Synthesis and antibacterial activity of novel 4-{4-(methylamino)thieno[3,2-d]pyrimidin-2-yl}-benzohydrazide derivatives

Giri, Tapan Kumar; Sailaja, G.; Eppakayala, Laxminarayana; Chary, M. Thirumala; Ramesh, M.

doi:10.1134/s1070363217060238

Cited by 4 publications

(3 citation statements)

References 8 publications

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“…Compound 58d reduced parasitemia by more than 99.8% when administered orally (50 mg/kg once daily for 4 days). This administration scheme led to a mean survival time of 23 González Cabrera et al were interested in similar derivatives but including an amine function at position 4 of the thienopyrimidine core [35,54]. A SAR study demonstrated the influence of various substituents at positions 2, 4, and 6 of the thieno [3,2-d]pyrimidine ring (Table 5).…”

Section: % Inhibition Pf3d7mentioning

confidence: 99%

“…Among these three compounds, only 2,4-dichlorothieno [3,2-d]pyrimidine (Figure 8) showed a low antibacterial activity against one bacterial strain, B. subtilis with 43% inhibition at 100 μM. [3,2-d]pyrimidine derivatives including an acyl hydrazone moiety as potential antibacterial agents [23]. All derivatives were evaluated in vitro against E. coli, Pseudomonas sp., S. aureus, and Bacillus sp.…”

Section: Ampicillinmentioning

confidence: 99%

“…However, the exhibited antibacterial activities were twice lower than the reference drug streptomycin. Giri et al identified new thieno [3,2-d]pyrimidine derivatives including an acyl hydrazone moiety as potential antibacterial agents [23]. All derivatives were evaluated in vitro against E. coli, Pseudomonas sp., S. aureus, and Bacillus sp.…”

Section: Ampicillinmentioning

confidence: 99%

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Thienopyrimidine: A Promising Scaffold to Access Anti-Infective Agents

et al. 2021

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Thienopyrimidines are widely represented in the literature, mainly due to their structural relationship with purine base such as adenine and guanine. This current review presents three isomers—thieno[2,3-d]pyrimidines, thieno[3,2-d]pyrimidines and thieno[3,4-d]pyrimidines—and their anti-infective properties. Broad-spectrum thienopyrimidines with biological properties such as antibacterial, antifungal, antiparasitic and antiviral inspired us to analyze and compile their structure–activity relationship (SAR) and classify their synthetic pathways. This review explains the main access route to synthesize thienopyrimidines from thiophene derivatives or from pyrimidine analogs. In addition, SAR study and promising anti-infective activity of these scaffolds are summarized in figures and explanatory diagrams. Ligand–receptor interactions were modeled when the biological target was identified and the crystal structure was solved.

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Section: % Inhibition Pf3d7mentioning

confidence: 99%

Section: Ampicillinmentioning

confidence: 99%

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Thienopyrimidine: A Promising Scaffold to Access Anti-Infective Agents

et al. 2021

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Fused Thienopyrimidines as Versatile Pharmacophores for the Development of Cyclooxygenase‐2 Inhibitors

Thakur,

Arora,

Katiyar

et al. 2024

ChemistrySelect

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Inflammation is an essential body immune system response against various infections and tissue injuries and maintains normal homeostasis. Alterations in inflammatory responses lead to multiple disorders like heart diseases, obesity, diabetes, cancer, stroke, and neurodegenerative disorders. Cyclooxygenases (COXs), the enzymes, exist in two isoforms (COX‐1 and COX‐2) that catalyze the rate‐determining step of prostaglandin biogenesis and play a significant role in inflammation. COX‐2 inhibitors, although effective anti‐inflammatory agents are considered to be highly unsafe for long‐term usage due to their possible side and adversative effects. Recently, fused‐thienopyrimidines have emerged as a privileged scaffold with excellent anti‐inflammatory potential. In the present review, we have emphasized the recent developments in the design and synthetic strategies of fused‐thienopyrimidine derivatives and their detailed structure‐activity‐relationship (SAR) studies. The primary goal of this review is to provide restructuring knowledge about this template, which could prove beneficial and valuable for chemists working in the anti‐inflammatory area.

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Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C₂₆H₁₇N₅O₄

Wei

Jing³

2022

Zeitschrift Für Kristallographie - New Crystal Structures

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C46H38N10S2, triclinic, P 1 ‾ $P\overline{1}$ (no. 2), a = 8.9297(12) Å, b = 10.9926(15) Å, c = 12.6758(18) Å, α = 104.532(2)°, β = 96.312(2)°, γ = 112.398(2)° V = 1083.8(3) Å3, Z = 2, R gt (F) = 0.0398, wR ref (F 2) = 0.1195, T = 296(2) K.

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Synthesis and antibacterial activity of novel 4-{4-(methylamino)thieno[3,2-d]pyrimidin-2-yl}-benzohydrazide derivatives

Cited by 4 publications

References 8 publications

Thienopyrimidine: A Promising Scaffold to Access Anti-Infective Agents

Thienopyrimidine: A Promising Scaffold to Access Anti-Infective Agents

Fused Thienopyrimidines as Versatile Pharmacophores for the Development of Cyclooxygenase‐2 Inhibitors

Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C₂₆H₁₇N₅O₄

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Synthesis and antibacterial activity of novel 4-{4-(methylamino)thieno[3,2-d]pyrimidin-2-yl}-benzohydrazide derivatives

Cited by 4 publications

References 8 publications

Thienopyrimidine: A Promising Scaffold to Access Anti-Infective Agents

Thienopyrimidine: A Promising Scaffold to Access Anti-Infective Agents

Fused Thienopyrimidines as Versatile Pharmacophores for the Development of Cyclooxygenase‐2 Inhibitors

Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4

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Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C₂₆H₁₇N₅O₄