1-(2-羟基乙氧基甲基)-5-苯基硒基嘧啶-2,4-二酮 | 153081-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1-(2-羟基乙氧基甲基)-5-苯基硒基嘧啶-2,4-二酮
• 英文名称: 1-<(2-hydroxyethoxy)methyl>-5-(phenylselenyl)uracil
• 英文别名: 5-(phenylselenenyl)acyclouridine；1-[(2-hydroxyethoxy)methyl]-5-(phenylselenenyl)uracil；1-((2-Hydroxyethoxy)methyl)-5-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione；1-(2-hydroxyethoxymethyl)-5-phenylselanylpyrimidine-2,4-dione
• CAS: 153081-01-7
• 化学式: C₁₃H₁₄N₂O₄Se
• 分子量: 341.225
• InChiKey: KFSPSGWABMNFIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.84
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯基氯化硒 、 1-(2-羟基乙氧基甲基)嘧啶-2,4-二酮 以 吡啶 、 乙醇 、 苯 为溶剂， 以76%的产率得到1-(2-羟基乙氧基甲基)-5-苯基硒基嘧啶-2,4-二酮
  参考文献：
  名称：

  Enzyme inhibitors, their synthesis and methods for use

  摘要：

  提供了一种新型化合物，可有效抑制DHUDase或UrdPase的活性。这些化合物具有一般式 ##STR1## 其中 X 是 S 或 Se；Y 是 I、F、Cl、Br、甲氧基、苄基、硒苯基或噻吩基，R.sub.1 是具有一般式 ##STR2## 的醋酸尾部，其中 R.sub.2 是 H、CH.sub.2 OH 或 CH.sub.2 NH.sub.2 ；R.sub.3 是 OH、NH.sub.2 或 OCOCH.sub.2 CH.sub.2 CO.sub.2 H；R.sub.4 是 O、S 或 CH.sub.2。这些化合物可以与各种化疗药物一起用于制备药物组合物，以增加治疗的功效。这些化合物还可以用于通过联合给药或顺序给药酶抑制化合物和有效治疗癌症、病毒、真菌、细菌或寄生虫感染的化疗药物来治疗患者的方法。这些化合物还可以用于增强成像。此外，它们可以单独用于预防和/或治疗嘧啶分解和其他生理紊乱。

  公开号：

  US05476855A1

文献信息

• Phenylselenenyl- and phenylthio-substituted pyrimidines as inhibitors of dihydrouracil dehydrogenase and uridine phosphorylase
  作者：Naganna M. Goudgaon、Fardos N. M. Naguib、Mahmoud H. el Kouni、Raymond F. Schinazi

  DOI：10.1021/jm00078a015

  日期：1993.12

  Lithiation of 5-bromo-2,4-bis (benzyloxy) pyrimidine (3) with n-BuLi at -80 degrees C followed by the addition of diphenyl diselenide or diphenyl disulfide as an electrophile furnished the corresponding 5-(phenylhetera)-2,4-bis(benzyloxy) pyrimidine, which on exposure to trimethylsilyl iodide in CH2-Cl-2 at room temperature yielded the 5-(phenylhetera)uracils in 70-75% yield. Similarly, the 6-(phenylhetera) uracils were prepared from 6-bromo-2,4-bis (benzyloxy) pyrimidine (10). 1-[(2-Hydroxyethoxy)methyl] -5-(phenylselenenyl)uracil (PSAU, 18) and 1-(ethoxymethyl)-5- (phenylselenenyl)uracil (17) were synthesized by the electrophilic addition of benzeneselenenyl chloride to the acyclic uracils under basic conditions. These compounds were evaluated for their ability to inhibit dihydrouracil dehydrogenase (DHUDase, E.C. 1.3.1.2), orotate phosphoribosyltransferase (OPRTase, E.C. 2.4.2.10), uridine phosphorylase (UrdPase, E.C. 2.4.2.3), and thymidine phosphorylase (dThdPase, E.C. 2.4.2.4). 5-(Phenylselenenyl)uracil (PSU, 6) and 5-(phenylthio)uracil (PTU, 7) inhibited DHUDase with apparent K-i values of 4.8 and 5.4 mu M, respectively. The corresponding 6-analogues, compounds 13 and 14, demonstrated inhibitory activity against OPRTase. PTU as well as PSU and its riboside, 2'-deoxyriboside, and acyclonucleosides were inhibitors of UrdPase, with PSAU (18) being the most potent with an apparent K-i value of 3.8 mu M. None of the compounds evaluated had any effect on dThdPase. Interestingly, most of the compounds showed modest selective anti-human-immunodeficiency-virus activity in acutely infected primary human lymphocytes.
• Goudgaon Naganna M., Naguib Fardos N. M., Kouni Mahmoud H. el, Schimazi R+, J. Med. Chem, 36 (1993) N 26, S 4250-4254
  作者：Goudgaon Naganna M., Naguib Fardos N. M., Kouni Mahmoud H. el, Schimazi R+

  DOI：——

  日期：——