5-<(2-Hydroxy-5-nitrophenyl)methylene>-2,4,6(1H,3H)-pyrimidinetrione

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-<(2-Hydroxy-5-nitrophenyl)methylene>-2,4,6(1H,3H)-pyrimidinetrione
• 英文别名: 5-(2-hydroxy-5-nitrobenzylidene)pyrimidine-2.4.6(1H.3H.5H)-trione；5-[(2-Hydroxy-5-nitrophenyl)methylidene]-1,3-diazinane-2,4,6-trione
• 化学式: C₁₁H₇N₃O₆
• mdl: MFCD00477464
• 分子量: 277.193
• InChiKey: RWQZDFKRLTZNJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  巴比妥酸 、 5-硝基水杨醛 以 乙醇 为溶剂， 反应 0.5h， 以95%的产率得到5-<(2-Hydroxy-5-nitrophenyl)methylene>-2,4,6(1H,3H)-pyrimidinetrione
  参考文献：
  名称：

  A simple approach towards the synthesis of oxadeazaflavines

  摘要：

  The synthesis of oxadeazaflavine (2H-chromeno[2,3-d]pyrimidine-2,4(3H)-dione) derivatives (1a, 1b and 1c) from barbituric acid and salicylaldehydes as starting materials was shown to be possible using water as solvent at room temperature. The orange intermediate formed, an anthocyanidin-like precursor of the desired products, gave reasonable yields of the oxadeazaflavines when treated with acetic acid-acetic anhydride mixture. When the reaction was carried out at 100-degrees-C the corresponding 1,5-dihydro-5(5'-barbituryl)-2H-chromeno[2,3-d]pyrimidine-2,4(3H)-diones (4a, 4b and 4c) were obtained. The reaction of barbituric acid with nitrosalicylaldehydes, at either 25 or 100-degrees-C, leads only to the corresponding arylidenebarbituric acids.

  DOI：

  10.1016/s0040-4020(01)80384-7

文献信息

• [EN] PYRIMIDINE DERIVATIVES FOR USE AS ANTIBIOTICS<br/>[FR] DÉRIVÉS DE PYRIMIDINE À UTILISER EN TANT QU'ANTIBIOTIQUES
  申请人：UNIV ASTON

  公开号：WO2010136804A1

  公开（公告）日：2010-12-02

  The invention provides a compound of formula (i): wherein R1 and R2 are independently selected from hydrogen, methyl, ethyl, propyl and butyl; R3 is selected from substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 1-naphthyl, substituted 2-naphthyl, and substituted phenyl, and X1 and X3 are independently selected from O or S, and X2 is O; and L is selected from C1 to C3 alkyl, C1 to C3 alkoxyl, C2 or C3 alkenyl, and C2 or C3 alkynyl; and the bond connecting L to the ring is a single or a double bond; wherein when the bond connecting L to the pyrimidine ring is a double bond, the substituted phenyl is not a monosubstituted 2- or 4- halobenzene; and wherein the substituted phenyl is not a toluene, anisole, phenol, dimethylaniline, guaiacol, or benzyl phenyl ether moiety; or a pharmaceutically, or veterinarily, acceptable derivative thereof. The use of such compounds as medicaments, in particular as antibiotics, specifically antibiotics for the inhibition of bacterial DHODase is also described, as are compositions (pharmaceutical and anti-infective) containing the compositions, articles or surfaces coated impregnated with the anti- infective compositions. Finally, the invention provides methods for the treatment of a disease and methods for preventing bacterial transmission including the compounds of formula 1.

  这项发明提供了一个式（i）的化合物：其中R1和R2分别选自氢、甲基、乙基、丙基和丁基；R3选自取代或未取代的蒽基、取代或未取代的芘基、取代或未取代的咔唑基、取代或未取代的咪唑基、取代或未取代的菲基、取代或未取代的芴基、取代或未取代的1-萘基、取代的2-萘基和取代的苯基，X1和X3分别选自O或S，X2为O；L选自C1到C3烷基、C1到C3烷氧基、C2或C3烯基和C2或C3炔基；连接L到环的键为单键或双键；当连接L到嘧啶环的键为双键时，取代的苯基不是单取代的2-或4-卤苯；取代的苯基不是甲苯、甲酚、二甲基苯胺、愈创木酚或苄基苯醚基团；或其药学或兽医学上可接受的衍生物。还描述了这些化合物作为药物的用途，特别是作为抗生素，特别是用于抑制细菌DHODase的抗生素，以及含有这些化合物的组合物（药用和抗感染），涂有抗感染组合物的物品或表面。最后，该发明提供了一种治疗疾病的方法和预防细菌传播的方法，包括式1的化合物。
• Medicinal Drug with Activity against Gram Positive Bacteria, Mycobacteria and Fungi
  申请人：LEVINA Elizabeth

  公开号：US20160000786A1

  公开（公告）日：2016-01-07

  The present invention discloses a nanocomposite material having single-walled aluminosilicate nanotube in polymer, a membrane comprising such nanocomposite material, and the method of making the nanocomposite material, in which the composite material has high volume fraction of well-dispersed nanotubes. A gel-phased single-walled aluminosilicate nanotube is first prepared and then mixed with a polymer matrix to yield the composite material.

  本发明披露了一种在聚合物中具有单壁氧化铝硅酸盐纳米管的纳米复合材料，以及包括这种纳米复合材料的膜和制备纳米复合材料的方法。该复合材料具有高体积分数的良好分散的纳米管。首先制备了凝胶相单壁氧化铝硅酸盐纳米管，然后与聚合物基体混合以得到复合材料。
• Benzopyrano derivatives, pharmaceutical compositions containing them and processes for preparing the compounds and compositions
  申请人：Technobiotic Ltd.

  公开号：EP0008277A1

  公开（公告）日：1980-02-20

  Novel compounds of the formula wherein each of R3 and R5 represents hydrogen or loweralkyl, n Is an integer from one to four and R represents hydrogen, ' loweralkyl, lowercycloalkyl, lowercycloalkyl-loweralkyl, acyloxyloweralkyl, hydroxyloweralkyl, lower-alkoxyloweralkyl, nitro, halogeno, haloloweralkyl, hydroxy, loweralkoxy, acylaminoloweralkyl, aminoloweralkyl, mono- or diloweralkylaminoloweralkyl, alkanoyloxy, carboxy, loweralkoxycarbonyl, acyl, formyl, cyano or a carboxamido moiety of the structure wherein A is straight or branched chain alkyl with up to 12 carbon atoms, lowercycloalkyl, lowercycloalkylloweralkyl, loweralkoxyloweralkyl, hydroxyloweralkyl, fluoroloweralkyl, loweralkenyl, loweralkylthioloweralkyl, loweralkylsulfoxyloweralkyl, loweralkylsulfonylloweralkyl, thiazolyt, oxazolyl, thiadiazolyl, methylthiadiazolyl, furyl, pyrazolyl, tetrazolyl, methyltetrazolyl, hydroxypyrimidinyl, phenyl, pyrimidinyl-dione, or the grouping wherein E is a straight or branched chain or cyclic loweralkylene, x is zero or one and Q is hydroxy, loweralkoxy, amino or mono- or diloweralkylamino; or the grouping -E-Re, wherein E is as defined above and is optionally substituted by hydroxy and/or phenyl, R8 is phenyl, thiazolyl, oxazolyl, thiadiazolyl, methylthiadiazolyl, tetrazolyl, methyltetrazolyl, furyl, pyridiyl, methylpyridiyl or piperidinyl; and B is hydrogen, loweralkyl, lowercycloalkyl, lowercycioalkylioweralkyl, or loweralkenyl; or A and B, when taken together with the nitrogen atom to which they are attached, represent imidazolyl, morpholinyl, pyrrolidinyl, piperidinyl or piperazinyl said heterocyclic rings being optionally substituted by hydroxy, loweralkyl or hydroxyloweralkyl; and pharmaceutically acceptable salts thereof. The preparation of these compounds by five methods is described, in particular one inventive method which comprises reacting a correspondingly R-substituted salicylaldehyde and barbituric acid in an alcoholic solvent in the presence of a sulfonic acid. Representative compounds of the invention have been shown to exhibit anti-allergy reactions and are thus useful in treating, such diseases as asthma, allergic rhinitis, urticaria and ulcerative colitis.

  式中的新型化合物 其中 R3 和 R5 各自代表氢或低级烷基，n 是 1 至 4 的整数，R 代表氢、'低级烷基、低级环烷基、低级环烷基-低级烷基、酰氧基低级烷基、羟基低级烷基、低级烷氧基低级烷基、硝基、卤素、卤代低级烷基、羟基、低级烷氧基、酰基氨基低级烷基、氨基低级烷基、单烷基或稀释低级烷基氨基低级烷基、烷酰氧基、羧基、低级烷氧基羰基、酰基、甲酰基、氰基或结构为羧酰胺的分子 其中 A 是碳原子数不超过 12 个的直链或支链烷基、低级环烷基、低级环烷氧基低级烷基、低级烷氧基低级烷基、羟基低级烷基、氟代低级烷基、低级烯基、低级烷硫基低级烷基、噻唑基、噁唑基、噻二唑基、甲硫二唑基、呋喃基、吡唑基、四唑基、甲基四唑基、羟基嘧啶基、苯基、嘧啶基二酮或以下基团 其中 E 为直链或支链或环状低级烯烃，x 为 0 或 1，Q 为羟基、低级烷氧基、氨基或单或稀烷基氨基；或基团-E-Re，其中 E 如上文所定义并可选被羟基和/或苯基取代，R8 为苯基、噻唑基、噁唑基、噻二唑基、甲硫二唑基、四唑基、甲基四唑基、呋喃基、吡啶基、甲基吡啶基或哌啶基；而 B 是氢、低级烷基、低级环烷基、低级环烷基低级烷基或低级烯基；或者 A 和 B 连同它们所连接的氮原子代表咪唑基、吗啉基、吡咯烷基、哌啶基或哌嗪基，所述杂环可任选被羟基、低级烷基或羟基低级烷基取代；以及它们的药学上可接受的盐。 本发明描述了通过五种方法制备这些化合物的方法，特别是一种创造性的方法，该方法包括在磺酸存在下，在醇溶剂中使相应的 R 取代水杨醛和巴比妥酸反应。本发明的代表性化合物已被证明具有抗过敏反应，因此可用于治疗哮喘、过敏性鼻炎、荨麻疹和溃疡性结肠炎等疾病。
• Medicinal drug with activity against gram positive bacteria, mycobacteria and fungi
  申请人：Levina Elizabeth

  公开号：US10265318B2

  公开（公告）日：2019-04-23

  A medicinal drug is provided with activity against gram positive bacteria, mycobacteria and fungi characterized in that it is a compound of the class of pyrimidine derivatives of salicylic aldehyde and perhydropyrimidine-2,4,6-triones selected from a group consisting of tautomeric forms, salt forms, and a cyclic form of pyrylium salts, and with the general formula: where X1, X3 are selected from the group containing: H, halogen; NO2; X2, X4 are selected from the group containing: H, halogen; Z is selected from the group containing: O, NNH2, NOH, perhydropyrimidine-5-ylidene-2,4.6-trione, perhydropyrimidine-5-ylidene-2,4.6-trione, substituted at the nitrogen atom with alkyl, aryl or aralkyl group; Y is selected from the group containing: H, Na, Li, K. Further, methods for treating infections, tonsillitis, pneumonia, or wound infections caused by Gram-positive bacteria, mycobacteria and fungi are provided using a therapeutically effective amount of the compound.

  提供了一种对革兰氏阳性菌、分枝杆菌和真菌具有活性的药物，其特征在于它是一种水杨醛和过氢嘧啶-2,4,6-三酮的嘧啶衍生物类化合物，该化合物从同分异构体、盐类和环状嘧啶盐组成的组中选出，通式为 其中 X1、X3 选自以下组别H、卤素 X2、X4 选自包含以下物质的组H、卤素； Z 选自包含以下物质的组O、NNH2、NOH、全氢嘧啶-5-亚基-2,4.6-三酮、全氢嘧啶-5-亚基-2,4.6-三酮，在氮原子上被烷基、芳基或芳烷基取代； Y 选自以下组别H、Na、Li、K。 此外，还提供了使用治疗有效量的化合物治疗革兰氏阳性菌、分枝杆菌和真菌引起的感染、扁桃体炎、肺炎或伤口感染的方法。
• A simple approach towards the synthesis of oxadeazaflavines
  作者：José Daniel Figueroa-Villar、Elizabete R. Cruz

  DOI：10.1016/s0040-4020(01)80384-7

  日期：1993.4

  The synthesis of oxadeazaflavine (2H-chromeno[2,3-d]pyrimidine-2,4(3H)-dione) derivatives (1a, 1b and 1c) from barbituric acid and salicylaldehydes as starting materials was shown to be possible using water as solvent at room temperature. The orange intermediate formed, an anthocyanidin-like precursor of the desired products, gave reasonable yields of the oxadeazaflavines when treated with acetic acid-acetic anhydride mixture. When the reaction was carried out at 100-degrees-C the corresponding 1,5-dihydro-5(5'-barbituryl)-2H-chromeno[2,3-d]pyrimidine-2,4(3H)-diones (4a, 4b and 4c) were obtained. The reaction of barbituric acid with nitrosalicylaldehydes, at either 25 or 100-degrees-C, leads only to the corresponding arylidenebarbituric acids.