3-(N,N-diethylamino)carbonyloxymethyl-1-(3,4,5-trimethoxythiobenzoyl)piperazine | 253873-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(N,N-diethylamino)carbonyloxymethyl-1-(3,4,5-trimethoxythiobenzoyl)piperazine
• 英文别名: 4-(3',4',5'-trimethoxythiobenzoyl)-2-(N,N-diethylaminocarbonyloxymethyl)piperazine；[4-(3,4,5-trimethoxybenzenecarbothioyl)piperazin-2-yl]methyl N,N-diethylcarbamate
• CAS: 253873-22-2
• 化学式: C₂₀H₃₁N₃O₅S
• 分子量: 425.549
• InChiKey: XBUIOXKRJOONNC-UHFFFAOYSA-N

物化性质

• 沸点：
  538.9±60.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(N,N-diethylamino)carbonyloxymethyl-1-(3,4,5-trimethoxythiobenzoyl)piperazine 、 3,4,5-三甲氧基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以41%的产率得到3-(N,N-diethylamino)carbonyloxymethyl-4-(3,4,5-trimethoxybenzoyl)-1-(3,4,5-trimethoxythiobenzoyl)piperazine
  参考文献：
  名称：

  Structure–activity relationships in platelet-activating factor. Part 13: Synthesis and biological evaluation of piperazine derivatives with dual anti-PAF and anti-HIV-1 or pure antiretroviral activity

  摘要：

  HIV-1 infection of the brain and PAF neurotoxicity are implicated in AIDS dementia complex. We previously reported that a trisubstituted piperazine derivative is able to diminish both HIV-1 replication in monocyte-derived macrophages and PAF-induced platelet aggregation. We report in this work new compounds obtained by modifying its piperazine substituents. The structure-activity relationship study shows that a better dual activity or even pure antiretroviral compounds can be obtained in this series. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.031
• 作为产物：
  描述：

  3-(N,N-diethylamino)carbonyloxymethyl-1-(3,4,5-trimethoxybenzoyl)piperazine 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 以62.4%的产率得到3-(N,N-diethylamino)carbonyloxymethyl-1-(3,4,5-trimethoxythiobenzoyl)piperazine
  参考文献：
  名称：

  Structure–activity relationships in platelet-activating factor. Part 13: Synthesis and biological evaluation of piperazine derivatives with dual anti-PAF and anti-HIV-1 or pure antiretroviral activity

  摘要：

  HIV-1 infection of the brain and PAF neurotoxicity are implicated in AIDS dementia complex. We previously reported that a trisubstituted piperazine derivative is able to diminish both HIV-1 replication in monocyte-derived macrophages and PAF-induced platelet aggregation. We report in this work new compounds obtained by modifying its piperazine substituents. The structure-activity relationship study shows that a better dual activity or even pure antiretroviral compounds can be obtained in this series. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.031

文献信息

• Piperazine derivatives inhibiting human immunodeficiency virus replication
  申请人：Universite Paris 7 - Denis Diderot

  公开号：US06531476B1

  公开（公告）日：2003-03-11

  The invention concerns the use of a piperazine derivative of formula (I) wherein: A and B=C═O, C═S or CR7R8 with R7=H, methyl, cyano, cyanomethyl, CO2CH3 or (C═O)CH3 and R8=H or phenyl; R1 to R6=H, OH, or C1-C5 alkoxy; X represents: either C═O, O(C═O), O(C═S), O(SO2), NH(C═O), NH(C═S), NH(SO2), S(C═O) or S(C═S), then Y=NR9R10, CR9R10R11 in which R9, R10 and R11=H, C1-C5 alkyl, C2-C5 alkenyl, or C2-C5 alkynyl or Y=nitrogenous heterocycle comprising 5 to 10 atoms; or X represents O, S, O(C═O)O, NH(C═O)O, or S(C═O)O, then Y=CR9R10R11 with R9, R10, R11 as above; or one of its pharmaceutically acceptable salts for preparing a medicine inhibiting HIV. The invention is useful for treating HIV infection.

  这项发明涉及使用式（I）的哌嗪衍生物，其中：A和B=C═O，C═S或CR7R8，其中R7=H，甲基，氰基，氰甲基，CO2CH3或（C═O）CH3，R8=H或苯基；R1至R6=H，OH或C1-C5烷氧基；X代表：C═O，O（C═O），O（C═S），O（SO2），NH（C═O），NH（C═S），NH（SO2），S（C═O）或S（C═S），然后Y=NR9R10，CR9R10R11，其中R9，R10和R11=H，C1-C5烷基，C2-C5烯基或C2-C5炔基或Y=含有5至10个原子的氮杂环；或X代表O，S，O（C═O）O，NH（C═O）O或S（C═O）O，然后Y=CR9R10R11，其中R9，R10，R11如上；或其制备药用可接受的盐之一，用于制备抑制HIV的药物。这项发明对治疗HIV感染很有用。
• [EN] PIPERAZINE DERIVATIVES INHIBITING HUMAN IMMUNODEFICIENCY VIRUS REPLICATION<br/>[FR] DERIVES DE LA PIPERAZINE POUR L'INHIBITION DE LA REPLICATION DU VIRUS DE L'IMMUNODEFICIENCE HUMAINE
  申请人：UNIV PARIS 7 DENIS DIDEROT

  公开号：WO2000001677A1

  公开（公告）日：2000-01-13

  L'invention se rapporte à l'utilisation d'un dérivé de la pipérazine de formule (I), avec: A et B = C=O, C=S ou CR7R8 avec R7 = H, méthyle, cyano, cyanométhyle, CO2CH3 ou (C=O)CH3, et R8 = H ou phényle; R1 à R6 = H, OH ou alkoxy en C1 à C5; X représente: soit C=O, O(C=O), O(C=S), O(SO2), NH(C=O), NH(C=S), NH(SO2), S(C=O) ou S(C=S), alors Y = NR9R10, CR9R10R11 = H, alkyle en C1 à C5, alcényle en C2 à C5 ou alcynyle en C2 à C5 ou hétérocycle azoté comprenant 5 à 10 atomes; soit O, S, O(C=O)O, NH(C=O)O ou S(C=O)O, alors Y = CR9R10R11 avec R9, R10, R11 comme précédemment; ou l'un des ses sels pharmaceutiquement acceptables, pour la préparation d'un médicament pour inhiber la réplication du VIH. Application: traitement de l'infection par le VIH.

  本发明涉及使用式（I）的哌嗪衍生物，其中：A和B = C=O，C=S或CR7R8，其中R7 = H，甲基，氰基，氰甲基，CO2CH3或（C=O）CH3，而R8 = H或苯基; R1到R6 = H，OH或C1到C5的烷氧基; X表示：C=O，O（C=O），O（C=S），O（SO2），NH（C=O），NH（C=S），NH（SO2），S（C=O）或S（C=S）中的任意一种，那么Y = NR9R10，CR9R10R11 = H，C1到C5的烷基，C2到C5的烯基或C2到C5的炔基或含有5到10个原子的氮杂环; 或O，S，O（C=O）O，NH（C=O）O或S（C=O）O中的任意一种，那么Y = CR9R10R11，其中R9，R10，R11如前所述; 或其药学上可接受的盐之一，用于制备抑制HIV复制的药物。应用：治疗HIV感染。
• DERIVES DE LA PIPERAZINE POUR L'INHIBITION DE LA REPLICATION DU VIRUS DE L'IMMUNODEFICIENCE HUMAINE
  申请人：UNIVERSITE PARIS 7 - Denis DIDEROT

  公开号：EP1095029A1

  公开（公告）日：2001-05-02
• US6531476B1
  申请人：——

  公开号：US6531476B1

  公开（公告）日：2003-03-11
• Structure–activity relationships in platelet-activating factor. Part 13: Synthesis and biological evaluation of piperazine derivatives with dual anti-PAF and anti-HIV-1 or pure antiretroviral activity
  作者：Nawal Serradji、Okkacha Bensaid、Marc Martin、Wafa Sallem、Nathalie Dereuddre-Bosquet、Houcine Benmehdi、Catherine Redeuilh、Aazdine Lamouri、Georges Dive、Pascal Clayette、Françoise Heymans

  DOI：10.1016/j.bmc.2006.07.031

  日期：2006.12

  HIV-1 infection of the brain and PAF neurotoxicity are implicated in AIDS dementia complex. We previously reported that a trisubstituted piperazine derivative is able to diminish both HIV-1 replication in monocyte-derived macrophages and PAF-induced platelet aggregation. We report in this work new compounds obtained by modifying its piperazine substituents. The structure-activity relationship study shows that a better dual activity or even pure antiretroviral compounds can be obtained in this series. (c) 2006 Elsevier Ltd. All rights reserved.