(Z)-5-<(2,3-dimethyl-6-nitrophenyl)methylene>-2,3-imidazolidinedione | 109133-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (Z)-5-<(2,3-dimethyl-6-nitrophenyl)methylene>-2,3-imidazolidinedione
• 英文别名: (Z)-5-[(2,3-dimethyl-6-nitrophenyl)methylene]-2,3-imidazolidinedione；(5Z)-5-[(2,3-dimethyl-6-nitrophenyl)methylidene]imidazolidine-2,4-dione
• CAS: 109133-81-5
• 化学式: C₁₂H₁₁N₃O₄
• 分子量: 261.237
• InChiKey: XHSCTCAIAUBTGK-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-二甲基-6-硝基苯胺 在 盐酸 、 sodium hydroxide 、 硼烷四氢呋喃络合物 、 sodium ethanolate 、 copper(l) cyanide 、 溶剂黄146 、 pyridinium chlorochromate 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 6.25h， 生成 (Z)-5-<(2,3-dimethyl-6-nitrophenyl)methylene>-2,3-imidazolidinedione
  参考文献：
  名称：

  1,3-二氢-2H-咪唑并[4,5-b]喹啉-2-酮类-血小板cAMP磷酸二酯酶抑制剂和诱导的聚集。

  摘要：

  合成了一系列1,3-二氢-2H-咪唑并[4,5-b]喹啉-2-酮衍生物，并作为粗制人血小板磷酸二酯酶制剂对cAMP水解的抑制剂以及对ADP-和胶原-抑制剂的评估。诱导兔血小板聚集。母体结构7a显示出有效的抑制活性，其通过在5-，6-，7-和8-位上引入烷基，烷氧基或卤素取代基而增强。N-1或N-3处的甲基化产生较弱的cAMP PDE抑制剂和血小板聚集。发现1,3,9,9a-四氢-2H-咪唑并[4,5-b]喹啉-2-酮（6）与它们的完全氧化同类物（7）等价。根据体外的血小板抑制特性，在血栓形成动物模型中预防血栓形成的功效以及良好的血液动力学特征，即1,3-二氢-7，选择8-二甲基-2H-咪唑并[4,5-b]喹啉-2-酮（7o，BMY 20844）进行毒理学评估和临床试验。描述了7o的有效合成。

  DOI：

  10.1021/jm00113a033

文献信息

• Diethyl 2,4-dioxoimidazolidine-5-phosphonates: Horner-Wadsworth-Emmons reagents for the mild and efficient preparation of C-5 unsaturated hydantoin derivatives
  作者：Nicholas A. Meanwell、Herbert R. Roth、Edward C. R. Smith、Donald L. Wedding、J. J. Kim Wright

  DOI：10.1021/jo00024a036

  日期：1991.11

  The phosphonates 19 and 20 were prepared from hydantoin and 1-methylhydantoin, respectively, by way of bromination at C-5 and a subsequent Michaelis-Arbuzov reaction with triethyl phosphite. The Horner-Wadsworth-Emmons-type reagents 19 and 20 were found to react readily with aromatic and aliphatic aldehydes, in the presence of a base, to produce C-5 unsaturated hydantoin derivatives 22 and 26, generally in high yield. The products 22 and 26 were frequently isolated as mixtures of E and Z isomers depending upon the identity of the aldehyde and phosphonate. The isomeric configuration of the products was determined from an analysis of NMR spectral data. Long-range C-13-H-1 coupling constants between the C-4 carbonyl of the hydantoin ring and the olefinic proton were found to be diagnostic of isomer geometry. Conditions were also developed that allowed coupling of 19 and 20 with cyclic and acyclic ketones and alpha-dicarbonyl compounds to afford the corresponding olefinic products. C-5 unsaturated hydantoin derivatives are of synthetic utility as precursors to alpha-amino acid derivatives, pyruvates, and the imidazo[4,5-b]quinolin-2-one heterocyclic ring system, a class of potent inhibitors of low Km cAMP phosphodiesterase and the chromophore present in the siderophore azotobactin.
• US4668686A
  申请人：——

  公开号：US4668686A

  公开（公告）日：1987-05-26
• 1,3-Dihydro-2H-imidazo[4,5-b]quinolin-2-ones - inhibitors of blood platelet cAMP phosphodiesterase and induced aggregation
  作者：Nicholas A. Meanwell、Herbert R. Roth、Edward C. R. Smith、Donald L. Wedding、J. J. Kim Wright、J. Stuart Fleming、Elizabeth Gillespie

  DOI：10.1021/jm00113a033

  日期：1991.9

  5-b]quinolin-2-one derivatives was synthesized and evaluated as inhibitors of cAMP hydrolysis by a crude human platelet phosphodiesterase preparation and as inhibitors of ADP- and collagen-induced aggregation of rabbit blood platelets. The parent structure 7a, demonstrated potent inhibitory activity that was enhanced by the introduction of alkyl, alkoxy, or halogen substituents at the 5-, 6-, 7-, and 8-positions

  合成了一系列1,3-二氢-2H-咪唑并[4,5-b]喹啉-2-酮衍生物，并作为粗制人血小板磷酸二酯酶制剂对cAMP水解的抑制剂以及对ADP-和胶原-抑制剂的评估。诱导兔血小板聚集。母体结构7a显示出有效的抑制活性，其通过在5-，6-，7-和8-位上引入烷基，烷氧基或卤素取代基而增强。N-1或N-3处的甲基化产生较弱的cAMP PDE抑制剂和血小板聚集。发现1,3,9,9a-四氢-2H-咪唑并[4,5-b]喹啉-2-酮（6）与它们的完全氧化同类物（7）等价。根据体外的血小板抑制特性，在血栓形成动物模型中预防血栓形成的功效以及良好的血液动力学特征，即1,3-二氢-7，选择8-二甲基-2H-咪唑并[4,5-b]喹啉-2-酮（7o，BMY 20844）进行毒理学评估和临床试验。描述了7o的有效合成。