tert-butyl 5-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxylate | 402848-98-0

• 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: tert-butyl 5-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxylate
• 英文别名: tert-butyl 5-methyl-2,4-dioxo-pyrimidine-1-carboxylate；tert-butyl 5-methyl-2,4-dioxopyrimidine-1-carboxylate
• CAS: 402848-98-0
• 化学式: C₁₀H₁₄N₂O₄
• 分子量: 226.232
• InChiKey: YSXJYFVSYDCLLB-UHFFFAOYSA-N

物化性质

• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  2-8°C，干燥

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxylate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 RS 100975
  参考文献：
  名称：

  Synthesis, pharmacology and pharmacokinetics of 3-(4-Aryl-piperazin-1-ylalkyl)-uracils as uroselective α1A-antagonists

  摘要：

  Predominance in the urethra and prostate of the alpha(1A)-adrenoceptor subtype, which is believed to be the receptor mediating noradrenaline induced smooth muscle contraction in these tissues, led to the preparation of alpha(1A)-selective antagonists to be tested as uroselective compounds for the treatment of benign prostatic hyperplasia. Thus, a number of selective alpha(1A)-adrenoceptor antagonists were synthesized and assayed in vitro for potency and selectivity. Dog pharmacokinetic parameters of 12 (RO700004) and its metabolite 40 (RO1104253) were established. The relative selectivity of intravenously administered 12, 40 and standard prazosin to inhibit hypogastric nerve stimulation-induced increases in intraurethral prostatic pressure versus phenylephrine-induced increases in diastolic blood pressure in anesthetized dogs was 76, 71 and 0.6, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00305-6
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 胸腺嘧啶 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以33%的产率得到tert-butyl 5-methyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxylate
  参考文献：
  名称：

  尿嘧啶及其衍生物的烷基化/酰化产物的多样性：合成和结构研究

  摘要：

  叔丁基二碳酸酯（BOC 2与尿嘧啶（U），胸腺嘧啶（T）和6-甲基尿嘧啶（6-MU）O）和乙基碘（ETI）反应以下在吡啶/ DMF的溶剂，并用DMAP作为常规程序进行催化剂。在20种合成化合物中，在C5位置被Boc-吡啶部分取代的6-甲基尿嘧啶的衍生物出乎意料地出现。NMR光谱证实了所有尿嘧啶衍生物的分子结构。并行量子力学DFT计算支持了实验结果。

  DOI：

  10.1039/c8ob02552e

文献信息

• Synthesis of (Carbo)nucleoside Analogues by [3+2] Annulation of Aminocyclopropanes
  作者：Sophie Racine、Florian de Nanteuil、Eloisa Serrano、Jérôme Waser

  DOI：10.1002/anie.201404832

  日期：2014.8.4

  (Carbo)nucleoside derivatives constitute an important class of pharmaceuticals, yet there are only few convergent methods to access new analogues. Here, we report the first synthesis of thymine‐, uracil‐, and 5‐fluorouracil‐substituted diester donor–acceptor cyclopropanes and their use in the indium‐ and tin‐catalyzed [3+2] annulations with aldehydes, ketones, and enol ethers. The obtained diester products

  （碳）核苷衍生物构成一类重要的药物，但只有很少的融合方法来获得新的类似物。在这里，我们报道了胸腺嘧啶，尿嘧啶和5-氟尿嘧啶取代的二酯供体-受体环丙烷的首次合成及其在铟和锡催化的[3 + 2]环合中用醛，酮和烯醇醚的合成。 。所获得的二酯产物可以容易地脱羧并还原为相应的醇。该方法仅需四个或五个步骤即可获得各种新的（碳）核苷类似物，对于合成生物活性化合物的库非常有用。
• Influence of theN3-Protection Group onN1- vs.O2-Alkylation in the Mitsunobu Reaction
  作者：Olaf R. Ludek、Chris Meier

  DOI：10.1002/ejoc.200500801

  日期：2006.2

  The influence of the N3-protection group of thymine on the regioselectivity of the N1- vs. O2-alkylation under Mitsunobu conditions is described. A series of N3-protected thymine derivatives 8a–f was prepared and coupled to cyclopentanol as model compound for carbocyclic nucleoside precursors. Finally, the N3-BOM group was selected to improve our previously reported synthetic strategy to carbocyclic

  描述了在 Mitsunobu 条件下胸腺嘧啶的 N3-保护基团对 N1-与 O2-烷基化的区域选择性的影响。制备了一系列 N3 保护的胸腺嘧啶衍生物 8a-f，并与环戊醇偶联作为碳环核苷前体的模型化合物。最后，选择 N3-BOM 组来改进我们之前报道的碳环胸苷 (carba-dT) 合成策略。此外，2,6-二甲基-Bz 基团专门导致了carba-dT 的O2-类似物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• ACID CERAMIDASE INHIBITORS AND THEIR USE AS MEDICAMENTS
  申请人：FONDAZIONE ISTITUTO ITALIANO DI TECHNOLOGIA

  公开号：US20150111892A1

  公开（公告）日：2015-04-23

  The present invention concerns, in a first aspect, compounds of Formula I as defined herein, pharmaceutically acceptable salts thereof and pharmaceutical compositions containing such compounds. The present invention also relates to compounds of Formula I for use as acid ceramidase inhibitors, and in the treatment of cancer and other disorders in which modulation of the levels of ceramide is clinically relevant.

  本发明涉及第一方面的I式化合物，其定义如本文所述，其药用盐以及含有这种化合物的药物组合物。本发明还涉及I式化合物的用途，用作酸酶抑制剂，以及在癌症和其他需要临床相关的调节酸酶水平的疾病治疗中的用途。
• [EN] ACID CERAMIDASE INHIBITORS AND THEIR USE AS MEDICAMENTS<br/>[FR] INHIBITEURS DE LA CÉRAMIDASE ACIDE ET LEUR UTILISATION COMME MÉDICAMENTS
  申请人：FOND ISTITUTO ITALIANO DI TECNOLOGIA

  公开号：WO2013178576A1

  公开（公告）日：2013-12-05

  The present invention concerns, in a first aspect, compounds of Formula I as defined herein, pharmaceutically acceptable salts thereof and pharmaceutical compositions containing such compounds. The present invention also relates to compounds of Formula I for use as acid ceramidase inhibitors, and in the treatment of cancer and other disorders in which modulation of the levels of ceramide is clinically relevant.

  本发明涉及第一方面的Formula I化合物，其定义如下，以及其药用盐和含有这种化合物的药物组合物。本发明还涉及Formula I化合物作为酸酶抑制剂的用途，以及在治疗癌症和其他需要临床上调节酸酶水平的疾病中的应用。
• Synthesis of Betulin 28-(2-Bromoacetate) Conjugates with Uracil and its Methyl-Substituted Homologs
  作者：S. N. Dubovitskii、N. G. Komissarova、O. V. Shitikova、L. V. Spirikhin、M. F. Abdullin、M. S. Yunusov

  DOI：10.1007/s10600-015-1325-5

  日期：2015.5

  A series of potentially biologically active betulin derivatives containing various C-28 2-uracilacetoxy substituents were synthesized.

  合成了一系列含有各种 C-28 2-尿嘧啶乙酰氧基取代基的潜在生物活性桦木脑衍生物。