(4-amino-5-fluoro-1,2-dihydropyrimidin-2-one)*(5-fluoro-2,4-(1H,3H)-pyrimidinedione)

• 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: (4-amino-5-fluoro-1,2-dihydropyrimidin-2-one)*(5-fluoro-2,4-(1H,3H)-pyrimidinedione)
• 英文别名: 6-amino-5-fluoro-1H-pyrimidin-2-one;5-fluoro-1H-pyrimidine-2,4-dione
• 化学式: C₄H₃FN₂O₂*C₄H₄FN₃O
• 分子量: 259.172
• InChiKey: UISCMAXQLBTDKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.31
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-氟脲嘧啶 、 氟胞嘧啶 以 水 为溶剂， 生成 (4-amino-5-fluoro-1,2-dihydropyrimidin-2-one)*(5-fluoro-2,4-(1H,3H)-pyrimidinedione)
  参考文献：
  名称：

  Controlled Synthesis of New 5-Fluorocytosine Cocrystals Based on the pK_a Rule

  摘要：

  5-Fluorocytosine (5-FC) was investigated for the controlled synthesis of cocrystals by applying the pK(a) rule. Five cocrystals were designed and developed with adipic, succinic, terephtalic, benzoic, and malic acids, all exhibiting negative Delta pK(a) values ranging from close to zero up to roughly -1. The synthesized cocrystals were analyzed by single crystal X-ray diffraction, and the observed supramolecular synthons were compared to the reported structures containing 5-FC. In the first four cocrystals, the intermolecular interactions between adjacent 5-FC molecules form two different homodimers showing R-2(2)(8) motifs and assembled via complementary N-H center dot center dot center dot O and N-H center dot center dot center dot N hydrogen bonds, respectively. However, in the cocrystal with malic acid (Delta pK(a) = -0.1), an intermediate supramolecular synthon pattern between salts and cocrystals is observed. In this crystal packing, the homodimer of 5-FC molecules held by the N-H center dot center dot center dot O interactions is preserved, but a new heterodimer is formed between 5-FC and the acid molecule, such as the ones observed for 5-FC salts. These differences were analyzed using UNI Force Field Calculations to establish the intermolecular potentials of the synthons. As an application, we synthesized a cocrystal of 5-FC with 5-fluorouracil. This can be considered the first step toward the application of 5-FC for the design of new tailor-made drugs.

  DOI：

  10.1021/cg500502j

文献信息

• SENSITIZING CELLS TO COMPOUNDS USING LIPID-MEDIATED GENE AND COMPOUND DELIVERY
  申请人：Inex Pharmaceuticals Corp.

  公开号：EP1053022A2

  公开（公告）日：2000-11-22
• A COMBINED GROWTH FACTOR-DELETED AND THYMIDINE KINASE-DELETED VACCINIA VIRUS VECTOR
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1180157A1

  公开（公告）日：2002-02-20
• METHOD FOR DETECTION OF CANCER CELLS USING VIRUS
  申请人：MEMORIAL SLOAN-KETTERING CANCER CENTER

  公开号：EP1979000B1

  公开（公告）日：2011-07-13
• PEPTIDE CLEARING AGENTS
  申请人：Mologic Ltd

  公开号：EP2470216A1

  公开（公告）日：2012-07-04
• BIOMARKERS AND THERAPEUTIC TARGETS FOR SARCOMA
  申请人：Oxford University Innovation Limited

  公开号：EP3107936A1

  公开（公告）日：2016-12-28