(2-Pyrazinyl)oxamsaeure-ethylester | 54166-59-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2-Pyrazinyl)oxamsaeure-ethylester
• 英文别名: pyrazin-2-yl-oxalamic acid ethyl ester；(2-Pyrazinyl)oxamic acid ethyl ester；Ethyl 2-oxo-2-(pyrazin-2-ylamino)acetate
• CAS: 54166-59-5
• 化学式: C₈H₉N₃O₃
• 分子量: 195.178
• InChiKey: XHRJEJHQOVRQQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-Pyrazinyl)oxamsaeure-ethylester 生成 N-Pyrazin-2-yl-oxalamic acid
  参考文献：
  名称：

  抗过敏药的研究。I.新型吡嗪衍生物的合成和抗过敏活性。

  摘要：

  合成了各种吡嗪衍生物，并检查了它们的抗过敏活性。带有5-四唑基的化合物对过敏性组胺释放的抑制活性比相应的羧基衍生物更有效。在吡嗪环和5-四唑基之间作为间隔基引入-CONH-或-NHCO-大大提高了活性。N-（1H-替硝唑-5-基）-2-吡嗪甲酰胺（I-3）估计显示出与色甘酸二钠（DSCG）几乎相同的效价。研究了通过将一些取代基引入I-3的吡嗪环的3位，5位或6位而修饰的各种衍生物之间的构效关系。当取代基如甲基，氯，甲氧基，在3-或5-位引入甲基氨基和二甲基氨基。相反，具有各种烷基氨基的6-取代或多或少地增加了活性。其中，6-二甲基氨基（I-17c）和6-（1-吡咯烷基）（I-34）衍生物被证明是最有效的。测定I-17c和I-34的IC 50值（对变应性组胺释放产生50％抑制的浓度）分别为4.7×10（-10）和4.6×10（-10）M。这两种化合物不仅通过静脉内途径（两种化合物的ED50 =

  DOI：

  10.1248/cpb.38.201
• 作为产物：
  描述：

  氨基吡嗪 、 草酰氯单乙酯 以 二氯甲烷 为溶剂， 生成 (2-Pyrazinyl)oxamsaeure-ethylester
  参考文献：
  名称：

  新的一锅三组分合成4 H-吡啶并[1,2- a ]嘧啶，4 H-嘧啶并[1,2- a ]嘧啶和4 H-吡嗪并[1,2- a ]嘧啶类

  摘要：

  一种新的，单釜和4的三组分合成ħ -吡啶并[1,2-一个]嘧啶，4 ħ嘧啶并[1,2一]嘧啶，和4- ħ -吡嗪并[1,2一]描述了嘧啶。通过将异氰酸酯加到乙炔二羧酸二烷基酯上而形成的反应性1：1两性离子中间体被N-（2-杂芳基）酰胺捕获，制得烯酮胺中间体，将其环化，然后在反应条件下重排，得到标题化合物在温和的反应条件下，收率很高。X射线单晶分析最终证实了所获得的桥头双环6-6杂环化合物的结构。

  DOI：

  10.1016/j.tet.2007.08.024

文献信息

• Discovery of Cytochrome P450 4F11 Activated Inhibitors of Stearoyl Coenzyme A Desaturase
  作者：Sarah E. Winterton、Emanuela Capota、Xiaoyu Wang、Hong Chen、Prema L. Mallipeddi、Noelle S. Williams、Bruce A. Posner、Deepak Nijhawan、Joseph M. Ready

  DOI：10.1021/acs.jmedchem.8b00052

  日期：2018.6.28

  Stearoyl-CoA desaturase (SCD) catalyzes the first step in the conversion of saturated fatty acids to unsaturated fatty acids. Unsaturated fatty acids are required for membrane integrity and for cell proliferation. For these reasons, inhibitors of SCD represent potential treatments for cancer. However, systemically active SCD inhibitors result in skin toxicity, which presents an obstacle to their development

  硬脂酰辅酶A去饱和酶（SCD）催化饱和脂肪酸向不饱和脂肪酸转化的第一步。膜完整性和细胞增殖需要不饱和脂肪酸。由于这些原因，SCD抑制剂代表了潜在的癌症治疗方法。但是，具有内在活性的SCD抑制剂会导致皮肤毒性，这对它们的发展构成了障碍。我们最近描述了一系列草酸二酰胺，它们通过CYP4F11介导的代谢转化为癌症子集内的活性SCD抑制剂。在本文中，我们描述了草酸二酰胺和相关N-酰基脲的优化，以及与代谢活化和SCD抑制有关的结构-活性关系的分析。
• Pyridyl oxamic acid derivatives and use in the prevention of allergic
  申请人：American Home Products Corporation

  公开号：US04054661A1

  公开（公告）日：1977-10-18

  Anti-allergic agents of aromatic and heterocyclic oxamic acid derivation present the following formula: ##STR1## in which A is a member selected from the group consisting of 2-thiazolyl, 2-pyridyl, 2-pyridyl-N-oxide, 6-(lower)alkyl-2-pyridyl, 3-cyano-2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 2-pyrazinyl, .alpha.-naphthyl, .beta.naphthyl, phenyl, 2,6-dichlorophenyl, and substituted phenyl moieties containing from one to three substituents in any of the 2,3,4 and 5 positions of the phenyl ring, independently selected from the group consisting of lower alkyl, lower alkylthio, lower alkylsulfinyl, lower alkoxy, hydroxy(lower)-alkoxy, 2-(lower alkoxy oxalyloxy) ethoxy, benzyloxy, N-mono-and di-lower alkylamino(lower)-alkoxy, halo, sulfamyl, polyhalo(lower)alkyl, carbamyl, N-lower alkylcarbamyl, nitro, mono-and di-lower alkylamino, phenylazo, carboxy, lower alkylcarbonyl, cyano, carb(lower)alkoxy, phenoxy(lower)alkoxy, lower alkoxyoxalamido and lower alkoxyoxalamidophenoxy radicals; B, when taken alone, is a member selected from the group consisting of --OH, lower alkoxy, --NH.sub.2, --NHOH, cyclohexyloxy and phenoxy; and Y is a member selected from the group consisting of oxygen and when taken with B and the carbon atom to which they are attached, forms the moiety ##STR2##

  芳香族和杂环氧酰胺衍生的抗过敏剂具有以下公式：##STR1## 其中A是从2-噻唑基，2-吡啶基，2-吡啶基-N-氧化物，6-（较低）烷基-2-吡啶基，3-氰基-2-吡啶基，3-吡啶基，4-吡啶基，2-吡嘧啶基，2-吡嗪基，α-萘基，β-萘基，苯基，2,6-二氯苯基和取代苯基中选择的一种成员，所述取代苯基包含一个到三个取代基，所述取代基独立地选择自较低烷基，较低硫代烷基，较低磺代烷基，较低烷氧基，羟基（较低）-烷氧基，2-（较低烷氧基氧乙酰氧基）乙氧基，苄氧基，N-单和二-较低烷基氨基（较低）-烷氧基，卤，磺酰胺，多卤（较低）烷基，氨基甲酰，N-较低烷基氨基甲酰，硝基，单和二-较低烷基氨基，苯基偶氮，羧基，较低烷基羰基，氰基，羰基（较低）烷氧基，苯氧基（较低）烷氧基，较低烷氧基草酰胺基和较低烷氧基草酰胺基苯氧自由基；B，单独时，是从-OH，较低烷氧，-NH.sub.2，-NHOH，环己氧基和苯氧基中选择的一种成员；Y是从氧中选择的一种成员，当与B和它们连接的碳原子一起被选取时，形成如下部分：##STR2##
• Oxamic acid derivatives
  申请人：American Home Products Corporation

  公开号：US04160100A1

  公开（公告）日：1979-07-03

  Anti-allergic agents of aromatic and heterocyclic oxamic acid derivation present the following formula: ##STR1## in which A is a member selected from the group consisting of 2-thiazolyl, 2-pyridyl, 2-pyridyl-N-oxide, 6-(lower)alkyl-2-pyridyl, 3-cyano-2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 2-pyrazinyl, .alpha.-naphthyl, .beta.-naphthyl, phenyl, 2,6-di-chlorophenyl, and substituted phenyl moieties containing from one to three substituents in any of the 2,3,4 and 5 positions of the phenyl ring, independently selected from the group consisting of lower alkyl, lower alkylthio, lower alkylsulfinyl, lower alkoxy, hydroxy(lower)alkoxy, 2-(lower alkoxy oxalyloxy) ethoxy, benzyloxy, N-mono-and di-lower alkylamino(lower)alkoxy, halo, sulfamyl, polyhalo(lower)alkyl, carbamyl, N-lower alkylcarbamyl, nitro, mono-and di-lower alkylamino, phenylazo, carboxy, lower alkylcarbonyl, cyano, carb(lower)alkoxy, phenoxy(lower)alkoxy, lower alkoxyoxalamido and lower alkoxyoxalamidophenoxy radicals; B, when taken alone, is a member selected from the group consisting of --OH, lower alkoxy, --NH.sub.2, --NHOH, cyclohexyloxy and phenoxy; and Y is a member selected from the group consisting of oxygen and when taken with B and the carbon atom to which they are attached, forms the moiety ##STR2##

  芳香族和杂环氧酰胺衍生的抗过敏剂具有以下化学式：##STR1## 其中A是从以下组中选择的成员：2-噻唑基、2-吡啶基、2-吡啶-N-氧化物、6-（较低）烷基-2-吡啶基、3-氰基-2-吡啶基、3-吡啶基、4-吡啶基、2-嘧啶基、2-吡嗪基、α-萘基、β-萘基、苯基、2,6-二氯苯基和含有1至3个取代基的取代苯基，这些取代基独立地选自下列组成的组：较低烷基、较低烷硫基、较低烷基亚硫酰基、较低烷氧基、羟基（较低）烷氧基、2-（较低烷氧羰酰氧基）乙氧基、苄氧基、N-单和双较低烷基氨基（较低）烷氧基、卤素、磺酰基、多卤素（较低）烷基、氨基甲酰基、N-较低烷基甲酰基、硝基、单和双较低烷基氨基、苯基偶氮基、羧基、较低烷基羰基、氰基、羰（较低）烷氧基、苯氧基（较低）烷氧基、较低烷氧羰胺基和较低烷氧羰胺苯氧基基团；B单独时，是从以下组成的组中选择的成员：--OH、较低烷氧、--NH.sub.2、--NHOH、环己氧基和苯氧基；Y是从以下组成的组中选择的成员：氧，当与B和它们连接的碳原子一起取得时，形成如下团 ##STR2##
• Oxamic acid derivatives for the prevention of immediate type
  申请人：American Home Products Corporation

  公开号：US03966965A1

  公开（公告）日：1976-06-29

  Anti-allergic agents of ##EQU1## and heterocyclic oxamic acid derivation present the following formula: IN WHICH A is a member selected from the group consisting of 2-thiazolyl, 2-pyridyl, 2-pyridyl-N-oxide, 6-(lower)alkyl-2-pyridyl, 3-cyano-2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 2-pyrazinyl, .alpha.-naphthyl, .beta.-naphthyl, phenyl, 2,6-dichlorophenyl, and substituted phenyl moieties containing from one to three substituents in any of the 2,3,4 and 5 positions of the phenyl ring, independently selected from the group consisting of lower alkyl, lower alkylthio, lower alkylsulfinyl, lower alkoxy, hydroxy(lower)-alkoxy, 2-(lower alkoxy oxalyloxy) ethoxy, benzyloxy, N-mono-and di-lower alkylamino(lower)-alkoxy, halo, sulfamyl, polyhalo(lower)alkyl, carbamyl, N-lower alkylcarbamyl, nitro, mono- and di-lower alkylamino, phenylazo, carboxy, lower alkylcarbonyl, cyano, carb(lower)alkoxy, phenoxy(lower)alkoxy, lower alkoxyoxalamido and lower alkoxyoxalamidophenoxy radicals; B, when taken alone, is a member selected from the group consisting of -OH, lower alkoxy, --NH.sub.2, --NHOH, cyclohexyloxy and phenoxy; and Y is a member selected from the group consisting of oxygen and when taken with B and the carbon atom to which they are attached, forms the moiety ##EQU2##

  ##EQU1##的抗过敏剂和杂环氧酰胺衍生物具有以下公式：其中A是从2-噻唑基，2-吡啶基，2-吡啶-N-氧化物，6-（较低）烷基-2-吡啶基，3-氰基-2-吡啶基，3-吡啶基，4-吡啶基，2-吡嘧啶基，2-吡啶基，α-萘基，β-萘基，苯基，2,6-二氯苯基和取代苯基等组成的群中选择的成员，其中该苯环的2,3,4和5位置中的任意位置都包含从一个到三个取代基的取代基，这些取代基独立地从较低烷基，较低硫代烷基，较低磺酰基，较低烷氧基，羟基（较低）-烷氧基，2-（较低烷氧基氧代羰基）乙氧基，苄氧基，N-单和二-较低烷基氨基（较低）-烷氧基，卤素，磺酰基，多卤代（较低）烷基，氨基甲酰基，N-较低烷基氨基甲酰基，硝基，单和双-较低烷基氨基，苯基偶氮基，羧基，较低烷基羰基，氰基，羰基（较低）烷氧基，苯氧基（较低）烷氧基，较低烷氧氧代草酰胺基和较低烷氧氧代草酰胺苯氧基自由基；B，当单独取时，是从-OH，较低烷氧基，-NH.sub.2，-NHOH，环己氧基和苯氧基等组成的群中选择的成员；Y是从氧中选择的成员，当与B和它们连接的碳原子一起取时，形成上述公式。
• US3966965A
  申请人：——

  公开号：US3966965A

  公开（公告）日：1976-06-29