4-(4-{6-[(4-methoxybenzyl)imino]-2,3,4,6-tetrahydrobenzo[e]pyrimido[1,2-c][1,3]thiazin-9-yl}benzoyl)benzyl {13-oxo-17-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-3,6,9-trioxa-12-azaheptadecyl}carbamate | 1428649-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 4-(4-{6-[(4-methoxybenzyl)imino]-2,3,4,6-tetrahydrobenzo[e]pyrimido[1,2-c][1,3]thiazin-9-yl}benzoyl)benzyl {13-oxo-17-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-3,6,9-trioxa-12-azaheptadecyl}carbamate
• CAS: 1428649-06-2
• 化学式: C₅₂H₆₁N₇O₉S₂
• 分子量: 992.23
• InChiKey: OUGHZCIPVUXYDT-NVVQJRFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  70.0
• 可旋转键数：
  25.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  190.51
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  4-(4-{6-[(4-methoxybenzyl)imino]-2,3,4,6-tetrahydrobenzo[e]pyrimido[1,2-c][1,3]thiazin-9-yl}benzoyl)benzyl {13-oxo-17-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-3,6,9-trioxa-12-azaheptadecyl}carbamate 在 三氟乙酸 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以35%的产率得到[4-[4-(6-imino-3,4-dihydro-2H-pyrimido[1,2-c][1,3]benzothiazin-9-yl)benzoyl]phenyl]methyl N-[2-[2-[2-[2-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]ethoxy]ethoxy]ethoxy]ethyl]carbamate
  参考文献：
  名称：

  Design and synthesis of biotin- or alkyne-conjugated photoaffinity probes for studying the target molecules of PD 404182

  摘要：

  To investigate the mechanism of action of the potent antiviral compound PD 404182, three novel photo-affinity probes equipped with a biotin or alkyne indicator were designed and synthesized based on previous structure-activity relationship studies. These probes retained the potent anti-HIV activity of the original pyrimidobenzothiazine derivatives. In photoaffinity labeling studies using HIV-1-infected H9 cells (H9IIIB), eight potential proteins were observed to bind PD 404182. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.016
• 作为产物：
  描述：

  4-[(tert-butyldiphenylsilyloxy)methyl]-N-methoxy-N-methylbenzamide 在 吡啶 、 四(三苯基膦)钯 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 四丁基氟化铵 、 叔丁基锂 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 正戊烷 为溶剂， 反应 4.43h， 生成 4-(4-{6-[(4-methoxybenzyl)imino]-2,3,4,6-tetrahydrobenzo[e]pyrimido[1,2-c][1,3]thiazin-9-yl}benzoyl)benzyl {13-oxo-17-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-3,6,9-trioxa-12-azaheptadecyl}carbamate
  参考文献：
  名称：

  Design and synthesis of biotin- or alkyne-conjugated photoaffinity probes for studying the target molecules of PD 404182

  摘要：

  To investigate the mechanism of action of the potent antiviral compound PD 404182, three novel photo-affinity probes equipped with a biotin or alkyne indicator were designed and synthesized based on previous structure-activity relationship studies. These probes retained the potent anti-HIV activity of the original pyrimidobenzothiazine derivatives. In photoaffinity labeling studies using HIV-1-infected H9 cells (H9IIIB), eight potential proteins were observed to bind PD 404182. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.016