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Synthesis, characterization, X-ray diffraction studies and biological evaluation of tert-butyl 4-(2-ethoxy-2-oxoethyl)-piperazine-1-carboxylate and tert-butyl 4-(2-hydrazino-2-oxoethyl)piperazine-1-carboxylate
Research on Chemical Intermediates ( IF 2.8 ) Pub Date : 2016-04-21 , DOI: 10.1007/s11164-016-2542-7
Bhuvan Kulkarni , Sharada Thimmappaiah , Harisha Padigar , Suchetan Parameshwar Adimule , Naveen Shivalingegowda , Lokanath Krishnappagowda Neratur , Manjunatha Kumsi

Two derivatives of N-Boc piperazine, an ester derivative, i.e., tert-butyl 4-(2-ethoxy-2-oxoethyl)-piperazine-1-carboxylate (1), and, a hydrazide derivative tert-butyl 4-(2-hydrazino-2-oxoethyl)piperazine-1-carboxylate (2) were synthesized and were characterized by FT-IR, 1H & 13C NMR and LCMS spectroscopic studies. The structures of both 1 and 2 were further confirmed by single crystal X-ray diffraction analysis. The molecule of 1 is linear in shape with the ethyl acetate moiety adopting fully extended conformation, while the molecule of 2 is L-shaped with the molecule being twisted at the C10 atom. The crystal structure of 1 adopts a two-dimensional zig-zag architecture featuring C–H…O intermolecular interactions, while that of 2 features strong N–H…O hydrogen bonds and intermolecular interactions of the type N–H…N and C–H…N, resulting in a two-dimensional structure. Furthermore, a detailed analysis of the intermolecular interactions and crystal packing of 1 and 2 via Hirshfeld surface analysis and fingerprint plots was performed. The antibacterial and antifungal activities of both the compounds have been studied against several microorganisms, and were found to be moderately active.



中文翻译:

4-(2-乙氧基-2-氧乙基)-哌嗪-1-羧酸叔丁酯和4-(2-肼基-2-氧乙基)哌嗪-叔丁基叔丁酯的合成,表征,X射线衍射研究和生物学评价1-羧酸盐

N-Boc哌嗪的两种衍生物,一种酯衍生物,即4-(2-乙氧基-2-氧乙基)-哌嗪-1-羧酸叔丁酯(1),和酰肼衍生物4-(2合成了-肼基-2-氧代乙基)哌嗪-1-甲酸酯(2),并通过FT-IR,1 H和13表征C NMR和LCMS光谱研究。通过单晶X射线衍射分析进一步证实了1和2的结构。1的分子呈线性,乙酸乙酯部分采用完全延伸的构象,而2的分子呈L形,分子在C10原子处扭曲。1的晶体结构采用具有Z–H…O分子间相互作用的二维之字形结构,而2的晶体结构则具有强大的N–H…O氢键以及N–H…N和C–型的分子间相互作用。 H…N,形成二维结构。此外,还通过Hirshfeld表面分析和指纹图谱对1和2的分子间相互作用和晶体堆积进行了详细分析。

更新日期:2016-04-21
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