[1,2,4]三唑并[1,5-a]喹喔啉-2-羧酸,4,5-二氢-4-羰基-,乙基酯 | 150454-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: [1,2,4]三唑并[1,5-a]喹喔啉-2-羧酸,4,5-二氢-4-羰基-,乙基酯
• 英文名称: ethyl 4,5-dihydro-4-oxo-1,2,4-triazolo<1,5-α>quinoxaline-2-carboxylate
• 英文别名: ethyl 4,5-dihydro-4-oxo-1,2,4-triazolo<1,5-a>quinoxaline-2-carboxylate；ethyl 4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylate；ethyl 4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxalin-2-carboxylate；Ethyl 4-oxo-4,5-dihydro-[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylate；ethyl 4-oxo-5H-[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylate
• CAS: 150454-81-2
• 化学式: C₁₂H₁₀N₄O₃
• 分子量: 258.236
• InChiKey: PTTFPEJFOCLEGM-UHFFFAOYSA-N

物化性质

• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  86.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [1,2,4]三唑并[1,5-a]喹喔啉-2-羧酸,4,5-二氢-4-羰基-,乙基酯 在 氨 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以68%的产率得到4-oxo-5H-[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxamide
  参考文献：
  名称：

  1,2,4-Triazolo[1,5-a]quinoxaline as a Versatile Tool for the Design of Selective Human A₃ Adenosine Receptor Antagonists:  Synthesis, Biological Evaluation, and Molecular Modeling Studies of 2-(Hetero)aryl- and 2-Carboxy-Substitued Derivatives

  摘要：

  A number of 4-oxo-substituted 1,2,4-triazolo[1,5-alquinoxaline derivatives bearing at position-2 the claimed (hetero)aryl moiety (compounds 1-15) but also a carboxylate group (16-28, 3236) or a hydrogen atom (29-31) were designed as human A(3) (hA(3)) adenosine receptor (AR) antagonists. This study produced some interesting compounds and among them the 2-(4methoxyphenyl)-1,2,4-triazolo[1,5-alquinoxalin-4-one (8), which can be considered one of the most potent and selective hA(3) adenosine receptor antagonists reported till now. Moreover, as a new finding, replacement of the classical 2-(hetero)aryl moiety with a 2-carboxylate function (compounds 16-28 and 32-36) maintained good hA(3) AR binding activity but, most importantly and interestingly, produced a large increase in bA(3) versus hA(1) selectivity. A receptor-based SAR analysis provided new interesting insights about the steric and electrostatic requirements that are important for the anchoring of these derivatives at the hA(3) receptor recognition site, thus highlighting the versatility of the triazoloquinoxaline scaffold for obtaining potent and selective hA(3) AR antagonists.

  DOI：

  10.1021/jm0504149
• 作为产物：
  描述：

  ethyl N¹-(2-nitrophenyl)-N³-ethoxalyloxamidrazonate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 180.0~190.0 ℃ 、151.99 kPa 条件下， 反应 1.5h， 生成 [1,2,4]三唑并[1,5-a]喹喔啉-2-羧酸,4,5-二氢-4-羰基-,乙基酯
  参考文献：
  名称：

  Catarzi, Daniela; Cecchi, Lucia; Colotta, Vittoria, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 5, p. 1161 - 1163

  摘要：

  DOI：

文献信息

• The chemoselective reduction of nitro compounds: scope of the electrochemical method
  作者：JM Chapuzet、R Labrecque、M Lavoie、E Martel、J Lessard

  DOI：10.1051/jcp/1996930601

  日期：——

  The selective electrohydrogenation of nitro aliphatic and nitro aromatic functional groups in molecules containing other groups that are easy to hydrogenate (activated double bond, carbon-iodine bond, nitrile,) has been sucessfully carried out in slightly acidic (pH = 3) or neutral (pH = 5-6) methanol-water solutions at Devarda copper and Raney cobalt electrodes. The electrochemical synthesis of a quinolone 15 and a quinoxaline 18 is also reported. Preliminary results on the preparative electroreduction of 5-nitroindole 21 on Hg in aqueous methanol with HBr as supporting electrolyte are presented and dicussed for the first time.

  在含有其他易氢化基团（活化双键、碳-碘键、氰基）的分子中，对硝基脂肪族和硝基芳香族官能团的选择性电氢化已在微酸性（pH = 3）或中性（pH = 5-6）的甲醇-水溶液中，在德尔瓦铜和拉尼钴电极上成功进行。本文还报道了喹诺酮15和喹喉18的电化学合成。首次介绍了在含氢溴酸的甲醇水溶液中，在汞上进行5-硝基吲哚21的制备电还原的初步结果，并进行了讨论。
• 1,2,4-Triazolo[1,5-a]quinoxaline derivatives: synthesis and biological evaluation as adenosine receptor antagonists
  作者：Daniela Catarzi、Vittoria Colotta、Flavia Varano、Guido Filacchioni、Claudia Martini、Letizia Trincavelli、Antonio Lucacchini

  DOI：10.1016/j.farmac.2003.09.005

  日期：2004.2

  of a previously reported series of analogous size and shape, thus suggesting a similar A(1)-binding mode. In particular, the binding data indicate that alkylation of the 4-amino group of these derivatives lead to potent A(1)-receptor antagonists. Moreover, as new results, this study has pointed out that the ethyl 2-carboxylate group can advantageously replace the 2-(hetero)aryl ring of previously reported

  由于大多数已报道的腺苷受体拮抗剂是2-（杂）芳基取代的三环杂芳族衍生物，因此在本研究中，我们报道了一组新的4-氨基-1,2,4-三唑并合成和生物学评估[在位置2处含有羧酸乙酯基团或氢原子的1，5-a]喹喔啉。这些化合物的结构活性关系与先前报道的一系列类似的大小和形状一致，因此表明了相似的A（1）结合模式。特别地，结合数据表明这些衍生物的4-氨基的烷基化导致有效的A（1）-受体拮抗剂。此外，作为新的结果，该研究指出，2-羧酸乙酯基团可以有利地取代先前报道的三唑并喹喔啉衍生物的2-（杂）芳基环，
• Catarzi, Daniela; Cecchi, Lucia; Colotta, Vittoria, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 5, p. 1161 - 1163
  作者：Catarzi, Daniela、Cecchi, Lucia、Colotta, Vittoria、Filacchioni, Guido、Melani, Fabrizio

  DOI：——

  日期：——
• Synthesis, Ionotropic Glutamate Receptor Binding Affinity, and Structure−Activity Relationships of a New Set of 4,5-Dihydro-8-heteroaryl-4-oxo-1,2,4-triazolo[1,5-<i>a</i>]quinoxaline-2-carboxylates Analogues of TQX-173
  作者：Daniela Catarzi、Vittoria Colotta、Flavia Varano、Guido Filacchioni、Alessandro Galli、Chiara Costagli、Vincenzo Carlà

  DOI：10.1021/jm010862q

  日期：2001.9.1

  A seires of 4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates analogues of TQX-173 (1b), bearing different nitrogen-containing heterocycles at position-8, were synthesized as AMPA receptor antagonists. All the reported compounds were also biologically evaluated for their binding at glycine/NMDA and KA receptors to better assess their selectivity toward the AMPA receptor. Structure-activity relationships (SAR) on these TQX derivatives have evidenced that the precise positioning of the nitrogen atoms and the specific electronic topography of the 8-heteroaromatic ring are both important for the anchoring to the AMPA receptor. In fact, it has been well-established that the presence of a N-3-nitrogen-containing heterocycle at position-8 of the TQX framework is an essential feature for potent and selective AMPA receptor antagonists. Functional antagonism at both AMPA receptor and NMDA receptor-ion channel complex was evaluated by assessing the ability of some selected compounds to inhibit depolarization induced by 5 muM AMPA or NMDA in mouse cortical wedge preparations.
• Catarzi; Cecchi; Colotta, Il Farmaco, 1993, vol. 48, # 8, p. 1065 - 1078
  作者：Catarzi、Cecchi、Colotta、Melani、Filacchioni、Martini、Giusti、Lucacchini

  DOI：——

  日期：——