2-ethoxalylaminobenzonitrile | 54249-43-3

• 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-ethoxalylaminobenzonitrile
• 英文别名: ethyl 2'-cyanooxanilate；2'-Cyanooxanilic acid ethyl ester；2'-Cyanooxanilsaeure-ethylester；Ethyl [(2-cyanophenyl)amino](oxo)acetate；ethyl 2-(2-cyanoanilino)-2-oxoacetate
• CAS: 54249-43-3
• 化学式: C₁₁H₁₀N₂O₃
• mdl: MFCD00835333
• 分子量: 218.212
• InChiKey: LYNISAGITOKJKO-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91 °C(Solv: ethanol (64-17-5))
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-ethoxalylaminobenzonitrile 以 1,4-二氧六环 、 水 为溶剂， 反应 1.5h， 生成 (2-cyano-phenyl)-oxalamic acid
  参考文献：
  名称：

  一系列含有γ-氨基酸部分的胱天蛋白酶抑制剂治疗胆汁淤积性肝病的构效关系研究

  摘要：

  已经合成了一系列含有γ-氨基酸部分的胱天蛋白酶抑制剂。对其抗凋亡细胞活性的构效关系进行了系统的研究。这些努力导致了化合物20o作为有效的半胱天冬酶抑制剂的发现，证明了临床前改善总胆红素功效并显着改善了药代动力学。

  DOI：

  10.1016/j.bmcl.2018.04.002
• 作为产物：
  描述：

  2-carbamoyloxanilic acid ethyl ester 以 乙醚 、 水 、 乙酸酐 、 苯 为溶剂， 生成 2-ethoxalylaminobenzonitrile
  参考文献：
  名称：

  Oxamic acid derivatives for the prevention of immediate type

  摘要：

  ##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。

  公开号：

  US03966965A1

文献信息

• Oxanilic acids, a new series of orally active antiallergic agents
  作者：John H. Sellstedt、Charles J. Guinosso、Albert J. Begany、Stanley C. Bell、Marvin Rosenthale

  DOI：10.1021/jm00243a014

  日期：1975.9

  antiallergic activity using the rat passive cutaneous anaphylaxis (PCA) test. Many of the oxanilic acid esters are active orally, with the most active species having an aryl 2'-carbamoyl group and a 3'-methoxy group. Hydrolysis of the ester from the oxanilic ester moiety causes a loss of oral activity.

  制备了大量的草酸苯甲酸酯和N-杂芳基草酰胺酸酯，并通过大鼠被动皮肤过敏反应（PCA）测试发现具有抗过敏活性。许多草酰苯甲酸酯具有口服活性，最活泼的物种具有芳基2'-氨基甲酰基和3'-甲氧基。酯从草酰胺酯部分水解会导致口服活性下降。
• 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 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。
• Chemical Hybridizing Agents for Chickpea (<i>Cicer arietinum</i> L.):  Leads from QSAR Analysis of Ethyl Oxanilates and Pyridones
  作者：Kajal Chakraborty、C. Devakumar

  DOI：10.1021/jf052435h

  日期：2006.3.1

  In the self-pollinated crops such as chickpea, induction of male sterility by deployment of chemical hybridizing agents (CHAs) facilitating "two-line" approach holds immense potential in heterosis breeding. A total of 40 test CHAs comprising 20 ethyl oxanilates and 20 pyridones were screened as potential CHAs on chickpea (variety BG 1088) at 500, 800, and 1000 ppm. Three test compounds mostly having either F (4)/Br (5)/CF3 (19) at the para position of the aryl ring from a pool of 20 ethyl oxanilates were identified as the most potent CHAs causing >= 99% induction of pollen sterility and > 90% total flower sterility at 1000-ppm test concentration. Among pyridone derivatives, N-(4-chlorophenyl)-5-carbethoxy-4,6-dimethyl, 1, 2-dihydropyrid-2-one (26) was found to be the most active. Quantitative structure activity relationship (QSAR) analysis has revealed a direct involvement of Swain-Lupton field constant, F, with the target bioactivity which implied that field rather than resonance effect (R) had a positive effect on the activity. The real guiding principle for selectivity was found out to be the hydrophobic parameter pi value. The QSAR models indicated that increased steric bulk at the 4-position on the phenyl ring is associated with enhanced activity. The CHAs appeared to act by mimicking UDP-glucose, the key substrate in the synthesis of callose, or lead to an imbalance in acid-base equilibrium in pollen mother cells resulting in dissolution of callose wall by premature callase secretion.
• N-(Aminophenyl)oxamic acids and esters as potent, orally active antiallergy agents
  作者：Dieter H. Klaubert、John H. Sellstedt、Charles J. Guinosso、Robert J. Capetola、Stanley C. Bell

  DOI：10.1021/jm00138a020

  日期：1981.6