Synthesis, characterization, antibacterial and antifungal activity of thienopyrimidines and triazolothienopyrimidines

Panchamukhi, Shridhar I.; Iqbal, Ahsan; Khan, Ashraf Y.; Kalashetti, M. B.; Khazi, I. M.

doi:10.1007/s11094-011-0545-7

Cited by 14 publications

(6 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The inhibitors molecules induce cell death by trapping the gyrase DNA complex, inducing oxidative damage, and preventing DNA replication. 4 Thienopyrimidines represent important chemical class in drug discovery due to vast range of pharmacological properties including antiallergic, 5 antiviral, [6][7] anti-in-flammatory, [8][9][10][11][12] analgesic, [13][14] antispasmodic, antibacterial, [14][15] antifungal, 16 antimicrobial, [17][18][19][20][21] antidiabetic, 22 antioxidant, 23 antitumor, [24][25][26][27][28][29] antipsychotic 30 etc. This useful activity of thienopyrimidine generates our interest in developing a tool for screening novel thienopyrimidine analogs are promise antibacterial agent.…”

Section: Introductionmentioning

confidence: 99%

Combined 3D-QSAR and Molecular Docking Analysis of Thienopyrimidine Derivatives as Staphylococcus aureus Inhibitors

Ouassaf¹,

Belaidi

Khamouli³

et al. 2021

ACSi

View full text Add to dashboard Cite

The discovery of antibacterials is considered one of the greatest medical achievements of all time. In this work, a combination of three computational analyzes: 3D-QSAR, molecular docking and ADME evaluation were applied in thienopyrimidine derivatives intended toward gram-positive bacterium Staphylococcus aureus. The validity of 3D-QSAR model was tested with a set of data which is divided into a training and a test set. The two models constructed (CoMFA and CoMSIA) show good statistical reliability (q2 = 0.758; r2 = 0.96; r2pred = 0.783) and (q2 = 0.744; r2 = 0.97; r2pred = 0.625) respectively. In addition, docking methods were applied to understand the structural features responsible for the affinity of the ligands in the binding of S. aureus DNA gyrase. Drug likeness and ADME analysis applied in this series of new proposed compounds, have shown that the five lead molecules would have the potential to be effective drugs and could be used as a starting point for designing compounds against Staphylococcus aureus.

show abstract

Section: Introductionmentioning

confidence: 99%

Combined 3D-QSAR and Molecular Docking Analysis of Thienopyrimidine Derivatives as Staphylococcus aureus Inhibitors

Ouassaf¹,

Belaidi

Khamouli³

et al. 2021

ACSi

View full text Add to dashboard Cite

show abstract

“…This led the medicinal chemist to take a deep interest in molecular modification of thienopyrimidines which resulted in several marketed drugs containing thienopyrimidine scaffolds [17] . Thienopyrimidines are active analgesics, [18] anti‐pyretic, [19] anti‐hypertensive, [20] anti‐inflammatory, [21] anti‐bacterial, [22] anti‐fungal, [23] anti‐viral [24] and potent anti‐histaminic agents [25] . Selected examples of thienopyrimidines as potent pharmacological agents are shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Thieno[3,2‐d]pyrimidine Derivatives through Sequential S_NAr and Suzuki Reactions as Selective h‐NTPDase Inhibitors

et al. 2023

View full text Add to dashboard Cite

In this study various of thieno[3,2‐d]pyrimidine derivatives have been synthesized by treating different secondary amines through aromatic nucleophilic substitution reaction (SNAr) followed by Suzuki reaction with aryl and heteroaryl boronic acids. A bis‐Suzuki coupling was also performed to generate bis‐aryl thienopyrimidine derivatives. The synthesized compounds were screened for the hydrolytic activity of h‐NTPdase1, h‐NTPdase2, h‐NTPdase3, and h‐NTPdase8. The compound N‐benzyl‐N‐methyl‐7‐phenylthieno[3,2‐d]pyrimidin‐4‐amine 3 j selectively inhibits the activity of h‐NTPdase1 with IC50 value of 0.62±0.02 μM whereas, the compound 4 d was the most potent inhibitor of h‐NTPdase2 with sub‐micromolar IC50 value of 0.33±0.09 μM. Similarly, compounds 4 c and 3 b were found to be selective inhibitors for isozymes h‐NTPdase3 (IC50=0.13±0.06 μM) and h‐NTPdase8 (IC50=0.32±0.10 μM), respectively. The molecular docking study of the compounds with the highest potency and selectivity revealed the interactions with the important amino acid residues.

show abstract

“…[2][3][4] On the other hand, the classes of tricyclic compounds bearing thienopyrimidine scaffolds have been the focus of great interest because of their pharmacological activities, such as antitumor, [5][6][7][8][9] antiallergic, anti-inflammatory, analgesic, antifungal and antibacterial activities. [10][11][12][13][14][15][16][17][18][19][20] Consequently, thienopyrimidines have become an important class of compounds in drug discovery programs and the medicinal chemistry. [21][22][23][24][25] In continuation of our previous work on biologically active nitrogen and sulfur heterocycles, [26][27][28][29] it was of interest to synthesize some novel thieno [2,3-d:4,5-d`]dipyrimidine derivatives and evaluate these compounds for their cytotoxic activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Cytotoxic Activity of Some Novel Thieno[2,3-d:4,5-d’]Dipyrimidine Derivatives

El‐Sayed¹,

Fadda²

2018

ACSi

View full text Add to dashboard Cite

Synthesis of some novel tricyclic compounds bearing thienodipyrimidine moiety by the reaction of ethyl 6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[3,2-d]pyrimidine-7-carboxylate (1) with different types of aromatic amines to give the corresponding carboxamide derivatives 2-11, which cyclized with triethyl orthoformate in acetic anhydride to afford thieno[2,3-d:4,5-d']dipyrimidine derivatives 12-15 is described. Similarly, thieno[2,3-d:4,5-d']dipyrimidine derivative 17 was also prepared via the reaction of carboxamide derivative 2 with chloroacetyl chloride in chloroform to give thieno[3,2-d]pyrimidine-7-carboxamide derivative 16, followed by a cyclization in boiling acetic anhydride. The structure of these compounds was confirmed on the basis of their spectral and analytical data such as IR, 1 H-NMR, 13 C-NMR spectroscopy and mass spectral data. The synthesized compounds were screened for their cytotoxic activity.

show abstract

Synthesis, characterization, antibacterial and antifungal activity of thienopyrimidines and triazolothienopyrimidines

Cited by 14 publications

References 5 publications

Combined 3D-QSAR and Molecular Docking Analysis of Thienopyrimidine Derivatives as Staphylococcus aureus Inhibitors

Combined 3D-QSAR and Molecular Docking Analysis of Thienopyrimidine Derivatives as Staphylococcus aureus Inhibitors

Synthesis of Thieno[3,2‐d]pyrimidine Derivatives through Sequential S_NAr and Suzuki Reactions as Selective h‐NTPDase Inhibitors

Synthesis and Cytotoxic Activity of Some Novel Thieno[2,3-d:4,5-d’]Dipyrimidine Derivatives

Contact Info

Product

Resources

About

Synthesis, characterization, antibacterial and antifungal activity of thienopyrimidines and triazolothienopyrimidines

Cited by 14 publications

References 5 publications

Combined 3D-QSAR and Molecular Docking Analysis of Thienopyrimidine Derivatives as Staphylococcus aureus Inhibitors

Combined 3D-QSAR and Molecular Docking Analysis of Thienopyrimidine Derivatives as Staphylococcus aureus Inhibitors

Synthesis of Thieno[3,2‐d]pyrimidine Derivatives through Sequential SNAr and Suzuki Reactions as Selective h‐NTPDase Inhibitors

Synthesis and Cytotoxic Activity of Some Novel Thieno[2,3-d:4,5-d’]Dipyrimidine Derivatives

Contact Info

Product

Resources

About

Synthesis of Thieno[3,2‐d]pyrimidine Derivatives through Sequential S_NAr and Suzuki Reactions as Selective h‐NTPDase Inhibitors