Synthesis of Lanso Aminopyrimidines as Dominant Chemotherapeutic Agents for Leukaemia

Pandya, Mayank; Dholaria, Piyush; Kapadiya, Khushal M.

doi:10.1134/s1070428020110147

Cited by 4 publications

(2 citation statements)

References 17 publications

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“…Hybridization and dimerization concepts were introduced to avail the benefit of two or more heterocycles in a single molecular framework. Because of the previous rationale, and in continuation of ongoing research to find diverse structural leads with potential chemotherapeutic and antitubercular activities, 52 53 54 55 56 in the present study, a new series of hybrids ([6,6′-biimidazo[1,2- a ]pyridine]-2,2′-dicarboxamide, 7a – j ) were obtained from ethyl 6-bromoimidazo[1,2- a ]pyridine-2-carboxylate through self-dimerization by Suzuki–Miyaura cross-coupling reaction in a four-step procedure. These compounds were further screened for their in vitro anticancer activity against a panel of 60 human cancer cell lines (nine cancer panels) and H 37 Rv anti-tubercular screening.…”

Section: Chemistrymentioning

confidence: 99%

Regioselective Pd-Catalyzed Suzuki–Miyaura Borylation Reaction for the Dimerization Product of 6-Bromoimidazo[1,2-a]pyridine-2-carboxylate: Mechanistic Pathway, Cytotoxic and Tubercular Studies

Sanghavi

Kapadiya

Sriram

et al. 2023

Synlett

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In the pharmaceutical industry, boronic acid and esters play an important role in API-based synthesis. The most efficient way of preparing various active agents is palladium-catalyzed Suzuki–Miyaura borylation reactions. Herein, we report the formation of dimerization product [6,6′-biimidazo[1,2-a]pyridine]-2,2′-dicarboxamide derivatives 7a–j from 6-bromoimidazo[1,2-a]pyridine-2-carboxylate by employing the same conditions. A regioselective borylation of ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate (3) was examined for the formation of ethyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-2-carboxylate (4a) but it was found to be directed towards the dimerization product 5. The nitrogen-rich system was incorporated into potential anti-cancer and anti-TB agents through acid amine coupling reactions between acid 6 and various amines (dialkyl/cyclic sec./tert.) to form the final adducts 7. Five derived scaffolds were identified as moderately active in TB activity against the H37Rv strain, while two compounds were found to be particularly potent in NCI-60 anti-cancer screening in nine cancer panels.

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Section: Chemistrymentioning

confidence: 99%

Regioselective Pd-Catalyzed Suzuki–Miyaura Borylation Reaction for the Dimerization Product of 6-Bromoimidazo[1,2-a]pyridine-2-carboxylate: Mechanistic Pathway, Cytotoxic and Tubercular Studies

Sanghavi

Kapadiya

Sriram

et al. 2023

Synlett

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“…To extend our efforts towards promising anticancer agents using various natural/nonnatural precursors [48][49][50], herein, we have reported a new class of Gabapentin base hybridpeptide derivatives (11a-11j) and were evaluated for anticancer screening against MCF-7 breast cancer cells line. The structure of newly synthesized peptides was assigned based on IR,…”

Section: Introductionmentioning

confidence: 99%

Anti-Cancer Activity of Gabapentin and Chiral Amino Acids-Based Hybrid-Peptides against MCF-7 Breast Cancer Cell-Line

Pansuriya

Kapadiya

Rathod

et al. 2021

JPRI

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Aims: Herein, we report the cytotoxicity of gabapentin-based peptides (11a-11j) using L-alanine and L-phenyl alanine chiral amino acids for peptide bond formation in ten efficient and straightforward steps. The in vitro MTT assays of derived molecules on the MCF-7 cell line (a human breast adenocarcinoma cell line) exhibited enhanced antitumor activity compared to the control (100% cell proliferation). Methods: The ten steps synthetic methods were adapted for the synthesis of the Gabapentin-based peptide derivatives through BOC- deBOC methods and using EDC-HCl, DMAP and commercially available solvents. All the synthesized peptides were unambiguously characterized with the help of spectroscopic (IR, 1H NMR, 13C-NMR, mass spectra, and elemental) data analysis. Results: The Compounds 11a, 11b, 11h,11i, and 11j showed a remarkable antiproliferative (cell death) activity, with % cell proliferation values ranging from 25-38 %. Conclusion: The study showed that the compounds with some specific functionalities like, benzylic and trifluoromethyl functionality enhanced the potency with comparable %cell proliferation and cell death. Based on the findings in this work and their easily accessible molecular structures, compounds 11a and 11j are worthy of further biological investigations.

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Facile Microwave Synthesis of Pd-Catalyzed Suzuki Reaction for Bis-6-Aryl Imidazo[1,2-a]Pyridine-2-Carboxamide Derivatives with PEG3 Linker

Sanghavi

Dhuda

Kapadiya

2022

Polycyclic Aromatic Compounds

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Synthesis of Lanso Aminopyrimidines as Dominant Chemotherapeutic Agents for Leukaemia

Cited by 4 publications

References 17 publications

Regioselective Pd-Catalyzed Suzuki–Miyaura Borylation Reaction for the Dimerization Product of 6-Bromoimidazo[1,2-a]pyridine-2-carboxylate: Mechanistic Pathway, Cytotoxic and Tubercular Studies

Regioselective Pd-Catalyzed Suzuki–Miyaura Borylation Reaction for the Dimerization Product of 6-Bromoimidazo[1,2-a]pyridine-2-carboxylate: Mechanistic Pathway, Cytotoxic and Tubercular Studies

Anti-Cancer Activity of Gabapentin and Chiral Amino Acids-Based Hybrid-Peptides against MCF-7 Breast Cancer Cell-Line

Facile Microwave Synthesis of Pd-Catalyzed Suzuki Reaction for Bis-6-Aryl Imidazo[1,2-a]Pyridine-2-Carboxamide Derivatives with PEG3 Linker

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