Synthesis of novel pyrazoline based bis (1,2,3-triazole) scaffolds via click chemistry
A series of novel bis(1,2,3-triazoles) derivatives 7a–m were synthesized by the 1,3-dipolar cycloaddition (click-reaction) of 1-methyl-3,5-bis(2- -(prop-2-yn-1-yloxy)phenyl)-4,5-dihydro-1H-pyrazole (5) with various aralkyl azides 6a–m in the presence of sodium ascorbate and copper sulphate with good...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Serbian Chemical Society
2017-01-01
|
| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.doiserbia.nb.rs/img/doi/0352-5139/2017/0352-51391600076K.pdf |
| _version_ | 1819054715876409344 |
|---|---|
| author | Kiran Kothuri Ashok Dongamanti Rao Boddu Ananda Sarasija Madderla Rao Alapati Srinivas |
| author_facet | Kiran Kothuri Ashok Dongamanti Rao Boddu Ananda Sarasija Madderla Rao Alapati Srinivas |
| author_sort | Kiran Kothuri |
| collection | DOAJ |
| description | A series of novel bis(1,2,3-triazoles) derivatives 7a–m were synthesized by the 1,3-dipolar cycloaddition (click-reaction) of 1-methyl-3,5-bis(2- -(prop-2-yn-1-yloxy)phenyl)-4,5-dihydro-1H-pyrazole (5) with various aralkyl azides 6a–m in the presence of sodium ascorbate and copper sulphate with good yields. The required precursor 5 was synthesized by reacting (E)-1,3- -bis(2-hydroxyphenyl)prop-2-en-1-one (3) with methylhydrazine hydrate via 2,2′-(1-methyl-4,5-dihydro-1H-pyrazole-3,5-diyl)diphenol 4, followed by reaction with propargyl bromide. The homogeneity of all the newly synthesized compounds was checked by TLC. The IR, NMR, mass spectral data and elemental analysis were in accord with the assigned structure. The title compounds were evaluated for their antibacterial activity against various bacterial strains, i.e., Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis; compounds 7f–7h and 7j were found to be moderately active against the bacteria, when compared with that of the standard drug. Furthermore, the same library of compounds was evaluated for their antioxidant activity using the nitric oxide radical scavenging activity. The results of the study showed that compounds 7e–7h and 7k–7m showed good radical scavenging activity. |
| first_indexed | 2024-12-21T12:56:02Z |
| format | Article |
| id | doaj.art-cae15db30b674738a593f24f18c6cd14 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-12-21T12:56:02Z |
| publishDate | 2017-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-cae15db30b674738a593f24f18c6cd142022-12-21T19:03:20ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212017-01-0182324125110.2298/JSC160216076A0352-51391600076KSynthesis of novel pyrazoline based bis (1,2,3-triazole) scaffolds via click chemistryKiran Kothuri0Ashok Dongamanti1Rao Boddu Ananda2Sarasija Madderla3Rao Alapati Srinivas4Osmania University, Department of Chemistry, Green and Medicinal Chemistry Laboratory, Hyderabad, Telangana, India + Department of Chemistry, JNTU-H, Hyderabad, Telangana, IndiaOsmania University, Department of Chemistry, Green and Medicinal Chemistry Laboratory, Hyderabad, Telangana, IndiaOsmania University, Department of Chemistry, Green and Medicinal Chemistry Laboratory, Hyderabad, Telangana, IndiaOsmania University, Department of Chemistry, Green and Medicinal Chemistry Laboratory, Hyderabad, Telangana, IndiaVagdevi InnoScience Private Limited, 5-A/8, IDA Nacharam, Hyderabad, Telangana, IndiaA series of novel bis(1,2,3-triazoles) derivatives 7a–m were synthesized by the 1,3-dipolar cycloaddition (click-reaction) of 1-methyl-3,5-bis(2- -(prop-2-yn-1-yloxy)phenyl)-4,5-dihydro-1H-pyrazole (5) with various aralkyl azides 6a–m in the presence of sodium ascorbate and copper sulphate with good yields. The required precursor 5 was synthesized by reacting (E)-1,3- -bis(2-hydroxyphenyl)prop-2-en-1-one (3) with methylhydrazine hydrate via 2,2′-(1-methyl-4,5-dihydro-1H-pyrazole-3,5-diyl)diphenol 4, followed by reaction with propargyl bromide. The homogeneity of all the newly synthesized compounds was checked by TLC. The IR, NMR, mass spectral data and elemental analysis were in accord with the assigned structure. The title compounds were evaluated for their antibacterial activity against various bacterial strains, i.e., Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis; compounds 7f–7h and 7j were found to be moderately active against the bacteria, when compared with that of the standard drug. Furthermore, the same library of compounds was evaluated for their antioxidant activity using the nitric oxide radical scavenging activity. The results of the study showed that compounds 7e–7h and 7k–7m showed good radical scavenging activity.http://www.doiserbia.nb.rs/img/doi/0352-5139/2017/0352-51391600076K.pdfclick chemistrychalcones1,2,3-triazolespyrazolinesantibacterial |
| spellingShingle | Kiran Kothuri Ashok Dongamanti Rao Boddu Ananda Sarasija Madderla Rao Alapati Srinivas Synthesis of novel pyrazoline based bis (1,2,3-triazole) scaffolds via click chemistry Journal of the Serbian Chemical Society click chemistry chalcones 1,2,3-triazoles pyrazolines antibacterial |
| title | Synthesis of novel pyrazoline based bis (1,2,3-triazole) scaffolds via click chemistry |
| title_full | Synthesis of novel pyrazoline based bis (1,2,3-triazole) scaffolds via click chemistry |
| title_fullStr | Synthesis of novel pyrazoline based bis (1,2,3-triazole) scaffolds via click chemistry |
| title_full_unstemmed | Synthesis of novel pyrazoline based bis (1,2,3-triazole) scaffolds via click chemistry |
| title_short | Synthesis of novel pyrazoline based bis (1,2,3-triazole) scaffolds via click chemistry |
| title_sort | synthesis of novel pyrazoline based bis 1 2 3 triazole scaffolds via click chemistry |
| topic | click chemistry chalcones 1,2,3-triazoles pyrazolines antibacterial |
| url | http://www.doiserbia.nb.rs/img/doi/0352-5139/2017/0352-51391600076K.pdf |
| work_keys_str_mv | AT kirankothuri synthesisofnovelpyrazolinebasedbis123triazolescaffoldsviaclickchemistry AT ashokdongamanti synthesisofnovelpyrazolinebasedbis123triazolescaffoldsviaclickchemistry AT raobodduananda synthesisofnovelpyrazolinebasedbis123triazolescaffoldsviaclickchemistry AT sarasijamadderla synthesisofnovelpyrazolinebasedbis123triazolescaffoldsviaclickchemistry AT raoalapatisrinivas synthesisofnovelpyrazolinebasedbis123triazolescaffoldsviaclickchemistry |