tert-butyl N-[(1S)-1-(5-methyl-4-oxothieno[2,3-d][1,3]oxazin-2-yl)ethyl]carbamate | 179762-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: tert-butyl N-[(1S)-1-(5-methyl-4-oxothieno[2,3-d][1,3]oxazin-2-yl)ethyl]carbamate
• CAS: 179762-34-6
• 化学式: C₁₄H₁₈N₂O₄S
• 分子量: 310.374
• InChiKey: BCKCGDYAAUOIHB-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 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：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S)-1-(5-methyl-4-oxothieno[2,3-d][1,3]oxazin-2-yl)ethyl]carbamate 在 sodium cyanoborohydride 、 N,N-二异丙基乙胺 作用下， 生成 5-methyl-2-[(1S)-1-[[(E)-3-phenylprop-2-enyl]amino]ethyl]thieno[2,3-d][1,3]oxazin-4-one
  参考文献：
  名称：

  Inhibition of herpes proteases and antiviral activity of 2-substituted thieno[2,3-d]oxazinones

  摘要：

  Cinnamyl derivatives of thieno[2,3-d]oxazinones are mechanism-based inhibitors of the HSV-2, VZV and CMV herpes proteases which demonstrate nanomolar potency. Compounds 5 and 28 inhibit protease processing in HSV-2 infected cells with a selectivity index of at least 30. (C) 1999 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0960-894x(99)00004-9
• 作为产物：
  描述：

  2-氨基-4-甲基-噻吩-3-羧酸乙酯 在 N-甲基吗啉 、 三苯基膦 、 氯甲酸异丁酯 作用下， 以 四氯化碳 为溶剂， 生成 tert-butyl N-[(1S)-1-(5-methyl-4-oxothieno[2,3-d][1,3]oxazin-2-yl)ethyl]carbamate
  参考文献：
  名称：

  Inhibition of herpes proteases and antiviral activity of 2-substituted thieno[2,3-d]oxazinones

  摘要：

  Cinnamyl derivatives of thieno[2,3-d]oxazinones are mechanism-based inhibitors of the HSV-2, VZV and CMV herpes proteases which demonstrate nanomolar potency. Compounds 5 and 28 inhibit protease processing in HSV-2 infected cells with a selectivity index of at least 30. (C) 1999 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0960-894x(99)00004-9

文献信息

• Inhibition of human cytomegalovirus protease by enedione derivatives of thieno[2,3-d]oxazinones through a novel dual acylation/alkylation mechanism
  作者：Ivan L. Pinto、Richard L. Jarvest、Brian Clarke、Christine E. Dabrowski、Ashley Fenwick、Michele M Gorczyca、L.John Jennings、Patrick Lavery、Edmund J Sternberg、David G. Tew、Andrew West

  DOI：10.1016/s0960-894x(99)00005-0

  日期：1999.2

  Enedione derivatives of thieno[2,3-d]oxazinones are nanomolar inhibitors of CMV protease which act through a novel dual acylation of the catalytic serine and alkylation of the protease cysteine 161 via a Michael addition to the enedione moiety of the inhibitor. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Inhibition of herpes proteases and antiviral activity of 2-substituted thieno[2,3-d]oxazinones
  作者：Richard L. Jarvest、Ivan L. Pinto、Stephen M. Ashman、Christine E. Dabrowski、Annabellee V. Fernandez、L.John Jennings、Patrick Lavery、David G. Tew

  DOI：10.1016/s0960-894x(99)00004-9

  日期：1999.2

  Cinnamyl derivatives of thieno[2,3-d]oxazinones are mechanism-based inhibitors of the HSV-2, VZV and CMV herpes proteases which demonstrate nanomolar potency. Compounds 5 and 28 inhibit protease processing in HSV-2 infected cells with a selectivity index of at least 30. (C) 1999 Elsevier Science Ltd. Ail rights reserved.