(N-tert-butoxycarbonyl)suberedamine A | 1378296-81-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (N-tert-butoxycarbonyl)suberedamine A
• 英文别名: tert-butyl N-[(2S)-3-(3-bromo-4-methoxyphenyl)-1-[2-[3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl]ethylamino]-1-oxopropan-2-yl]carbamate
• CAS: 1378296-81-1
• 化学式: C₂₈H₃₈Br₃N₃O₅
• 分子量: 736.339
• InChiKey: JYVNZBBWPAHETI-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (N-tert-butoxycarbonyl)suberedamine A 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以94%的产率得到suberedamine A
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Purpurealidin E-Derived Marine Sponge Metabolites: Aplysamine-2, Aplyzanzine A, and Suberedamines A and B

  摘要：

  Five purpurealidin-derived marine secondary sponge metabolies have been synthesized through the carbodiimide coupling of an appropriate bromotyrosine unit. The structure elucidations have been confirmed through direct comparison with spectroscopic data of isolated natural products. Aplyzanzine A has been shown to be the most active product against a broad bacterial and fungal screen, demonstrating MIC values 2 to 4 times lower than the other metabolites in this study. Compounds 2, 3, 4a, and 5-7 exhibit a modest inhibition against slow growing mycobacteria (MIC 25-50 mu g/mL), including Mycobacterium tuberculosis. iso-Anomoian A and suberedamine B showed antitumor activity in the NCI-DTP60 cell line screen at single-digit micromolar concentrations, with iso-anomoian A inhibiting 53 cell lines. These molecules present novel scaffolds for further optimization.

  DOI：

  10.1021/np300102z
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-3-bromo-O-methyl-(S)-tyrosine methyl ester 在 水 、 sodium hydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (N-tert-butoxycarbonyl)suberedamine A
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Purpurealidin E-Derived Marine Sponge Metabolites: Aplysamine-2, Aplyzanzine A, and Suberedamines A and B

  摘要：

  Five purpurealidin-derived marine secondary sponge metabolies have been synthesized through the carbodiimide coupling of an appropriate bromotyrosine unit. The structure elucidations have been confirmed through direct comparison with spectroscopic data of isolated natural products. Aplyzanzine A has been shown to be the most active product against a broad bacterial and fungal screen, demonstrating MIC values 2 to 4 times lower than the other metabolites in this study. Compounds 2, 3, 4a, and 5-7 exhibit a modest inhibition against slow growing mycobacteria (MIC 25-50 mu g/mL), including Mycobacterium tuberculosis. iso-Anomoian A and suberedamine B showed antitumor activity in the NCI-DTP60 cell line screen at single-digit micromolar concentrations, with iso-anomoian A inhibiting 53 cell lines. These molecules present novel scaffolds for further optimization.

  DOI：

  10.1021/np300102z