A new synthetic route for the preparation of 2,2′,5′-trimethyl-7-oxo-4,7-dihydro-[6,7′-bipyrazolo[1,5-a]pyrimidine]-3,3′-dicarbonitrile, structural elucidation, Hirshfeld surface analysis, energy framework, density functional theory and molecular docking investigations

被引：2

作者：

El Hafi, Mohamed ^{[1
]}

Lahmidi, Sanae ^{[1
]}

Boulhaoua, Mohammed ^{[1
,2
]}

El Ghayati, Lhoussaine ^{[1
]}

Albalwi, Hanan ^{[3
]}

Anouar, El Hassane ^{[3
]}

Alharthi, Abdulrahman I. ^{[3
]}

Mague, Joel T. ^{[4
]}

Essassi, El Mokhtar ^{[1
]}

Lai, Chin-Hung ^{[5
,6
]}

机构：

[1] Mohammed V Univ Rabat, Dept Chem, Lab Heterocycl Organ Chem, Fac Sci, BP 1014, Rabat, Morocco

[2] ELTE Eotvos Lor & Univ, Inst Chem, Dept Inorgan Chem, Budapest, Hungary

[3] Prince Sattam Bin Abdulaziz Univ, Coll Sci & Humanites Al Kharj, Dept Chem, Al Kharj 11942, Saudi Arabia

[4] Tulane Univ, Dept Chem, New Orleans, LA USA

[5] Chung Shan Med Univ, Dept Med Appl Chem, Taichung, Taiwan

[6] Chung Shan Med Univ Hosp, Dept Med Educ, Taichung, Taiwan

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2022年 / 69卷 / 04期

关键词：

crystal structure; DFT calculations; energy framework; molecular docking; pyrazolopyrimidine derivatives; CRYSTAL-STRUCTURE; PI-INTERACTIONS; DFT CALCULATIONS; ARYLATION; SERIES;

D O I：

10.1002/jccs.202100509

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new bipyrazolo [1,5-a]pyrimidine derivative, 2,2 ',5 '-trimethyl-7-oxo-4,7-dihydro-[6,7 '-bipyrazolo[1,5-a]pyrimidine]-3,3 '-dicarbonitrile dihydrate acetic acid solvate (3) has been synthesized via two different methods and characterized by single-crystal X-ray diffraction (XRD) and spectroscopic techniques. A plausible reaction mechanism in the synthesis of 3 through the two synthetic routes used has been proposed. The XRD analysis reveals that the two bicyclic moieties in 3 are close to perpendicular to one another. Some formal double bonds appear localized while others appear to involve some delocalization. In the crystal structure, a layer structure is formed by O-HMIDLINE HORIZONTAL ELLIPSISO, O-HMIDLINE HORIZONTAL ELLIPSISN and N-HMIDLINE HORIZONTAL ELLIPSISO hydrogen bonds, along with weak C-HMIDLINE HORIZONTAL ELLIPSISO and pi-stacking interactions. The energy framework indicates that the packing of 3 is mainly determined by dispersion interactions between molecules. The frontier molecular orbital analysis shows that 3 may act more as a nucleophile than an electrophile. The analysis of the Hirshfeld surface maps and 2D fingerprint plots of 3 reveal that intermolecular hydrogen bonding and HMIDLINE HORIZONTAL ELLIPSISH, NMIDLINE HORIZONTAL ELLIPSISH and OMIDLINE HORIZONTAL ELLIPSISH contacts are the major ones between the units of 3. The antibacterial activity of 3 is explored by its molecular docking into the binding site of tyrosyl-tRNA synthetase, where it formed a stable complex with the amino acids of tyrosyl-tRNA synthetase mainly through hydrogen bonding.

引用

页码：717 / 730

页数：14