(Z)-5-(naphthalene-2-ylmethylidene)imidazolidine-2,4-dione | 140894-72-0

• 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-(naphthalene-2-ylmethylidene)imidazolidine-2,4-dione
• 英文别名: (Z)-5-(naphthalene-2-ylmethylene)imidazolidine-2,4-dione；(5Z)-5-(naphthalen-2-ylmethylidene)imidazolidine-2,4-dione
• CAS: 140894-72-0
• 化学式: C₁₄H₁₀N₂O₂
• 分子量: 238.246
• InChiKey: HSXQWEKSYKYNFL-WQLSENKSSA-N

物化性质

• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-5-(naphthalene-2-ylmethylidene)imidazolidine-2,4-dione 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 (Z)-1-<2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-D-erythro-pentofuranosyl>-5-(2-naphthylmethylene)-2,4-imidazolidinedione
  参考文献：
  名称：

  Hydantoin analogs of thymidine

  摘要：

  Hydantoin nucleosides were synthesized from a protected methyl 2-deoXy-D-ribofuranoside in a Friedel-Crafts catalyzed silyl-Hilbert-Johnson reaction as modified by Vorbruggen. Atypical byproducts are accounted for by assuming the initial step being a ring opening of the sugar to give an acyclic glycos-1-yl cation.

  DOI：

  10.1021/jo00074a028
• 作为产物：
  描述：

  海因 、 2-萘甲醛 在 碳酸氢钠 、 C.I.酸性橙108 作用下， 以 水 、 乙醇 为溶剂， 反应 16.0h， 以27%的产率得到(Z)-5-(naphthalene-2-ylmethylidene)imidazolidine-2,4-dione
  参考文献：
  名称：

  [EN] METHODS OF USE FOR OPSIN BINDING LIGANDS
  [FR] PROCÉDÉS D'UTILISATION DE LIGANDS DE LIAISON DE L'OPSINE

  摘要：

  公开了利用公式I1 II、III、IV和/或V的化合物治疗与在眼睛中积聚的有毒视觉循环产物有关的眼科疾病的方法，这些产物与暴露于光线的医疗程序期间的视觉循环反应有关，最常见的是各种形式的眼科手术，并稳定突变视蛋白的正确折叠。还描述了在这些方法中有用的化合物和组合物，无论是单独使用还是与其他治疗剂结合使用，以及筛选用于上述治疗的新药物的方法。

  公开号：

  WO2010074746A1

文献信息

• [EN] METHODS OF USE FOR OPSIN BINDING LIGANDS<br/>[FR] PROCÉDÉS D'UTILISATION DE LIGANDS DE LIAISON DE L'OPSINE
  申请人：BIKAM PHARMACEUTICALS INC

  公开号：WO2010074746A1

  公开（公告）日：2010-07-01

  Methods of use of compounds of the Formula I1 II, III, IV and/or V are disclosed for treating ophthalmic conditions related to the production of toxic visual cycle products that accumulate in the eye, and are associated with reactions of the visual cycle during medical procedures that expose the eye to light, most commonly the various forms of ophthalmic surgery and stabilize the proper folding of mutant opsins. Compounds and compositions useful in the these methods, either alone or in combination with other therapeutic agents, are also described, along with methods of screening for new agents useful in said treatments.

  公开了利用公式I1 II、III、IV和/或V的化合物治疗与在眼睛中积聚的有毒视觉循环产物有关的眼科疾病的方法，这些产物与暴露于光线的医疗程序期间的视觉循环反应有关，最常见的是各种形式的眼科手术，并稳定突变视蛋白的正确折叠。还描述了在这些方法中有用的化合物和组合物，无论是单独使用还是与其他治疗剂结合使用，以及筛选用于上述治疗的新药物的方法。
• [EN] NOVEL N3-AMINOALKYL DERIVATIVES OF 5-ARYLIDENEHYDANTOIN, PHARMACEUTICAL COMPOSITION CONTAINING THE ABOVE AND APPLICATION THEREOF<br/>[FR] NOUVEAUX DÉRIVÉS N3-AMINOALKYLE DE 5-ARYLIDÈNEHYDANTOÏNE, COMPOSITION PHARMACEUTIQUE CONTENANT CES DERNIERS ET APPLICATION ASSOCIÉE
  申请人：UNIWERSYTET JAGIELLOŃSKI

  公开号：WO2015065212A1

  公开（公告）日：2015-05-07

  The invention discloses novel 3-aminoalkyl derivatives of 5-arylidenehydantoin of formula I, pharmaceutical composition containing these derivatives and the use thereof in inhibition of efflux of drugs used to prevent and treat diseases of bacterial and/or cancer origin.

  本发明公开了式I的新型5-芳基亚醰基脲的3-氨基烷基衍生物，包含这些衍生物的药物组合物以及将其用于抑制用于预防和治疗细菌和/或癌症起源疾病的药物外流的用途。
• Verfahren zur selektiven Hydrierung von aktivierten, ethylenisch ungesättigten Verbindungen
  申请人：RÜTGERSWERKE AKTIENGESELLSCHAFT

  公开号：EP0695749A1

  公开（公告）日：1996-02-07

  Die Erfindung betrifft ein neues Verfahren zur selektiven Hydrierung von aktivierten, ethylenisch ungesättigten Verbindungen in Gegenwart von Unterphosphoriger Säure, Carbonsäure und katalytischen Mengen Jod oder Jodwasserstoff. Insbesondere betrifft diese Erfindung ein Verfahren zur Hydrierung von Verbindungen mit entsprechenden Doppelbindungen an einem heterocyclischen Ring unter Erhalt eines empfindlichen, aromatischen Rings oder Ringsystems bzw. ohne überlicherweise als Katalysatorgifte wirkende Abbauprodukte, wie z.B. Schwefelverbindungen, freizusetzen.

  本发明涉及一种在次磷酸、羧酸和催化量的碘或碘化氢存在下选择性氢化活化的乙烯基不饱和化合物的新工艺。 特别是，本发明涉及一种氢化杂环上具有相应双键的化合物的工艺，同时保留敏感的芳香环或环系统，或不释放通常作为催化剂毒物的降解产物，如硫化合物。
• Anticonvulsant Activity of Phenylmethylenehydantoins:  A Structure−Activity Relationship Study
  作者：Jeyanthi Chinnappa Thenmozhiyal、Peter Tsun-Hon Wong、Wai-Keung Chui

  DOI：10.1021/jm030450c

  日期：2004.3.1

  Phenylmethylenehydantoins (PMHs) and their des-phenyl analogues were synthesized and evaluated for anticonvulsant activity using the maximal electroshock seizure (MES) assay. The phenyl rings of PMHs were substituted with a wide spectrum of groups, and the selection of substituents was guided by Craig's plot. Phenylmethylenehydantoins substituted with alkyl (2, 3, 5, 6, 12, 14), halogeno (35, 38, 41), trifluoromethyl (11), and alkoxyl (23) groups at the phenyl ring were found to exhibit good anticonvulsant activity with EDMES(2.5) ranging from 28 to 90 mg/kg. Substitution of polar groups such as -NO2, -CN, and -OH was found to be less active or inactive on PMHs. Replacement of the phenyl ring with heteroaromatic rings reduced or caused the loss of anticonvulsant activity. The study identified two PMHs, 14 (EDMES(2.5) = 28 +/- 2 mg/kg) and 12 (EDMES(2.5) = 39 4 mg/kg), to be the most active candidates of the series, which are comparable to phenytoin (55, EDMES(2.5) = 30 +/- 2 mg/kg) in their protection against seizure. Multivariate analysis performed on the whole series of 54 PMHs further supported the finding that the alkylated phenylmethylenehydantoins are the best acting compounds. The SAR model derived on the basis of 12 of the most active phenylmethylenehydantoins demonstrated good predicting ability (root-mean-square error of prediction (RMSEP) = 0.134; RMSEE = 0.057) and identified LUMO energy and the log P as critical parameters for their anticonvulsant activity.
• Hydantoin analogs of thymidine
  作者：Ahmed A. El-Barbary、Ahmed I. Khodair、Erik B. Pedersen

  DOI：10.1021/jo00074a028

  日期：1993.10

  Hydantoin nucleosides were synthesized from a protected methyl 2-deoXy-D-ribofuranoside in a Friedel-Crafts catalyzed silyl-Hilbert-Johnson reaction as modified by Vorbruggen. Atypical byproducts are accounted for by assuming the initial step being a ring opening of the sugar to give an acyclic glycos-1-yl cation.