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Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

Premansh Dudhe, Mena Asha Krishnan, Kratika Yadav, Diptendu Roy, Krishnan Venkatasubbaiah, Biswarup Pathak and Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463. https://doi.org/10.3762/bjoc.17.101

Supporting Information

Supporting Information File 1: Copies of ¹H, ¹³C NMR spectra of 1a–h, 3aa–ac, 3ba–bc, 3da, 3ea, 3ga, 12a–b, 12e–f, 12i, 14d, 14g and 15, UV calibration curves in different organic solvents for γ-carboline 3ac, and single-crystal XRD data of 3ac.
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Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

Premansh Dudhe, Mena Asha Krishnan, Kratika Yadav, Diptendu Roy, Krishnan Venkatasubbaiah, Biswarup Pathak and Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463. https://doi.org/10.3762/bjoc.17.101

How to Cite

Dudhe, P.; Krishnan, M. A.; Yadav, K.; Roy, D.; Venkatasubbaiah, K.; Pathak, B.; Chelvam, V. Beilstein J. Org. Chem. 2021, 17, 1453–1463. doi:10.3762/bjoc.17.101

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TY  - JOUR
A1  - Dudhe, Premansh
A1  - Krishnan, Mena Asha
A1  - Yadav, Kratika
A1  - Roy, Diptendu
A1  - Venkatasubbaiah, Krishnan
A1  - Pathak, Biswarup
A1  - Chelvam, Venkatesh
T1  - Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation
JF  - Beilstein Journal of Organic Chemistry
PY  - 2021///
VL  - 17
SP  - 1453
EP  - 1463
SN  - 1860-5397
DO  - 10.3762/bjoc.17.101
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.17.101
KW  - γ-carboline
KW  - cascade reaction
KW  - cell uptake
KW  - cytotoxicity
KW  - fluorescence
N2  - 1,5-Disubstituted indole-2-carboxaldehyde derivatives 1a–h and glycine alkyl esters 2a–c are shown to undergo a novel cascade imination-heterocylization in the presence of the organic base DIPEA to provide 1-indolyl-3,5,8-substituted γ-carbolines 3aa–ea in good yields. The γ-carbolines are fluorescent and exhibit anticancer activities against cervical, lung, breast, skin, and kidney cancer cells.
ER  -

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Scholarly Works

Suzdalev, K. F.; Krachkovskaya, A. V.; Lysenko, E. A.; Demidov, O. P. Modeling stages of domino reaction of thiopyrano[4,3- b ]indole-3(5 H )-thiones and dimethyl acetylenedicarboxylate: a new synthetic route to γ-carbolines with thione group. Journal of Sulfur Chemistry 2023, 45, 364–377. doi:10.1080/17415993.2023.2282667
Wang, R.; Huang, R.; Yuan, Y.; Wang, Z.; Shen, K. The anti-breast cancer potential of indole/isatin hybrids. Archiv der Pharmazie 2023, 356, e2300402. doi:10.1002/ardp.202300402
Pavithra, E.; Kannadasan, S.; Shanmugam, P. Synthesis of 5-aryl-3,3'-bis-indolyl and bis-7-aza-indolyl methanone derivatives from 5-bromo-7-azaindoles via sequential methylenation using microwave irradiation, CAN oxidation, and Suzuki coupling reactions. RSC advances 2022, 12, 30712–30721. doi:10.1039/d2ra05849a

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