N-[2-(1-piperazinylethyl)]-N'-[2-(5-bromopyridyl)]thiourea | 214753-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N-[2-(1-piperazinylethyl)]-N'-[2-(5-bromopyridyl)]thiourea
• 英文别名: 1-(5-Bromo-2-pyridyl)-3-(2-piperazin-1-ylethyl)thiourea；1-(5-bromopyridin-2-yl)-3-(2-piperazin-1-ylethyl)thiourea
• CAS: 214753-81-8
• 化学式: C₁₂H₁₈BrN₅S
• 分子量: 344.278
• InChiKey: DUFCTLAQMYFYBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(1-piperazinylethyl)]-N'-[2-(5-bromopyridyl)]thiourea 在 甲醇 、 氰化钠 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Certain Heterodimers Expected as HIV-1 Reverse Transcriptase Inhibitors

  摘要：

  Expected for the ability to inhibit HIV replication, we report the synthesis of two heterodimers of the general formula: [2NRTI]-C5-GLY-SUCCINYL-Npiperazinyl-[NNRTI] (18, 19) containing both a Nucleoside Reverse Transcriptase Inhibitor (10, 11) and a Non-Nucleoside Reverse Transcriptase Inhibitor (8) [Trovirdine Analogue belonging of the phenethyl thiazolyl thiourea class] connected through the "succinyl-glycine" spontaneously cleavable linker.

  DOI：

  10.1081/ncn-120022675
• 作为产物：
  描述：

  N-氨乙基哌嗪 、 imidazole-1-carbothionic acid (5-bromopyridin-2-yl)amide 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 N-[2-(1-piperazinylethyl)]-N'-[2-(5-bromopyridyl)]thiourea
  参考文献：
  名称：

  Structure-based design of N-[2-(1-piperidinylethyl)]-N′-[2-(5-bromopyridyl)]-thiourea and N-[2-(1-piperazinylethyl)]-N′-[2-(5-bromopyridyl)]-thiourea as potent non-nucleoside inhibitors of HIV-1 reverse transcriptase

  摘要：

  A novel computer model of the HIV reverse transcriptase (RT) non-nucleoside inhibitor (NNI) binding pocket, which was generated using high resolution crystal structure information from 9 individual RT/NNI complexes, revealed previously unrecognized ligand derivatization sites for phenethylthiazolylthiourea (PETT) derivatives. Spatial gaps surrounding the pyridyl ring of the active PETT derivative trovirdine were discovered during modeling procedures. Docking studies using the computer-generated model of the binding pocket (composite binding pocket) suggested that the replacement of the planar pyridyl ring of trovirdine with a nonplanar piperidinyl or piperazinyl ring, which occupy larger volumes, would better fill the spacious Wing 2 region of the butterfly-shaped NNI binding pocket. The anti-HIV activity of the synthesized heterocyclic compounds N-[2-(1-piperidinylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea and N-[2-(1-piperazinylethyl)]-N'-[2(5-bromopyridyl)]-thiourea was examined in HTLVIIIB-infected peripheral blood mononuclear cells. Both compounds were more potent than trovirdine and abrogated HIV replication at nanomolar concentrations without any evidence of cytotoxicity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00384-9

文献信息

• SYNTHESIS AND ANTI-HIV ACTIVITY OF [D4U]-[TROVIRDINE ANALOGUE] AND [D4T]-[TROVIRDINE ANALOGUE] HETERODIMERS AS INHIBITORS OF HIV-1 REVERSE TRANSCRIPTASE
  作者：D. Gavriliu、C. Fossey、A. Ciurea、Z. Delbederi、E. Sugeac、D. Ladurée、S. Schmidt、G. Laumond、A. M. Aubertin

  DOI：10.1081/ncn-120015066

  日期：2002.11

  A series of eleven heterodimers containing both a nucleoside analogue (d4U, d4T) and a non-nucleoside type inhibitor (Trovirdine analogue) were synthesized and evaluated for their ability to inhibit HIV replication. Unfortunately, the (N-3)d4U-Trovirdine conjugates (9a-e) and (N-3)d4T-Trovirdine conjugates (10a-f) were found to be inactive suggesting that the two individual inhibitor compounds do not

  合成了一系列同时含有核苷类似物（d4U，d4T）和非核苷类抑制剂（特洛维定类似物）的十一种异二聚体，并评估了它们抑制HIV复制的能力。不幸的是，发现（N-3）d4U-Trovirdine缀合物（9a-e）和（N-3）d4T-Trovirdine缀合物（10a-f）没有活性，这表明两种单独的抑制剂化合物在它们各自的抑制剂中不能同时结合各个站点。