ethyl 13,16-bis(2-ethoxy-2-oxoethyl)-6-methyl-1-(1-methyl-4-(1-methyl-4-(1-methyl-1H-imidazole-2-carboxamido)-1H-pyrrole-2-carboxamido)-1H-pyrrol-2-yl)-1,11-dioxo-2,6,10,13,16-pentaazaoctadecan-18-oate | 144181-99-7

• 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: ethyl 13,16-bis(2-ethoxy-2-oxoethyl)-6-methyl-1-(1-methyl-4-(1-methyl-4-(1-methyl-1H-imidazole-2-carboxamido)-1H-pyrrole-2-carboxamido)-1H-pyrrol-2-yl)-1,11-dioxo-2,6,10,13,16-pentaazaoctadecan-18-oate
• CAS: 144181-99-7
• 化学式: C₄₀H₆₁N₁₁O₁₀
• 分子量: 855.992
• InChiKey: ZQQMLVNSGMPDOC-UHFFFAOYSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.45
• 重原子数：
  61.0
• 可旋转键数：
  27.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  232.7
• 氢给体数：
  4.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  ethyl 13,16-bis(2-ethoxy-2-oxoethyl)-6-methyl-1-(1-methyl-4-(1-methyl-4-(1-methyl-1H-imidazole-2-carboxamido)-1H-pyrrole-2-carboxamido)-1H-pyrrol-2-yl)-1,11-dioxo-2,6,10,13,16-pentaazaoctadecan-18-oate 在 lithium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以27%的产率得到[[2-(Bis-carboxymethyl-amino)-ethyl]-({3-[methyl-(3-{[1-methyl-4-({1-methyl-4-[(1-methyl-1H-imidazole-2-carbonyl)-amino]-1H-pyrrole-2-carbonyl}-amino)-1H-pyrrole-2-carbonyl]-amino}-propyl)-amino]-propylcarbamoyl}-methyl)-amino]-acetic acid
  参考文献：
  名称：

  Design of peptides that bind in the minor groove of DNA at 5'-(A,T)G(A,T)C(A,T)-3' sequences by a dimeric side-by-side motif

  摘要：

  The designed peptides pyridine-2-carboxamide-netropsin (2-PyN) and 1-methylimidazole-2-carboxamide-netropsin (2-ImN) are crescent-shaped synthetic analogs of the natural products netropsin (N) and distamycin A (D). Footprinting experiments indicate that the peptides 2-PyN and 2-ImN bind specifically the 5 base pair sequence 5'-TGTCA-3'. Affinity cleaving data suggest that the complexes, 2-ImN.5'-TGTCA-3' and 2-PyN.5'-TGTCA-3', are composed of two equivalent orientations which disfavor a 1:1 model. The footprinting and affinity cleaving data are in accord with a 2:1 complex where a novel side-by-side antiparallel dimer binds in the minor groove of double-helical DNA.

  DOI：

  10.1021/ja00049a006
• 作为产物：
  描述：

  1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxylic acid 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、2.07 MPa 条件下， 反应 45.42h， 生成 ethyl 13,16-bis(2-ethoxy-2-oxoethyl)-6-methyl-1-(1-methyl-4-(1-methyl-4-(1-methyl-1H-imidazole-2-carboxamido)-1H-pyrrole-2-carboxamido)-1H-pyrrol-2-yl)-1,11-dioxo-2,6,10,13,16-pentaazaoctadecan-18-oate
  参考文献：
  名称：

  Design of peptides that bind in the minor groove of DNA at 5'-(A,T)G(A,T)C(A,T)-3' sequences by a dimeric side-by-side motif

  摘要：

  The designed peptides pyridine-2-carboxamide-netropsin (2-PyN) and 1-methylimidazole-2-carboxamide-netropsin (2-ImN) are crescent-shaped synthetic analogs of the natural products netropsin (N) and distamycin A (D). Footprinting experiments indicate that the peptides 2-PyN and 2-ImN bind specifically the 5 base pair sequence 5'-TGTCA-3'. Affinity cleaving data suggest that the complexes, 2-ImN.5'-TGTCA-3' and 2-PyN.5'-TGTCA-3', are composed of two equivalent orientations which disfavor a 1:1 model. The footprinting and affinity cleaving data are in accord with a 2:1 complex where a novel side-by-side antiparallel dimer binds in the minor groove of double-helical DNA.

  DOI：

  10.1021/ja00049a006