Chalcone Derivatives 3a Research Articles

Exploring Regio- and Stereoselectivity in [3+2] Cycloaddition: Molecular Electron Density Theory Approach for Novel Spirooxindole-Based Benzimidazole with Pyridine Spacer

A new ethylene derivative was synthesized as a precursor for the [3+2] cycloaddition (32CA) reaction to access a novel spirooxindole embodied with benzimidazole with a pyridine spacer. The chalcone derivatives 3a–j is obtained with condensation of the acetyl derivative with aryl aldehydes. The one-pot multi-component reaction of the ethylene derivative, 5-Cl-isatin, and octahydroindole-2-carboxylic acid enables the construction of a highly functionalized quaternary center spirooxindole scaffold in a high chemical yield. A study using the Molecular Electron Density Theory (MEDT) explains the complete regio- and stereoselectivity of the reaction, resulting in the exclusive formation of the ortho/endo-cycloadduct under kinetic control. The low activation Gibbs free energy is the result of the supernucleophilic character of the in situ-generated azomethine ylide and the strong electrophilic character of the ethylene derivatives.

Design, Synthesis, and SAR Studies of Some Novel Chalcone Derivatives for Potential Insecticidal Bioefficacy Screening on Spodoptera frugiperda (Lepidoptera: Noctuidae).

Spodoptera frugiperda is a species of the order Lepidoptera. It is one of the species of fall armyworm moths distinguished by its larval life stage, is found in different regions of Africa, and can cause incredible damage. This is the first report produced by the preparation of an indexed combinatorial library of novel chalcone derivatives 3a-k via treatment of 4-formylphenyl4-methylbenzenesulfonate (1) with some acetyl compounds 2a-k in the presence of NaOH. The structures of the synthesized compounds were proven by different spectroscopic techniques such as infrared, 1H NMR, 13C NMR, and elemental analyses. In this work, we studied their toxicity effect against S. frugiperda, followed by a structure-reaction relationship. Moreover, newly prepared chalcone derivatives were tested as insecticides using S. frugiperda. It has been found that most compounds have good to excellent potential effectiveness. Among all of the compounds, 3b, 3g, and 3j exhibited excellent effectiveness. Furthermore, compound 3c showed the most activity, with LC50 = 9.453 ppm of the second instar larva and LC50 = 66.930 of the fourth instar larva .

Synthesis of bis chalcones and transformation into bis heterocyclic compounds with expected antimicrobial activity

One-pot synthesis of novel derivatives of bis-chalcones has been achieved by condensation of 1,4-diacetylbenzene with different aldehydes in basic media. The reaction of chalcone derivatives 3a,b with thioglycolic acid gives compounds 4a,b. This, when reacted with ethyl cyanoacetate in presence of ammonium acetate gives the corresponding cyanopyridine derivatives 5a,b. Furthermore, bis-chalcone 3a,b has been cyclized to pyrazole analogs by using 2,4-dinitrophenylhydrazine to give compounds 7a,b in good yields. All products have been characterized by IR, 1H and 13C NMR, and elemental analysis. The newly synthesised compounds have been screened for anti-bacterial activity.

Design and synthesis of heterocyclic Compounds from 1,4-diacetylbenzene with Expected Antimicrobial Activity

In this present work, synthesized a novel derivatives of bis-chalcones via condensation of 1,4-diacetylbenzene with different aldehydes in basic media. The reaction of chalcone derivatives 3a,b with thioglycolic acid gave compounds 4a,b. That was reacted with ethyl cyanoacetate in presence of ammonium acetate to give the corresponding cyanopyridine derivatives 5a,b. Furthermore, bis-chalcone 3a,b was cyclization to pyrazole analogs by using 2,4-dinitrophenylhydrazine to give compounds 7a,b in good yields. All products were characterized by IR spectrum, 1HNMR, 13CNMR, and elemental analysis. The new compounds have been screened as anti-bacterial activity

Synthesis of four pyrene-containing chalcone derivatives: Achieving excellent third-order nonlinear optical properties by optimizing halopyridines

Four chalcone derivatives 3a–3d based on pyrenyl donor and different halopyridyl acceptors were synthesized successfully. The resultant chromophores 3a–3d were characterized by nuclear magnetic resonance (NMR), high resolution mass spectra (HR-MS) and ultraviolet (UV) spectra. The theoretical calculations and thermal properties of the materials 3a–3d were systematically studied to illustrate structure-performance relationship. Further, a novel and unique method, 4f phase coherent imaging technology, was introduced to investigate the third-order nonlinear optical properties of title compounds 3a–3d with 4 ns laser pulses at 460 nm. The thermal properties, the theoretical calculations and the experimental results consistently indicate that the compound 3b, namely 3-(5-bromopyridin-2-yl)-1-(pyren-1-yl) prop-2-en-1-one, is a more promising candidate for optoelectronic and nonlinear optical devices. Its third-order nonlinear absorption coefficient (β), refraction index (n2) and polarization (χ(33)) are found to be up to such order of magnitude as 10−9 m/W, 10−16 m2/W and 10−11 esu, respectively.

Design, synthesis and anticancer evaluation of novel pyrazole, pyrazolo[3,4-d]pyrimidine and their glycoside derivatives

ABSTRACTThe chalcone derivatives 3a,b were cyclized upon reaction with thiourea to give the pyrazolo[3,4-d]pyrimidine derivatives 5a,b. Condensation of 5a,b and their hydrazide derivatives 8a,b with cyclic and acyclic glucose gave the condensed S- and N-glycosides 7a,b and 9a,b, respectively. Reaction of 3b with ethyl cyanoacetate followed by reaction with cyclic glucose afforded a mixture of the O- and/or N-glycoside isomers 12 and 13, respectively. The pyrazolo[3,4-c]pyrazole derivative 14 was also obtained from the reaction of 3b with hydrazine hydrate. A number of the synthesized compounds were screened for their antitumor activity against three different tumor cell lines HEPG2 (liver), HCT116 (colon) and MCF-7 (breast) with a docking study against CDK2.

Synthesis and antimicrobial activity of novel chalcone derivatives

A series of novel 3-[N, N-bis(2-hydroxyethyl)-amino]-chalcone derivatives 3a–3j were synthesized by the aldol condensation of [N, N-bis(2-hydroethyl)-3-amino]-acetophenone 2 with aromatic aldehydes. Their structures were further confirmed by ESI-HRMS, 1H NMR, IR and elemental analysis. X-ray analysis reveals crystal 3b is a monoclinic system with P21/n space group. The antimicrobial activities of the newly synthesized chalcones in vitro were evaluated and the results indicated that most compounds presented moderate to good antimicrobial activities, especially the antifungal capability. Compounds 3a, 3d, 3f and 3g revealed obvious potency against Candida albicans with MIC values of 32 μg/mL, which were better compared with others.

Potent anti-inflammatory and analgesic activities of new derivatives of chalcone, pyridine, pyrazole, and isoxazole incorporated into 5,6,7,8-tetrahydronaphthalene

Objective Synthesis of new series of 5,6,7,8-tetrahydronaphthalene derivatives conjugated with chalcone, pyridine, pyrazole and isoxazole functionalities hoping to circumvent the unwanted ulcerogenic and other side effects of the already used nonsteroidal anti-inflammatory drugs. Background Most currently used nonsteroidal anti-inflammatory drugs (NSAIDs) suffer from limitation in their therapeutic uses, since they cause gastrointestinal and renal side effects related to inhibition of cyclooxygenase1 (Cox1) in tissues where prostaglandins exert physiological effects. Methodology Reaction of 2-acetyl tetralin (1) with some aromatic aldehydes in the presence of malononitrile yielded 2-amino-3-cyanopyridine derivatives 2a–c. Condensation of compound 1 with aromatic aldehydes afforded the chalcone derivatives 3a–c. Then, compound 3a reacted with hydrazine hydrate or phenyl hydrazine and yielded pyrazoline derivatives 4 or 5, respectively. Also, the reaction of compound 3c with hydroxylamine hydrochloride afforded the isoxazole derivative 6. Anti-inflammatory properties of the synthesized compounds were evaluated in vivo utilizing formalin induced paw edema method in rats, analgesic activities were tested via both hot plate and writhing methods. Results Derivatives 2c and 3c revealed promising results when the anti-inflammatory, analgesic, and ulcerogenic activities of the synthesized compounds were evaluated. All of the compounds induced significant central and peripheral analgesia. The derivatives 2a, 2c, 3a, 3b, 3c, 5, and 6 showed higher activity than the standard ibuprofen.

Synthesis of some novel benzofuran-2-yl(4,5-dihyro-3,5-substituted diphenylpyrazol-1-yl) methanones and studies on the antiproliferative effects and reversal of multidrug resistance of human MDR1-gene transfected mouse lymphoma cells in vitro

A new series of benzofuran-2-yl(4,5-diydro-3,5-substituted diphenylpyrazol-1-yl) methanone derivatives 8a– x by the reaction of the benzofuran-2-carbohydrazides 7 with various chalcone derivatives 3a– x using microwave irradiation has been described. The effect of synthesized compounds 8a– v was studied against human cancer cell lines for their antiproliferative activity and reversal of multidrug resistance on human MDR1-gene transfected mouse lymphoma cells. Among the 24 compounds, the 8c and 8h showed good antiproliferative activity 8b, 8f and 8k were exhibited good MDR reversal activity. The main significance of the process is easy workup process, short reaction time and high yield of the new compounds for biological interest. However, the studies on genetically modified multidrug resistant cancer cells are costly and time consuming.

Unexpected lactonization accompanying addition of ethyl acetoacetate to chalcones derived from 3-acetylthiophene

Chalcone derivatives containing thiophene ring were prepared by the condensation of 3-acetylthiophene with aromatic aldehydes in excellent yields. The addition of ethyl acetoacetate to chalcone derivatives 3a–3h in the presence of solid NaOH in CH2Cl2 resulted in the formation of the mixture of bicyclic lactone derivatives 5a–5h and 6-(ethoxycarbonyl)cyclohexenone derivatives 6a–6h.