Synthesis, DFT calculations, In silico studies, and biological evaluation of pyrano[2,3-c]pyrazole and pyrazolo[4'3':5,6]pyrano[2,3-d]pyrimidine derivatives

被引：12

作者：

Abouelenein, Mohamed G. ^{[1
]}

Ismail, Abd El-Hamid A. ^{[1
]}

Aboelnaga, Asmaa ^{[2
]}

Tantawy, Mohamed A. ^{[3
,4
]}

El-Ebiary, Nora M. A. ^{[5
]}

El-Assaly, Samy A. ^{[6
]}

机构：

[1] Menoufia Univ, Fac Sci, Chem Dept, Shibin Al Kawm, Menofia, Egypt

[2] Ain Shams Univ, Fac Womens Arts Sci & Educ, Chem Dept, Heliopolis 11757, Egypt

[3] Natl Res Ctr, Hormones Dept, Med Res Div, Giza 12622, Egypt

[4] Natl Res Ctr, Ctr Excellence Adv Sci, Stem Cells Lab, Giza 12622, Egypt

[5] Natl Res Ctr, Chem Industnes Res Inst, Green Chem Dept, Giza, Egypt

[6] Natl Res Ctr NRC, Nat & Microbial Prod Chem Dept, Giza, Egypt

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2023年 / 1275卷

关键词：

Isatin; Pyrano[2; 3-c]pyrazole; DFT calculations; Pyrimidine; Cancer; Molecular docking; ONE-POT; MULTICOMPONENT SYNTHESIS; STRUCTURAL FEATURES; MOLECULAR DOCKING; CATALYST; ACID; PYRANOPYRAZOLES; ANTIBACTERIAL; INHIBITORS; PYRAZOLE;

D O I：

10.1016/j.molstruc.2022.134587

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：

An eco-friendly approach was conducted for synthesizing pyrano[2,3-c]pyrazoles M1 -M25 via a one-pot reaction of hydrazine hydrate 99%, ethyl acetoacetate or diethyl malonate, carbonyl group source, and active methylene compounds. Besides, pyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidines M26 -M31 was synthe-sized via intramolecular cyclization of M10 and M13 . Thereafter, the antimicrobial, antioxidant, and anti-cancer activities of the titled compounds were evaluated utilizing an array of techniques. Fortunately, the vast majority of the compounds exhibited promising biological activities. Over and above, in silico study was employed to determine the expected mode of action of the synthesized compounds. M21 was the most promising anti-bacterial agent, while M5 was the most cytotoxic compound. Finally, DFT theoretical calculations were used to study the stability and structural parameters of the newly synthesized com-pounds. DFT calculations showed the energy gaps between the HOMO-LUMO with all the investigated compounds in a range of 4.04-5.66 eV allowing for easy exchange of electrons and the reactivity.(c) 2022 Elsevier B.V. All rights reserved.

引用

页数：22

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