3-(1,1-dioxo-7-methyl-1,4-dihydrobenzo[1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester | 477932-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: 3-(1,1-dioxo-7-methyl-1,4-dihydrobenzo[1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester
• CAS: 477932-76-6
• 化学式: C₁₂H₁₄N₂O₄S
• 分子量: 282.32
• InChiKey: BZDBXQVMENVSLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(1,1-dioxo-7-methyl-1,4-dihydrobenzo[1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester 、 1-苄基-1H-吡啶并[2,3-d][1,3]噁嗪-2,4-二酮 在 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 1-benzyl-4-hydroxy-3-(7-methyl-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-1,8-naphthyridin-2(1H)-one
  参考文献：
  名称：

  Inhibitors of HCV NS5B polymerase: Synthesis and structure–activity relationships of N-1-benzyl and N-1-[3-methylbutyl]-4-hydroxy-1,8-naphthyridon-3-yl benzothiadiazine analogs containing substituents on the aromatic ring

  摘要：

  A series of non-nucleoside HCV NS5B polymerase inhibitors based on the N-1-benzyl or N-1-[3-methylbutyl]-4-hydroxy-1,8-naphthyridon-3-yl benzothiadiazine core substituted in the D-ring aromatic moiety have been prepared and evaluated. Aromatic substituents extending from position 7 of the D-ring exhibited excellent potency against both genotypes 1a and 1b. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.022
• 作为产物：
  描述：

  N-(p-toluenyl)-N'-(chlorosulfonyl)-urea 在 三氯化铝 、 硫酸 、 sodium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 3-(1,1-dioxo-7-methyl-1,4-dihydrobenzo[1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Inhibitors of HCV NS5B polymerase: Synthesis and structure–activity relationships of N-1-benzyl and N-1-[3-methylbutyl]-4-hydroxy-1,8-naphthyridon-3-yl benzothiadiazine analogs containing substituents on the aromatic ring

  摘要：

  A series of non-nucleoside HCV NS5B polymerase inhibitors based on the N-1-benzyl or N-1-[3-methylbutyl]-4-hydroxy-1,8-naphthyridon-3-yl benzothiadiazine core substituted in the D-ring aromatic moiety have been prepared and evaluated. Aromatic substituents extending from position 7 of the D-ring exhibited excellent potency against both genotypes 1a and 1b. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.022

文献信息

• Substituted benzothiadizine inhibitors of Hepatitis C virus polymerase
  作者：Antony N. Shaw、Rosanna Tedesco、Ramesh Bambal、Deping Chai、Nestor O. Concha、Michael G. Darcy、Dashyant Dhanak、Kevin J. Duffy、Duke M. Fitch、Adam Gates、Victor K. Johnston、Richard M. Keenan、Juili Lin-Goerke、Nannan Liu、Robert T. Sarisky、Kenneth J. Wiggall、Michael N. Zimmerman

  DOI：10.1016/j.bmcl.2009.05.091

  日期：2009.8

  The synthesis and optimisation of HCV NS5B polymerase inhibitors with improved potency versus the existing compound 1 is described. Substitution in the benzothiadiazine portion of the molecule, furnishing improvement in potency in the high protein Replicon assay, is highlighted, culminating in the discovery of 12h, a highly potent oxyacetamide derivative. (C) 2009 Elsevier Ltd. All rights reserved.