2-Substituted perimidines: Zwitterionic tauterism in solid state, substituent effect on their crystal packing and biological activity

被引：3
|
作者：
Augusto Fernandez-Gijon, Cesar [1 ]
Olvera-Mancilla, Jessica [1 ]
Le Lagadec, Ronan [2 ]
Barba-Behrens, Norah [3 ]
Rico-Bautista, Hugo [3 ]
Toscano, Ruben A. [2 ]
Alexandrova, Larissa [1 ]
机构：
[1] Univ Nacl Autonoma Mexico, Inst Invest Mat, AP 70-360, Coyoacan 04510, Mexico
[2] Univ Nacl Autonoma Mexico, Inst Quim, Circuito Exterior S-N,Ciudad Univ, Coyoacan 04510, Mexico
[3] Univ Nacl Autonoma Mexico, Fac Quim, Dept Quim Inorgan & Nucl, AP 70-360, Coyoacan 04510, Mexico
来源：
JOURNAL OF MOLECULAR STRUCTURE | 2022年 / 1252卷
关键词：
X-RAY; 1,8-DIAMINONAPHTHALENE; DIFFRACTION; DERIVATIVES; MOLECULE; NMR;
D O I：
10.1016/j.molstruc.2021.132056
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Structural and electronic properties of five 2-substituted 1H-perimidines: 3-(1H-perimidin-2-yl)propanoic acid (SPm), (Z)-3-(1H-perimidin-2-yl)acrylic acid) (MPm), (Z)-3-(1H-perimidin-2-yl)but-2-enoic acid (CPm-1), (Z)-2-methyl-3-(1H-perimidin-2-yl)acrylic acid (CPm-2) and 2-((1H-perimidin-2-yl)methyl)acrylic acid (IPm) have been studied. All perimidines bear aliphatic acidic substituents at 2-position andare distinguished by a carbon-carbon double bond in the substituents. The crystallographic X-ray diffraction analysis revealed that they exist in the solid state as zwitterions. Primary screening of 2-substituted 1H-perimidines against different cancer cell lines were also realized. The results obtained are discussed in terms of the structure-property relationships and compared with density functional theory calculations. Additionally, the effect of inclusion of water molecules in the crystal lattice on the molecular packing is analyzed. (C) 2021 Elsevier B.V. All rights reserved.
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页数：9
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