5-(phenylthio)uracil | 1137-90-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-(phenylthio)uracil
• 英文别名: 5-(phenylthio)pyrimidine-2,4(1H,3H)-dione；5-phenylsulfanyl-1H-pyrimidine-2,4-dione
• CAS: 1137-90-2
• 化学式: C₁₀H₈N₂O₂S
• 分子量: 220.252
• InChiKey: MFORXTHLVUSZNY-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：

  5-(phenylthio)uracil 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 17.5h， 生成
  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：

  5-(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72%的产率得到5-(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。
• Photoinitiated Synthesis of Sulfides in Water
  作者：Sergio A. Rodriguez、Leandro D. Mena、Maria T. Baumgartner

  DOI：10.1071/ch15496

  日期：——

  Herein, we report a synthetic route to obtain aryl sulfides using inexpensive and non-toxic reactants and water as solvent, that avoids the use of catalysts or heating. The photoinduced reaction between soluble substrates and a series of thiols in alkaline aqueous medium produces the corresponding sulfides in moderate to good yields.

  在此，我们报告了一种合成途径，该途径使用廉价且无毒的反应物和水作为溶剂来获得芳基硫，从而避免了使用催化剂或加热。可溶性底物与碱性水溶液介质中的一系列硫醇之间的光诱导反应以中等至良好的产率产生相应的硫化物。
• 制备5-硫/硒修饰尿嘧啶衍生物的方法
  申请人：中国科学院化学研究所

  公开号：CN109651267B

  公开（公告）日：2020-05-19

  本发明属于有机化学领域，具体涉及一种高效制备5‑硫/硒修饰尿嘧啶衍生物的方法。所述方法为：在碘源、氧化剂存在下，在溶剂中，使得式I所示硫酚类化合物或式II所示二硒醚类化合物与式III所示尿嘧啶反应，得到式IV所示5‑硫修饰尿嘧啶衍生物或式V所示5‑硒修饰尿嘧啶衍生物。本发明提供了一种无金属催化，无预先官能化的一步法制备硫/硒修饰尿嘧啶类化合物的通用方法，该方法绿色简洁可行，原料简单易得，底物范围广，应用前景广泛。
• A NaI/H₂O₂-Mediated Sulfenylation and Selenylation of Unprotected Uracil and Its Derivatives
  作者：Xue-Dong Li、Yu-Ting Gao、Ying-Jie Sun、Xiao-Yang Jin、Dong Wang、Li Liu、Liang Cheng

  DOI：10.1021/acs.orglett.9b02183

  日期：2019.9.6

  efficient iodide-catalyzed/hydrogen peroxide mediated sulfenylation and selenylation of unprotected uracil and its derivatives with simple thiols and diselenides was established. This coupling tolerates a broad variety of functional groups to provide diverse 5-sulfur/selenium-substituted uracil derivatives in good to excellent yields (up to 93%).

  建立了有效的碘化物催化/过氧化氢介导的未保护的尿嘧啶及其衍生物与简单硫醇和二硒化物的亚磺酰化和硒基化反应。这种偶联耐受多种官能团，以良好至极佳的收率（高达93％）提供各种5-硫/硒取代的尿嘧啶衍生物。
• Recyclable Iron/Graphite Catalyst for C-S Cross Coupling of Thiols with Aryl Halides under Ligand-Free Conditions
  作者：Kakulapati Rao、Vijay Akkilagunta、Vutukuri Reddy

  DOI：10.1055/s-0029-1219801

  日期：2010.5

  A recyclable iron/graphite (Fe/Cg) catalyst for the efficient C-S cross-coupling of various iodoarenes with aromatic/ aliphatic thiols has been developed under ligand-free conditions (26 examples, up to 99% yield). The catalyst can be easily recovered and recycled up to seven cycles without loss of activity.

  在无配体条件下开发了一种可回收的铁/石墨 (Fe/Cg) 催化剂，用于各种碘芳烃与芳香族/脂肪族硫醇的高效 CS 交叉偶联（26 个例子，产率高达 99%）。催化剂可以很容易地回收和循环使用多达七个循环而不会损失活性。