1-(N(3)-methylthymin-1-yl)-3-(N(3)-methyluracil-1-yl)propane | 31167-29-0

• 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-(N(3)-methylthymin-1-yl)-3-(N(3)-methyluracil-1-yl)propane
• 英文别名: 5-methyl-1H,1'H-1,1'-propane-1,3-diyl-bis-pyrimidine-2,4-dione；1-[3-(2,4-Dioxopyrimidin-1-yl)propyl]-5-methylpyrimidine-2,4-dione
• CAS: 31167-29-0
• 化学式: C₁₂H₁₄N₄O₄
• 分子量: 278.268
• InChiKey: KIKRFLBBHPIQHF-UHFFFAOYSA-N

物化性质

• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(N(3)-methylthymin-1-yl)-3-(N(3)-methyluracil-1-yl)propane 在 水 、 溴 作用下， 生成
  参考文献：
  名称：

  Dezor-Mazur, Maria; Kazmierczak, Franciszek; Golankiewicz, Krzysztof, Heterocycles, 1984, vol. 22, # 12, p. 2739 - 2750

  摘要：

  DOI：
• 作为产物：
  描述：

  在 Tetraacetyl-D-arabinoflavin 、 高氯酸 作用下， 以 乙腈 为溶剂， 生成 1-(N(3)-methylthymin-1-yl)-3-(N(3)-methyluracil-1-yl)propane
  参考文献：
  名称：

  A possible chain reaction in photosensitized splitting of pyrimidine dimers by a protonated, oxidized flavin

  摘要：

  Pyrimidine dimer cycloreversion was photosensitized by protonated 2',3',4',5'-tetraacetylriboflavin (ac4rfH+), whereas the protonated flavin radical (ac4rfH2.+) failed to sensitize detectable dimer splitting. In acetonitrile containing 0.075% perchloric acid, the ac4rf absorption bands at 375 nm and 445 nm are replaced by a new band at 390 nm due to ac4rfH+. Irradiation of ac4rfH+ in the presence of cis,syn- or trans,syn-1,3-dimethyluracil dimer resulted in efficient cycloreversion to 1,3-dimethyluracil, probably induced by electron abstraction from the dimer by ac4rfH+ to produce the dimer radical cation. The quantum yeilds of splitting were large (PHI(spl) = 0.35 and 1.5 for cis,syn and trans,syn isomers, respectively, at [dimer] = 1.2 mM). Splitting quantum yields increased with dimer concentration in a quadratic fashion. These results are consistent with the occurrence of a chain reaction propagated by monomer.+ + dimer --> monomer + dimer.+ in the case of the dimethyluracil dimers. The fluorescence of the protonated flavin (lambda(em) = 507 nm) was found to be quenched by the dimers. In the presence of small amounts of added water, however, both the fluorescence quenching and splitting were abolished. Two cis,syn dimers in which the N(1)- and N(1')-atoms were tethered via a trimethylene bridge exhibited quantum yields of approximately 0.02 at the above dimer concentration. A compound in which ac4rf is covalently bound to a pyrimidine dimer was also found to undergo splitting in acidified acetonitrile (PHI = 0.03). These values are more than 1 order of magnitude greater than those reported for unprotonated flavins.

  DOI：

  10.1021/jo00034a021

文献信息

• Triplet Energy Transfer versus Excited State Cyclization as the Controlling Step in Photosensitized Bipyrimidine Dimerization
  作者：Ofelia R. Alzueta、M. Consuelo Cuquerella、Miguel A. Miranda

  DOI：10.1021/acs.joc.9b01423

  日期：2019.11.1

  triplet energy transfer is the rate controlling step, (b) excited state cyclization is the rate controlling step, and (c) the rate controlling step switches along the reaction. Thus, by introducing variations in the substitution at C5, the length of the linking bridge, or the substrate concentration, it is possible to switch from a process governed by the intrinsic dimerization step to an energy transfer-controlled

  聚亚甲基连接的联嘧啶模型已设计为具有不同的C5取代基和桥长度。用联嘧啶模型选择性辐照2'-甲氧基苯乙酮（2M），即使存在庞大的取代基也能得到环丁烷嘧啶二聚体。C5处的取代影响嘧啶（Pyr）的相对三重态能量（ET（rel））以及分子间能量转移和分子内三重态Pyr *猝灭的空间位阻。光物理研究表明，烷基取代导致ET（rel）值显着降低。证明了Pyr衍生物对2M的三重激发态的猝灭，并建立了它们的猝灭速率常数（kq）。作为一般趋势，含胸腺嘧啶的化合物的kq值高于109 M-1 s-1，而在尿嘧啶和叔丁基尿嘧啶类似物中，kq显着降低。这些数据是在三种不同的情况下进行解释的：（a）三重态能量转移是速率控制步骤，（b）激发态环化是速率控制步骤，并且（c）速率控制步骤随反应而变化。因此，通过在C5处的取代，连接桥的长度或底物浓度上引入变化，可以从由固有二聚化步骤控制的过程切换至能量转移控制的过程。
• AGENTS THAT PREVENT OR REPAIR SKIN DAMAGE
  申请人：Regents of the University of Minnesota

  公开号：US20140350036A1

  公开（公告）日：2014-11-27

  The invention provides compounds of formula I: or a salt thereof as described herein. The invention also provides dermatological compositions comprising a compound of formula I or mixtures of one or more compounds of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods for protecting skin or DNA from photodamage or repairing photodamaged skin or DNA.

  本发明提供了以下式I的化合物：或其盐，如本文所述。本发明还提供了包含式I化合物或一种或多种式I化合物的混合物的皮肤学组合物，制备式I化合物的方法，用于制备式I化合物的中间体以及保护皮肤或DNA免受光损伤或修复光损伤皮肤或DNA的治疗方法。
• US9403778B2
  申请人：——

  公开号：US9403778B2

  公开（公告）日：2016-08-02