N-[N-BOC-(4-aminobutyl)-N-methylpyrrole-4-(N-methylimidazole-2-carboxamido)-2-carboxamido]glutaramide monocarboxylic acid | 413577-43-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[N-BOC-(4-aminobutyl)-N-methylpyrrole-4-(N-methylimidazole-2-carboxamido)-2-carboxamido]glutaramide monocarboxylic acid
• 英文别名: 5-[[1-Methyl-2-[[1-methyl-5-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butylcarbamoyl]pyrrol-3-yl]carbamoyl]imidazol-4-yl]amino]-5-oxopentanoic acid
• CAS: 413577-43-2
• 化学式: C₂₅H₃₇N₇O₇
• 分子量: 547.611
• InChiKey: GQURZKPEHAXWIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  186
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[N-BOC-(4-aminobutyl)-N-methylpyrrole-4-(N-methylimidazole-2-carboxamido)-2-carboxamido]glutaramide monocarboxylic acid 在 palladium on activated charcoal 盐酸 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 Pentanedioic acid {2-[5-(4-amino-butylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-imidazol-4-yl}-amide [2-(3-chloromethyl-6-hydroxy-2,3-dihydro-indole-1-carbonyl)-benzofuran-5-yl]-amide; hydrochloride
  参考文献：
  名称：

  Sequence selective recognition of DNA by hairpin conjugates of a racemic seco-cyclopropaneindoline-2-benzofurancarboxamide and polyamides

  摘要：

  Conjugates of racemic seco-cyclopropaneindoline-2-benzofurancarboxamide (CI-Bf) and four diamides (ImIm 1, ImPy 2, PyIm 3, and PyPy 4, where Py is pyrrole, and Im is imidazole), linked by a gamma-aminobutyrate group were synthesized. In addition to alkylating at adenine-N3 positions within an A(5) sequence, the imidazole-containing compounds 1 and 2 were found to also alkylate purine-N3 positions within a sequence 3'-GGGGGGA(888)CTGCTC(894)-5'. A model for the binding of hairpin conjugates I and 2 with the 3'-GACT-5' sequence is proposed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00341-4
• 作为产物：
  描述：

  [4-({1-Methyl-4-[(1-methyl-4-nitro-1H-imidazole-2-carbonyl)-amino]-1H-pyrrole-2-carbonyl}-amino)-butyl]-carbamic acid tert-butyl ester 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 生成 N-[N-BOC-(4-aminobutyl)-N-methylpyrrole-4-(N-methylimidazole-2-carboxamido)-2-carboxamido]glutaramide monocarboxylic acid
  参考文献：
  名称：

  Sequence selective recognition of DNA by hairpin conjugates of a racemic seco-cyclopropaneindoline-2-benzofurancarboxamide and polyamides

  摘要：

  Conjugates of racemic seco-cyclopropaneindoline-2-benzofurancarboxamide (CI-Bf) and four diamides (ImIm 1, ImPy 2, PyIm 3, and PyPy 4, where Py is pyrrole, and Im is imidazole), linked by a gamma-aminobutyrate group were synthesized. In addition to alkylating at adenine-N3 positions within an A(5) sequence, the imidazole-containing compounds 1 and 2 were found to also alkylate purine-N3 positions within a sequence 3'-GGGGGGA(888)CTGCTC(894)-5'. A model for the binding of hairpin conjugates I and 2 with the 3'-GACT-5' sequence is proposed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00341-4

文献信息

• Compositions and methods of the use thereof achiral analogues of CC-1065 and the duocarmycins
  申请人：Taiho Pharmaceutical Co. Ltd.

  公开号：US06660742B2

  公开（公告）日：2003-12-09

  The present invention relates to novel achiral seco-analogues of DNA minor groove and sequence-selective alkylating agents (+)-CC1065 and the duocarmycins, depicted as general class I, II, III, IV and V: wherein X is a good leaving group, such as a chloride, a bromide, an iodide, a mesylate, a tosylate, an acetate, a quaternary ammonium moiety, a mercaptan, an alkylsulfoxyl, or an alkylsulfonyl group, preferably either a chloride, a bromide, or an iodide group. R1 is a suitable minor groove binding agent to enhance the interactions of the achiral seco-cyclopropaneindole (Cl) or an achiral seco-duocarmycin with specific sequences of DNA.

  该发明涉及一种新颖的DNA次级沟和序列选择性烷基化剂（+）-CC1065和duocarmycins的不对称环丙烷各向同性衍生物，表示为一般的I、II、III、IV和V类：其中X是一个良好的离去基团，如氯化物、溴化物、碘化物、甲磺酸酯、对甲苯磺酸酯、乙酸酯、季铵基团、巯基、烷基亚砜基或烷基磺酰基，最好是氯化物、溴化物或碘化物基团。R1是一个适当的次级沟结合剂，用于增强不对称环丙烷吲哚（Cl）或不对称duocarmycin与DNA特定序列的相互作用。