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ChemInform Abstract: One Pot Synthesis of Fused Chromene-pyrano-pyrimidines and Evaluation of Their Antimicrobial Activity.
Abstract
An efficient synthesis of novel fused chromeno-pyrano-pyrimidines 6a-j has been achieved by a mild sodium acetate catalyzed one pot sequential multi-component reaction. All the compounds have been isolated as pure products from the reaction mixture in goodyield. The synthesized compounds have been evaluated for their antimicrobial activity against gram negative E. coli strain wherein compounds 6b, 6c and 6f display noteworthy antimicrobial activity. Minimum inhibitory concentrations of the compounds are reported.
... Previous studies have indicated that monocarbonyl analogs of curcumin (MACs) without the β-diketone moiety have shown better anti-inflammatory and antibacterial activities than curcumin. [15] Coumarin is another naturally occurring compound that acquires a wide spectrum of pharmacological and physiological activities which include antibacterial, [16,17] antitumor, [18] antioxidant, [19,20] and anti-inflammatory. [21,22] Coumarin is found naturally in many plants and could be used as an important component of various functional materials. ...
... Although these compounds have been widely studied individually due to their inherent pharmacological properties but only recently, fused structures incorporating both pyrimidine and chromene moieties were synthesized. Several studies have been conducted previously for antimicrobial activities, and the majority had focused on the synthesis of Chromeno-pyrano-pyrimidines, chromenopyrimidine-amine and Pyrimidine-thienopyridine derivatives [24][25][26]. The synthesized compounds have been evaluated for their antimicrobial activities respectively. ...
The aim of the study is to design and synthesize the new bioactive heterocyclic compounds.
Pyrimidine is an important class of heterocyclic compound that are known to possess important pharmacological and antimicrobial properties. 2H-chromenes are also known to possess antimicrobial properties. Chromeno pyrimidines are compounds having both pyrimidines and 2H-chromenes in their structures. Hence, the synthesis of novel chromeno pyrimidine containing chloro, fluoro, trifluoromethyl groups have been carried out by multi-step organic
synthesis, in order to study their interesting antimicrobial properties. The synthesized compounds were characterized by 1H NMR, 13C NMR, 19F NMR, FT-IR, GC-MS and elemental analysis. They were screened for their antibacterial activities against Gram-positive
(Staphylococcus aureus, Bacillus subtilis), Gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria and antifungal activities against Aspergillus niger and Candida albicans by cup plate method. The fluoro and trifluro methyl derivatives showed the highest antimicrobial activity compared to the others. The trifluoro derivative (6c2) exhibited excellent results with the highest inhibition zone of 26mm in 100 µg/ mL against Bacillus subtilis and
23mm in 100 µg/ mL against Pseudomonas aeruginosa.
Keywords: Chremeno pyramidines, antibacterial, antifungal, synthesis, novel drugs.
... These derivatives have shown a remarkably broad spectrum of pharmacological and physiological activities and they are used as anticoagulant (Abdelhafez et al., 2010;Au and Rettie, 2008;Ganguly et al., 2013;Guo et al., 2013;Palareti and Legnani, 1996;Pelz et al., 2005;Simon and Shaughnessy, 2004;Van Walraven et al., 2002), antibacterial (Brahmbhatt et al., 2013;Cespedes et al., 2006;El-Dean et al., 2013;Kidwai et al., 2014;Kumari et al., 2013;Musthafa et al., 2013;Pansuriya and Patel, 2007;Prasad et al., 2014), antifungal (Chohan et al., 2006;Rehman et al., 2005), antiviral (Kirkiacharian et al., 2008;Zavrsnik et al., 2011), antitumor (Arya et al., 2014;Bi et al., 2013;Dorababu et al., 2013;Farghaly et al., 2014;Kawaii et al., 2001;Kumar et al., 2013;Pingaew et al., 2014;Salinas-Jazmin et al., 2010;Loa et al., 2009), anticonvulsant (Jaweed Mukarram et al., 2005), antiprotozoal (Tasdemir et al., 2006), insecticidal , fungicide (Oliva et al., 2003), antimycobacterial (Abou-Melha and Faruk, 2008;Kotharkar and Shinde, 2006;Mostafa, 2008;Sukdolak et al., 2005;Zavrsnik et al., 2008), antimutagenic (Edenharder and Tang, 1997), antioxidant (Foti et al., 1996;Jung and Park, 2009;Kaneko et al., 2001;Senol et al., 2010;Vukovic et al., 2010aVukovic et al., , 2010b, and anti-inflammatory agents (Ahmad et al., 2009;Luchini et al., 2008). Also, in recent years there are references to derivatives with HIV protease inhibitors (Chiang et al., 2007;Khan et al., 2004aKhan et al., , 2004bKostova et al., 2004;Liu et al., 2009;Manolov et al., 2004;Mao et al., 2002;Mitra et al., 1998;Raleva et al., 2005;Skulnick et al., 1996;Su et al., 2006), and tyrosine kinase inhibitors (Yang et al., 1999). ...
This review aims to document the publications concerning 4-hydroxycoumarin, its synthesis, chemical reactivity and reactions during the period from 1996 up to now.
Chromenes are a significant family of heterocyclic chemicals that have a wide range of biological applications, a simple chemical structure, and only mildly undesirable side effects. The synthesis of a wide range of chromene analogs that displayed unexpected behaviors via numerous mechanisms was investigated by a number of different research teams, which led to the discovery of multiple pathways for their synthesis. In addition, different chromene-fused heterocycles exhibit a wide variety of fascinating biological actions, including those that are anticancer, anticonvulsant, antibacterial, anticholinesterase, antituberculosis, and anti-diabetic. In light of this, the purpose of this study is to highlight the many synthesis techniques and antibacterial activity associated with chromene-fused heterocyclic compounds. Moreover, such research can open avenues for exploring other therapeutic applications of these compounds in various disease areas, as their biological activities extend beyond antibacterial effects.
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A number of derivatives of isoxazolo[4,3‐ d ]pyrimidine and isoxazolo[4,5‐ d ]pyrimidine were prepared with potential anticancer activity. Condensation of 4‐amino‐5‐benzoyl‐isoxazolo‐3‐carboxylic acid hydrazide with ethyl orthoformate and then with different amines gave a series of 3‐benzoyl‐7‐oxo‐7 H ‐isoxazolo[4,3‐ d ]pyrimidin‐6‐yl‐aryliden‐formamidine. A series of 5‐aminomethyl‐7‐phenyl‐isoxazolo[4,5‐ d ]pyrimidine‐3‐carboxamide was obtained from 4‐amino‐5‐benzoylisoxazole‐3‐carboxamide with acetonitrile, and chloroacetonitrile with gaseous hydrogen chloride. Some of these compounds were tested for their cytotoxic activity. J. Heterocyclic Chem., (2010).
Procedures were developed for the synthesis of substituted bis(2,5-dimethyl-3-thienyl)furans based on 1,2-bis(2,5-dimethyl-3-thienyl)-2-hydroxyethanone. Dithienylethene structures in which the ethene fragment is involved in the furan or furopyrimidine system possess photochromic properties and their open forms exhibit fluorescence.
Piperidinylpyrimidine derivatives, previously prepared as inhibitors of TNF-alpha production, were evaluated for their inhibitory activity against HIV-1 LTR activation. Some of these derivatives inhibited activation of HIV-1 LTR-directed CAT gene expression induced by PMA in Jurkat cells. In this report, we describe SAR in this series of compounds and show that the 3,4-methylenedioxybenzoyl (piperonyloyl) group on the nitrogen of piperidine and lipophilic substitution at the C(6)-position of pyrimidine are important for this inhibitory activity. Some of the synthesized compounds also inhibited HIV-1 LTR transactivation induced by viral protein Tat. These results suggest that piperidinylpyrimidines are useful as potent AIDS therapeutics that directly inhibit HIV-1 LTR activation and indirectly suppress TNF-alpha production.
Dicamphanoyl khellactone (DCK) is a coumarin derivative that can potently inhibit HIV-1 replication. DCK does not inhibit RNA-dependent DNA synthesis. However, an HIV reverse transcriptase (RT) inhibitor-resistant strain, HIV-1/RTMDR1, is resistant to DCK. Thus, it is possible that HIV-1 RT is the target of DCK. To test this possibility, DCK-resistant viruses were selected in the presence of DCK. Our results indicate that a single amino acid mutation, E138K in HIV-1 RT, is sufficient to confer DCK resistance. Interestingly, a DCK derivative, 3'R,4'R-Di-O-(-)-camphanoyl-2-ethyl-2',2'-dimethyldihydropyrano[2,3-f]chromone (DCP8), is effective against HIV-1/RTMDR1. However, the DCK-escape virus carrying the E138K mutation remains resistant to DCP8. Since DCK did not inhibit the RNA-dependent DNA polymerase activity of HIV-1 RT when using poly-rA or poly-rC as template, we evaluated the effect of DCK on the DNA-dependent DNA polymerase activity of HIV-1 RT. Our results indicate that DCK can inhibit the DNA-dependent DNA polymerase activity of HIV-1 RT. In conclusion, DCK is a unique HIV-1 RT inhibitor that inhibits the DNA-dependent DNA polymerase activity. In contrast, DCK did not significantly affect the RNA-dependent DNA polymerase activity when poly-rA or poly-rC was used as templates. An E138K mutation in the non-nucleoside RT inhibitors (NNRTIs) binding pocket of HIV-1 RT confers resistance to DCK and its chromone derivative, DCP8.
The six novel 4-methylcoumarins bearing different functionalities such as amino, hydroxy, N-acetyl, acetoxy and nitro have been synthesized and confirmed on the basis of their spectral data (1H-, 13C-NMR, UV, IR and EI mass). They were examined for the first time for their effect on NADPH dependent liver microsomal lipid peroxidation in vitro, and the results were compared with other model 4-methylcoumarin derivatives to establish the structure-activity relationship. Our studies demonstrated that amino group is an effective substitute for the hydroxyl group for antioxidant property and produced a dramatic inhibition of lipid peroxidation. Ortho dihydroxy and ortho hydroxy-amino coumarins were found to possess highest antioxidant and radical scavenging activities.
Coumarin and its derivative 7-hydroxycoumarin (7-OHC) have antitumor and antimetastatic properties. The purpose of this study was to investigate the possible effects of these compounds on expression of the bcl-2 and Bax oncoproteins in two human lung cancer cell lines, A427 and Calu-1. The cells were cultured in vitro for 24 h in RPMI 1640 with 1.5% (v/v) ethanol, 1.0 mM ethanolic coumarin or 1.0 mM ethanolic 7-OHC. Viability was determined in each cell line by an MTT assay. Total protein was extracted from cell lysates and the bcl-2 and Bax oncoproteins were identified. Western blotting showed a decrease in bcl-2 and an increase in Bax in A427 cells cultured with coumarin or 7-OHC. Neither drug changed bcl-2 expression in Calu-1 cells compared to solvent controls, and Bax expression was only slightly increased by coumarin. We conclude that 7-OHC is a more potent inhibitor of cell proliferation than coumarin and has more marked effects on oncoprotein expression. Also, the A427 cell line was more sensitive to the drugs than Calu-1.
The multiple parallel synthesis of a series of N,S-bis-alkylated thiopyrazolo[3,4-d]pyrimidines, based on sequential S- then N-alkylation, is reported. These compounds showed significant anti-mycobacterial activity (MICs down to 2mug/ml) and their potential as significant drug-like leads is substantiated through cytotoxicity evaluation and in silico profiling.