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Microwave-Assisted Facile Synthesis and In vitro Anti- microbial Activities of Some Novel Isoxazole Derivatives via Chalcones
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Isoxazole is an azole with an oxygen atom next to the nitrogen. Isoxazole rings are found in some natural products, such as ibotenic acid and also found in a number of drugs, including COX-2 inhibitor valdecoxib. Furoxan, a nitric oxide donor is containing isoxazolyl group & found in many β-lactamase resistant antibiotics, such as cloxacillin, dicloxacillin and flucloxacillin. The synthetic androgenic steroid danazol also has an isoxazole ring. The substituted isoxazoles are well developed in literature to posses significant biological activities. The disubstituted and trisubstituted isoxazoles have been reported to exhibit broad range of biological activities such as antimicrobial activity, analgesic activity, antiinflammatory activity, antioxidant activity, anticancer activity, CNS activity, antitubercular activity and miscellaneous activities like GABA agonistic activity, inhibitory activity, antihypertensive activity, and glutamate transporter activity. The present review summarizes up to date information of various biological activities of isoxazole analogs.
Isoxazole is a five membered heterocyclic compound having various pharmacological actions. The great interest associated with isoxazoles and their derivatives is based on their versatility as synthetic building blocks, their latent functionalities as enaminones, 1,3-dicarbonyl compounds, γ-amino alcohols, and β-hydroxy nitriles have been widely exploited for the synthesis of other heterocycles and complex molecules. This review paper comprises of up to date information on isoxazole analogs. More emphasis was given to critical discussion on the synthetic strategy of isoxazole derivative, their utility as building blocks in their transformation to more biologically potent molecules. Results of isoxazole derivatives and their substitutions effect on diverse biological activities also presented.
Chalcones (1,3-diaryl-2-propen-1-ones) and their heterocyclic analogues, belong to the flavonoid family, which possess a number of interesting biological properties such as antioxidant, cytotoxic, anticancer, antimicrobial, antiprotozoal, antiulcer, antihistaminic and anti-inflammatory activities. Several pure chalcones have been approved for clinical use or tested in humans. Clinical trials have shown that these compounds reached reasonable plasma concentration and are well-tolerated. For this reason they are an object of continuously growing interest amongst the scientists. However, much of the pharmacological potential of chalcones is still not utilized. The purpose of this review is to provide an overview of the pharmacological activity of naturally occurring and synthetic chalcones. This review highlights more recent pharmacological screening of these compounds, their mechanisms of action and relevant structure-activity relationships.
Despite the impressive scientific and technological advances of recent decades, no effective treatment is currently available for Chagas disease. Our research group has been studying the design and synthesis of analogues of natural lignans aiming to identify compounds with antiparasitic activity. This article reports the synthesis of 42 novel bis-heterocyclic derivatives and the structure-activity relationship study conducted based on results of biological assays against Trypanosoma cruzi amastigotes. Thirty-seven compounds were active, and eight of them had GI50 values lower than 100 μM (GI50 88.4-12.2 μM). A qualitative structure activity relationship study using three dimensional descriptors was carried out and showed a correlation between growth inhibitory potency and the presence of bulky hydrophobic groups located at rings A and D of the compounds. Compound 3-(3,4-dimethoxyphenyl)-5-((4-(4-pentylphenyl)-1H-1,2,3-triazol-1-yl)methyl)isoxazole (31) was the most active in the series (GI50 12.2 μM), showing, in vitro, low toxicity and potency similar to benznidazole (GI50 10.2 μM). These results suggest that this compound can be a promising scaffold for the design of new trypanocidal compounds.
Isoxazole compounds exhibit a wide spectrum of targets and broad biological activities. Developing compounds with heterocycle rings has been one of the trends. The integration of isoxazole ring can offer improved physical-chemical properties. Because of the unique profiles, isoxazole ring becomes a popular moiety in compounds design. In this review article, the major focus has been paid to the applications of isoxazole compounds in treating multiple diseases, including anticancer, antimicrobial, anti-inflammatory, etc. Strategies for compounds design for preclinical, clinical, and FDA approved drugs were discussed. Also, the emphasis has been addressed to the future perspectives and trend for the application.
Chalcone or (E)-1,3-diphenyl-2-propene-1-one scaffold has gained considerable scientific interest in medicinal chemistry owing to its simple chemistry, ease in synthesizing a variety of derivatives and exhibiting a broad range of promising pharmacological activities by modulating several molecular targets. A number of natural and (semi-) synthetic chalcone derivatives have demonstrated admirable anti-inflammatory activity due to their inhibitory potential against various therapeutic targets like cyclooxygenase (COX), lipooxygenase (LOX), interleukins (IL), prostaglandins (PGs), nitric oxide synthase (NOS), leukotriene D4 (LTD4), nuclear factor-κB (NF-κB), intracellular cell adhesion molecule-1 (ICAM-1), vascular cell adhesion molecule-1 (VCAM-1), monocyte chemoattractant protein-1 (MCP-1) and TLR4/MD-2, etc. The chalcone scaffold with hydroxyl, methoxyl, carboxyl, prenyl group and/or heterocyclic ring substitution like thiophene/ furan/indole showed promising anti-inflammatory activity. In this review, a comprehensive study (from the year 1991 to 2016) on multi-targets of inflammatory interest, related inflammation reactions and their treatment by chalcone-based inhibitors acting on various molecular targets entailed in inflammation, structure-activity relationships (SARs), mechanism of actions (MOAs), and patents are highlighted.
Nitrogen containing heterocyclic rings with an oxygen atom is considered as one of the best combination in medicinal chemistry due to their diversified biological activities. Isoxazole, a five membered heterocyclic azole ring is found in naturally occuring ibetonic acid along with some of the marketed drugs such as valdecoxib, flucloxacillin, cloxacillin, dicloxacillin, and danazol. It is also significant for showing antipsychotic activity in risperidone and anticonvulsant activity in zonisamide, the marketed drugs. This review article covers research articles reported till date covering biological activity along with SAR of fused isoxazole derivatives.
The reaction of 5-amino-3-methylisoxazole (1) with formalin and secondary amines gave the corresponding Mannich bases 3, 4, 5, 6. Alkylation of isoxazole derivative 1 with Mannich bases hydrochloride gave unsubstituted isoxazolo[5,4-b]pyridine derivatives 8a, 8b via alkylation at position 4. Moreover, coupling reaction of 1 with different diazonium salts gave the corresponding mono and bisazo dyes of isoxazole derivative. The newly synthesized compounds were screened for their antitumor activity compared with 5-fluorouracil as a well-known cytotoxic agent using Ehrlich ascites carcinoma cells. Interestingly, the obtained results showed clearly that compounds 3, 15, 8b, 4, 8a, and 5 exhibited high antitumor activity than 5-fluorouracil.
The synthesis and characterization of some novel isoxazoles derivatives have been presented. Acylation of resorcinol followed by nuclear prenylation with isoprene gives Chroman. Chroman on treatment with p-substituted benzaldehydes affords substituted chalcones. Isoxazoles have been prepared from chalcones by treating with hydroxylamine hydrochloride. The structure of isoxazoles has been characterized by spectral analysis.
A series of chlorosubstituted 4-aroylisoxazoles have been synthesized by the interaction of chlorosubstituted-3- aroylflavones with hydroxylaminehydrochloride refluxing in ethanol medium with 0.5 ml of piperidine for two hours.Chlorosubstituted-3-aroylflavones were prepared by refluxing the chlorosubstituted-3-aroylflavanones with iodine crystal. Initially chlorosubstituted-3-aroylflavanones have been prepared by the interaction of different aldehydes with 1-(2'-hydroxy-3',5'-dichlorophenyl)-3-phenyl-1,3-propanedione. Constitutions of synthesized compounds have been confirmed on the basis of elemental analysis, molecular weight determination, UV-visible, I.R. and 1H-NMR spectral studies. The titled compounds were evaluated for their antimicrobial activity against fungi species such as Aspergillus niger, Rhizopus species, Curvularia lunata, Drechslera tetramera, Fusarium species, Bipolaris sorokeniana.
For Abstract see ChemInform Abstract in Full Text.
Heterocyclic compounds possess a cyclic structure with two or more different kinds of atoms in the ring. This work is devoted to organic heterocyclic compounds in which the ring contains at least one carbon atom; all atoms other than carbon are considered as heteroatoms. Carbon is still by far the most common ring atom in heterocyclic compounds, but the number and variety of heteroatoms in the rings of known compounds has increased as the years go by and thus there is a steady transition to include the expanding domain of inorganic heterocyclic systems. Since rings can be of any size, from three-membered upwards, and since the heteroatoms can be drawn in almost any combination from a large number of the elements (though nitrogen, oxygen, and sulfur are still by far the most common), the number of possible heterocyclic systems is almost limitless. An enormous number of heterocyclic compounds is known and this number continues to increase very rapidly. The literature of the subject is correspondingly vast and of the three major divisions of organic chemistry, aliphatic, carbocyclic, and heterocyclic, the last is by far the largest. Over 31 million compounds are now recorded in Chemical Abstracts and a very large proportion of these are heterocyclic.
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