Modified 7-Chloro-11<i>H</i>-indeno[1,2-b]quinoxaline Heterocyclic System for Biological Activities
Recent advances in functionalized organic Spiro heterocyclic compounds composed of nitrogen bonded five- and six-membered rings have been made, establishing them as a synthetic target in organic-based biomedical applications. In this work, we report a synthesis of spirocyclic compounds under a one-p...
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MDPI AG
2022-02-01
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| Online Access: | https://www.mdpi.com/2073-4344/12/2/213 |
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| author | Nakul Kumar Gajendra Kumar Inwati Emad M. Ahmed Chhagan Lal Bharat Makwana Virendra K. Yadav Saiful Islam Hyun-Jo Ahn Krishna K. Yadav Byong-Hun Jeon |
| author_facet | Nakul Kumar Gajendra Kumar Inwati Emad M. Ahmed Chhagan Lal Bharat Makwana Virendra K. Yadav Saiful Islam Hyun-Jo Ahn Krishna K. Yadav Byong-Hun Jeon |
| author_sort | Nakul Kumar |
| collection | DOAJ |
| description | Recent advances in functionalized organic Spiro heterocyclic compounds composed of nitrogen bonded five- and six-membered rings have been made, establishing them as a synthetic target in organic-based biomedical applications. In this work, we report a synthesis of spirocyclic compounds under a one-pot reaction using 1,3-dipolar cycloaddition in a regio and diastereoselective manner. The higher atomic economy with higher yield (95%) and regio and stereoselectivity were achieved by a multi-component reaction of L-proline (1), Indenoquinoxaline (2), and the dipolarophile of malononitrile (3) solvents followed by reflux conditions. The reaction intermediate comprised azomethineylides derived from reactive primary amines, and the spiro derivatives were synthesized up to a ≈ 95% yield. The structural and characteristic chemical components of the as-prepared Spiro compounds were characterized by <sup>1</sup>H-NMR, FTIR, and Mass spectroscopy. The functionalized spiro-pyrrolizidines were found to be effective for biological uses by considering their in vitro screening and antimicrobial impacts. Spiro constituents were found to be much more effective for Gram-positive bacteria due to the stronger lipophilic character of the molecules, and they resulted feasible membrane permeation in a biological system. Based on the planarity geometry of the Spiro pyrrolizidines, meta-substitution possesses steric hindrance and hence shows less effectiveness compared to para-substitution on the same nucleus, which shows a marginal steric effect. The biological studies showed that the derived spiro heterocyclic systems have an inhibitory effect of 50%. |
| first_indexed | 2024-03-09T22:21:25Z |
| format | Article |
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| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-09T22:21:25Z |
| publishDate | 2022-02-01 |
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| series | Catalysts |
| spelling | doaj.art-a865437729d644f6863e32f195b60c2d2023-11-23T19:13:08ZengMDPI AGCatalysts2073-43442022-02-0112221310.3390/catal12020213Modified 7-Chloro-11<i>H</i>-indeno[1,2-b]quinoxaline Heterocyclic System for Biological ActivitiesNakul Kumar0Gajendra Kumar Inwati1Emad M. Ahmed2Chhagan Lal3Bharat Makwana4Virendra K. Yadav5Saiful Islam6Hyun-Jo Ahn7Krishna K. Yadav8Byong-Hun Jeon9School of Pure and Applied Sciences, Sabarmati University, Ahmedabad 380009, GJ, IndiaDepartment of Chemistry, HVHP Institute of Post Graduate Studies and Research, Sarva Vishwavidyalaya, Kadi 382715, GJ, IndiaDepartment of Physics, College of Science, Taif University, P.O. Box 11099, Taif 21944, Makkah, Saudi ArabiaDepartment of Chemistry, Harcourt Butler Technical University, Kanpur 208002, UP, IndiaDepartment of Chemistry, HVHP Institute of Post Graduate Studies and Research, Sarva Vishwavidyalaya, Kadi 382715, GJ, IndiaDepartment of Microbiology, School of Sciences, P P. Savani University, Surat 394125, GJ, IndiaCivil Engineering Department, College of Engineering, King Khalid University, Abha 61411, Asir, Saudi ArabiaDepartment of Earth Resources and Environmental Engineering, Hanyang University, Seoul 04763, KoreaFaculty of Science and Technology, Madhyanchal Professional University, Ratibad, Bhopal 462044, MP, IndiaDepartment of Earth Resources and Environmental Engineering, Hanyang University, Seoul 04763, KoreaRecent advances in functionalized organic Spiro heterocyclic compounds composed of nitrogen bonded five- and six-membered rings have been made, establishing them as a synthetic target in organic-based biomedical applications. In this work, we report a synthesis of spirocyclic compounds under a one-pot reaction using 1,3-dipolar cycloaddition in a regio and diastereoselective manner. The higher atomic economy with higher yield (95%) and regio and stereoselectivity were achieved by a multi-component reaction of L-proline (1), Indenoquinoxaline (2), and the dipolarophile of malononitrile (3) solvents followed by reflux conditions. The reaction intermediate comprised azomethineylides derived from reactive primary amines, and the spiro derivatives were synthesized up to a ≈ 95% yield. The structural and characteristic chemical components of the as-prepared Spiro compounds were characterized by <sup>1</sup>H-NMR, FTIR, and Mass spectroscopy. The functionalized spiro-pyrrolizidines were found to be effective for biological uses by considering their in vitro screening and antimicrobial impacts. Spiro constituents were found to be much more effective for Gram-positive bacteria due to the stronger lipophilic character of the molecules, and they resulted feasible membrane permeation in a biological system. Based on the planarity geometry of the Spiro pyrrolizidines, meta-substitution possesses steric hindrance and hence shows less effectiveness compared to para-substitution on the same nucleus, which shows a marginal steric effect. The biological studies showed that the derived spiro heterocyclic systems have an inhibitory effect of 50%.https://www.mdpi.com/2073-4344/12/2/213spiro heterocyclicsquinoxalin-11-oneone-pot synthesisazomethineylidesbiomedical uses |
| spellingShingle | Nakul Kumar Gajendra Kumar Inwati Emad M. Ahmed Chhagan Lal Bharat Makwana Virendra K. Yadav Saiful Islam Hyun-Jo Ahn Krishna K. Yadav Byong-Hun Jeon Modified 7-Chloro-11<i>H</i>-indeno[1,2-b]quinoxaline Heterocyclic System for Biological Activities Catalysts spiro heterocyclics quinoxalin-11-one one-pot synthesis azomethineylides biomedical uses |
| title | Modified 7-Chloro-11<i>H</i>-indeno[1,2-b]quinoxaline Heterocyclic System for Biological Activities |
| title_full | Modified 7-Chloro-11<i>H</i>-indeno[1,2-b]quinoxaline Heterocyclic System for Biological Activities |
| title_fullStr | Modified 7-Chloro-11<i>H</i>-indeno[1,2-b]quinoxaline Heterocyclic System for Biological Activities |
| title_full_unstemmed | Modified 7-Chloro-11<i>H</i>-indeno[1,2-b]quinoxaline Heterocyclic System for Biological Activities |
| title_short | Modified 7-Chloro-11<i>H</i>-indeno[1,2-b]quinoxaline Heterocyclic System for Biological Activities |
| title_sort | modified 7 chloro 11 i h i indeno 1 2 b quinoxaline heterocyclic system for biological activities |
| topic | spiro heterocyclics quinoxalin-11-one one-pot synthesis azomethineylides biomedical uses |
| url | https://www.mdpi.com/2073-4344/12/2/213 |
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