Ultrasonic-Assisted Synthesis and Quantum Chemical Analysis of Spiro[Indoline-3,3′-Pyrazol]-2-One Derivatives as Effective Bactericidal and Viricidal Agents

Abstract

The present work described a novel synthesis of spiro[indoline-3,3′-pyrazol]-2-one derivatives 2, 4, 5, and 7 via a one-pot reaction of chalcones or β-aroyl acrylic acid 1a–c, isatin, and hydrazine derivatives e.g. hydrazine hydrate, methyl hydrazine, phenylhydrazine or acetohydrazide in sonicated reaction condition. The unexpected product 1,3-oxazino[3,2-a]indol-10-yl-ethanone derivative 6 can be generated instead of N-acetyl spiro[indoline-3,3′-pyrazol]-2-one as desired. Also, the Spiropyrazole-fused furanone and pyridazinone ring can be made. Owing to their unique 3-dimensional structures, spirooxindoles have been found as lucky chemotypes for antiviral drug enhancement in an attempt to achieve these spiropyrazole derivatives 2–10 with hydrophobic groups. Furthermore, the density functional theory (DFT) was used to elucidate the electronic and structural features of spiropyrazole derivatives and their reactive species, which supports the proposed mechanism of antibacterial and antiviral capabilities.

Keywords:

• Antibacterial activity
• antiviral activity
• DFT
• MCRs
• Spiroheterocycles

Acknowledgment

The authors look forward to sincere gratitude to Flow Cytometry Unit, National Cancer Institute, Cairo University and STDF project No. 37139 for helpful and acheivement of the manuscript.

Disclosure statement

No potential conflict of interest was reported by the authors.

Ethical standards

All animal studies have been approved by the appropriate ethics committee and have therefore been performed following the ethical standards laid down in the 1964 Declaration of Helsinki.

Authors contributions

The listed authors contributed to this work as described in the following: Sameh A. Rizk gave the concepts of the work, methodology and interpreted the results, and prepared the manuscript, Salwa S. Abdelwahab carried out the synthetic work, interpreted the results assisted in antiviral results and prepared the manuscript and Abdullah M. Abdo interpreted methodology, antibacterial and antiviral results and collaborated in the manuscript preparation. All authors read and approved the final manuscript.