Microwave-assisted one-pot efficient synthesis of functionalized 2-oxo-2-phenylethylidenes-linked 2-oxo-benzo[1,4]oxazines and 2-oxo-quino[1,4]oxalines: Synthetic Applications, Antioxidant activity, SAR and Cytotoxic Studies
A microwave-assisted, environmentally benign green protocol for the synthesis of functionalized (Z)-3-(2-oxo-2-phenylethylidene)-3, 4-dihydro-2H-benzo[b][1,4]oxazin-2-ones 11a-n in excellent yields (upto 97%) and (Z)-3-(2-oxo-2-phenylethylidene)-3,4-dihydroquinoxalin-2(1H)-ones 14a-h (upto 96% yield...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Slovenian Chemical Society
2017-12-01
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| Series: | Acta Chimica Slovenica |
| Subjects: | |
| Online Access: | https://journals.matheo.si/index.php/ACSi/article/view/3709 |
| _version_ | 1818312328228110336 |
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| author | Vashundhra Sharma Pradeep K. Jaiswal Dharmendra K. Yadav Mukesh Saran Jaroslav Prikhodko Manas Mathur Ajit K. Swami Irina V. Mashevskaya Sandeep Chaudhary |
| author_facet | Vashundhra Sharma Pradeep K. Jaiswal Dharmendra K. Yadav Mukesh Saran Jaroslav Prikhodko Manas Mathur Ajit K. Swami Irina V. Mashevskaya Sandeep Chaudhary |
| author_sort | Vashundhra Sharma |
| collection | DOAJ |
| description | A microwave-assisted, environmentally benign green protocol for the synthesis of functionalized (Z)-3-(2-oxo-2-phenylethylidene)-3, 4-dihydro-2H-benzo[b][1,4]oxazin-2-ones 11a-n in excellent yields (upto 97%) and (Z)-3-(2-oxo-2-phenylethylidene)-3,4-dihydroquinoxalin-2(1H)-ones 14a-h (upto 96% yield) are reported. The practical applicability of developed methodology were also confirmed by the gram scale synthesis of 11a, 14c and 14e; synthesis of anticancer alkaloid Cephalandole A 16 (89% yield). All the synthesized compounds 11a-n, 14a-h and 16 were assessed for their in vitro antioxidant activities in DPPH radical scavenging and FRAP assay. In DPPH assay, compounds 11a, 14c and 14e, the most active compounds of the series, were found to show IC50 value of 10.20 ± 0.08 μg/mL, 9.89 ± 0.15 μg/mL and 8.97 ± 0.13 μg/mL, respectively in comparison with standard reference (ascorbic acid, IC50 = 4.57 μg/mL). Whereas, in FRAP antioxidant assay seven compounds (11c, 11e, 11i, 11k, 11l, 14d and 14h) displayed higher antioxidant activity comparison than reference standard BHT (C0.5FRAP = 546.2 μM). Moreover, the cytotoxic studies of the compounds 11a, 14c, 14e and 14h were found to be non-toxic in nature in 3T3 fibroblast cell lines using MTT assay. |
| first_indexed | 2024-12-13T08:16:06Z |
| format | Article |
| id | doaj.art-389eafba28a244dcb645a6ef1d25fbb2 |
| institution | Directory Open Access Journal |
| issn | 1318-0207 1580-3155 |
| language | English |
| last_indexed | 2024-12-13T08:16:06Z |
| publishDate | 2017-12-01 |
| publisher | Slovenian Chemical Society |
| record_format | Article |
| series | Acta Chimica Slovenica |
| spelling | doaj.art-389eafba28a244dcb645a6ef1d25fbb22022-12-21T23:54:07ZengSlovenian Chemical SocietyActa Chimica Slovenica1318-02071580-31552017-12-01644988100410.17344/acsi.2017.3709525Microwave-assisted one-pot efficient synthesis of functionalized 2-oxo-2-phenylethylidenes-linked 2-oxo-benzo[1,4]oxazines and 2-oxo-quino[1,4]oxalines: Synthetic Applications, Antioxidant activity, SAR and Cytotoxic StudiesVashundhra Sharma0Pradeep K. Jaiswal1Dharmendra K. Yadav2Mukesh Saran3Jaroslav Prikhodko4Manas Mathur5Ajit K. Swami6Irina V. Mashevskaya7Sandeep Chaudhary8Laboratory of Organic and Medicinal Chemistry Department of Chemistry Malaviya National Institute of Technology (MNIT) Jaipur Jawaharlal Nehru Marg, Jaipur-302017, Rajasthan, INDIALaboratory of Organic and Medicinal Chemistry Department of Chemistry Malaviya National Institute of Technology (MNIT) JaipurDepartment of Biochemistry, All India Institute of Medical Sciences (AIIMS), Jodhpur, Rajasthan-342005, India. College of Pharmacy, Gachon University of Medicine and Science, Room # 502, Hambakmoeiro 191, Yeonsu-gu, Incheon city, 406-799, Korea.Department of Advance Molecular Microbiology, Seminal Applied Sciences Pvt. Ltd. Jaipur-302015, India.Department of Organic Chemistry Faculty of Chemistry Perm State University, 15 Bukireva, Perm 614990, Russian FederationDepartment of Advance Molecular Microbiology, Seminal Applied Sciences Pvt. Ltd. Jaipur-302015, IndiaDepartment of Advance Molecular Microbiology, Seminal Applied Sciences Pvt. Ltd. Jaipur-302015, IndiaeDepartment of Organic Chemistry, Faculty of Chemistry, Perm State University, 15 Bukireva, Perm 614990, Russian Federation.Laboratory of Organic and Medicinal Chemistry Assistant Professor, Department of Chemistry Adjunct Faculty, Materials Research Centre Malaviya National Institute of Technology (MNIT) Jaipur Jawaharlal Nehru Marg, Jaipur-302017, Rajasthan, INDIA Email: schaudhary.chy@mnit.ac.in, sandeep.chaudhary2311@gmail.com Phone No: +91-141-2713319 (O); +91-8764028344 (M); +91-9549657339 (M) Fax No: +91-141-2529029 Website: SCH Research GroupA microwave-assisted, environmentally benign green protocol for the synthesis of functionalized (Z)-3-(2-oxo-2-phenylethylidene)-3, 4-dihydro-2H-benzo[b][1,4]oxazin-2-ones 11a-n in excellent yields (upto 97%) and (Z)-3-(2-oxo-2-phenylethylidene)-3,4-dihydroquinoxalin-2(1H)-ones 14a-h (upto 96% yield) are reported. The practical applicability of developed methodology were also confirmed by the gram scale synthesis of 11a, 14c and 14e; synthesis of anticancer alkaloid Cephalandole A 16 (89% yield). All the synthesized compounds 11a-n, 14a-h and 16 were assessed for their in vitro antioxidant activities in DPPH radical scavenging and FRAP assay. In DPPH assay, compounds 11a, 14c and 14e, the most active compounds of the series, were found to show IC50 value of 10.20 ± 0.08 μg/mL, 9.89 ± 0.15 μg/mL and 8.97 ± 0.13 μg/mL, respectively in comparison with standard reference (ascorbic acid, IC50 = 4.57 μg/mL). Whereas, in FRAP antioxidant assay seven compounds (11c, 11e, 11i, 11k, 11l, 14d and 14h) displayed higher antioxidant activity comparison than reference standard BHT (C0.5FRAP = 546.2 μM). Moreover, the cytotoxic studies of the compounds 11a, 14c, 14e and 14h were found to be non-toxic in nature in 3T3 fibroblast cell lines using MTT assay.https://journals.matheo.si/index.php/ACSi/article/view/3709Benzo[1,4]oxazines2-oxo-benzo[1,4] oxazines2-oxo-quino[1,4]oxalinesAntioxidantMicrowave-Assisted Organic Synthesis (MAOS)DPPHFRAP |
| spellingShingle | Vashundhra Sharma Pradeep K. Jaiswal Dharmendra K. Yadav Mukesh Saran Jaroslav Prikhodko Manas Mathur Ajit K. Swami Irina V. Mashevskaya Sandeep Chaudhary Microwave-assisted one-pot efficient synthesis of functionalized 2-oxo-2-phenylethylidenes-linked 2-oxo-benzo[1,4]oxazines and 2-oxo-quino[1,4]oxalines: Synthetic Applications, Antioxidant activity, SAR and Cytotoxic Studies Acta Chimica Slovenica Benzo[1,4]oxazines 2-oxo-benzo[1,4] oxazines 2-oxo-quino[1,4]oxalines Antioxidant Microwave-Assisted Organic Synthesis (MAOS) DPPH FRAP |
| title | Microwave-assisted one-pot efficient synthesis of functionalized 2-oxo-2-phenylethylidenes-linked 2-oxo-benzo[1,4]oxazines and 2-oxo-quino[1,4]oxalines: Synthetic Applications, Antioxidant activity, SAR and Cytotoxic Studies |
| title_full | Microwave-assisted one-pot efficient synthesis of functionalized 2-oxo-2-phenylethylidenes-linked 2-oxo-benzo[1,4]oxazines and 2-oxo-quino[1,4]oxalines: Synthetic Applications, Antioxidant activity, SAR and Cytotoxic Studies |
| title_fullStr | Microwave-assisted one-pot efficient synthesis of functionalized 2-oxo-2-phenylethylidenes-linked 2-oxo-benzo[1,4]oxazines and 2-oxo-quino[1,4]oxalines: Synthetic Applications, Antioxidant activity, SAR and Cytotoxic Studies |
| title_full_unstemmed | Microwave-assisted one-pot efficient synthesis of functionalized 2-oxo-2-phenylethylidenes-linked 2-oxo-benzo[1,4]oxazines and 2-oxo-quino[1,4]oxalines: Synthetic Applications, Antioxidant activity, SAR and Cytotoxic Studies |
| title_short | Microwave-assisted one-pot efficient synthesis of functionalized 2-oxo-2-phenylethylidenes-linked 2-oxo-benzo[1,4]oxazines and 2-oxo-quino[1,4]oxalines: Synthetic Applications, Antioxidant activity, SAR and Cytotoxic Studies |
| title_sort | microwave assisted one pot efficient synthesis of functionalized 2 oxo 2 phenylethylidenes linked 2 oxo benzo 1 4 oxazines and 2 oxo quino 1 4 oxalines synthetic applications antioxidant activity sar and cytotoxic studies |
| topic | Benzo[1,4]oxazines 2-oxo-benzo[1,4] oxazines 2-oxo-quino[1,4]oxalines Antioxidant Microwave-Assisted Organic Synthesis (MAOS) DPPH FRAP |
| url | https://journals.matheo.si/index.php/ACSi/article/view/3709 |
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