Microwave-Assisted Improved Regioselective Synthesis of 3-Benzoyl Indolizine Derivatives

Sumanth, Gopavaram; Saini, Surbhi Mahender; Lakshmikanth, Kyatagani; Mangubhai, Gayakvad Sunitaben; Shivaprasad, Kondreddy; Chandrashekharappa, Sandeep

doi:10.1016/j.molstruc.2023.135561

Cited by 12 publications

(3 citation statements)

References 34 publications

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“…Indolizine is a bridged nitrogen-containing bicyclic heterocyclic moiety (de Souza et al, 2016;Lakshmikanth et al, 2023;Sumanth et al, 2023). It is a 10π electron conjugated planar electronic structure, also known as a bioisostere of indole (Sandeep et al, 2013a(Sandeep et al, , 2014Shivaprasad et al, 2023;Sumanth et al, 2023;Venugopala et al, 2018). The structure is aromatic in nature and has planarity.…”

Section: Introductionmentioning

confidence: 99%

“…Heterocyclic compounds are of great interest in organic chemistry, having various applications in natural products and synthetic pharmaceuticals (Dorai et al., 2023; Ningegowda et al., 2020; Uppar et al., 2021; Uppar, Chandrashekharappa, et al., 2020; Uppar, Mudnakudu‐Nagaraju, et al., 2020; Venugopala et al., 2020). Indolizine is a bridged nitrogen‐containing bicyclic heterocyclic moiety (de Souza et al., 2016; Lakshmikanth et al., 2023; Sumanth et al., 2023). It is a 10 π electron conjugated planar electronic structure, also known as a bioisostere of indole (Sandeep et al., 2013a, 2014; Shivaprasad et al., 2023; Sumanth et al., 2023; Venugopala et al., 2018).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization, and anti‐inflammatory properties of novel ethyl 3‐benzoyl‐7‐(trifluoromethyl)indolizine‐1‐carboxylate derivatives: In silico and in vitro analysis

Singh,

Kushwaha,

Tandon

et al. 2024

Chem Biol Drug Des

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Series of 7‐(Trifluoromethyl) substituted indolizine 4a‐g was synthesized using the one‐pot method. Spectroscopic techniques such as IR, 1H‐NMR, 13C‐NMR, and HRMS were used for the structure confirmation of newly synthesized compounds. These 4a‐g compounds were tested for their anti‐inflammatory activity. In this study, we identified novel indolizine derivative compounds 4a‐g selectively targeting COX‐2 enzyme, tumor necrosis factor‐α (TNF‐α) and, interleukin‐6 (IL‐6). The in silico docking studies of 4a‐g showed that these compounds have a higher affinity for COX‐2 enzyme, TNF‐ α, and IL‐6. In silico ADME profile analysis predicts that these compounds have good gastrointestinal tract and blood–brain barrier absorption. In vitro studies showed that compound 4d significantly reduces the level of COX‐2 enzymes as compared to indomethacin. Compounds 4e, 4f, and 4a were also found to significantly reduce the level of TNF‐α, while compounds 4f, 4g, and 4d, showed a reduction in the level of IL‐6 when compared to indomethacin. Compounds 4a, 4d, and 4f also reduces nitric oxide (NO) level, compared to indomethacin. Overall, the current study illustrates significant anti‐inflammatory activities of these novel 7‐(Trifluoromethyl) substituted indolizine derivatives.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and anti‐inflammatory properties of novel ethyl 3‐benzoyl‐7‐(trifluoromethyl)indolizine‐1‐carboxylate derivatives: In silico and in vitro analysis

Singh,

Kushwaha,

Tandon

et al. 2024

Chem Biol Drug Des

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“…This study is a continuation of our research work in the design and preparation of the nitrogen-containing heterocyclic compound 'Indolizine' as an anti-TB agent. Indolizines are prime focussed due to their interest in synthetic chemistry (Lakshmikanth et al, 2023;Sandeep et al, 2013aSandeep et al, , 2014Sumanth et al, 2023;Venugopala et al, 2018) with medicinal applications like tuberculosis (Khedr et al, 2018;Sandeep Chandrashekharappa et al, 2019;Venugopala, Tratrat, Pillay, et al, 2019), antioxidant (Vijayakumar Uppar, 2020), anticancer , anti-microbial (Sandeep et al, 2013b;Uppar et al, 2021;Vijayakumar Uppar, 2020), anti-inflammatory (Chandrashekharappa, Venugopala, Tratrat, et al, 2018;Sandeep et al, 2017;, larvicidal (Chandrashekharappa, Venugopala, Nayak, et al, 2018;Uppar et al, 2020) and NmeNANAS inhibitor (Alwassil et al, 2019). In this work, we have designed, characterized and evaluated a series of morpholine-containing indolizine derivatives (5a-o) (Table 1) for their anti-tubercular potential.…”

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confidence: 99%

Design, synthesis and characterization of ethyl 3‐benzoyl‐7‐morpholinoindolizine‐1‐carboxylate as anti‐tubercular agents: In silico screening for possible target identification

Tiwari,

Mangubhai,

Kidwai

et al. 2024

Chem Biol Drug Des

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A thorough search for the development of innovative drugs to treat tuberculosis, especially considering the urgent need to address developing drug resistance, we report here a synthetic series of ethyl 3‐benzoyl‐7‐morpholinoindolizine‐1‐carboxylate analogues (5a‐o) as potent anti‐tubercular agents. These morpholino‐indolizines were synthesized by reacting 4‐morpholino pyridinium salts, with various electron‐deficient acetylenes to afford the ethyl 3‐benzoyl‐7‐morpholinoindolizine‐1‐carboxylate analogues (5a‐o). All synthesized intermediate and final compounds are characterized by spectroscopic methods such as 1H NMR, 13C NMR and HRMS and further examined for their anti‐tubercular activity against the M. tuberculosis H37Rv strain (ATCC 27294—American type cell culture). All the compounds screened for anti‐tubercular activity in the range of 6.25–50 μM against the H37Rv strain of Mycobacterium tuberculosis. Compound 5g showed prominent activity with MIC99 2.55 μg/mL whereas compounds 5d and 5j showed activity with MIC99 18.91 μg/mL and 25.07 μg/mL, respectively. In silico analysis of these compounds revealed drug‐likeness. Additionally, the molecular target identification for Malate synthase (PDB 5CBB) is attained by computational approach. The compound 5g with a MIC99 value of 2.55 μg/mL against M. tuberculosis H37Rv emerged as the most promising anti‐TB drug and in silico investigations suggest Malate synthase (5CBB) might be the compound's possible target.

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Larvicidal activity, molecular docking, and molecular dynamics studies of 7-(trifluoromethyl)indolizine derivatives against Anopheles arabiensis

Singh,

Tiwari,

Deb

et al. 2024

Mol Divers

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Microwave-Assisted Improved Regioselective Synthesis of 3-Benzoyl Indolizine Derivatives

Cited by 12 publications

References 34 publications

Synthesis, characterization, and anti‐inflammatory properties of novel ethyl 3‐benzoyl‐7‐(trifluoromethyl)indolizine‐1‐carboxylate derivatives: In silico and in vitro analysis

Synthesis, characterization, and anti‐inflammatory properties of novel ethyl 3‐benzoyl‐7‐(trifluoromethyl)indolizine‐1‐carboxylate derivatives: In silico and in vitro analysis

Design, synthesis and characterization of ethyl 3‐benzoyl‐7‐morpholinoindolizine‐1‐carboxylate as anti‐tubercular agents: In silico screening for possible target identification

Larvicidal activity, molecular docking, and molecular dynamics studies of 7-(trifluoromethyl)indolizine derivatives against Anopheles arabiensis

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