1,3-bis(trimethylsilyl)uracil | 3442-82-8

• 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: 1,3-bis(trimethylsilyl)uracil
• 英文别名: bis(trimethylsilyl)uracil；bis(TMS)uracil；2,4(1H,3H)-Pyrimidinedione, 1,3-bis(trimethylsilyl)-；1,3-bis(trimethylsilyl)pyrimidine-2,4-dione
• CAS: 3442-82-8
• 化学式: C₁₀H₂₀N₂O₂Si₂
• 分子量: 256.452
• InChiKey: WPNJNSFRHGSSCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  [(2S,3S)-3-(chloromethoxy)-4-diethoxyphosphorylbutan-2-yl]oxymethylbenzene 、 1,3-bis(trimethylsilyl)uracil 在 四乙基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 1-<<(3S)-(benzyloxy)-1-(diethylphosphonyl)-(2R)-butoxy>methyl>uracil
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1‘,2‘-Seconucleo-5‘-phosphonates

  摘要：

  A series of 1',2'-seconucleophosphonate analogues were prepared containing adenine, cytosine, thymine, and uracil as the nucleobase. The synthetic methodology is efficient and uses chloromethyl ethers derived from the chirons diethyl (3S)-(benzyloxy)-(2R)-hydroxybutanephosphonate (1) and diethyl (3S),4-bis(benzyloxy)-(2R)-hydroxybutanephosphonate (2). Selected deblocked derivatives, i.e., two monoesters (13 and 14), four phosphonic acids (15-18), and one cyclic phosphonate (23), were screened for in vitro activity against certain RNA, adeno, and HIV viruses. All of them were found to be devoid of activity.

  DOI：

  10.1021/jm9506783
• 作为产物：
  描述：

  N,O-双三甲硅基乙酰胺 、 尿嘧啶 以 乙腈 为溶剂， 生成 1,3-bis(trimethylsilyl)uracil
  参考文献：
  名称：

  A General Synthesis of C2'-Deuterated Ribonucleosides

  摘要：

  DOI：

  10.1021/jo00095a060
• 作为试剂：
  描述：

  苯基氯化硒 、 乙酰化葡萄烯糖 在 silver trifluoromethanesulfonate 、 1,3-bis(trimethylsilyl)uracil 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 1-(2'-deoxy-2'-phenylselenenyl-3',4',6'-tri-O-acetyl-β-D-gluco-pyranosyl)-uracil 、 1-(2'-deoxy-2'-phenylselenenyl-3',4',6'-tri-O-acetyl-α-D-manno-pyranosyl)-uracil 、 1-(4',6'-O-diacetyl-2',3'-dideoxy-β-D-erythro-hex-2-enopyranosyl)uracil
  参考文献：
  名称：

  Synthesis of 2′-deoxy-pyranosyl nucleosides from glycals through consecutive addition of phenylselenenyl chloride and glycosylation. A study of factors controlling the stereoselectivity

  摘要：

  2'-Deoxy-2'-phenylselenenyl-pyranosyl nucleosides have been synthesised in a stereoselective way starting from glycals using selenium reagents, and converted into 2'-deoxynucleosides by treatment with tributyltin hydride. The stereoselectivity of the reaction has been shown to be dependent on the protecting groups, the structure of the starting glycal, the phenylselenenyl reagent and the solvent. Nucleosides of beta-gluco beta-galacto and alpha-arabino configuration are principally obtained, starting from the corresponding benzyl protected glycals, using PhSeCl as an activating reagent and ehter as the solvent.

  DOI：

  10.1016/s0040-4020(01)89572-7

文献信息

• The Syntheses of Purine and Pyrimidine Secoribo-nucleosides: Acyclo-uridine Derivative of Cyclophosphamide
  作者：Maryam Zakerinia、Hady Davary、Gholam H. Hakimelahi

  DOI：10.1002/hlca.19900730418

  日期：1990.6.20

  The synthesis of secoribo-nucleoside analogues is described. Compounds 4 and 5 possess interesting antiviral effects in vitro. A procedure is also developed for the conversion of acyclo-uridine nucleoside 7 to a novel derivative of cyclophosphamide 8.

  描述了secoribo-核苷类似物的合成。化合物4和5在体外具有令人感兴趣的抗病毒作用。还开发了将无环尿苷核苷7转化为环磷酰胺8的新型衍生物的程序。
• 用于抗病毒治疗的被取代的N4-羟基胞苷衍 生物及其前药
  申请人：常州安蒂卫生物科技有限公司

  公开号：CN111548384B

  公开（公告）日：2021-04-27

  本发明涉及具有式I结构的被取代的N4‑羟基胞苷衍生物、前药及其药物组合物，以及使用该组合物用于治疗病毒感染的方法，所述式I结构的被取代的N4‑羟基胞苷衍生物结构为：本发明所述药物组合物用于制备治疗副粘液病毒科、正粘液病毒科、冠状病毒科和丝状病毒科病毒，特别是制备治疗新型冠状病毒(COVID‑19或SARS‑Cov‑2)和流感病毒感染的药物，所述药物组合物具有代谢稳定性高、口服吸收性高、生物利用度高、清除率高、肺分布高、广谱低毒、心脏毒性低等优点。
• Design, synthesis, and antiviral properties of 4′-substituted ribonucleosides as inhibitors of hepatitis C virus replication: The discovery of R1479
  作者：David B. Smith、Joseph A. Martin、Klaus Klumpp、Stewart J. Baker、Peter A. Blomgren、Rene Devos、Caroline Granycome、Julie Hang、Christopher J. Hobbs、Wen-Rong Jiang、Carl Laxton、Sophie Le Pogam、Vincent Leveque、Han Ma、Graham Maile、John H. Merrett、Arkadius Pichota、Keshab Sarma、Mark Smith、Steven Swallow、Julian Symons、David Vesey、Isabel Najera、Nick Cammack

  DOI：10.1016/j.bmcl.2007.02.004

  日期：2007.5

  A series of 4'-substituted ribonucleoside derivatives has been prepared and evaluated for inhibition of hepatitis C virus (HCV) RNA replication in cell culture. The most potent and non-cytotoxic derivative was compound 28 (4'-azidocytidine, R1479) with an IC(50) of 1.28 microM in the HCV replicon system. The triphosphate of compound 28 was prepared and shown to be an inhibitor of RNA synthesis mediated

  制备了一系列的4'-取代核糖核苷衍生物，并评估了其在细胞培养中对丙型肝炎病毒（HCV）RNA复制的抑制作用。最有效和无细胞毒性的衍生物是化合物28（4'-叠氮基吡啶，R1479），在HCV复制子系统中的IC（50）为1.28 microM。制备了化合物28的三磷酸酯，并显示出它是由NS5B（IC（50）= 320 nM）介导的RNA合成抑制剂，NS5B是HCV编码的RNA聚合酶。有关类似物的数据已被用来对这一系列核苷的活性产生一些初步的要求。
• Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases
  作者：I. A. Mikhailopulo、N. E. Poopeiko、T. I. Prikota、G. G. Sivets、E. I. Kvasyuk、J. Balzarini、Erik De Clercq

  DOI：10.1021/jm00111a040

  日期：1991.7

  A series of 3'-deoxy-3'-fluoro- and 2'-azido-2',3'-dideoxy-3'-fluoro-D-ribofuranosides of natural heterocyclic bases have been synthesized with the use of universal carbohydrate precursors, viz., 1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3-fluoro-D-ribofuranose and methyl 2-azido-5-O-benzoyl-2,3-dideoxy-3-fluoro-beta-D-ribofuranoside, respectively. The cytostatic and antiviral activity of the compounds was

  已使用通用碳水化合物前体合成了一系列天然杂环碱的3'-脱氧3'-氟和2'-叠氮基2'，3'-二脱氧3'-氟-D-呋喃核糖苷，即1-O-乙酰基-2,5-二-O-苯甲酰基-3-脱氧-3-氟-D-呋喃核糖和甲基2-叠氮基-5-O-苯甲酰基-2,3-二脱氧-3-氟-β-D-核呋喃糖苷。分别针对多种肿瘤细胞系和DNA / RNA病毒评估了该化合物的细胞抑制活性和抗病毒活性。从细胞抑制活性和抗病毒活性的观点来看，作为最活性的化合物出现了3'-脱氧-3'-氟腺苷。它以0.2-2微克/ mL的浓度抑制某些肿瘤细胞系（例如鼠白血病L1210和人T淋巴细胞MT-4）的增殖，
• Synthesis and Properties of 4′-ThioLNA/BNA
  作者：Rion Maeda、Noriko Saito-Tarashima、Hideaki Wakamatsu、Yoshihiro Natori、Noriaki Minakawa、Yuichi Yoshimura

  DOI：10.1021/acs.orglett.1c01306

  日期：2021.5.21

  applicable to oligonucleotide therapeutics, we designed a 4′-thio analogue of an LNA/BNA monomer. Synthesis of 4′-hydroxymethyl-4′-thioribonucleoside was achieved by a tandem ring-contraction-aldol reaction of a 5-thiopyranose derivative and the subsequent Pummerer-type thioglycosylation reaction of the corresponding sulfoxide. Treatment of 4′-hydroxymethyl-4′-thiopyrimidine nucleosides with diphenyl

  为了开发适用于寡核苷酸治疗的新核苷类似物，我们设计了LNA / BNA单体的4'-硫代类似物。4'-羟甲基-4'-硫代核糖核苷的合成是通过5-硫代吡喃糖衍生物的串联环缩合-醛醇缩合反应和随后的相应亚砜的Pummerer型硫代糖基化反应实现的。在催化NaHCO 3存在下用碳酸二苯酯处理4'-羟甲基-4'-硫代嘧啶核苷，得到所需的4'-thioLNA / BNA单体，将其引入寡核苷酸中。