-7
• 化学式: C₂₃H₂₇FN₄O₆S
• 分子量: 506.555
• InChiKey: XJLGXHIRSHTRPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  730.7±70.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)
• 溶解度：
  在DMSO中的溶解度为10 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  8

安全信息

• 安全说明：
  S22,S24/25

反应信息

• 作为产物：
  描述：

  3-(3-methoxypropyl)-8-cyclopentylxanthine 在 三溴化硼 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(8-环戊基-2,6-二氧代-1-丙基-7H-嘌呤-3-基)丙基4-氟磺酰基苯甲酸酯
  参考文献：
  名称：

  Synthesis and use of FSCPX, an irreversible adenosine A1 antagonist, as a ‘Receptor Knock-Down’ tool

  摘要：

  A new preparative synthetic route for the irreversible adenosine A1 antagonist 8-cyclopentyl-3-N-[3-((3-(4-fluorosulphonyl)benzoyl)-oxy)-propyl]-1-N-propyl-xanthine (FSCPX, 1) is described. The availability of ample amounts of the irreversible antagonist FSCPX allowed us to use FSCPX as a research tool for adenosine A1 receptors in in vivo experiments. After verification of the irreversible antagonistic function of FSCPX in in vitro experiments, FSCPX was used successfully as a 'receptor knock-down' tool in in vivo experiments on conscious rats.

  DOI：

  10.1016/s0960-894x(01)00069-5

文献信息

• Substituted 1,3-Dipropylxanthines as Irreversible Antagonists of A1 Adenosine Receptors
  作者：Peter J. Scammells、Stephen P. Baker、Luiz Belardinelli、Ray A. Olsson

  DOI：10.1021/jm00043a010

  日期：1994.8

  This report describes the synthesis of 29 xanthines containing a chemoreactive chloroaryl beta-chloroethylamino, alpha,beta-unsaturated carbonyl bromoacetyl, 3-(fluorosulfonyl)benzoyl, or 4-(fluorosulfonyl)benzoyl group as part of an exocyclic 1-, 3-, or 8-substituent. The xanthines inhibited the binding of [H-3]-8-cyclopentyl-1,3-dipropylxanthine ([H-3]CPX) to the A(1) adenosine receptor (A(1)AR) of DDT1 MF2 cells at IC(50)s in the low-nanomolar to low-micromolar range. Seven of the 29 analogues irreversibly inhibited the binding of [H-3]CPX without changing the K-D of that ligand; five were 1,3-dipropylxantines having the following reactive groups as 8-substituents: (bromoacetamido)methyl (24), (bromoacetamido)ethyl (25), (bromoacetamido)propyl (26), [4-(fluorosulfonyl)benzamido]methyl (33) or 3-[[4-(fluorosulfonyl)benzoyl]oxy]cyclopentyl (42). Both 8-cyclopentyl-3-[3-[[4-(fluorosulfonyl)benzoyl]oxy]propyl]-1-propylxanthine (53) and 8-cyclopentyl-3-bis[3-[[4-(fluorosulfonyl)benzoyl]oxy]propyl]xanthine (55) inhibited [H-3]CPX binding irreversibly. Five of the ligands, including 26, 33 (IC50 = 49 mu M), and 53 (IC50 = 9 mu M), antagonized the binding of [H-3]NECA to the A(2a)AR of PC12 cells, but unlike binding to the A(1)AR, binding to the A(2a)AR was completely reversible. The potency of 33 (IC50 = 2 mu M, 72% loss of CPX binding at 1 mu M) and 53 (IC50 - 0.01 mu M, 74% loss of CPX binding at 0.05 mu M) and their seletivity for the A(1)AR suggest that those two ligands may be useful in studies of the structure and function of that receptor.
• Scammells Peter J., Baker Stephen P., Belardinelli Luiz, Olsson Ray A., J. Med. Chem, 37 (1994) N 17, S 2704-2712
  作者：Scammells Peter J., Baker Stephen P., Belardinelli Luiz, Olsson Ray A.

  DOI：——

  日期：——
• METHODS OF USE AND KIT FOR MEASUREMENT OF LIPOPOLYSACCHARIDE WITH A TIME RESOLVED FLUORESCENCE BASED ASSAY
  申请人：Endacea, Inc.

  公开号：EP2616817A2

  公开（公告）日：2013-07-24
• [EN] HTLV-I-CELL BINDING AND INHIBITION<br/>[FR] LIAISON ET INHIBITION DE CELLULE DU VIRUS DU LYMPHOME HUMAIN A CELLULES T DE TYPE 1 (HTLV-I)
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2004070000A2

  公开（公告）日：2004-08-19

  The present invention provides methods of inhibiting HLV-1 infection in cells by physically blocking binding of HTLV-I to the cells using adenosine receptor antagonists and methods of lowering HTLV-I proviral load or HTLV-I titer in HTLV-I individuals by physically blocking binding of HTLV-I to cells in the individuals adenosine receptor antagonists.
• [EN] METHODS OF USE AND KIT FOR MEASUREMENT OF LIPOPOLYSACCHARIDE WITH A TIME RESOLVED FLUORESCENCE BASED ASSAY<br/>[FR] MÉTHODES D'UTILISATION DES MESURES DES LIPOPOLYSACCHARIDES PAR DOSAGE PAR FLUORESCENCE EN TEMPS RÉSOLU ET KIT AFFÉRENT
  申请人：ENDACEA INC

  公开号：WO2012037361A2

  公开（公告）日：2012-03-22

  The present invention relates to the methods of use for measurement of lipopolysaccharide (LPS) and methods of use for diagnosis of sepsis and LPS-related conditions. Specifically the present invention relates to a time resolved fluorescence (TRF) based assay for the measurement of LPS and methods of use for the measurement of LPS to diagnose sepsis, Gram-negative bacterial infections, and LPS-related conditions.