1-(Tetrahydro-2-furyl)-thymin | 17902-22-6

• 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-(Tetrahydro-2-furyl)-thymin
• 英文别名: 5-methyl-1-(oxolan-2-yl)pyrimidine-2,4-dione
• CAS: 17902-22-6
• 化学式: C₉H₁₂N₂O₃
• 分子量: 196.206
• InChiKey: RAAYJODWWOGQAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(Tetrahydro-2-furyl)-thymin 在 lithium hydroxide 、 sodium hydride 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(2-carboxy-4,5-dibromothiophen-3-yl-methyl)-5-methyl-1-(tetrahydrofuran-2-yl)pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of N³-Substituted Willardiine Derivatives:  Role of the Substituent at the 5-Position of the Uracil Ring in the Development of Highly Potent and Selective GLU_K5 Kainate Receptor Antagonists

  摘要：

  Some N-3-substituted analogues of willardiine such as 11 and 13 are selective kainate receptor antagonists. In an attempt to improve the potency and selectivity for kainate receptors, a range of analogues of 11 and 13 were synthesized with 5-substituents on the uracil ring. An X-ray crystal structure of the 5-methyl analogue of 13 bound to GLU(K5) revealed that there was allowed volume around the 4- and 5-positions of the thiophene ring, and therefore the 4,5-dibromo and 5-phenyl (67) analogues were synthesized. Compound 67 (ACET) demonstrated low nanomolar antagonist potency on native and recombinant GLU(K5)-containing kainate receptors (K-B values of 7 +/- 1 and 5 +/- 1 nM for antagonism of recombinant human GLU(K5) and GLU(K5)/GLU(K2), respectively) but displayed IC50 values > 100 mu M for antagonism of GLU(A2), GLU(K6), or GLU(K6)/GLU(K2).

  DOI：

  10.1021/jm061041u
• 作为产物：
  描述：

  胸腺嘧啶 在 硫酸氢铵 、 六甲基二硅氮烷 作用下， 以 乙腈 为溶剂， 反应 36.0h， 生成 1-(Tetrahydro-2-furyl)-thymin
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of N³-Substituted Willardiine Derivatives:  Role of the Substituent at the 5-Position of the Uracil Ring in the Development of Highly Potent and Selective GLU_K5 Kainate Receptor Antagonists

  摘要：

  Some N-3-substituted analogues of willardiine such as 11 and 13 are selective kainate receptor antagonists. In an attempt to improve the potency and selectivity for kainate receptors, a range of analogues of 11 and 13 were synthesized with 5-substituents on the uracil ring. An X-ray crystal structure of the 5-methyl analogue of 13 bound to GLU(K5) revealed that there was allowed volume around the 4- and 5-positions of the thiophene ring, and therefore the 4,5-dibromo and 5-phenyl (67) analogues were synthesized. Compound 67 (ACET) demonstrated low nanomolar antagonist potency on native and recombinant GLU(K5)-containing kainate receptors (K-B values of 7 +/- 1 and 5 +/- 1 nM for antagonism of recombinant human GLU(K5) and GLU(K5)/GLU(K2), respectively) but displayed IC50 values > 100 mu M for antagonism of GLU(A2), GLU(K6), or GLU(K6)/GLU(K2).

  DOI：

  10.1021/jm061041u

文献信息

• [EN] MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS OLIGOMÈRES MODIFIÉS ET LEURS UTILISATIONS
  申请人：IONIS PHARMACEUTICALS INC

  公开号：WO2021030763A1

  公开（公告）日：2021-02-18

  The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard nucleoside. An oligomeric compound comprising a modified oligonucleotide consisting of 12-30 linked nucleosides, wherein at least one nucleoside of the modified oligonucleotide is a stereo-non-standard nucleoside; and wherein the oligomeric compound is selected from among an RNAi compound, a modified CRISPR compound, and an artificial mRNA compound.

  本公开提供了包含至少一种立体非标准核苷酸的修饰寡核苷酸的寡聚化合物。包括由12-30个连接的核苷酸组成的修饰寡核苷酸的寡聚化合物，其中修饰寡核苷酸的至少一个核苷酸是立体非标准核苷酸；且所述寡聚化合物选自RNAi化合物、修饰CRISPR化合物和人工mRNA化合物。
• Method for the preparation of derivatives of uracil
  申请人：Toshin Chemical Co., Ltd.

  公开号：US04159378A1

  公开（公告）日：1979-06-26

  A novel and very elegant method is proposed for the preparation of N.sub.1 -(2-tetrahydrofuryl)-5-substituted or -unsubstituted uracil, especially, N.sub.1 -(2-tetrahydrofuryl)-5-fluorouracil, by the reaction of the corresponding 5-substituted uracil compound with 2,3-dihydrofuran. The reaction is performed in the presence of a chlorosilane compound, e.g. dimethyldichlorosilane, and a catalytic amount of an organic amine compound and can proceed very rapidly without disadvantageous side reactions to give the objective compound with high purity in a high yield.

  提出了一种新颖而非常优雅的方法，用于制备N.sub.1-(2-四氢呋喃基)-5-取代或未取代尿嘧啶，特别是N.sub.1-(2-四氢呋喃基)-5-氟尿嘧啶，通过相应的5-取代尿嘧啶化合物与2,3-二氢呋喃的反应。在氯硅烷化合物（例如二甲基二氯硅烷）和有机胺化合物的催化下进行反应，可以非常迅速地进行，没有不利的副反应，从而以高纯度和高产率得到目标化合物。
• Lee, Chun Ho; Kim, Joong Young; Kim, Wan Joo, Heterocycles, 1990, vol. 31, # 2, p. 211 - 214
  作者：Lee, Chun Ho、Kim, Joong Young、Kim, Wan Joo、Kim, Yong Hae

  DOI：——

  日期：——
• NOMURA HIROAKI; YOSHIOKA YOSHIO; MINAMI ISAO, CHEM. AND PHARM. BULL., 1979, 27, NO 4, 899-906
  作者：NOMURA HIROAKI、 YOSHIOKA YOSHIO、 MINAMI ISAO

  DOI：——

  日期：——
• US5075446A
  申请人：——

  公开号：US5075446A

  公开（公告）日：1991-12-24