4-(4-benzhydrylpiperazino)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-benzhydrylpiperazino)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine
• 英文别名: 4-[4-(Diphenylmethyl)piperazinyl]-1-phenylpyrazolo[5,4-d]pyrimidine；4-(4-benzhydrylpiperazin-1-yl)-1-phenylpyrazolo[3,4-d]pyrimidine
• 化学式: C₂₈H₂₆N₆
• mdl: MFCD00319774
• 分子量: 446.555
• InChiKey: NQBUVYWRXKJRRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二苯氯甲烷 在 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 4.0h， 生成 4-(4-benzhydrylpiperazino)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of pyrazolo[3,4-d]pyrimidines: a novel class of potent enterovirus inhibitors

  摘要：

  A series of pyrazolo[3,4-d]pyrimidines were synthesized. and their antiviral activity was evaluated in a plaque reduction assay. It is very interesting that this class of compounds provide remarkable evidence that they are very specific for human enteroviruses, in particular, coxsackieviruses. Some derivatives proved to be highly effective in inhibiting enterovirus replication at nanomolar concentrations. SAR studies revealed that the phenyl group at the N-I position and the hydrophobic diarylmethyl group at the piperazine largely influenced the in vitro antienteroviral activity of this new class of potent antiviral agents. It was found that the pyrazolo[3,4-d]pyrimidines with a thiophene substituent, such as compounds 20 24, in general exhibited high activity against coxsackievirus B3 (IC50 = 0.063-0.089 muM) and moderate activity against enterovirus 71 (IC50 = 0.32-0.65 muM) with no apparent cytotoxic effect toward RD (rhabdomyosarcoma) cell lines (CC50>25 muM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.092

文献信息

• ANTI-ENTEROVIRUS COMPOUNDS
  申请人：——

  公开号：US20040204400A1

  公开（公告）日：2004-10-14

  This invention features, among others, a pyrazolopyrimidine compound of formula (A): 1 A is (CH 2 ) q —CHR a R b ; each of R 1 and R 2 , independently, is hydrogen, halogen, cyano, nitro, or alkyl; or R 1 and R 2 taken together is (CH 2 ) r ; each of R 3 and R 4 , independently, is hydrogen, halogen, cyano, nitro, or alkyl; each of R 5 , R a , and R b , independently, is aryl, aralkyl, or heteroaryl, optionally substituted with halogen, cyano, nitro, alkyl, aryl, aralkyl, heteroaryl, OR, O(O)CR, C(O)R, C(O)OR, C(O)NRR′, SR, S(O)R, S(O)OR, NRR′, NR(O)CR′, NRC(O)OR′, or NRC(O)NR′R″; each of m, n, o, p, and r, independently, is 0 or 1, and q is 0, 1, or 2; in which each of R, R′, and R″, independently, is hydrogen or alkyl, provided that the sum of m, n, o, and p is 1, 2, 3, or 4.

  该发明涉及一种式（A）的吡唑吡咯啉化合物：1A为（CH2）q—CHRaRb；R1和R2中的每一个独立地为氢、卤素、氰基、硝基或烷基；或者R1和R2一起为（CH2）r；R3和R4中的每一个独立地为氢、卤素、氰基、硝基或烷基；R5、Ra和Rb中的每一个独立地为芳基、芳基烷基或杂环芳基，可选择地用卤素、氰基、硝基、烷基、芳基、芳基烷基、杂环芳基、OR、O（O）CR、C（O）R、C（O）OR、C（O）NRR′、SR、S（O）R、S（O）OR、NRR′、NR（O）CR′、NRC（O）OR′或NRC（O）NR′R″取代；m、n、o、p和r中的每一个独立地为0或1，q为0、1或2；其中R、R′和R″中的每一个独立地为氢或烷基，前提是m、n、o和p的总和为1、2、3或4。
• US6815444B2
  申请人：——

  公开号：US6815444B2

  公开（公告）日：2004-11-09
• Design, synthesis, and structure–activity relationships of pyrazolo[3,4-d]pyrimidines: a novel class of potent enterovirus inhibitors
  作者：Jyh-Haur Chern、Kak-Shan Shia、Tsu-An Hsu、Chia-Liang Tai、Chung-Chi Lee、Yen-Chun Lee、Chih-Shiang Chang、Sung-Nien Tseng、Shin-Ru Shih

  DOI：10.1016/j.bmcl.2004.02.092

  日期：2004.5

  A series of pyrazolo[3,4-d]pyrimidines were synthesized. and their antiviral activity was evaluated in a plaque reduction assay. It is very interesting that this class of compounds provide remarkable evidence that they are very specific for human enteroviruses, in particular, coxsackieviruses. Some derivatives proved to be highly effective in inhibiting enterovirus replication at nanomolar concentrations. SAR studies revealed that the phenyl group at the N-I position and the hydrophobic diarylmethyl group at the piperazine largely influenced the in vitro antienteroviral activity of this new class of potent antiviral agents. It was found that the pyrazolo[3,4-d]pyrimidines with a thiophene substituent, such as compounds 20 24, in general exhibited high activity against coxsackievirus B3 (IC50 = 0.063-0.089 muM) and moderate activity against enterovirus 71 (IC50 = 0.32-0.65 muM) with no apparent cytotoxic effect toward RD (rhabdomyosarcoma) cell lines (CC50>25 muM). (C) 2004 Elsevier Ltd. All rights reserved.