Four pyrrole derivatives used as building blocks in the synthesis of minor-groove binders.
Four pyrrole derivatives used as building blocks in the synthesis of minor-groove binders.
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DOI：
10.1107/s2056989017001177
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发表时间：
2017-02-01
期刊：
影响因子：
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通讯作者：
Suckling CJ
中科院分区：
文献类型：
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作者：
Kennedy AR;Khalaf AI;Scott FJ;Suckling CJ
标题硝基物是用于合成修饰的DNA小沟结合剂的中间体。它们是4-硝基-1H-吡咯-2-羧酸乙酯、其衍生物4-硝基-1-（4-戊炔基）-1H-吡咯-2-羧酸乙酯、N-[3-（二甲基氨基）丙酰基]-1-异戊基-4-硝基-1H-吡咯-2-甲酰胺和1-（3-叠氮基丙酰基）-4-（1-甲基-4-硝基-1H-吡咯-2-甲酰胺基）-N-[2-（吗啉-4-基）乙酰基]-1H-吡咯-2-甲酰胺。标题硝基三吡咯基化合物，C7 H8 N2 O 4，（I）（4-硝基-1H-吡咯-2-羧酸乙酯），其衍生物C12 H14 N2 O 4，（II）[4-硝基-1-（4-异丙基乙炔基）-1H-吡咯-2-羧酸酯]，C15 H26 N4 O3，（III）{N-[3-（二异丙基甲基氨基）丙基]-1-异戊基-4-硝基-1H-吡咯-2-甲酰胺}，和C20 H27 N9 O 5，（IV）{1-（3-叠氮基异丙基）-4-（1-甲基-4-硝基-1H-吡咯-2-甲酰胺基）-N-[2-（吗啉-4-基）乙基]-1H-吡咯-2-甲酰胺}是用于合成修饰的DNA小沟结合剂的中间体。在所有四种化合物中，硝基位于吡咯环的平面内。在化合物（I）和（II）中，酯基也位于吡咯环的平面中。在化合物（III）中，其他两个取代基均位于吡咯环的平面之外。在化合物（IV）的情况下，共面性延伸到第二个吡咯环并通过两个酰胺基团。在所有四种化合物的晶体中，层状结构通过（I）、（III）和（IV）的N-H-O和C-H-O氢键的组合形成，但通过（II）的仅C-H-O氢键形成。
The title nitropyrrole-based compounds are intermediates used in the synthesis of modified DNA minor-groove binders. They are ethyl 4-nitro-1H-pyrrole-2-carboxylate, its derivative ethyl 4-nitro-1-(4-pentynyl)-1H-pyrrole-2-carboxylate, N-[3-(dimethylamino)propyl]-1-isopentyl-4-nitro-1H-pyrrole-2-carboxamide and 1-(3-azidopropyl)-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-N-[2-(morpholin-4-yl)ethyl]-1H-pyrrole-2-carboxamide. The title nitropyrrole-based compounds, C7H8N2O4, (I) (ethyl 4-nitro-1H-pyrrole-2-carboxylate), its derivative C12H14N2O4, (II) [ethyl 4-nitro-1-(4-pentynyl)-1H-pyrrole-2-carboxylate], C15H26N4O3, (III) {N-[3-(dimethyamino)propyl]-1-isopentyl-4-nitro-1H-pyrrole-2-carboxamide}, and C20H27N9O5, (IV) {1-(3-azidopropyl)-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-N-[2-(morpholin-4-yl)ethyl]-1H-pyrrole-2-carboxamide}, are intermediates used in the synthesis of modified DNA minor-groove binders. In all four compounds, the nitro groups lie in the plane of the pyrrole ring. In compounds (I) and (II), the ester groups also lie in the plane of the pyrrole ring. In compound (III), both of the other substituents lie out of the plane of the pyrrole ring. In the case of compound (IV), the coplanarity extends to the second pyrrole ring and through both amide groups. In the crystals of all four compounds, layer-like structures are formed, via a combination of N—H⋯O and C—H⋯O hydrogen bonds for (I), (III) and (IV), but by only C—H⋯O hydrogen bonds for (II).