Volume 353, Issue 12 2000192
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Synthesis of novel 4,5-dihydropyrrolo[1,2-a]quinoxalines, pyrrolo[1,2-a]quinoxalin]-2-ones and their antituberculosis and anticancer activity

Vitthal B. Makane

Vitthal B. Makane

Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, India

Academy of Scientific and Innovative Research, Ghaziabad, Uttar Pradesh, India

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Eruva Vamshi Krishna

Eruva Vamshi Krishna

Department of Applied Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, India

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Uattam B. Karale

Uattam B. Karale

Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, India

Academy of Scientific and Innovative Research, Ghaziabad, Uttar Pradesh, India

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Dattatraya A. Babar

Dattatraya A. Babar

Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, India

Academy of Scientific and Innovative Research, Ghaziabad, Uttar Pradesh, India

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Saradhi Kalari

Saradhi Kalari

Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, India

Academy of Scientific and Innovative Research, Ghaziabad, Uttar Pradesh, India

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Estharla M. Rekha

Estharla M. Rekha

Department of Pharmacy, Birla Institute of Technology and Science-Pilani, Hyderabad, Telangana, India

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Manjulika Shukla

Manjulika Shukla

Department of Microbiology, CSIR-Central Drug Research Institute, Lucknow, Uttar Pradesh, India

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Grace Kaul

Grace Kaul

Department of Microbiology, CSIR-Central Drug Research Institute, Lucknow, Uttar Pradesh, India

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Dharmarajan Sriram

Dharmarajan Sriram

Department of Pharmacy, Birla Institute of Technology and Science-Pilani, Hyderabad, Telangana, India

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Sidharth Chopra

Sidharth Chopra

Department of Microbiology, CSIR-Central Drug Research Institute, Lucknow, Uttar Pradesh, India

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Sunil Misra

Sunil Misra

Academy of Scientific and Innovative Research, Ghaziabad, Uttar Pradesh, India

Department of Applied Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, India

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Haridas B. Rode

Corresponding Author

Haridas B. Rode

Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, India

Academy of Scientific and Innovative Research, Ghaziabad, Uttar Pradesh, India

Correspondence Haridas B. Rode, Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad, Telangana 500 007, India.

Email: [email protected]

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First published: 12 August 2020
Citations: 14

Abstract

A facile strategy was developed for the synthesis of biologically important 4,5-dihydropyrrolo[1,2-a]quinoxalines and pyrrolo[1,2-a]quinoxalin]-2-ones by treating 2-(1H-pyrrol-1-yl)anilines with imidazo[1,2-a]pyridine-3-carbaldehyde or isatin, using amidosulfonic acid (NH3SO3) as a solid catalyst in water at room temperature. The protocol has been extended to electrophile ninhydrin. The catalyst could be recycled for six times without the loss of activity. The compounds were evaluated for their antituberculosis, antibacterial, and anticancer activities. It is worth noting that compounds 3d and 3e demonstrated a minimum inhibitory concentration value of 6.25 µM against Mycobacterium tuberculosis H37Rv, whereas compounds 3d, 3g, 5d, 5e, and 5i showed a remarkable inhibition of A549, DU145, HeLa, HepG2, MCF-7, and B16-F10 cell lines, respectively. Staphylococcus aureus was inhibited by compounds 5b, 5e, 5d, 5g, and 5l at 32 µg/ml.

CONFLICTS OF INTERESTS

The authors declare that there are no conflicts of interests.

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