25870-74-0

Upstream product

• 115848-67-4 4-methyl-4'-(4-methyl-benzylidenamino)-chalcone 
• 13909-56-3 4'-Nitro-4-methyl-chalkon 
• 104-87-0 4-methyl-benzaldehyde 
• 99-92-3 p-aminobenzophenone 
• 100-19-6 (4-nitrophenyl)ethanone 

Downstream Products

• 911237-90-6 2-amino-4-(4-aminophenyl)-6-(4-methylphenyl)pyrimidine 
• 25870-86-4 1-(4-isothiocyanatophenyl)-3-(4-methylphenyl)-2-propen-1-one 

Relevant academic research and scientific papers

Synthesis, Antiproliferative and Cytotoxic Activities, DNA Binding Features and Molecular Docking Study of Novel Enamine Derivatives

Novel enamine derivatives were synthesized from the reaction of lactone and chalcones and their antiproliferative and cytotoxic activities against six cancer cell lines (e. g., HeLa, HT29, A549, MCF7, PC3 and Hep3B) and one normal cell lines (e. g., FL) were investigated along with their mode of interactions with CT-DNA. Most of the enamine derivatives with IC50 values of 86–168 μM demonstrated much stronger antiproliferative activity than the starting molecules against the cancer cells. While, among the enamine derivatives, four compounds displayed higher cytotoxic potency than the control drugs (5-fluorouracil and cisplatin) against the Hep3B cell lines, these compounds did not exhibit any significant toxicity against normal cells, FL. The UV/VIS spectral data suggest that eight compounds cause hypochromism with a slight bathochromic shift (～6 nm), indicating that they bind to the DNA by way of an intercalative or minor groove binding mode. The binding constants of the compounds are in the range of 0.1×103 M?1–2.3×104 M?1. The antiproliferative activity of studied enamine derivatives could possibly be due to their DNA binding as well as their cytotoxic properties. In addition to these assays, the chalcones and enamine derivatives were investigated by molecular docking to calculate the synergistic effect of antiproliferative activities against six human cancer cell lines.

EGFR inhibitors and apoptotic inducers: Design, synthesis, anticancer activity and docking studies of novel xanthine derivatives carrying chalcone moiety as hybrid molecules

One of the helpful ways to improve the effectiveness of anticancer agents and weaken drug resistance is to use hybrid molecules. therefore, the current study intended to introduce 20 novel xanthine/chalcone hybrids 9–28 of promising anticancer activity. Compounds 10, 11, 13, 14, 16, 20 and 23 exhibited potent inhibition of cancer cells growth with IC50 ranging from 1.0 ± 0.1 to 3.5 ± 0.4 μM compared to doxorubicin with IC50 ranging from 0.90 ± 0.62 to 1.41 ± 0.58 μM and that compounds 11 and 16 were the best. To verify the mechanism of their anticancer activity, compounds 10, 11, 13, 14, 16, 20 and 23 were evaluated for their EGFR inhibitory effect. The study results revealed that compound 11 showed IC50 = 0.3 μM on the target enzyme which is more potent than staurosporine reference drug (IC50 = 0.4 μM). Accordingly, the apoptotic effect of the most potent compounds 11 was extensively investigated and showed a marked increase in Bax level up to 29 folds, and down-regulation in Bcl2 to 0.28 fold, in comparison to the control. Furthermore, the effect of compound 11 on Caspases 3 and 8 was evaluated and was found to increase their levels by 8 and 14 folds, respectively. Also, the effect of compound 11 on the cell cycle and its cytotoxic effect were examined. Moreover, a molecular docking study was adopted to confirm mechanism of action.

3-Aminomethyl pyridine chalcone derivatives: Design, synthesis, DNA binding and cytotoxic studies

Herein we report design, synthesis, and anticancer activity of compounds 6a–h and 11a–j. Compounds 6a–f were designed based on 3-aminomethyl pyridine attached to different acetamide derivatives and in compounds 6g–h it was attached to coumarin moiety. Coumarin containing compounds 6g–h showed very poor anticancer activity against both A549 (Lungs cancer cell line), and MCF-7 (Breast cancer cell line) cell lines in MTT assay. Compounds 11a–j were designed as derivatives of 3-aminomethyl pyridine and 4-amino chalcones. A series of chalcone derivatives of 3-aminomethyl pyridine 11a–j have been synthesized and screened for their in vitro anticancer activity and DNA binding affinity. Most of the compounds showed very good antimitotic activity against A549 cell line as compared to fluorouracil. Compounds 11g and 11i were selected for DNA-binding studies as they showed excellent activity against cancer cell lines in MTT assay. CT-DNA binding affinity of compounds 11g and 11i have been investigated by UV based DNA titration and fluorescence emission study against DNA-EtBr complex. Interestingly, compound 11i has displayed excellent antiproliferative activity, with IC50 0.0067?±?0.0002?μm, against MCF-7 cell line. Compound 11i has been studied for its cytotoxicity using MTT, LDH, as well as EtBr/AO assay and was found to induce apoptosis in the cancerous cell line.

Design, Synthesis, and Antiviral Activity of Novel Chalcone Derivatives Containing a Purine Moiety

To find new antiviral agents, novel chalcone derivatives containing a purine moiety were designed and synthesized by combining bioactive substructures. The antiviral activities of the derivatives against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) were evaluated. Results showed that most of the derivatives showed antiviral activities. Compounds 3n and 3p exhibited excellent curative, protective and inactivation activities against TMV, with the EC50 values of 452.4, 416.2, 241.2 and 438.7, 418.6, 261.7 μg?mL?1, respectively, which were better than those of ribavirin (585.8, 436.0 and 268.7 μg?mL?1). Compounds 3n and 3p showed remarkable curative and protective activities against CMV. Compound 3n showed a moderate affinity to TMV coat protein, with binding constant Ka and Kd values of 1.5 × 104 L?mol?1 and 79.8 μmol?L?1, respectively. These findings provided an important structural insight for further designs of highly active chalcone derivatives and a basis for further study on their mechanism of action.

Naphthoquinone-based chalcone hybrids and derivatives: Synthesis and potent activity against cancer cell lines

Novel naphthoquinone-based chalcones were prepared from the reaction between 3-bromo-nor-β-lapachone and amino-chalcones. Lapachone derivatives are also described here. All the substances were evaluated against cancer and normal cell lines and several compounds demonstrated potent antitumor activity. This journal is

On the investigation of hybrid quinones: Synthesis, electrochemical studies and evaluation of trypanocidal activity

In our continued search for novel trypanocidal compounds, arylamine, chalcone, triazolic, triazole-carbohydrate and chalcogenium derivatives containing a naphthoquinone scaffold were prepared; in addition to electrochemical studies, these compounds were evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease. Among the thirty-eight compounds herein evaluated, six were found to be more potent against trypomastigotes than the standard drug benznidazole, with IC50/24 h values between 52.9 and 89.5 μM.

Synthesis of amino chalcones in presence of ionic liquid as soluble support

A microwave-assisted liquid phase synthesis of aminochalcones was developed by using aldehyde-functionalized ionic liquid as soluble support. Ionic liquid bound aminoacetophenone was treated with aromatic aldehyde to give supported chalcone derivatives. After cleavage, the target compounds were obtained in 83-92 % yields and ≥ 95 % purities without column chromatographic purification. The recovered aldehyde-functionalized ionic liquid could be reused for several times without affecting its activity and the yields of desired compounds were between 86-89 %. These results indicated that the presented method could be applied efficiently to the liquid phase combinatorial chemistry based on aldol condensation.

A study of anti-inflammatory and analgesic activity of new 2,4,6-trisubstituted pyrimidines

Chalcone derivatives (3a - m) were prepared by condensing 4-aminoacetophenone with various substituted aromatic and hetero aromatic aldehydes according to Claisen-Schmidt condensation. These chalcones, on reaction with guanidine hydrochloride under basic alcoholic conditions gave 2,4,6-trisubstituted pyrimidines (5a - m) in quantitative yields. All the newly synthesized pyrimidines were characterized by means of IR, 1H- and 13CNMR, Electron Ionization (EI)-mass and elemental analyses and screened for anti-inflammatory and analgesic activities by in vivo. 2-Amino-4-(4-aminophenyl)-6-(2,4-dichlorophenyl)pyrimidine (5b) and 2-amino-4-(4-aminophenyl)- 6-(3-bromophenyl) pyrimidine (5d) were found to be the most potent anti-inflammatory and analgesic activity compared with ibuprofen, reference standard. And also it was found that compound 5b identified as lead structure among all in both the activities. Pyrimidines which showed good anti-inflammatory activity also displayed better analgesic activity.

Synthesis and antimicrobial activity of some new 2,4,6-trisubstituted pyrimidines

Chalcone derivatives [3(a-m)] were prepared by condensing 4-aminoacetophenone with various substituted aromatic and hetero aromatic aldehydes in dilute ethanolic potassium hydroxide solution at room temperature according to Claisen-Schmidt condensation. These chalcones react with guanidine hydrochloride in a basic alcoholic media to give 2,4,6-trisubstituted pyrimidines [5(a-m)]. All these pyrimidines were characterized by means of their IR, 1H NMR and elemental analyses and screened for their antimicrobial activity. Some of these compounds showed significant antimicrobial activity.

Synthesis and analgesic activity of some chalcones

A series of novel 1-(4′-aminophenyl)-3-(substituted aryl/heteroaryl)-2-propen-1-ones (1-16) have been synthesized by treating 4-amino acetophenone with various substituted aromatic and unsubstituted heterocyclic aldehydes in presence of methanol and aqueous alkaline solution at room temperature. Their structures were confirmed by IR, 1H NMR, 13C NMR, EI-MS spectra and elemental analyses data. The synthesized compounds were investigated for their analgesic activity. Compounds 6 and 15 exhibited maximum analgesic activity. Chalcones with electron releasing substituent like amino, hydroxyl, methyl, halogens etc exhibited good analgesic activity.