6-(phenylthio)uracil | 15422-05-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-(phenylthio)uracil
• 英文别名: 6-phenylsulfanyl-1H-pyrimidine-2,4-dione
• CAS: 15422-05-6
• 化学式: C₁₀H₈N₂O₂S
• 分子量: 220.252
• InChiKey: ZNLSBGQCJIWHCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(phenylthio)uracil 在 盐酸 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 28.0h， 生成 trans-1-(4'-hydroxy-2'-buten-1'-yl)-6-(thiophenyl)uracil
  参考文献：
  名称：

  Rajaratnam, Ragine; Phadtare, Shashi, Pharmacy and Pharmacology Communications, 1998, vol. 4, # 4, p. 205 - 209

  摘要：

  DOI：
• 作为产物：
  描述：

  6-(phenylthio)-2,4-bis(benzyloxy)pyrimidine 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到6-(phenylthio)uracil
  参考文献：
  名称：

  Phenylselenenyl- and phenylthio-substituted pyrimidines as inhibitors of dihydrouracil dehydrogenase and uridine phosphorylase

  摘要：

  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.

  DOI：

  10.1021/jm00078a015

文献信息

• Synthesis of substituted uracils by the reactions of halouracils with selenium, sulfur, oxygen and nitrogen nucleophiles under focused microwave irradiation
  作者：Woei-Ping Fang、Yuh-Tsyr Cheng、Yann-Ru Cheng、Yie-Jia Cherng

  DOI：10.1016/j.tet.2005.01.085

  日期：2005.3

  Under microwave irradiation, the nucleophilic substitution reactions of halouracils with selenium, sulfur, oxygen and nitrogen nucleophiles was complete within several minutes with yields up to 99%. The method using microwave irradiation is superior to those conducted under conventional heating processes.

  在微波辐射下，氟脲与硒，硫，氧和氮亲核试剂的亲核取代反应在几分钟内完成，收率高达99％。使用微波辐射的方法优于在常规加热过程下进行的方法。
• EFFICIENT SYNTHESIS OF NOVEL 6-PHENYLTHIO-2,4- DISUBSTITUTED PYRIMIDINES
  作者：Ν. M. Goudgaon、CH Upendar Reddy

  DOI：10.1515/hc.2008.14.6.443

  日期：2008.1

  substitution reaction of 6-phenylthio2,4-dichloropyrimidine with a oxygen nucleophile like sodium benzylate and nitrogen nucleophiles like heterocyclic primary amines, aliphatic primary amines and substituted aromatic primary amines furnished the target compounds, 6-phenylthio2,4-disubstituted pyrimidines respectively in 40-80% yield. Introduction In the last few years, uracil and pyrimidinone analogs substituted

  6-苯硫基-2,4-二取代嘧啶从巴比妥酸开始，分五步制备。巴比妥酸与 POCl 3 在 N，V-二甲基苯胺存在下的反应提供 2,4,6-三氯嘧啶，其与水溶液反应。NaOH回流产生6-氯尿嘧啶。6-氯尿嘧啶与苯硫酚在碱性条件下反应得到6-苯基硫尿嘧啶，在回流下使用过量POCl 3 氯化得到关键合成子6-苯硫基2,4-二氯嘧啶。6-苯硫基2,4-二氯嘧啶与氧亲核试剂如苄酸钠和氮亲核试剂如杂环伯胺、脂肪族伯胺和取代的芳香伯胺的芳香亲核取代反应提供了目标化合物6-苯硫基，4-二取代的嘧啶分别以 40-80% 的产率得到。介绍 在过去几年中，Ce 位取代的尿嘧啶和嘧啶酮类似物已成为化疗领域潜在的抗病毒药物。在重要的 6-取代尿嘧啶衍生物中，1-[(2-羟乙基)甲基]-6苯基硫尿嘧啶 (HEPT) 及其类似物 6-苄基-1-(乙氧基甲基)-5-异丙基尿嘧啶 (Emivirine, EMV) 已被选为治疗获得性免疫缺陷病毒
• Invariant and Variable Supramolecular Self-Assembly in 6-Substituted Uracil Derivatives: Insights from X-ray Structures and Quantum Chemical Study
  作者：Lamya H. Al-Wahaibi、Sai Ramya Sree Bysani、Samar S. Tawfik、Mohammed S. M. Abdelbaky、Santiago Garcia-Granda、Ali A. El-Emam、M. Judith Percino、Subbiah Thamotharan

  DOI：10.1021/acs.cgd.0c01583

  日期：2021.6.2

  interactions come from H···O contacts in 1, and these contacts were reduced due to the presence of methyl substitutions in 2 and 3. This reduction is compensated by the increase of the same amount of H···H contacts in these structures. Further, the PIXEL energy and DFT calculations at the M06-2X-D3/cc-pVTZ level of theory were used to characterize the dimeric topology formed in structures of 1–3. The intermolecular

  本研究开发了三种新的6-(芳硫基)尿嘧啶衍生物，即6-(苯硫基)嘧啶-2,4(1 H ,3 H )-二酮( 1 )、C 10 H 8 N 2 O 2 S；6-( p -tolylthio)pyrimidine-2,4(1 H ,3 H )-dione ( 2 ), C 11 H 10 N 2 O 2 S；和 6-(3,5-二甲基苯硫基)嘧啶-2,4(1 H ,3 H )-二酮 ( 3 ), C 12 H 12 N 2 O 2S，已经合成。这些化合物的单晶结构揭示了一个不变的分子带，其中包含交替的R 2 2 (8) 合成子，由1和3 中的N-H···O 氢键形成。这种交替的氢键模式在2 中消失了；相反，会生成一个新的合成子。晶格能计算表明，甲基取代衍生物（2和3）比化合物1具有更高的稳定能。. 静电势图揭示了羰基氧接受倾向的差异。Hirshfeld 表面和 2D 指纹图分析表明，主要的分子间相互作用来自1
• Reductive debromination and coupling reaction in the thermolysis of 5-bromouracils in N,N-dialkylamides. Cleavage of the C(5)–bromine bond by an initial electron-transfer process
  作者：Magiochi Sako、Mikio Suzuki、Miyuki Tanabe、Yoshifumi Maki

  DOI：10.1039/p19810003114

  日期：——

  Thermolysis of various 5-bromouracils (1) in N,N-dialkylamides results in the formation of methylenebisuracils (2) and reductive debrominated products (3)via cleavage of the C(5)–Br bond; the latter involves a one-electron transfer process. The product distribution between (2) and (3) depends upon the nature of substituents in the uracil ring.

  N，N-二烷基酰胺中的各种5-溴尿嘧啶（1）的热解通过C（5）-Br键的裂解形成亚甲基双尿嘧啶（2）和还原性溴化产物（3）；后者涉及单电子转移过程。（2）和（3）之间的产物分布取决于尿嘧啶环中取代基的性质。
• SYNTHESIS OF CERTAIN 6-(ARYLTHIO)URACILS AS POTENTIAL ANTIVIRAL AGENTS
  作者：Ali A. El-emam、Magda N.A. Nasr、Erik B. Pedersen、Tarek Fouad、Claus Nielsen

  DOI：10.1080/10426500108040231

  日期：2001.8.1

  Abstract A series of 6-(Arylthio)uracils have been prepared via condensation of 6-chlorouracil or 5-ethyl-6-chlorouracil with the corresponding thiophenol derivatives in pyridine or ethanolic potassium hydroxide. The synthesized compounds were tested for their antiviral activity. Some of the 5-ethyl-6-(arylthio)uracil derivatives 10a-g showed moderate activities against hepatitis B Virus (HBV) and

  摘要 通过6-氯尿嘧啶或5-乙基-6-氯尿嘧啶与相应的苯硫酚衍生物在吡啶或乙醇氢氧化钾中缩合制备了一系列6-(芳硫基)尿嘧啶。测试合成的化合物的抗病毒活性。一些 5-乙基-6-（芳硫基）尿嘧啶衍生物 10a-g 对乙型肝炎病毒 (HBV) 和 HIV-1 病毒显示出中等活性。