ethyl 2-acetyl-3-ureido-2-propenoate | 6319-01-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 2-acetyl-3-ureido-2-propenoate
• 英文别名: ethyl ureidomethyleneacetoacetate；2-acetyl-3-ureido-acrylic acid ethyl ester；2-Acetyl-3-ureido-acrylsaeure-aethylester；ethyl ureidomethylene ethanoylacetate；Carbamidomethylenacetessigsaeureethylester；ethyl 2-[(carbamoylamino)methylidene]-3-oxobutanoate
• CAS: 6319-01-3
• 化学式: C₈H₁₂N₂O₄
• 分子量: 200.194
• InChiKey: RHSGRHXESJMSEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.31
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  98.49
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetyl-3-ureido-2-propenoate 在 氢氧化钾 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,3-bis(4-fluorobenzyl)-5-acetyluracil
  参考文献：
  名称：

  HIV Integrase Inhibitors with Nucleobase Scaffolds:  Discovery of a Highly Potent Anti-HIV Agent

  摘要：

  HIV integrase is essential for HIV replication. However, there are currently no integrase inhibitors in clinical use for AIDS. We have discovered a conceptually new beta-diketo acid that is a powerful inhibitor of both the 3'-processing and strand transfer steps of HIV-1 integrase. The in vitro anti-HIV data of this inhibitor were remarkable as exemplified by its highly potent antiviral therapeutic efficacy against HIVTEKI and HIV-1(NL4-3) replication in PBMC (TI > 4,000 and > 10,000, respectively).

  DOI：

  10.1021/jm0508890
• 作为产物：
  描述：

  尿素 、 2-乙氧亚甲基乙酰乙酸乙酯 生成 ethyl 2-acetyl-3-ureido-2-propenoate
  参考文献：
  名称：

  Cervinka,O. et al., Zeitschrift fur Chemie, 1971, vol. 11, # 1, p. 11 - 12

  摘要：

  DOI：

文献信息

• Inhibitors of NF-κB and AP-1 Gene Expression:  SAR Studies on the Pyrimidine Portion of 2-Chloro-4-trifluoromethylpyrimidine-5-[<i>N</i>-(3‘,5‘-bis(trifluoromethyl)phenyl)carboxamide]
  作者：Moorthy S. S. Palanki、Paul E. Erdman、Leah M. Gayo-Fung、Graziella I. Shevlin、Robert W. Sullivan、Mark E. Goldman、Lynn J. Ransone、Brydon L. Bennett、Anthony M. Manning、Mark J. Suto

  DOI：10.1021/jm0001626

  日期：2000.10.1

  We investigated the structure-activity relationship studies of N-[3, 5-bis(trifluoromethyl)phenyl][2-chloro-4-(trifluoromethyl)pyrimidin-5 -yl]carboxamide (1), an inhibitor of transcription mediated by both NF-kappaB and AP-1 transcription factors, with the goal of improving its potential oral bioavailability. Compounds were examined for cell-based activity, were fit to Lipinski's rule of 5, and were

  我们研究了N- [3,5-双（三氟甲基）苯基] [2-氯-4-（三氟甲基）嘧啶-5-基]羧酰胺（1）的结构-活性关系研究。 NF-kappaB和AP-1转录因子，旨在提高其潜在的口服生物利用度。检查化合物的基于细胞的活性，符合Lipinski的5法则，并使用肠上皮细胞系Caco-2检查潜在的胃肠道通透性。使用溶液相组合方法，将选定的基团在嘧啶环的2-，4-和5-位取代。用氟代替2-氯为1可以得到活性相当的化合物。然而，在2-位的其他取代导致活性丧失。在4-位的三氟甲基基团可以被甲基，乙基，氯或苯基取代，而没有实质性的活性损失。位于5位的羧酰胺基对于活性至关重要。如果将其移动到6位，则活动丢失。1的2-甲基类似物（81）与1相比显示出可比的体外活性并改善了Caco-2的渗透性。
• Pyrimidine carboxylates and related compounds and methods for treating
  申请人：Signal Pharmaceuticals, Inc.

  公开号：US05935966A1

  公开（公告）日：1999-08-10

  Compounds having utility as anti-inflammatory agents in general and, more specifically, for the prevention and/or treatment of immunoinflammatory and autoimmune diseases are disclosed. The compounds are pyrimidine-containing compounds and, in one embodiment, are esters of the same. Methods are also disclosed for preventing and/or treating inflammatory conditions by administering to an animal in need thereof an effective amount of a compound of this invention, preferably in the form of a pharmaceutical composition.

  本文披露了作为抗炎药物的效用的化合物，特别是用于预防和/或治疗免疫炎症和自身免疫疾病的化合物。这些化合物是含嘧啶的化合物，在一个实施例中，它们是相同的酯。还披露了通过向需要的动物施用本发明的化合物的有效量，优选地以药物组合物的形式，来预防和/或治疗炎症病症的方法。
• Cyclization Dichotomy of Esters of 3-Ureido-2-cyano-2-propenoic and 3-Ureido-2-acyl-2-propenoic Acids
  作者：Miroslav Ledvina、Jiří Farkaš

  DOI：10.1135/cccc19941841

  日期：——

  The preparation of E and Z isomers of 3-ureido-2-cyano-2-propenoates Ia - Id and their base-catalyzed isomerization and cyclization to 5-carboxycytosine derivatives IIa - IIf and 5-cyanouracil derivatives IIIa and IIIb is described. Also described is the preparation of 3-ureido-2-acyl-2-propenoates Va - Vd and their base-catalyzed cyclization to 5-carboxy-2(1H)-pyrimidone derivatives VIa - VIc and 5-acyluracils VIIa - VIIc.

  描述了3-脲基-2-氰基-2-丙烯酸酯的Ia - Id的E和Z异构体的制备，以及它们的碱催化异构化和环化到5-羧基胞嘧啶衍生物IIa - IIf和5-氰基尿嘧啶衍生物IIIa和IIIb。还描述了3-脲基-2-酰基-2-丙烯酸酯Va - Vd的制备及其碱催化环化到5-羧基-2(1H)-嘧啶酮衍生物VIa - VIc和5-酰基尿嘧啶VIIa - VIIc。
• Investigation on possibility of rearrangement of pyrimidine-5-carboxylic acids esters
  作者：E. S. Scherbinina、D. V. Dar’in、P. S. Lobanov

  DOI：10.1007/s10593-010-0634-7

  日期：2010.12

  A previously reported rearrangement of pyrimidine-5-carboxylic acids esters to 5-acylpyrimidones does not, in fact, occur in any of the examples studied by us.

  实际上，在我们研究的任何实例中，实际上都没有发生以前报道的嘧啶5-羧酸酯重排为5-酰基嘧啶酮的情况。
• [EN] PYRIMIDINE CARBOXYLATES AND RELATED COMPOUNDS AND METHODS FOR TREATING INFLAMMATORY CONDITIONS<br/>[FR] CARBOXYLATES DE PYRIMIDINE ET COMPOSES APPARENTES ET PROCEDES POUR LE TRAITEMENT D'ETATS INFLAMMATOIRES
  申请人：SIGNAL PHARMACEUTICALS, INC.

  公开号：WO1998038171A1

  公开（公告）日：1998-09-03

  (EN) Compounds having utility as anti-inflammatory agents in general and, more specifically, for the prevention and/or treatment of immunoinflammatory and autoimmune diseases are disclosed. The compounds are pyrimidine-containing compounds and, in one embodiment, are esters of the same. Methods are also disclosed for preventing and/or treating inflammatory conditions by administering to an animal in need thereof an effective amount of a compound of this invention, preferably in the form of a pharmaceutical composition. (FR) Cette invention se rapporte à des composés utiles comme agents anti-inflammatoires en général et, plus particulièrement, pour la prévention et/ou le traitement de maladies immuno-inflammatoires et auto-immunes. Ces composés sont des composés contenant des pyrinidines et, dans un mode de réalisation, ce sont des esters de ces mêmes composés. Cette invention présente des procédés permettant de prévenir et/ou de traiter des états inflammatoires en administrant à un animal nécessitant un tel traitement une quantité efficace d'un composé de cette invention, de préférence sous la forme d'une composition pharmaceutique.

  具有抗炎作用的化合物，一般用于预防和/或治疗免疫炎症和自身免疫性疾病。这些化合物是含有嘧啶的化合物，其中一种实施方式是它们的酯类。该发明还揭示了通过向需要治疗的动物中投与本发明化合物的有效量，特别是以药物组成的形式，来预防和/或治疗炎症状况的方法。