ethyl 2-(2-chlorophenyl)-2-((dimethylamino)methyleneamino)acetate | 1352229-33-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(2-chlorophenyl)-2-((dimethylamino)methyleneamino)acetate
• 英文别名: Ethyl 2-(2-chlorophenyl)-2-(dimethylaminomethylideneamino)acetate；ethyl 2-(2-chlorophenyl)-2-(dimethylaminomethylideneamino)acetate
• CAS: 1352229-33-4
• 化学式: C₁₃H₁₇ClN₂O₂
• 分子量: 268.743
• InChiKey: OTUZAADMYUUYSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-chlorophenyl)-2-((dimethylamino)methyleneamino)acetate 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 5-(2-chlorophenyl)-4,5-dihydro-1,2,4-triazin-6(1H)-one
  参考文献：
  名称：

  Structure-based bioisosterism design, synthesis and biological evaluation of novel 1,2,4-triazin-6-ylthioacetamides as potent HIV-1 NNRTIs

  摘要：

  The development of new HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) offers the possibility of generating novel chemical entities of increased potency. Previous investigations in our laboratory resulted in the discovery of several novel series of arylazolylthioacetanilides as potent NNRTIs. In this study, based on the structure-based bioisosterism strategy, novel 1,2,4-triazin-6-yl thioacetamide derivatives were designed, synthesized and evaluated for their anti-HIV activity in MT-4 cells. Among them, the most promising compound was 8b15 with double-digit nanomolar activity against wild-type HIV-1 (EC50 = 0.018 +/- 0.007 mu M) and moderate activity against the double mutant strain RES056 (EC50 = 3.3 +/- 0.1 mu M), which indicated that 1,2,4-triazin-6-yl thioacetamide can be used as a novel scaffold to develop a new class of potent NNRTIs active against both wild-type and drug-resistant HIV-1 strains. In addition, preliminary structure-activity relationship (SAR) and molecular modeling results are also briefly discussed, which provide some useful information for the further design of novel NNRTIs. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.062
• 作为产物：
  描述：

  o-chlorophenylglycine 、 N,N-二甲基甲酰胺二甲基缩醛 反应 3.0h， 生成 ethyl 2-(2-chlorophenyl)-2-((dimethylamino)methyleneamino)acetate
  参考文献：
  名称：

  Structure-based bioisosterism design, synthesis and biological evaluation of novel 1,2,4-triazin-6-ylthioacetamides as potent HIV-1 NNRTIs

  摘要：

  The development of new HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) offers the possibility of generating novel chemical entities of increased potency. Previous investigations in our laboratory resulted in the discovery of several novel series of arylazolylthioacetanilides as potent NNRTIs. In this study, based on the structure-based bioisosterism strategy, novel 1,2,4-triazin-6-yl thioacetamide derivatives were designed, synthesized and evaluated for their anti-HIV activity in MT-4 cells. Among them, the most promising compound was 8b15 with double-digit nanomolar activity against wild-type HIV-1 (EC50 = 0.018 +/- 0.007 mu M) and moderate activity against the double mutant strain RES056 (EC50 = 3.3 +/- 0.1 mu M), which indicated that 1,2,4-triazin-6-yl thioacetamide can be used as a novel scaffold to develop a new class of potent NNRTIs active against both wild-type and drug-resistant HIV-1 strains. In addition, preliminary structure-activity relationship (SAR) and molecular modeling results are also briefly discussed, which provide some useful information for the further design of novel NNRTIs. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.062

文献信息

• Structure-based bioisosterism design, synthesis and biological evaluation of novel 1,2,4-triazin-6-ylthioacetamides as potent HIV-1 NNRTIs
  作者：Peng Zhan、Xiao Li、Zhenyu Li、Xuwang Chen、Ye Tian、Wenmin Chen、Xinyong Liu、Christophe Pannecouque、Erik De Clercq

  DOI：10.1016/j.bmcl.2012.09.062

  日期：2012.12

  The development of new HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) offers the possibility of generating novel chemical entities of increased potency. Previous investigations in our laboratory resulted in the discovery of several novel series of arylazolylthioacetanilides as potent NNRTIs. In this study, based on the structure-based bioisosterism strategy, novel 1,2,4-triazin-6-yl thioacetamide derivatives were designed, synthesized and evaluated for their anti-HIV activity in MT-4 cells. Among them, the most promising compound was 8b15 with double-digit nanomolar activity against wild-type HIV-1 (EC50 = 0.018 +/- 0.007 mu M) and moderate activity against the double mutant strain RES056 (EC50 = 3.3 +/- 0.1 mu M), which indicated that 1,2,4-triazin-6-yl thioacetamide can be used as a novel scaffold to develop a new class of potent NNRTIs active against both wild-type and drug-resistant HIV-1 strains. In addition, preliminary structure-activity relationship (SAR) and molecular modeling results are also briefly discussed, which provide some useful information for the further design of novel NNRTIs. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.