3-(3-Bromopropyl)-5,5-diphenylhydantoin | 42747-81-9

• 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: 3-(3-Bromopropyl)-5,5-diphenylhydantoin
• 英文别名: 3-(3-bromopropyl)-5,5-diphenylimidazolidine-2,4-dione；3-(3-bromo-propyl)-5,5-diphenyl-imidazolidine-2,4-dione；3-(3-bromopropyl)-5,5-diphenyl-2,4-imidazolidinedione；3-γ-Brompropyl-5,5-diphenyl-hydantoin；3-γ-Brompropyl-5,5-diphenylhydantoin
• CAS: 42747-81-9
• 化学式: C₁₈H₁₇BrN₂O₂
• 分子量: 373.249
• InChiKey: DDPNBGDEGSIABU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-Bromopropyl)-5,5-diphenylhydantoin 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 59.0h， 生成 3-{3-[4-(1-hydroxyethyl)-1H-1,2,3-triazol-1-yl]propyl}-5,5-diphenylimidazolidine-2,4-dione
  参考文献：
  名称：

  In vitroAnti-HMPV Activity of New Synthetic Phenytoin Derivatives

  摘要：

  New derivatives of synthetic 5,5-diphenylhydantoin (phenytoin) were prepared by N-alkylation with 1,3-dibromopropane. Subsequent treatment with sodium azide led to the respective azide. Reaction of the azide with phenylacetylene and 2-hydroxy-3-butyne and oxidation of the resulting alcohol with MnO2 resulted in three triazolic compounds that were evaluated in vitro for their antiviral activity against human metapneumovirus (HMPV). 5,5-Diphenyl-3-[3-(4-phenyl-1H-1,2,3-triazol-1-yl) propyl] imidazolidine-2,4-dione was the most active of the three compounds tested, with selectivity index of 129.87, even higher than ribavirin, the control substance. The three compounds showed activity in the early stages of viral replication presenting virucidal activity and binding to cellular receptors, preventing the adsorption of viral particles. These compounds showed higher activity in both experiments, inhibiting 98.3% of infection as virucidal and 98.9% when interacting with cellular receptors. Furthermore, they showed 73.8% of activity during the penetration of HMPV particles into cells. The derivative 3-{3-[4-(1-hydroxyethyl)-1H-1,2,3-triazol-1-yl] propyl}-5,5-diphenylimidazolidine-2,4-dione presented a mild anti-HMPV activity, with selectivity index of 2.74. 3-[3-(4-acetyl-1H-1,2,3-triazol-1-yl) propyl]-5,5-diphenylimidazolidine2,4- dione inhibited less than 50% of HMPV replication.

  DOI：

  10.5935/0103-5053.20150234
• 作为产物：
  描述：

  安息香精油 在 硝酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 3-(3-Bromopropyl)-5,5-diphenylhydantoin
  参考文献：
  名称：

  In vitroAnti-HMPV Activity of New Synthetic Phenytoin Derivatives

  摘要：

  New derivatives of synthetic 5,5-diphenylhydantoin (phenytoin) were prepared by N-alkylation with 1,3-dibromopropane. Subsequent treatment with sodium azide led to the respective azide. Reaction of the azide with phenylacetylene and 2-hydroxy-3-butyne and oxidation of the resulting alcohol with MnO2 resulted in three triazolic compounds that were evaluated in vitro for their antiviral activity against human metapneumovirus (HMPV). 5,5-Diphenyl-3-[3-(4-phenyl-1H-1,2,3-triazol-1-yl) propyl] imidazolidine-2,4-dione was the most active of the three compounds tested, with selectivity index of 129.87, even higher than ribavirin, the control substance. The three compounds showed activity in the early stages of viral replication presenting virucidal activity and binding to cellular receptors, preventing the adsorption of viral particles. These compounds showed higher activity in both experiments, inhibiting 98.3% of infection as virucidal and 98.9% when interacting with cellular receptors. Furthermore, they showed 73.8% of activity during the penetration of HMPV particles into cells. The derivative 3-{3-[4-(1-hydroxyethyl)-1H-1,2,3-triazol-1-yl] propyl}-5,5-diphenylimidazolidine-2,4-dione presented a mild anti-HMPV activity, with selectivity index of 2.74. 3-[3-(4-acetyl-1H-1,2,3-triazol-1-yl) propyl]-5,5-diphenylimidazolidine2,4- dione inhibited less than 50% of HMPV replication.

  DOI：

  10.5935/0103-5053.20150234

文献信息

• Hydantoins having RNase modulatory activity
  申请人：Olson W. Matthew

  公开号：US20050203156A1

  公开（公告）日：2005-09-15

  The present invention relates to hydantoin derivatives having RNase H, polymerase and/or HIV reverse transcriptase modulatory, and particularly, inhibitory activity. Included in the invention are the hydantoin derivatives, compositions containing the derivatives, methods of synthesis of the derivatives, screening methods to identify the derivatives, and methods of treatment using the hydantoin derivatives, including the treatment of HIV, AIDS and retrovirus-associated cancer.

  本发明涉及具有RNase H、聚合酶和/或HIV逆转录酶调节活性，特别是抑制活性的咪唑烷酮衍生物。该发明包括咪唑烷酮衍生物、含有这些衍生物的组合物、合成这些衍生物的方法、筛选方法以识别这些衍生物，以及使用这些咪唑烷酮衍生物进行治疗的方法，包括治疗HIV、艾滋病和逆转录病毒相关癌症的方法。
• Reaction of 5,5-diphenyl-2-thiohydantoin with 1,3-dibromopropane
  作者：K. Kieć-Kononowicz、A. Zejc、M. MikoŁajczyk、A. Zatorski、J. Karolak-Wojciechowska、M.W. Wieczorek

  DOI：10.1016/0040-4020(80)80063-9

  日期：1980.1

  The reaction between the potassium salt of 5,5-diphenyl-2-thiohydantoin (1) and 1,3-dibromopropane carried out in DME under anhydrous conditions has been found to give two isomeric diphenylimidazothiazines 2 and 3. When the reaction of 1 with 1,3-dibromopropane was performed in protic solvents (EtOH, HOH, NaOH) 2 and 3-(3-mercaptopropyl) - 5,5 - diphenylthiohydantoin (4) were formed. The latter is

  发现在无水条件下于DME中进行的5,5-二苯基-2-硫代乙内酰脲（1）的钾盐与1,3-二溴丙烷之间的反应产生了两种异构的二苯基咪唑并噻嗪2和3。当1与1，3-二溴丙烷的反应在质子溶剂（EtOH，HOH，NaOH）2中进行时，形成3-（3-巯基丙基）-5，5-二苯硫基乙内酰脲（4）。后者是3在反应条件下发生水解的产物。2,3,4,5-四氢-6,6-二苯基咪唑[2,1-b]-噻嗪-7（6H）-一（2）在空间群P2 1中结晶/ n，其中a = 10.812（3），b = 14.905（7），c = 9.885（4），β= 104.91（2）°。在5元环2是平面的，而6元噻嗪环采用沙发构象。
• Hydantoins Having RNase Modulatory Activity
  申请人：Olson Matthew W.

  公开号：US20100063118A1

  公开（公告）日：2010-03-11

  The present invention relates to hydantoin derivatives having RNase H, polymerase and/or HIV reverse transcriptase modulatory, and particularly, inhibitory activity. Included in the invention are the hydantoin derivatives, compositions containing the derivatives, methods of synthesis of the derivatives, screening methods to identify the derivatives, and methods of treatment using the hydantoin derivatives, including the treatment of HIV, AIDS and retrovirus-associated cancer.

  本发明涉及具有RNase H、聚合酶和/或HIV反转录酶调节活性的咪唑二酮衍生物，特别是具有抑制活性的咪唑二酮衍生物。该发明包括咪唑二酮衍生物、含有该衍生物的组合物、合成该衍生物的方法、筛选识别该衍生物的方法以及使用咪唑二酮衍生物的治疗方法，包括治疗HIV、艾滋病和逆转录病毒相关癌症的方法。
• KIEC-KONONOWICZ K.; ZEJC A.; PAWLOWSKI M., ACTA POL. PHARM., 43,(1986) N 2, 101-106
  作者：KIEC-KONONOWICZ K.、 ZEJC A.、 PAWLOWSKI M.

  DOI：——

  日期：——
• [EN] HYDANTOINS HAVING RNase MODULATORY ACTIVITY<br/>[FR] HYDANTOINES A ACTIVITE MODULATRICE DE LA RNASE
  申请人：WYETH CORP

  公开号：WO2005090316A1

  公开（公告）日：2005-09-29

  The present invention relates to hydantoin derivatives having RNase H, polymerase and/or HIV reverse transcriptase modulatory, and particularly, inhibitory activity. Included in the invention are the hydantoin derivatives, compositions containing the derivatives, methods of synthesis of the derivatives, screening methods to identify the derivatives, and methods of treatment using the hydantoin derivatives, including the treatment of HIV, AIDS and retrovirus­associated cancer.