(+/-)-1-(4-hydroxymethyl-2H,5H-dihydrothiophen-2-yl)-5-methyl-1H-pyrimidine-2,4-dione | 328386-40-9

• 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: (+/-)-1-(4-hydroxymethyl-2H,5H-dihydrothiophen-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[4-(Hydroxymethyl)-2,5-dihydrothiophen-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[4-(hydroxymethyl)-2,5-dihydrothiophen-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 328386-40-9
• 化学式: C₁₀H₁₂N₂O₃S
• 分子量: 240.283
• InChiKey: HBMCKEAJMLDEKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-hydroxymethyl-5H-furan-2-one 在 palladium on activated charcoal sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 氢气 、 二异丁基氢化铝 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 生成 (+/-)-1-(4-hydroxymethyl-2H,5H-dihydrothiophen-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  STRUCTURE-ACTIVITY RELATIONSHIPS OF APIO NUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS

  摘要：

  Several types of novel apio nucleosides were synthesized starting from 1,3-dihydroxyacetone and evaluated for antiviral activity. Among compounds tested, amino substituted apio dideoxynucleosides exhibited anti-HBV activity, while thioapio dideoxynucleosides were found to be active against HIV-1. Apio dideoxydidehydro nucleosides showed moderate to potent anti-HCMV activity, but their bioisosteric thioapio dideoxydidehydro nucleosides did not exhibit any significant antiviral activity.

  DOI：

  10.1081/ncn-100002344

文献信息

• Syntheses and Structure−Activity Relationships of Novel Apio and Thioapio Dideoxydidehydronucleosides as Anti-HCMV Agents
  作者：Lak Shin Jeong、Hea Ok Kim、Hyung Ryong Moon、Joon Hee Hong、Su Jeong Yoo、Won Jun Choi、Moon Woo Chun、Chong-Kyo Lee

  DOI：10.1021/jm000342f

  日期：2001.3.1

  acid produced from the basic hydrolysis of thioacetate 16. The majority of apio analogues synthesized in this study exhibited moderate to potent anti-HCMV activity, among which the 5-fluorouracil derivative 13c was found to be the most potent against HCMV, while thioapio analogues showed no activity against HCMV. However, all synthesized compounds did not exhibit any significant activities against HIV-1

  基于其中呋喃糖氧和2,3-二脱氧核糖的C2发生转位的apio双脱氧核苷，显示出有效的抗HIV活性和2'，3'-dideoxy-2'，3'-didehydronucleosides还显示出有效的抗HIV活性，我们合成了apio双脱氧二氢核苷，其中的氧原子与2,3-dideoxy-2,3-didehydro核糖的双键交换了。由于硫起氧的生物等排体的作用，因此也合成了硫代双脱氧二氢核苷。以苯基硒烯基化学为关键步骤，从1,3-二羟基丙酮开始合成Apio二脱氧二氢核苷13a-f。在路易斯酸存在下，在核苷碱基与乙酸苯硒烯基酯11缩合期间，异头物混合物的比例可在1：1至5：1之间变化。这与其他糖基供体例如5-O-（叔丁基二苯基甲硅烷基）-2-苯基硒烯基-2,3-二脱氧核糖基乙酸酯相反，其显示出优异的邻近基团效应（α：β= 1:99）。由内酯9经由硫代内酯17作为主要中间体合成了内酯9的硫代二脱氧二氢核苷