2'-Nitro-4'-(trifluoromethyl)oxanilic acid ethyl ester | 54166-79-9

• 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'-Nitro-4'-(trifluoromethyl)oxanilic acid ethyl ester
• 英文别名: Ethyl N-(2-nitro-4-trifluoromethylphenyl)oxamate；2'-Nitro-4'-(trifluormethyl)-oxanilsaeure-ethylester；Ethyl [2-nitro-4-(trifluoromethyl)anilino](oxo)acetate；ethyl 2-[2-nitro-4-(trifluoromethyl)anilino]-2-oxoacetate
• CAS: 54166-79-9
• 化学式: C₁₁H₉F₃N₂O₅
• 分子量: 306.198
• InChiKey: HPWJLXSOUJRZLN-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126 °C(Solv: ethanol (64-17-5))
• 密度：
  1.498±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-Nitro-4'-(trifluoromethyl)oxanilic acid ethyl ester 在 铁粉 、 溶剂黄146 作用下， 生成 1,4-二氢-6-(三氟甲基)喹喔啉-2,3-二酮
  参考文献：
  名称：

  Pyrrolylquinoxalinediones: A new class of AMPA receptor antagonists

  摘要：

  Pyrrolylquinoxalinediones were synthesized and their affinities for the AMPA receptor were determined. Most compounds showed moderate to good affinities. The acetic acid derivative 8b exhibited a K-i value of 70 nM and was equipotent to NBQX 1. Structure activity relationships are discussed. Selected compounds were tested for their potency to inhibit AMPA induced lethal convulsions in mice. In this in vivo model the compounds showed improved potency compared with NBQX. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00534-3
• 作为产物：
  描述：

  4-氯-3-硝基三氟甲苯 在 NH₂ 作用下， 生成 2'-Nitro-4'-(trifluoromethyl)oxanilic acid ethyl ester
  参考文献：
  名称：

  Pyrrolylquinoxalinediones: A new class of AMPA receptor antagonists

  摘要：

  Pyrrolylquinoxalinediones were synthesized and their affinities for the AMPA receptor were determined. Most compounds showed moderate to good affinities. The acetic acid derivative 8b exhibited a K-i value of 70 nM and was equipotent to NBQX 1. Structure activity relationships are discussed. Selected compounds were tested for their potency to inhibit AMPA induced lethal convulsions in mice. In this in vivo model the compounds showed improved potency compared with NBQX. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00534-3

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。
• Antisecretory oxamic acid esters
  申请人：American Home Products Corporation

  公开号：US04137325A1

  公开（公告）日：1979-01-30

  Variously substituted oxanilic acid esters possessing anti-secretary activity are useful anti-ulcer agents.

  各种替代氧基苯甲酸酯具有抗分泌活性，可用作抗溃疡药物。
• 2,3(1H,4H)quinoxalinedione
  申请人：BASF Aktiengesellschaft

  公开号：US05714489A1

  公开（公告）日：1998-02-03

  2,3(1H,4H)-quinoxalinediones of the formula I ##STR1## where R.sup.1 is hydrogen, an aliphatic radical which has up to 12 carbons and can be substituted by one of the following: phenyl, cyclopentyl, cyclohexyl or --CO--R.sup.3, --CO--O--R.sup.3 or --CO--NH--R.sup.3, where R.sup.3 is hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, benzyl or 1-phenylethyl, a cycloaliphatic radical with up to 12 carbons or phenyl, where the cyclic groups in R.sup.1 can have up to three of the following substituents: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro, cyano, --CO--O--R.sup.3 and --CO--NH--R.sup.3 ; R.sup.2 is 1-pyrrolyl which can have up to two of the following substituents: C.sub.1 -C.sub.4 -alkyl, phenyl, phenylsulfonyl, nitro, cyano and --CO--O--R.sup.3, --CO--NH--R.sup.3, --CH.sub.2 --O--R.sup.3, --O--R.sup.3 and --CH.dbd.NO--R.sup.3 R radicals are identical or different and are the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl, trichloromethyl, trifluoromethoxy, trichloromethoxy, fluorine, chlorine, bromine, iodine, nitro, cyano and --CO--O--R.sup.3 and --CO--NH--R.sup.3 as well as a fused-on benzene ring; n is 0-3, and 2,3(1H,4H)-quinoxalinediones I' ##STR2## where R.sup.1 has the stated meanings, are suitable as drugs in the treatment of neurodegenerative disorders and neurotoxic disturbances of the central nervous system.

  2,3(1H,4H)-喹诺醌二酮的结构如下：其中R.sup.1是氢，一个最多有12个碳原子并可被以下之一取代的脂肪基团：苯基、环戊基、环己基或--CO--R.sup.3、--CO--O--R.sup.3或--CO--NH--R.sup.3，其中R.sup.3是氢、C.sub.1-C.sub.4-烷基、苯基、苄基或1-苯乙基，一个最多有12个碳原子的环脂基团或苯基，其中R.sup.1中的环基团最多有以下三种取代基：C.sub.1-C.sub.4-烷基、C.sub.1-C.sub.4-卤代烷基、C.sub.1-C.sub.4-烷氧基、C.sub.1-C.sub.4-卤代烷氧基、卤素、硝基、氰基、--CO--O--R.sup.3和--CO--NH--R.sup.3；R.sup.2是1-吡咯基，最多可有以下两种取代基：C.sub.1-C.sub.4-烷基、苯基、苯基磺酰基、硝基、氰基和--CO--O--R.sup.3、--CO--NH--R.sup.3、--CH.sub.2--O--R.sup.3、--O--R.sup.3和--CH.dbd.NO--R.sup.3；R基团相同或不同，可为以下之一：C.sub.1-C.sub.4-烷基、C.sub.1-C.sub.4-烷氧基、三氟甲基、三氯甲基、三氟甲氧基、三氯甲氧基、氟、氯、溴、碘、硝基、氰基和--CO--O--R.sup.3和--CO--NH--R.sup.3，以及一个螺联苯环；n为0-3。具有上述含义的2,3(1H,4H)-喹诺醌二酮I'适用于治疗神经退行性疾病和中枢神经系统神经毒性障碍的药物。
• Pyrrolyl quinoxalindiones their production and use as AMPA receptor antagonists
  申请人：Abbott Laboratories

  公开号：US06277850B1

  公开（公告）日：2001-08-21

  Pyrrolylquinoxalinediones of the formula I and their tautomeric and isomeric forms, and their physiologically tolerated salts are described, where the variables have the following meaning: R1 hydrogen, C1-C6-alkyl, substituted by hydroxyl or carboxyl, R2 hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, a chlorine, fluorine or bromine atom, a trihalomethyl, cyano or nitro group or SO2—C1-C4-alkyl, R3 COOH or a radical which can be hydrolyzed to the carboxyl group, n 1 or 2.

  公式I的吡咯基喹喔啉二酮及其互变异构和同分异构形式以及其生理耐受的盐已被描述，其中变量的含义如下：R1为氢、C1-C6-烷基，被羟基或羧基取代，R2为氢、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、氯、氟或溴原子、三卤甲基、氰基或硝基，或SO2—C1-C4-烷基，R3为COOH或可水解为羧基的基团，n为1或2。
• Quinoxaline compounds and their preparation and use
  申请人：NOVO NORDISK A/S

  公开号：EP0377112A1

  公开（公告）日：1990-07-11

  Heterocyclic dihydroxyquinoxaline compounds having the formula wherein R¹ is hydroxy, alkoxy, aryloxy, aralkyloxy, cycloalkylalkoxy, cycloalkoxy, or acyloxy; and R⁵, R⁶, R⁷ and R⁸ independently are hydrogen, NO₂, halogen, CN, SO₂NR′R′, SO₂R′, CF₃, or OR′, wherein R′ is hydrogen or C1-4-alkyl. The invention also relates to a method of preparing the compounds, pharmaceutical compositions thereof, and their use. The compounds are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters, particularly the quisqualate receptors, and especially as neuroleptics.

  具有以下式子的杂环二羟基喹喔啉化合物 其中 R¹ 是羟基、烷氧基、芳氧基、烷氧基、环烷基烷氧基、环烷氧基或酰氧基；以及 R⁵、R⁶、R⁷ 和 R⁸ 独立地是氢、NO₂、卤素、CN、SO₂RN′R′、SO₂R′、CF₃ 或 OR′，其中 R′是氢或 C1-4 烷基。 本发明还涉及化合物的制备方法、其药物组合物及其用途。 本发明的化合物可用于治疗兴奋性神经递质，特别是喹乙醇受体活性亢进引起的病症，尤其可用作神经抑制剂。