1,3-二苄基-1-(7-氯噻唑并[5,4-d]嘧啶-2-基)硫脲 | 871266-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 1,3-噻唑并[5,4-d]嘧啶
• 中文名称: 1,3-二苄基-1-(7-氯噻唑并[5,4-d]嘧啶-2-基)硫脲
• 英文名称: 1,3-dibenzyl-1-(7-chloro[1,3]thiazolo[5,4-d]pyrimidin-2-yl)thiourea
• 英文别名: 1,3-dibenzyl-1-(7-chlorothiazolo[5,4-d]pyrimidin-2-yl)thiourea；1,3-dibenzyl-1-(7-chloro-[1,3]thiazolo[5,4-d]pyrimidin-2-yl)thiourea
• CAS: 871266-88-5
• 化学式: C₂₀H₁₆ClN₅S₂
• 分子量: 425.966
• InChiKey: GMRJTVNCPZHTOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,6-二氯-5-氨基嘧啶 、 异硫氰酸苯甲酯 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以94%的产率得到1,3-二苄基-1-(7-氯噻唑并[5,4-d]嘧啶-2-基)硫脲
  参考文献：
  名称：

  Single-Step Syntheses of 2-Amino-7-chlorothiazolo[5,4-d]pyrimidines:  Intermediates for Bivalent Thiazolopyrimidines

  摘要：

  A single-step process for the preparation of 2-amino-7-chlorothiazolo[5,4-d]pyrimidines, 2, was achieved by the reaction of the commercially available 4,6-dichloro-5-aminopyrimidine 1 with isothiocyanates. This mild reaction accommodates a variety of functionalized isothiocyanates and proceeds in good to excellent yields. The utility of such intermediates is exemplified by subsequent reaction with alkyl or arylamine nucleophiles to afford novel, differentially functionalized 2,7-diaminothiazolo[5,4-d]pyrimidines, 3.

  DOI：

  10.1021/jo0517702

文献信息

• Synthesis, antiproliferative and apoptosis-inducing activity of thiazolo[5,4-d]pyrimidines
  作者：Baljinder Singh、Santosh K. Guru、Smit Kour、Shreyans K. Jain、Rajni Sharma、Parduman R. Sharma、Shashank K. Singh、Shashi Bhushan、Sandip B. Bharate、Ram A. Vishwakarma

  DOI：10.1016/j.ejmech.2013.10.039

  日期：2013.12

  Thiazolo[5,4-d]pyrimidines are important class of heterocyclic compounds possessing diverse range of biological activities. Herein, we report an efficient synthesis of thiazolo[5,4-d]pyrimidines using recyclable KF/alumina catalyst. The reaction of 4,6-dichloro-5-aminopyrimidine with isothiocyanates in presence of 20 mol% KF/alumina produced thiazolo[5,4-d]pyrimidines in excellent yields without any

  噻唑并[5,4- d ]嘧啶是重要的一类具有多种生物活性的杂环化合物。在本文中，我们报告了使用可回收的KF /氧化铝催化剂高效合成噻唑并[5,4- d ]嘧啶的方法。4,6-二氯-5-氨基嘧啶在20 mol％KF /氧化铝存在下与异硫氰酸酯反应生成噻唑并[5,4- d]嘧啶类化合物，收率极高，无需任何色谱纯化。该方法操作简单，快速并且催化剂可以重复使用而没有任何明显的活性损失。在8种癌细胞系中测试了这些化合物的抗增殖活性，这些细胞系包括肺癌（NCI-H322和A549），表皮（A431），成胶质细胞瘤（T98G），胰腺（MIAPaCa-2），前列腺（PC-3），人白血病（HL-60）和乳腺癌（T47D）细胞。N，N'-二乙氨基取代的类似物2-（4-氯苯基氨基）-7-二乙氨基噻唑并[5,4- d ]嘧啶4k在肺（NCI-H322和A549），表皮（A431）中显示抗增殖活性和具有IC 50的
• Discovery of 7-(Prolinol-<i>N</i>-yl)-2-phenylamino-thiazolo[5,4-<i>d</i>]pyrimidines as Novel Non-Nucleoside Partial Agonists for the A_2A Adenosine Receptor: Prediction from Molecular Modeling
  作者：Sandip B. Bharate、Baljinder Singh、Sonja Kachler、Ana Oliveira、Vikas Kumar、Sonali S. Bharate、Ram A. Vishwakarma、Karl-Norbert Klotz、Hugo Gutiérrez de Terán

  DOI：10.1021/acs.jmedchem.6b00552

  日期：2016.6.23

  We describe the identification of 7-(prolinol-N-yl)-2-phenylamino-thiazolo[5,4-d]pyrimidines as a novel chemotype of non-nucleoside partial agonists for the A(2A) adenosine receptor (A(2A)AR). Molecular-modeling indicated that the (S)-2-hydroxymethylene-pyrrolidine could mimic the interactions of agonists' ribose, suggesting that this class of compounds could have agonistic properties. This was confirmed by functional assays on the A(2A)AR, where their efficacy could be associated with the presence of the 2-hydroxymethylene moiety. Additionally, the best compound displays promising affinity, selectivity profile, and physicochemical properties.