(3aR,4S,6R,6aS)-6-[[5-氨基-6-氯-2-(丙硫基)-4-嘧啶基]氨基]四氢-2,2-二甲基-4H-环戊烯并-1,3-二恶茂-4-醇 | 220241-60-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: (3aR,4S,6R,6aS)-6-[[5-氨基-6-氯-2-(丙硫基)-4-嘧啶基]氨基]四氢-2,2-二甲基-4H-环戊烯并-1,3-二恶茂-4-醇
• 中文别名: (3aR,4S,6R,6aS)-6-(5-胺基-6-氯-2-丙硫基-4-吡啶基)氨基四氢-2,2-二甲基-4H-环戊烯并-1,3-二氧杂环戊烷-4-醇；(3AR,4S,6R,6AS)-6-[[5-氨基-6-氯-2-(丙硫基)-4-嘧啶基]氨基]四氢-2,2-二甲基-4H-环戊烯并-1,3-二恶茂-4-醇
• 英文名称: (3aR,4S,6R,6aS)-6-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• 英文别名: (3aR,4S,6R,6aS)-6-[(5-amino-6-chloro-2-propylsulfanylpyrimidin-4-yl)amino]-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS: 220241-60-1
• 化学式: C₁₅H₂₃ClN₄O₃S
• 分子量: 374.892
• InChiKey: ZFIOCHSHJADREN-YKDSUIRESA-N

物化性质

• 沸点：
  567.9±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3aR,4S,6R,6aS)-6-[[5-氨基-6-氯-2-(丙硫基)-4-嘧啶基]氨基]四氢-2,2-二甲基-4H-环戊烯并-1,3-二恶茂-4-醇 在 sodium carbonate 、 亚硝酸异戊酯 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 17.0h， 生成 (3aR,4S,6R,6aS)-2,2-dimethyl-6-(7-phenoxy-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
  参考文献：
  名称：

  [EN] SYNTHESIS OF TRIAZOLOPYRIMIDINE COMPOUNDS
  [FR] SYNTHÈSE DE COMPOSÉS DE TRIAZOLOPYRIMIDINE

  摘要：

  本发明涉及有机合成领域，描述了特定三唑吡咯啉化合物及其中间体的合成，以及相关衍生物。

  公开号：

  WO2013060837A1
• 作为产物：
  描述：

  N-(((4S,5R)-2,2-dimethyl-5-vinyl-1 ,3-dioxolan-4-yl)methylene)-1-phenylmethanamine oxide 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 sodium iodide 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 19.0h， 生成 (3aR,4S,6R,6aS)-6-[[5-氨基-6-氯-2-(丙硫基)-4-嘧啶基]氨基]四氢-2,2-二甲基-4H-环戊烯并-1,3-二恶茂-4-醇
  参考文献：
  名称：

  Synthesis and biological evaluation of ticagrelor derivatives as novel antiplatelet agents

  摘要：

  Ticagrelor (1) is the first reversible P2Y12 receptor antagonist blocking adenine diphosphate (ADP)-induced platelet aggregation with rapid onset and offset of effects. In this study, synthesis of ticagrelor and its derivatives has been accomplished in a convergent way. The compound design was based on modifications of ticagrelor and its major metabolite (33) in order to ameliorate their pharmacokinetic properties and dosing profile. The final compounds (1a-g, 35a-g) were evaluated for their inhibitory effect on ADP-induced platelet aggregation in rats. The assay results showed that some compounds (e. g., 1b, 1d, 33, 35b, 35f) exhibited comparable potency with that of ticagrelor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.050

文献信息

• [EN] NEW PYRIMIDINE DERIVATIVES FOR PREVENTION AND TREATMENT OF GRAM-NEGATIVE BACTERIAL INFECTION, CONTAMINATION AND FOULING<br/>[FR] NOUVEAUX DÉRIVÉS DE PYRIMIDINE POUR LA PRÉVENTION ET LE TRAITEMENT D'UNE INFECTION, D'UNE CONTAMINATION ET DE SALISSURES PAR UNE BACTÉRIE À GRAM NÉGATIF
  申请人：UNIV LIEGE

  公开号：WO2020212553A1

  公开（公告）日：2020-10-22

  New pyrimidine derivatives together with a membrane penetrating agent, optionally with a detectable isotope and pharmaceutical composition for use in treatment or prevention of Gram-negative bacterial infection in a host mammal in need of such treatment or prevention and use as inhibitors of Gram-negative biofilm formation on a surface of biomaterial or medical device, particularly of cardiovascular device such as prosthetic heart valve or pacemakers. New pyrimidine derivatives together with a membrane penetrating agent; for use as radiotracer in diagnosing or prognosing Gram-negative bacterial infection in a host mammal.

  新的嘧啶衍生物与膜穿透剂一起，可选地带有可检测同位素和药物组合物，用于治疗或预防宿主哺乳动物体内需要此类治疗或预防的革兰氏阴性细菌感染，并用作抑制生物材料或医疗器械表面上的革兰氏阴性生物膜形成的抑制剂，特别是心血管器械，如假体心脏瓣膜或起搏器。新的嘧啶衍生物与膜穿透剂一起；用作放射示踪剂，用于诊断或预测宿主哺乳动物体内的革兰氏阴性细菌感染。
• Synthesis of Triazolopyrimidine Compounds
  申请人：LEK Pharmaceuticals d.d.

  公开号：EP2570405A1

  公开（公告）日：2013-03-20

  The present invention relates to the filed of organic synthesis and describes the synthesis of specific triazolopyrimidine compounds and intermediates thereof as well as related derivatives, suitable for the preparation of ticagrelor (TGC)

  本发明涉及有机合成领域，描述了特定三唑吡咯啉化合物及其中间体的合成，以及相关衍生物，适用于替卡格雷洛（TGC）的制备。
• Triazolo(4,5-d)pyrimidine compounds
  申请人：Astrazeneca UK Limited

  公开号：US06525060B1

  公开（公告）日：2003-02-25

  Triazolo[4,5-d]pyrimidine compounds, their use as medicaments, compositions containing them and processes for their preparation. The compounds of the invention have the formula (I) as follows: wherein R, X and R1 through R3 are as defined in the specification.

  Triazolo[4,5-d]嘧啶化合物，它们作为药物的用途，含有它们的组合物以及它们的制备方法。本发明的化合物具有以下式(I)： 其中R、X和R1至R3如规范中所定义。
• Synthesis and anticancer activities of novel 8-azapurine carbocyclic nucleoside hydrazones
  作者：Yeming Wang、Hong Yan、Chao Ma、Dan Lu

  DOI：10.1016/j.bmcl.2015.09.002

  日期：2015.10

  A series of novel 8-azapurine carbocyclic nucleoside hydrazones were synthesized through a useful procedure starting from amino alcohol and pyrimido dichloride. All the products were characterized by (1)H NMR, (13)C NMR and HRMS spectral analysis and the stereochemical structure of key intermediate was also confirmed by a single crystal X-ray diffraction crystallographic analysis. Moreover, the anticancer

  通过一种有用的方法，从氨基醇和嘧啶二氯化物开始合成了一系列新型的8-氮杂嘌呤碳环核苷。所有产物均通过（1）H NMR，（13）C NMR和HRMS光谱分析进行表征，并且还通过单晶X射线衍射晶体学分析证实了关键中间体的立体化学结构。此外，在体外评估了对人肝癌Huh-7细胞系和人乳腺癌A549细胞系的抗癌活性。
• Synthesis of ticagrelor analogues belonging to 1,2,3-triazolo[4,5-d]pyrimidines and study of their antiplatelet and antibacterial activity
  作者：Eric Goffin、Nicolas Jacques、Lucia Musumeci、Alain Nchimi、Cécile Oury、Patrizio Lancellotti、Bernard Pirotte

  DOI：10.1016/j.ejmech.2020.112767

  日期：2020.12

  bactericidal activity against gram-positive bacteria, a series of 1,2,3-triazolo[4,5-d]pyrimidines structurally related to ticagrelor were synthesized and examined as putative antiplatelet and antibacterial agents. The aim was to assess the possibility of dissociating the two biological properties and to find novel 1,2,3-triazolo[4,5-d]pyrimidines expressing antiplatelet activity and devoid of in vitro antibacterial

  基于最近的观察，抗血小板药替卡格雷和其代谢产物之一对革兰氏阳性菌具有杀菌活性，合成并研究了一系列与替卡格雷相关的1,2,3-三唑并[4,5- d ]嘧啶作为推定的抗血小板和抗菌剂。目的是评估解离这两种生物学特性的可能性，并找到表达抗血小板活性且缺乏体外作用的新型1,2,3-三唑并[4,5- d ]嘧啶抗菌活性。合成的新化合物是替卡格雷的已知代谢产物以及结构简化的类似物。发现其中一些表达抗血小板活性并失去抗菌活性，支持了两种活性未必联系在一起的观点。