4,6-Dihydroxy-5-nitro-2-[(phenylmethyl)thio]pyrimidine | 354582-76-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,6-Dihydroxy-5-nitro-2-[(phenylmethyl)thio]pyrimidine
• 英文别名: 5-Nitro-2-[(phenylmethyl)thio]-4,6-pyrimidinediol；2-(Benzylthio)-5-nitropyrimidine-4,6-diol；2-benzylsulfanyl-4-hydroxy-5-nitro-1H-pyrimidin-6-one
• CAS: 354582-76-6
• 化学式: C₁₁H₉N₃O₄S
• 分子量: 279.276
• InChiKey: JZLXPDXFQHWKND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,6-Dihydroxy-5-nitro-2-[(phenylmethyl)thio]pyrimidine 在 三氯氧磷 作用下， 反应 2.0h， 生成 4,6-Dichloro-5-nitro-2-[(phenylmethyl)thio]-pyrimidine
  参考文献：
  名称：

  噻唑并[5,4- d ]嘧啶衍生物的设计，合成及抗增殖活性

  摘要：

  通过基于生物学验证的支架的原子替换策略，设计了一系列噻唑并[5,4- d ]嘧啶衍生物，然后评估其在癌细胞系中的抗增殖活性。进行了结构活性关系研究，从而鉴定出了化合物22，该化合物对HGC-27表现出良好的抗增殖活性，IC 50值为1.22μM，对GES-1细胞的毒性低。机理研究表明，化合物22抑制HGC-27的菌落形成和迁移以及诱导细胞凋亡。免疫印迹实验证明化合物22上调Bax的表达，下调Bcl-2的表达水平并切割caspased-3 / 9。这些发现表明，化合物22可以用作设计用于治疗人胃癌的新药物的模板。原子替代策略可能是设计新的抗癌药物的可行策略，并且可能会在药物设计中找到其应用。

  DOI：

  10.1016/j.ejmech.2017.07.039
• 作为产物：
  描述：

  7,9-dihydro-6-[[(1R)-2-hydroxy-1-methylethyl]amino]-2-[(phenylmethyl)thio]-8H-purin-8-one 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 生成 4,6-Dihydroxy-5-nitro-2-[(phenylmethyl)thio]pyrimidine
  参考文献：
  名称：

  Pyrimidine compounds and their use as modulators of chemokine receptor activity

  摘要：

  这项发明提供了某些杂环化合物，其制备过程和中间体，包含它们的药物组合物以及它们在治疗中的应用；在式（I）中，A是式（a）或（b）的基团。

  公开号：

  US20030040523A1

文献信息

• Design, synthesis, and biological evaluation of new thiazolo[5,4-d]pyrimidine derivatives as potent antiproliferative agents
  作者：Zhong-Hua Li、Xue-Qi Liu、Peng-Fei Geng、Jin-Lian Ma、Tao-Qian Zhao、Hao-Ming Wei、Bin Yu、Hong-Min Liu

  DOI：10.1039/c7md00165g

  日期：——

  A series of thiazolo[5,4-d]pyrimidine derivatives were synthesized and evaluated for their antiproliferative activities against several human cancer cell lines. Structure–activity relationship studies were carried out, showing that most of the target compounds had good inhibition against the tested cell lines. Among them, compound 7i exhibited potent inhibition against human gastric cancer cells MGC-803

  合成了一系列噻唑并[5,4- d ]嘧啶衍生物，并评估了其对几种人类癌细胞系的抗增殖活性。进行了结构-活性关系研究，结果表明大多数目标化合物对受试细胞系均具有良好的抑制作用。其中，化合物7i对人胃癌细胞MGC-803和HGC-27表现出强抑制作用，IC 50值分别为4.64和5.07μM，在MGC-803和GES-1之间的选择性约为12倍，表明相对较低对正常细胞有毒性。化合物7i的效力和低毒性使噻唑洛[5,4- d]嘧啶是一种有吸引力的支架，用于设计选择性靶向MGC-803细胞的新衍生物。
• Design, synthesis and in vitro biological evaluation of novel [1,2,3]triazolo[4,5-d]pyrimidine derivatives containing a thiosemicarbazide moiety
  作者：Peng-Fei Geng、Xue-Qi Liu、Tao-Qian Zhao、Cong-Cong Wang、Zhong-Hua Li、Ji Zhang、Hao-Ming Wei、Biao Hu、Li-Ying Ma、Hong-Min Liu

  DOI：10.1016/j.ejmech.2018.01.031

  日期：2018.2

  A series of hybrid molecules containing [1,2,3]triazolo[4,5-d]pyrimidine and thiosemicarbazide moieties were designed, synthesized and evaluated for their antiproliferative activities against MGC-803, NCI-H1650 and PC-3 human cancer cells. Some of the synthesized compounds showed moderate to good activity against three selected cancer cell lines. Among these compounds, compound 29 displayed the most potent antiproliferative activity as well as good selectivity between cancer cells and normal cells. Further mechanism studies revealed that compound 29 could obviously inhibit the colony formation and migration of MGC-803 as well as induced apoptosis. (C) 2018 Elsevier Masson SAS. All rights reserved.
• PYRIMIDINE COMPOUNDS AND THEIR USE AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：AstraZeneca AB

  公开号：EP1257555B1

  公开（公告）日：2003-12-03
• US6958344B2
  申请人：——

  公开号：US6958344B2

  公开（公告）日：2005-10-25
• [EN] PYRIMIDINE COMPOUNDS AND THEIR USE AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] COMPOSES PYRIMIDINIQUES ET LEUR UTILISATION COMME MODULATEURS DE L'ACTIVITE DES RECEPTEURS DE CHIMIOKINE
  申请人：ASTRAZENECA AB

  公开号：WO2001058906A1

  公开（公告）日：2001-08-16

  The invention provides certain pyrimidine compounds, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy. Formula (I) in which: A is a group of formula (a), (b) or (c).