2-amino-5-(prop-2-yn-1-yl)pyrimidine-4,6-diol | 81887-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-amino-5-(prop-2-yn-1-yl)pyrimidine-4,6-diol
• 英文别名: 2-amino-4,6-dihydroxy-5-(prop-2-yn-1-yl)pyrimidine；2-Amino-6-hydroxy-5-(2-propynyl)-4-(3H)-pyrimidinone；2-amino-4-hydroxy-5-prop-2-ynyl-1H-pyrimidin-6-one
• CAS: 81887-04-9
• 化学式: C₇H₇N₃O₂
• 分子量: 165.151
• InChiKey: FZYMPCIFGOHPEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-5-(prop-2-yn-1-yl)pyrimidine-4,6-diol 在 硫酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 methyl 4-[(1S)-1-[(2-amino-6-methyl-furo[2,3-d]pyrimidin-4-yl)amino]ethyl]benzoate
  参考文献：
  名称：

  [EN] BAX INHIBITORS AND USES THEREOF
  [FR] INHIBITEURS DE BAX ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2021002986A3
• 作为产物：
  描述：

  盐酸胍 、 2-(2-丙炔-1-基)丙二酸二乙酯 在 sodium 作用下， 以 乙醇 为溶剂， 以96%的产率得到2-amino-5-(prop-2-yn-1-yl)pyrimidine-4,6-diol
  参考文献：
  名称：

  5-Substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4,6-dichloropyrimidines: synthesis and inhibitory effects on immune-activated nitric oxide production

  摘要：

  A series of 5-substituted 2-amino-4,6-dihydroxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, has been developed to convert the 2-amino-4,6-dihydroxypyrimidine analogs to novel 5-substituted 2-amino-4,6-dichloropyrimidines in high yields. Pilot screening for biological properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irrespective of the substituent at the 5 position, 2-amino-4,6-dichloropyrimidines inhibited immune-activated NO production. The most effective was 5-fluoro-2-amino-4,6-dichloropyrimidine with an IC ₅₀ of 2 µM (higher activity than the most potent reference compound) while the IC ₅₀s of other derivatives were within the range of 9-36 µM. The 2-amino-4,6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells. The Mechanism of action remains to be elucidated.

  DOI：

  10.1007/s00044-014-1018-9

文献信息

• [EN] PYRIMIDINE COMPOUNDS INHIBITING THE FORMATION OF NITRIC OXIDE AND PROSTAGLANDIN E2, METHOD OF PRODUCTION THEREOF AND USE THEREOF<br/>[FR] COMPOSÉS DE PYRIMIDINE INHIBANT LA FORMATION D'OXYDE NITRIQUE ET PROSTAGLANDINE E2, LEUR PROCÉDÉ DE PRODUCTION ET LEUR UTILISATION
  申请人：USTAV ORGANICKE CHEMIE A BIOCHEMIE AKADEMIE VED CR V V I

  公开号：WO2012116666A1

  公开（公告）日：2012-09-07

  The invention provides pyrimidine compounds of general formula (I), which reduce simultaneously the production of nitric oxide (NO) and prostaglandin E2 (PGE2). They have no negative effect on the viability of cells in concentrations decreasing the production of these factors by up to 50%; they are not cytotoxic. Furthermore, a method of preparation of the pyrimidine compounds of general formula (I), carrying 2-formamido group, a pharmaceutical composition comprising the substituted pyrimidine compounds according to the invention, and the use of these compounds for the treatment of inflammatory and cancer diseases are provided.˙

  该发明提供了一般式(I)的嘧啶化合物，可以同时减少一氧化氮（NO）和前列腺素E2（PGE2）的产生。它们在降低这些因子产生达到50%的浓度下对细胞的存活性没有负面影响；它们不具有细胞毒性。此外，还提供了一种制备一般式(I)的带有2-甲酰胺基团的嘧啶化合物的方法，一种包括根据该发明的取代嘧啶化合物的药物组合物，以及利用这些化合物治疗炎症和癌症疾病的方法。
• Herbicidal sulfonamides
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04487626A1

  公开（公告）日：1984-12-11

  This invention relates to a novel class of arylsulfonylureidofuro[2,3-d]pyrimidines, such as N'-[(4,6-dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]-N,N-dimethylbenz ene-1,2-sulfonamide, and their use as herbicides and plant growth regulants. These novel compounds can be prepared by reacting an appropriate furo[2,3-d]pyrimidin-2-amine with an appropriately substituted arylsulfonyl isocyanate or isothiocyanate.

  这项发明涉及一种新型的芳基磺酰脲基呋[2,3-d]嘧啶类化合物，例如N'-[(4,6-二甲基呋[2,3-d]嘧啶-2-基)氨基甲酰]-N,N-二甲基苯-1,2-磺酰胺，以及它们作为除草剂和植物生长调节剂的用途。这些新型化合物可以通过将适当的呋[2,3-d]嘧啶-2-胺与适当取代的芳基磺酰异氰酸酯或异硫氰酸酯反应而制备。
• ZIMMERMAN, W. T.
  作者：ZIMMERMAN, W. T.

  DOI：——

  日期：——
• PYRIMIDINE COMPOUNDS INHIBITING THE FORMATION OF NITRIC OXIDE AND PROSTAGLANDIN E2, METHOD OF PRODUCTION THEREOF AND USE THEREOF
  申请人：Ustav Organicke Chemie A Biochemie Akademie Ved Cr, v.v.i.

  公开号：EP2680847A1

  公开（公告）日：2014-01-08
• BAX INHIBITORS AND USES THEREOF
  申请人：CASE WESTERN RESERVE UNIVERSITY

  公开号：US20220389028A1

  公开（公告）日：2022-12-08

  A compound having formula (I) or (II) for use inhibiting Bax mediated cell death and/or apoptosis.