N(1),N(3)-二烯丙基胸腺嘧啶 | 114066-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: N(1),N(3)-二烯丙基胸腺嘧啶
• 中文别名: N(1),N(3)-二烯丙基胸苷
• 英文名称: N,N-1,3-bis(allyl)thymine
• 英文别名: 1,3-diallylthymine；N1,N3-diallylthymine；N(1),N(3)-Diallylthymine；5-methyl-1,3-bis(prop-2-enyl)pyrimidine-2,4-dione
• CAS: 114066-89-6
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: LPHRAHGTESHZNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-溴丙烯 、 胸腺嘧啶 生成 N(1),N(3)-二烯丙基胸腺嘧啶 、 1-烯丙基-5-甲基嘧啶-2,4(1H,3H)-二酮
  参考文献：
  名称：

  修饰寡核苷酸的硅前体的合成

  摘要：

  描述了用作修饰的反义寡核苷酸前体的四种硅核苷类似物的合成。

  DOI：

  10.1016/s0040-4039(00)78205-0

文献信息

• Potentiating effects of N1,N3-diallyluracil, N1,N3-diallylthymine and N1,N3-diallyl-6-methyluracil on pentobarbital-induced sleep and diazepam-induced motor incoordination.
  作者：YUJI TATEOKA、TOSHIYUKI KIMURA、KAZUHITO WATANABE、IKUO YAMAMOTO、ING KANG HO

  DOI：10.1248/cpb.35.4928

  日期：——

  N-Allyl derivatives of uracil (U), thymine (T) and 6-methyluracil (6-MU) were prepared, and their pharmacological activities (hypnotic activity and anticonvulsant activity against pentylenetetrazol (PTZ) -induced seizures) and interactions with three sedative-hypnotics [pentobarbital (PB), barbital (B) and diazepam (DZ)] were investigated in mice. N1, N3-Diallyluracil (DAU) alone exhibited hypnotic and anticonvulsant activities. None of the other allyl derivatives showed both pharmacological activities. As regards interactions, most of the compounds tested prolonged PB-induced sleep at either 80 or 160 mg/kg, i.p. Further, U, T, and 6-MU (160 mg/kg, i.p.) also prolonged the PB-induced sleeping time. DAU showed a prolonging effect on PB-induced sleep when given by intracerebroventricular (i.c.v.) injection. DAU, N1, N3-diallylthymine (DAT) and N1-monoallyluracil (N1-MAU) significantly prolonged the B-induced sleeping time at a dose of 160 mg/kg, i.p. Further, DAU and DAT (40 mg/kg, i.p.) enhanced DZ-induced motor incoordination. These results indicate that U and related compounds possess central nervous system (CNS) - depressant effects and DAU is the most potent among the N-allyl derivatives tested.

  制备了尿嘧啶（U）、胸腺嘧啶（T）和6-甲基尿嘧啶（6-MU）的N-烯丙基衍生物，及其药理活性（对戊四氮（PTZ）引起的癫痫发作的催眠活性和抗惊厥活性）以及与三种镇静剂的相互作用- 在小鼠身上研究了安眠药[戊巴比妥（PB）、巴比妥（B）和地西泮（DZ）]。 N1、N3-二烯丙基尿嘧啶（DAU）单独表现出催眠和抗惊厥活性。其他烯丙基衍生物均未表现出这两种药理活性。至于相互作用，大多数化合物在 80 或 160 mg/kg（腹膜内注射）下测试了 PB 诱导的睡眠延长。此外，U、T 和 6-MU（160 mg/kg，腹腔注射）也延长了 PB 诱导的睡眠时间。当通过脑室内 (i.c.v.) 注射时，DAU 对 PB 诱导的睡眠有延长作用。 DAU、N1、N3-二烯丙基胸腺嘧啶 (DAT) 和 N1-单烯丙基尿嘧啶 (N1-MAU) 在腹腔注射 160 mg/kg 的剂量下显着延长 B 诱导的睡眠时间。此外，DAU 和 DAT（40 mg/kg，腹腔注射）增强了 DZ 引起的运动不协调。这些结果表明 U 和相关化合物具有中枢神经系统 (CNS) 抑制作用，并且 DAU 是测试的 N-烯丙基衍生物中最有效的。
• Microwave-assisted N-allylation of uracil and thymine pyrimidine bases
  作者：L. Sacarescu、I. Atudosie、M. Simionescu、G. Sacarescu、V. Harabagiu

  DOI：10.1007/s10593-011-0804-2

  日期：2011.8

  This work presents a new synthetic approach to N(1)-allylation of pyrimidine nucleobases with allyl bromide. The increased efficiency of the proposed method is based on two specific elements: (a) the nucleoside N-deprotonation is carried out in a homogeneous system by using sodium methylsulfinylmethylide in DMSO; (b) the allylation reaction is microwave-assisted. This method ensures high yields (87-88%) of the monoallylated products and short reaction time (1.5 h as compared to tens of hours for classical methods), and provides protection against side reactions. NMR analysis of the crude reaction mixture indicated a ratio of 6 8 : 1 between N(1)-allyl derivatives and N(1),N(3)-diallyl derivatives.
• Gundersen, Lise-Lotte; Benneche, Tore; Rise, Frode, Acta Chemica Scandinavica, 1992, vol. 46, # 8, p. 761 - 771
  作者：Gundersen, Lise-Lotte、Benneche, Tore、Rise, Frode、Gogoll, Adolf、Undheim, Kjell

  DOI：——

  日期：——
• Synthesis of silicon precursors of modified oligonucleotides
  作者：Laurent Latxague、Jacques Thibon、Christel Guillot、Serge Moreau、Gérard Déleris

  DOI：10.1016/s0040-4039(00)78205-0

  日期：1994.8

  The synthesis of four silicon nucleoside analogues for use as modified antisense oligonucleotide precursors, is described.

  描述了用作修饰的反义寡核苷酸前体的四种硅核苷类似物的合成。