Non-nucleophilic base promoted synthesis of azo-linked oxazolone-pyrazole hybrids: Antimicrobial, antitubercular, anticancer evaluations and in-silico modeling insights
Ten new non-nucleophilic base (DBU) catalyzed oxazolone-bearing pyrazole derivatives were created to treat infectious diseases caused by bacterial, mycobacterial strains, and cancerous cell lines. Compounds 7b and 7c showed excellent antibacterial and antifungal activity. Compound 7b was highly effe...
Saved in:
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2024-12-01
|
| Series: | Results in Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715624005836 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1850105605205786624 |
|---|---|
| author | Bonny Y. Patel Vidhi Joshi Sangeetha Subramanian Gopal Italiya Prasanna Srinivasan Ramalingam Sivakumar Arumugam Sanjay D. Hadiyal Al-Anood Mohamed Al-Dies |
| author_facet | Bonny Y. Patel Vidhi Joshi Sangeetha Subramanian Gopal Italiya Prasanna Srinivasan Ramalingam Sivakumar Arumugam Sanjay D. Hadiyal Al-Anood Mohamed Al-Dies |
| author_sort | Bonny Y. Patel |
| collection | DOAJ |
| description | Ten new non-nucleophilic base (DBU) catalyzed oxazolone-bearing pyrazole derivatives were created to treat infectious diseases caused by bacterial, mycobacterial strains, and cancerous cell lines. Compounds 7b and 7c showed excellent antibacterial and antifungal activity. Compound 7b was highly effective against M. tuberculosis H37Rv, with a MIC of 0.06 μg/mL and significant binding affinities to AcrB of E. coli (−12 Kcal/mol), TriABC of P. aeruginosa (−12.5 Kcal/mol), and MepR of S. aureus (−10.6 Kcal/mol). Based on the findings, compounds 7b, 7c, and 7e exhibit proficient binding affinity with two essential targets, namely Enoyl-[acyl-carrier-protein] reductase and Topoisomerase I, of M. tuberculosis. Compound 7b showed superior cytotoxic activity against all cancer types except leukemia with GI50 values of 1.26–1.83 µM and LC50 values of 5.36–7.88 µM. Compound 7a demonstrated remarkable anticancer activity against colon, melanoma, ovarian, renal, and breast cancer cell lines with GI50 values of 1.60–2.55 µM. |
| format | Article |
| id | doaj-art-dfd0d6db19254da79e17176c8e52b2d8 |
| institution | OA Journals |
| issn | 2211-7156 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj-art-dfd0d6db19254da79e17176c8e52b2d82025-08-20T02:39:02ZengElsevierResults in Chemistry2211-71562024-12-011210188710.1016/j.rechem.2024.101887Non-nucleophilic base promoted synthesis of azo-linked oxazolone-pyrazole hybrids: Antimicrobial, antitubercular, anticancer evaluations and in-silico modeling insightsBonny Y. Patel0Vidhi Joshi1Sangeetha Subramanian2Gopal Italiya3Prasanna Srinivasan Ramalingam4Sivakumar Arumugam5Sanjay D. Hadiyal6Al-Anood Mohamed Al-Dies7School of Science, Department of Chemistry, RK University, Rajkot 360020, Gujarat, India; Corresponding author.Department of Chemistry, B.V. Shah (Vadi-Vihar) Science College, C.U. Shah University, Wadhwan City, Surendranagar 363001, Gujarat, IndiaSchool of Biosciences and Technology (SBST), Vellore Institute of Technology, Vellore, Tamil Nadu 632014, IndiaSchool of Biosciences and Technology (SBST), Vellore Institute of Technology, Vellore, Tamil Nadu 632014, IndiaSchool of Biosciences and Technology (SBST), Vellore Institute of Technology, Vellore, Tamil Nadu 632014, IndiaSchool of Biosciences and Technology (SBST), Vellore Institute of Technology, Vellore, Tamil Nadu 632014, IndiaDepartment of Chemistry, Atmiya University, Rajkot 360005, Gujarat, IndiaChemistry Department, Umm Al-Qura University, Al-Qunfudah University College, Saudi ArabiaTen new non-nucleophilic base (DBU) catalyzed oxazolone-bearing pyrazole derivatives were created to treat infectious diseases caused by bacterial, mycobacterial strains, and cancerous cell lines. Compounds 7b and 7c showed excellent antibacterial and antifungal activity. Compound 7b was highly effective against M. tuberculosis H37Rv, with a MIC of 0.06 μg/mL and significant binding affinities to AcrB of E. coli (−12 Kcal/mol), TriABC of P. aeruginosa (−12.5 Kcal/mol), and MepR of S. aureus (−10.6 Kcal/mol). Based on the findings, compounds 7b, 7c, and 7e exhibit proficient binding affinity with two essential targets, namely Enoyl-[acyl-carrier-protein] reductase and Topoisomerase I, of M. tuberculosis. Compound 7b showed superior cytotoxic activity against all cancer types except leukemia with GI50 values of 1.26–1.83 µM and LC50 values of 5.36–7.88 µM. Compound 7a demonstrated remarkable anticancer activity against colon, melanoma, ovarian, renal, and breast cancer cell lines with GI50 values of 1.60–2.55 µM.http://www.sciencedirect.com/science/article/pii/S2211715624005836AnticancerAntimicrobialAntitubercularMolecular dockingOxazolone-pyrazole |
| spellingShingle | Bonny Y. Patel Vidhi Joshi Sangeetha Subramanian Gopal Italiya Prasanna Srinivasan Ramalingam Sivakumar Arumugam Sanjay D. Hadiyal Al-Anood Mohamed Al-Dies Non-nucleophilic base promoted synthesis of azo-linked oxazolone-pyrazole hybrids: Antimicrobial, antitubercular, anticancer evaluations and in-silico modeling insights Results in Chemistry Anticancer Antimicrobial Antitubercular Molecular docking Oxazolone-pyrazole |
| title | Non-nucleophilic base promoted synthesis of azo-linked oxazolone-pyrazole hybrids: Antimicrobial, antitubercular, anticancer evaluations and in-silico modeling insights |
| title_full | Non-nucleophilic base promoted synthesis of azo-linked oxazolone-pyrazole hybrids: Antimicrobial, antitubercular, anticancer evaluations and in-silico modeling insights |
| title_fullStr | Non-nucleophilic base promoted synthesis of azo-linked oxazolone-pyrazole hybrids: Antimicrobial, antitubercular, anticancer evaluations and in-silico modeling insights |
| title_full_unstemmed | Non-nucleophilic base promoted synthesis of azo-linked oxazolone-pyrazole hybrids: Antimicrobial, antitubercular, anticancer evaluations and in-silico modeling insights |
| title_short | Non-nucleophilic base promoted synthesis of azo-linked oxazolone-pyrazole hybrids: Antimicrobial, antitubercular, anticancer evaluations and in-silico modeling insights |
| title_sort | non nucleophilic base promoted synthesis of azo linked oxazolone pyrazole hybrids antimicrobial antitubercular anticancer evaluations and in silico modeling insights |
| topic | Anticancer Antimicrobial Antitubercular Molecular docking Oxazolone-pyrazole |
| url | http://www.sciencedirect.com/science/article/pii/S2211715624005836 |
| work_keys_str_mv | AT bonnyypatel nonnucleophilicbasepromotedsynthesisofazolinkedoxazolonepyrazolehybridsantimicrobialantitubercularanticancerevaluationsandinsilicomodelinginsights AT vidhijoshi nonnucleophilicbasepromotedsynthesisofazolinkedoxazolonepyrazolehybridsantimicrobialantitubercularanticancerevaluationsandinsilicomodelinginsights AT sangeethasubramanian nonnucleophilicbasepromotedsynthesisofazolinkedoxazolonepyrazolehybridsantimicrobialantitubercularanticancerevaluationsandinsilicomodelinginsights AT gopalitaliya nonnucleophilicbasepromotedsynthesisofazolinkedoxazolonepyrazolehybridsantimicrobialantitubercularanticancerevaluationsandinsilicomodelinginsights AT prasannasrinivasanramalingam nonnucleophilicbasepromotedsynthesisofazolinkedoxazolonepyrazolehybridsantimicrobialantitubercularanticancerevaluationsandinsilicomodelinginsights AT sivakumararumugam nonnucleophilicbasepromotedsynthesisofazolinkedoxazolonepyrazolehybridsantimicrobialantitubercularanticancerevaluationsandinsilicomodelinginsights AT sanjaydhadiyal nonnucleophilicbasepromotedsynthesisofazolinkedoxazolonepyrazolehybridsantimicrobialantitubercularanticancerevaluationsandinsilicomodelinginsights AT alanoodmohamedaldies nonnucleophilicbasepromotedsynthesisofazolinkedoxazolonepyrazolehybridsantimicrobialantitubercularanticancerevaluationsandinsilicomodelinginsights |