One-Pot Multi-Component Synthesis and Biological Evaluation of Novel Indole-Pyrimidine Derivatives as Potent Anti-Cancer and Anti-Microbial Agents

Bhaskar, Juluru; Banala, Srinivas; Dasari, Gouthami; Suresh, Palaniswamy

doi:10.1134/s106816202104004x

Cited by 5 publications

(1 citation statement)

References 36 publications

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“…[37,38] They have always been considered as drugs and due to their anti-cancer and antibacterial properties. [39][40][41] Scheme 3 shows equilibrium between Pyrimidine-2 (1H) -one (PYH) (keto-amine form) and pyrimidin-2-ol (PY) (enol-imine form) which result from the transfer of proton between amine group and carbonyl group. In this research, the energy barrier of this transformation in the gas phase and the shortrange and long-range effects of various solvents on the energy barriers have been studied.…”

Section: Introductionmentioning

confidence: 99%

Solvent effects on direct and indirect tautomerism of pyrimidin‐2(1H)‐one/pyrimidin‐2‐ol

Hosseini

2022

J of Physical Organic Chem

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A theoretical study at the B3LYP/6‐311++G(d,p) level on tautomeric conversion of pyrimidin‐2(1H)‐one (PYH) to pyrimidin‐2‐ol (PY) was performed. Two mechanisms have been considered for this processes: (i) one in which the hydrogen is directly transferred, mechanisms A, through TS12 and (ii) another one in which a double hydrogen transfer takes place via TS1122, by formation of the corresponding dimer, mechanisms B. The results associated with the gas phase reveal that overcame to TS12 needs high activation free energies of 34.47 kcal/mol, as a consequence of the strain associated with the formation of the four‐membered transition state, while overcame to TS1122 requires much lower activation free energies, 4.97 kcal/mol. The effect of solvent on the studied tautomerization in implicit, explicit, and a combination of both implicit and explicit solvation models in various media (protic and aprotic polar solvents) has been considered. The results show that the use of a protic polar solvent reduces the energy barrier of the corresponding transition states in a very significant amount.

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Section: Introductionmentioning

confidence: 99%

Solvent effects on direct and indirect tautomerism of pyrimidin‐2(1H)‐one/pyrimidin‐2‐ol

Hosseini

2022

J of Physical Organic Chem

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In vitro Anticancer and Insilico Studies of Quinoxaline‐sulfonyl‐1,2,4‐triazole Hybrids

Dasari¹,

Banala²,

Nukala³

et al. 2022

ChemistrySelect

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New quinoxaline‐sulfonyl‐1,2,4‐triazole hybrids were synthesized (5 a–n) via systematic step‐wise sequence. Later, the in vitro cytotoxicity screening of all these compounds revealed that 2‐((4‐morpholino‐[1,2,4]triazolo[4,3‐a]quinoxalin‐1‐yl)sulfonyl)‐1‐(4‐nitrophenyl)ethenone (5 b), 1‐(4‐methoxy phenyl)‐2‐((4‐morpholino‐[1,2,4]triazolo[4,3‐a]quinoxalin‐1‐yl)sulfonyl) ethenone (5 d),4‐(2‐((4‐morpholino‐[1,2,4]triazolo[4,3‐a] quinoxaline‐1‐yl)sulfonyl)acetyl)benzonitrilen (5 g), 1‐(3,4‐dichloro phenyl)‐2‐((4‐morpholino[1,2,4]triazolo[4,3‐a]quinoxalin‐1‐yl) sulfonyl) ethenone (5 j) and 1‐(2,5‐dimethoxyphenyl)‐2‐((4‐morpholino[1,2,4]triazolo[4,3‐a]quinoxalin‐1‐yl)sulfonyl) ethenone (5 k) were found to more active against the four human cancer cell lines like Hep‐G2 (liver), A‐549 (lung), MCF‐7 (breast) and DU‐145 (prostate) with IC50 values ranging from 1.95±1.34 to 9.61 ±1.72 μM, whereas standard drug displayed IC50 values ranging from 1.97±0.45 to 3.08±0.13 μM. Predominately, compound 5 j displayed superior cytotoxicity against all cell lines than the standard etoposide. As well, the insilico studies of compounds 5 b, 5 d, 5 g, 5 j, and 5 k on EGFR receptor revealed that most potent compound 5 j strongly binds to protein EGFR (pdbid:4HJO). Finally, compounds 5 j and 5 g displayed superior inhibitory activity against tyrosine kinase EGFR than the standard erlotinib.

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Multicomponent reaction strategy to heterocyclic compounds in anticancer drug design

Majee,

Priya,

Kumar

et al. 2024

Green Approaches in Medicinal Chemistry for Sustainable Drug Design

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One-Pot Multi-Component Synthesis and Biological Evaluation of Novel Indole-Pyrimidine Derivatives as Potent Anti-Cancer and Anti-Microbial Agents

Cited by 5 publications

References 36 publications

Solvent effects on direct and indirect tautomerism of pyrimidin‐2(1H)‐one/pyrimidin‐2‐ol

Solvent effects on direct and indirect tautomerism of pyrimidin‐2(1H)‐one/pyrimidin‐2‐ol

In vitro Anticancer and Insilico Studies of Quinoxaline‐sulfonyl‐1,2,4‐triazole Hybrids

Multicomponent reaction strategy to heterocyclic compounds in anticancer drug design

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