2-thioxo-1,2,3,5,6,7-hexahydro-4H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-one | 236093-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-thioxo-1,2,3,5,6,7-hexahydro-4H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-one
• 英文别名: 4-sulfanylidene-3,5-diazatricyclo[9.4.0.02,7]pentadeca-1(15),2(7),11,13-tetraen-6-one
• CAS: 236093-42-8
• 化学式: C₁₃H₁₂N₂OS
• mdl: MFCD21567205
• 分子量: 244.317
• InChiKey: UFTJZHFZJNTYKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-thioxo-1,2,3,5,6,7-hexahydro-4H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-one 在 水 、 氯乙酸 作用下， 反应 12.0h， 以52%的产率得到6,7-dihydro-1H-benzo[6,7]cyclohepta[1,2-d]pyrimidine-2,4(3H,5H)-dione
  参考文献：
  名称：

  Synthesis and HIV-1 inhibitory properties of new tetrahydrobenzoquinazolinedione and tetrahydrobenzocycloheptenuracil derivatives and of their thioxo analogues

  摘要：

  Some new tetrahydrobenzoquinazolinediones 2a-4a, tetrahydrobenzocycloheptenuracils 5a, 6a and their thioxo analogues 2b-6b were synthesized within a project aimed at obtaining new HIV-1 tricyclic inhibitors whose scaffold includes a pyrimidine and a phenyl ring, which are present in various HIV-1 non-nucleoside inhibitors. Among the tetrahydrobenzaquinazolinediones 2a-4a, compounds 3a and 4a, in which the tricyclic system is respectively in an angular or linear arrangement, proved to possess a HIV-1 inhibitory activity which was in the micromolar range, while compound 2a, in which the tricyclic system is in the angular arrangement opposite to that of 3a, was found to be completely inactive. As regards the tetrahydrobenzocycloheptenuracil derivatives (5a and 6a), only 5a showed an inhibitory activity similar to that of 3a and 4a. Furthermore, all thioxo analogues 2b-6b were found to be devoid of any activity. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00024-5
• 作为产物：
  描述：

  methyl 5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate 、 硫脲 反应 2.0h， 以16%的产率得到2-thioxo-1,2,3,5,6,7-hexahydro-4H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-one
  参考文献：
  名称：

  Synthesis and HIV-1 inhibitory properties of new tetrahydrobenzoquinazolinedione and tetrahydrobenzocycloheptenuracil derivatives and of their thioxo analogues

  摘要：

  Some new tetrahydrobenzoquinazolinediones 2a-4a, tetrahydrobenzocycloheptenuracils 5a, 6a and their thioxo analogues 2b-6b were synthesized within a project aimed at obtaining new HIV-1 tricyclic inhibitors whose scaffold includes a pyrimidine and a phenyl ring, which are present in various HIV-1 non-nucleoside inhibitors. Among the tetrahydrobenzaquinazolinediones 2a-4a, compounds 3a and 4a, in which the tricyclic system is respectively in an angular or linear arrangement, proved to possess a HIV-1 inhibitory activity which was in the micromolar range, while compound 2a, in which the tricyclic system is in the angular arrangement opposite to that of 3a, was found to be completely inactive. As regards the tetrahydrobenzocycloheptenuracil derivatives (5a and 6a), only 5a showed an inhibitory activity similar to that of 3a and 4a. Furthermore, all thioxo analogues 2b-6b were found to be devoid of any activity. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00024-5

文献信息

• Macrocyclic Benzofused Pyrimidine Derivatives
  申请人：Altenbach Robert J.

  公开号：US20080188452A1

  公开（公告）日：2008-08-07

  Macrocyclic benzofused pyrimidine compounds, compositions comprising such compounds, methods for making the compounds, and methods of treating and preventing the progression of diseases, conditions and disorders using such compounds and compositions are described herein.

  本文描述了大环苯并嘧啶化合物、包含这种化合物的组合物、制备这种化合物的方法，以及使用这种化合物和组合物治疗和预防疾病、病症和障碍的方法。
• Macrocyclic benzofused pyrimidine derivatives
  申请人：Altenbach Robert J.

  公开号：US08735411B2

  公开（公告）日：2014-05-27

  Macrocyclic benzofused pyrimidine compounds, compositions comprising such compounds, methods for making the compounds, and methods of treating and preventing the progression of diseases, conditions and disorders using such compounds and compositions are described herein.

  本文描述了大环苯并嘧啶化合物，包括含有这种化合物的组合物，制备这些化合物的方法，以及使用这些化合物和组合物治疗和预防疾病、病状和障碍的方法。
• WO2008/60767
  申请人：——

  公开号：——

  公开（公告）日：——
• US8735411B2
  申请人：——

  公开号：US8735411B2

  公开（公告）日：2014-05-27
• Synthesis and HIV-1 inhibitory properties of new tetrahydrobenzoquinazolinedione and tetrahydrobenzocycloheptenuracil derivatives and of their thioxo analogues
  作者：Marco Macchia、Guido Antonelli、Aldo Balsamo、Silvia Barontini、Federico Calvani、Daniela Gentili、Adriano Martinelli、Armando Rossello、Ombretta Turriziani、Ramon Tesoro

  DOI：10.1016/s0014-827x(99)00024-5

  日期：1999.4

  Some new tetrahydrobenzoquinazolinediones 2a-4a, tetrahydrobenzocycloheptenuracils 5a, 6a and their thioxo analogues 2b-6b were synthesized within a project aimed at obtaining new HIV-1 tricyclic inhibitors whose scaffold includes a pyrimidine and a phenyl ring, which are present in various HIV-1 non-nucleoside inhibitors. Among the tetrahydrobenzaquinazolinediones 2a-4a, compounds 3a and 4a, in which the tricyclic system is respectively in an angular or linear arrangement, proved to possess a HIV-1 inhibitory activity which was in the micromolar range, while compound 2a, in which the tricyclic system is in the angular arrangement opposite to that of 3a, was found to be completely inactive. As regards the tetrahydrobenzocycloheptenuracil derivatives (5a and 6a), only 5a showed an inhibitory activity similar to that of 3a and 4a. Furthermore, all thioxo analogues 2b-6b were found to be devoid of any activity. (C) 1999 Elsevier Science S.A. All rights reserved.