2,2-dimethyl-5-(2-(naphthalen-1-yl)acetyl)-1,3-dioxane-4,6-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2-dimethyl-5-(2-(naphthalen-1-yl)acetyl)-1,3-dioxane-4,6-dione
• 英文别名: 2,2-Dimethyl-5-(2-naphthalen-1-ylacetyl)-1,3-dioxane-4,6-dione；2,2-dimethyl-5-(2-naphthalen-1-ylacetyl)-1,3-dioxane-4,6-dione
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: NKKAPZJAKSPPCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-(2-(naphthalen-1-yl)acetyl)-1,3-dioxane-4,6-dione 在 磺酰胺 作用下， 以 neat (no solvent) 为溶剂， 反应 1.5h， 生成 2,6-2H-5-(1-naphthalenylmethyl)-1,2,6-thiadiazine-1,1,3-trione
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Novel 3,5-Disubstituted-1,2,6-Thiadiazine-1,1-Dione Derivatives as HIV-1 NNRTIs

  摘要：

  On the basis of structural features, binding mode, and structure–activity relationship studies of two pyrimidine‐derived non‐nucleoside reverse‐transcriptase inhibitors, DABOs, and diaryl pyrimidines, a novel class of 1,2,6‐thiadiazine‐1,1‐dione derivatives were rationally designed using the strategies of bioisosterism and molecular hybridization, synthesized, and evaluated for their anti‐HIV activity in MT4 cell cultures. Three compounds were found to have moderate activity against HIV‐1 replication with EC50 values ranging from 23 to 32 μm. To further confirm the binding target, compound IIg was selected to conduct an HIV‐1 reverse‐transcriptase inhibitory assay. In addition, preliminary structure–activity relationship analysis among the newly synthesized compounds was discussed, and the binding mode of the active compound IIg was rationalized by molecular docking and physicochemical studies.

  DOI：

  10.1111/cbdd.12160
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 1-萘乙酸 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 5.33h， 生成 2,2-dimethyl-5-(2-(naphthalen-1-yl)acetyl)-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  新型4-氨基哌啶基连接的3,5-二取代-1,2,6-噻二嗪-1,1-二酮衍生物作为HIV-1 NNRTI的设计，合成和生物学评估

  摘要：

  基于DABO和DAPY型HIV-1 NNRTIs中特权片段的杂交，设计了一系列新的由4-氨基哌啶基连接的3,5-二取代-1,2,6-噻二嗪-1,1-二酮衍生物。 ，合成并评估了它们在MT-4细胞中的体外抗HIV活性。大多数目标化合物对WT HIV-1的抑制活性较弱。为了确定目标化合物的作用方式，选择了代表性的化合物Ba8和Bb8进行HIV-1 RT抑制测定。在该测定中，BA8和BB8显示良好的活性与IC 50倍的3.15和1.52的值 μ米， 分别。此外，还讨论了新合成化合物的初步结构-活性关系（SAR）分析和分子对接研究。

  DOI：

  10.1111/cbdd.12468

文献信息

• Design, Synthesis, and Biological Evaluation of Novel 3,5-Disubstituted-1,2,6-Thiadiazine-1,1-Dione Derivatives as HIV-1 NNRTIs
  作者：Ye Tian、Diwakar Rai、Peng Zhan、Christophe Pannecouque、Jan Balzarini、Erik De Clercq、Huiqing Liu、Xinyong Liu

  DOI：10.1111/cbdd.12160

  日期：2013.10

  On the basis of structural features, binding mode, and structure–activity relationship studies of two pyrimidine‐derived non‐nucleoside reverse‐transcriptase inhibitors, DABOs, and diaryl pyrimidines, a novel class of 1,2,6‐thiadiazine‐1,1‐dione derivatives were rationally designed using the strategies of bioisosterism and molecular hybridization, synthesized, and evaluated for their anti‐HIV activity in MT4 cell cultures. Three compounds were found to have moderate activity against HIV‐1 replication with EC50 values ranging from 23 to 32 μm. To further confirm the binding target, compound IIg was selected to conduct an HIV‐1 reverse‐transcriptase inhibitory assay. In addition, preliminary structure–activity relationship analysis among the newly synthesized compounds was discussed, and the binding mode of the active compound IIg was rationalized by molecular docking and physicochemical studies.
• Design, Synthesis, and Biological Evaluation of Novel 4-Aminopiperidinyl-linked 3,5-Disubstituted-1,2,6-thiadiazine-1,1-dione Derivatives as HIV-1 NNRTIs
  作者：Tao Liu、Boshi Huang、Ye Tian、Xin Liang、Hong Liu、Huiqing Liu、Peng Zhan、Erik De Clercq、Christophe Pannecouque、Xinyong Liu

  DOI：10.1111/cbdd.12468

  日期：2015.7

  4‐aminopiperidinyl‐linked 3,5‐disubstituted‐1,2,6‐thiadiazine‐1,1‐dione derivatives were designed, synthesized, and evaluated for their in vitro anti‐HIV activities in MT‐4 cells. Most of the target compounds showed weak inhibitory activity against WT HIV‐1. In order to confirm the mode of action of the target compounds, representative compounds Ba8 and Bb8 were selected to perform the HIV‐1 RT inhibitory assay. In

  基于DABO和DAPY型HIV-1 NNRTIs中特权片段的杂交，设计了一系列新的由4-氨基哌啶基连接的3,5-二取代-1,2,6-噻二嗪-1,1-二酮衍生物。 ，合成并评估了它们在MT-4细胞中的体外抗HIV活性。大多数目标化合物对WT HIV-1的抑制活性较弱。为了确定目标化合物的作用方式，选择了代表性的化合物Ba8和Bb8进行HIV-1 RT抑制测定。在该测定中，BA8和BB8显示良好的活性与IC 50倍的3.15和1.52的值 μ米， 分别。此外，还讨论了新合成化合物的初步结构-活性关系（SAR）分析和分子对接研究。