3-Benzyl-1-(2-hydroxy-ethoxymethyl)-2,2-dioxo-2,3-dihydro-1H-2λ⁶-benzo[1,2,6]thiadiazin-4-one | 221632-96-8

• 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: 3-Benzyl-1-(2-hydroxy-ethoxymethyl)-2,2-dioxo-2,3-dihydro-1H-2λ⁶-benzo[1,2,6]thiadiazin-4-one
• 英文别名: 1-[(2-Hydroxyethoxy)methyl]-3-benzyl-2,1,3-benzothiadiazin-4-one 2,2-dioxide；3-benzyl-1-(2-hydroxyethoxymethyl)-2,2-dioxo-2λ6,1,3-benzothiadiazin-4-one
• CAS: 221632-96-8
• 化学式: C₁₇H₁₈N₂O₅S
• 分子量: 362.406
• InChiKey: PJZSDJYSKZLYIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  95.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 3-Benzyl-1-(2-hydroxy-ethoxymethyl)-2,2-dioxo-2,3-dihydro-1H-2λ⁶-benzo[1,2,6]thiadiazin-4-one 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以75%的产率得到Benzoic acid 2-(3-benzyl-2,2,4-trioxo-3,4-dihydro-2H-2λ⁶-benzo[1,2,6]thiadiazin-1-ylmethoxy)-ethyl ester
  参考文献：
  名称：

  Novel Potential Agents for Human Cytomegalovirus Infection:  Synthesis and Antiviral Activity Evaluation of Benzothiadiazine Dioxide Acyclonucleosides

  摘要：

  The first acyclonucleosides based on the benzothiadiazine dioxide system were synthesized following the silylation procedure. Several acyclic moieties, including acetoxyethoxymethyl, benzyloxymethyl, and propargyloxymethyl groups, were introduced. Two synthetic strategies were designed to selectively obtain the N-1 or N-3 derivatives. Lipase-mediated deacylation was used for the deprotection of the acyclonucleosides. Some of the benzothiadiazine dioxide acyclonucleosides, in particular 16, proved active against human cytomegalovirus (CMV) at concentrations slightly higher than that found for ganciclovir [50% inhibitory concentration (IC50) = 3.5-3.7 mu g/mL, cytotoxicity (CC50) greater than or equal to 40 mu g/mL, MCC 20 mu g/mL]. Additionally, compound 16 inhibited the replication of human immunodeficiency virus type 1 (HTV-1) and HTV-2 in CEM cells at concentrations that were 5-fold lower than its cytotoxic concentration.

  DOI：

  10.1021/jm980327z
• 作为产物：
  描述：

  在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 2.0h， 生成 3-Benzyl-1-(2-hydroxy-ethoxymethyl)-2,2-dioxo-2,3-dihydro-1H-2λ⁶-benzo[1,2,6]thiadiazin-4-one
  参考文献：
  名称：

  Benzothiadiazine dioxide acyclonucleosides as lead compounds for the development of new agents against human cytomegalovirus and varicella-zoster virus infections

  摘要：

  The first acyclonucleosides derived from 2,1,3-benzothiadiazine dioxides were synthesized. From their antiviral activity evaluation results these compounds might be considered as new leads in the search for inhibitors of human cytomegalovirus (CMV) and varicella-zoster virus (VZV) infections. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00149-2

文献信息

• Benzothiadiazine dioxide acyclonucleosides as lead compounds for the development of new agents against human cytomegalovirus and varicella-zoster virus infections
  作者：Ana Martinez、Ana I. Esteban、Erik De Clercq

  DOI：10.1016/s0960-894x(97)00149-2

  日期：1997.4

  The first acyclonucleosides derived from 2,1,3-benzothiadiazine dioxides were synthesized. From their antiviral activity evaluation results these compounds might be considered as new leads in the search for inhibitors of human cytomegalovirus (CMV) and varicella-zoster virus (VZV) infections. (C) 1997 Elsevier Science Ltd.
• Novel Potential Agents for Human Cytomegalovirus Infection:  Synthesis and Antiviral Activity Evaluation of Benzothiadiazine Dioxide Acyclonucleosides
  作者：Ana Martinez、Ana I. Esteban、Ana Castro、Carmen Gil、Santiago Conde、Graciela Andrei、Robert Snoeck、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm980327z

  日期：1999.4.1

  The first acyclonucleosides based on the benzothiadiazine dioxide system were synthesized following the silylation procedure. Several acyclic moieties, including acetoxyethoxymethyl, benzyloxymethyl, and propargyloxymethyl groups, were introduced. Two synthetic strategies were designed to selectively obtain the N-1 or N-3 derivatives. Lipase-mediated deacylation was used for the deprotection of the acyclonucleosides. Some of the benzothiadiazine dioxide acyclonucleosides, in particular 16, proved active against human cytomegalovirus (CMV) at concentrations slightly higher than that found for ganciclovir [50% inhibitory concentration (IC50) = 3.5-3.7 mu g/mL, cytotoxicity (CC50) greater than or equal to 40 mu g/mL, MCC 20 mu g/mL]. Additionally, compound 16 inhibited the replication of human immunodeficiency virus type 1 (HTV-1) and HTV-2 in CEM cells at concentrations that were 5-fold lower than its cytotoxic concentration.