A Convenient Synthesis of New Annelated Pyrimidines and Their Biological Importance

Khan, Mohammad Wahiduzzaman; Uddin, Mohammed Kabir; Ali, Morshed; Rahman, Mohammad Shafiqur; Rashid, Mohammad A.; Chowdhury, Rasheduzzaman

doi:10.1002/jhet.1891

Cited by 7 publications

(3 citation statements)

References 31 publications

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“…To explore the effect of substituents on the benzene ring on the activity of CAM551, two monosubstituted derivatives 4a and 4b were synthesized, which are monosubstituted at the para position of the benzene ring (Scheme 1). Compound 2 was prepared as described by Khan et al [28] Compound 3 was synthesized from 5‐amino‐1‐methylpyrazole‐4‐carboxylic acid ethyl ester and 2‐azahexanone under the catalysis of phosphorus oxychloride, 1‐methyl‐6,7,8,9‐tetrahydropyrazolo[3,4‐ d ]pyrido‐[1,2‐ a ]pyrimidin‐4(1 H )‐one ( 3 ) was obtained. Compound 3 reacts with different substituted benzaldehyde under alkaline conditions to obtain a monosubstituted compound 4 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of tricyclic pyrazolopyrimidine arylidene ester derivatives and their cytotoxic and molecular docking evaluations

Lu,

Nie,

Tang

et al. 2024

Journal of Heterocyclic Chem

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Our research team has synthesized 33 tricyclic pyrazolopyrimidine arylidene ester derivatives using the lead compound CAM551 as a starting point. This was achieved by a designed five‐step synthesis strategy. The synthesized compounds' inhibitory activities against HT‐116 human colorectal adenocarcinoma cell line and HGC27 human gastric cancer cells were assessed through traditional MTT assays. The designed and synthesized compounds demonstrated superior inhibition against both types of cancer cells. Additionally, compound 7b, which contains a long‐chain substituent, exhibited improved inhibition against hepatocellular carcinoma cells and a greater safety profile. These findings indicate that compound 7b has the potential as an antitumor lead compound for future research.

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Section: Resultsmentioning

confidence: 99%

Synthesis of tricyclic pyrazolopyrimidine arylidene ester derivatives and their cytotoxic and molecular docking evaluations

Lu,

Nie,

Tang

et al. 2024

Journal of Heterocyclic Chem

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“…Under the same conditions reported to those employed above, treatment of imines with alkane and aromatic diamines led to new heterocyclic fused pyrimidinones (Scheme 6). The reaction of imines with ethylene diamine afforded the cyclized and stable products (13 and 14) 29,30 which result from the substitution of the cyano group by nucleophilic attack of the aliphatic amine of the intermediate (VIII) rather than the expected cyclic amidine described above. Finally, only the tetracyclic compound (15) was identified in 24% yield when imine (11) reacted with oaminobenzylamine.…”

Section: Scheme 5 Synthesis Of Methyl N-(4-chloro-5h-123-dithiazolmentioning

confidence: 93%

Synthesis of novel heterocyclic fused pyrimidin-4-one derivatives from imino-1,2,3-dithiazoles

Pereira¹,

Sarghe²,

Rouillard³

et al. 2017

Arkivoc

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Extending the potential applications of 4,5-dichloro-1,2,3-dithiazolium chloride chemistry, we investigated the synthesis of original derivatives of thieno [2,3-d]pyrimidin-4-one system by condensation of alkyl and aromatic diamines with 2-N-iminodithiazolothiophene derivatives. We continued our study for access to novel pyrazoloand pyrido-fused pyrimidinones using the potential applications of Appel's salt chemistry.

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“…Well-established procedures from the literature were applied for the synthesis of 50 [ 22 ] , 51 [ 15 ], 52 [ 23 ], and 53 [ 24 ].…”

Section: Methodsmentioning

confidence: 99%

Optimization of Pyrazole Compounds as Antibiotic Adjuvants Active against Colistin- and Carbapenem-Resistant Acinetobacter baumannii

et al. 2022

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The diffusion of antibiotic-resistant, Gram-negative, opportunistic pathogens, an increasingly important global public health issue, causes a significant socioeconomic burden. Acinetobacter baumannii isolates, despite causing a lower number of infections than Enterobacterales, often show multidrug-resistant phenotypes. Carbapenem resistance is also rather common, prompting the WHO to include carbapenem-resistant A. baumannii as a “critical priority” for the discovery and development of new antibacterial agents. In a previous work, we identified several series of compounds showing either direct-acting or synergistic activity against relevant Gram-negative species, including A. baumannii. Among these, two pyrazole compounds, despite being devoid of any direct-acting activity, showed remarkable synergistic activity in the presence of a subinhibitory concentration of colistin on K. pneumoniae and A. baumannii and served as a starting point for the synthesis of new analogues. In this work, a new series of 47 pyrazole compounds was synthesized. Some compounds showed significant direct-acting antibacterial activity on Gram-positive organisms. Furthermore, an evaluation of their activity as potential antibiotic adjuvants allowed for the identification of two highly active compounds on MDR Acinetobacter baumannii, including colistin-resistant isolates. This work confirms the interest in pyrazole amides as a starting point for the optimization of synergistic antibacterial compounds active on antibiotic-resistant, Gram-negative pathogens.

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A Convenient Synthesis of New Annelated Pyrimidines and Their Biological Importance

Cited by 7 publications

References 31 publications

Synthesis of tricyclic pyrazolopyrimidine arylidene ester derivatives and their cytotoxic and molecular docking evaluations

Synthesis of tricyclic pyrazolopyrimidine arylidene ester derivatives and their cytotoxic and molecular docking evaluations

Synthesis of novel heterocyclic fused pyrimidin-4-one derivatives from imino-1,2,3-dithiazoles

Optimization of Pyrazole Compounds as Antibiotic Adjuvants Active against Colistin- and Carbapenem-Resistant Acinetobacter baumannii

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