An efficient synthesis of new caffeine-based chalcones, pyrazolines and pyrazolo[3,4-b][1,4]diazepines as potential antimalarial, antitrypanosomal and antileishmanial agents

Insuasty, Braulio; Ramírez, Juan; Becerra, Diana; Echeverry, Carlos; Quiroga, Jairo; Abonı́a, Rodrigo; Robledo, Sara M.; Vélez, Iván Darío; Upegui, Yulieth; Muñoz, July A.; Ospina, Victoria; Nogueras, Manuel; Cobo, Justo

doi:10.1016/j.ejmech.2015.02.040

Cited by 81 publications

(41 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Non-specific absorbance was corrected by subtracting the O.D of the blank. Determinations were done by triplicate in at least two independent experiments [51].…”

Section: In Vitro Cytotoxicitymentioning

confidence: 99%

Triclosan-caffeic acid hybrids: Synthesis, leishmanicidal, trypanocidal and cytotoxic activities

Otero

García

Palacios

et al. 2017

European Journal of Medicinal Chemistry

Self Cite

View full text Add to dashboard Cite

The synthesis, cytotoxicity, anti-leishmanial and anti-trypanosomal activities of twelve triclosan-caffeic acid hybrids are described herein. The structure of the synthesized products was elucidated by a combination of spectrometric analyses. The synthesized compounds were evaluated against amastigotes forms of L. (V) panamensis, which is the most prevalent Leishmania species in Colombia, and against Trypanosoma cruzi, which is the pathogenic species to humans. Cytotoxicity was evaluated against human U-937 macrophages. Eight compounds were active against L. 26 and 28, the remaining compounds were toxic for mammalian cells, yet they have potential to be considered as candidates for anti-trypanosomal and anti-leishmanial drug development. The activity is dependent on the length of the alkyl linker with compound 19, bearing a four-carbon alkyl chain, the most performing hybrid. In general, hydroxyl groups increase both activity and cytotoxicity and the presence of the double bond in the side chain is not decisive for cytotoxicity and anti-protozoal activity.

show abstract

“…Non-specific absorbance was corrected by subtracting the O.D of the blank. Determinations were done by triplicate in at least two independent experiments [51].…”

Section: In Vitro Cytotoxicitymentioning

confidence: 99%

Triclosan-caffeic acid hybrids: Synthesis, leishmanicidal, trypanocidal and cytotoxic activities

Otero

García

Palacios

et al. 2017

European Journal of Medicinal Chemistry

Self Cite

View full text Add to dashboard Cite

show abstract

“…Reduction of 5-nitrofurfural (3) in presence of NaBH 4 in methanol at 0 °C for 30 min gave the desired (5-nitrofuran-2-yl)methanol (4). Treatment of alcohol 4 with triphenylphosphine and tribromoisocyanuric acid [19] in dichloromethane at room temperature for 4 h produced the desired bromide intermediate (5). Coupling of bromide 5 with apocynin (6) in presence of potassium carbonate in 2-methyltetrahydrofuran at reflux for 1 h gave the desired product 1-(4-((5-nitrofuran-2-yl)methoxy)-3-methoxyphenyl)ethanone (7).…”

Section: Resultsmentioning

confidence: 99%

“…They are significant as structural motifs among biologically active molecules and also for combinatorial assembly of heterocyclic scaffolds [2][3][4]. Chalcones containing several functional groups showed a wide spectrum of biological activities such as antileishmanial [5,6], antimalarial [5,7], anticancer [8,9], anti-HIV [10], antioxidant [11], inflammatory [12] antiprotozoal [13], antiulcer [14] and antimicrobial [15,16] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antiinflammatory Activity of Chalcone Derivatives Linked with Apocynin and 5-Nitrofuran Moiety

Reddy¹,

Kathale²

2018

Asian J. Chem.

View full text Add to dashboard Cite

The present paper describes the synthesis of some new chalcone derivatives i.e. 1-[3-methoxy-4-(5-nitro-furan-2-ylmethoxy)-phenyl]-3-(substituted phenyl)-propenone derivatives (9A-9K) from furfural and apocynin as starting materials. Claisen-Schmidt reaction of 1-(4-((5-nitrofuran-2-yl)methoxy)-3-methoxyphenyl)ethanone (7) with aromatic aldehydes (8A-K) under solvent free conditions using solid NaOH as catalyst at room temperature resulted in the formation of chalcone derivatives (9A-9K) in 86-96 % yield. These compounds were characterized by 1 H NMR, Mass and IR spectroscopy and were evaluated for their anti-inflammatory activity.Keywords: Anti-inflammatory activity, Apocynin, Chalcones, Furfural, Synthesis.Asian Journal of Chemistry; Vol. 30, No. 2 (2018), 312-316 Merck pre-coated plates (silica gel 60 F254) were used and spots were visualized under UV light. Merck silica gel 60 (230-400 mesh) was used for flash column chromatography and the eluting solvents are indicated in the procedures. Melting point determinations were performed by using Mel-temp apparatus and are uncorrected. 1H NMR spectra were recorded in Varian MR-400 MHz instrument. The mass spectra were recorded on Agilent ion trap MS and infrared spectra were recorded on a Perkin Elmer FT-IR spectrometer. 5-Nitrofurfural diacetate (2):A premixed solution of concentrated nitric acid (8.6 mL, 12.2 g, 193.62 mmol) and concentrated sulphuric acid (0.06 mL, 1.1 g, 11.2 mmol) was added drop-wise into acetic anhydride (90 mL) at 0 °C with stirring. To the above reaction mixture, furfural (1) (freshly distilled, 10.4 mL, 12.06 g, 125.5 mmol) was added dropwise over a period of 45 min and stirred for 1 h at 0 °C. Water (100 mL) was added to the mixture and stirred at room temperature for 30 min to obtain a white precipitate. To the reaction contents, 10 % NaOH solution was added until the pH of the mixture reached about 2.5 and the mixture was heated at 50°C for 1 h. After cooling to room temperature, the white precipitate formed was filtered, washed with water, recrystallized from anhydrous ethanol and dried to obtain diacetate compound 2. Yield: 24.84 g, 82 %. 5-Nitrofurfural (3):A mixture of 5-nitrofurfural diacetate (2) (10 g, 41.12 mmol) and 50 % aqueous sulphuric acid (100 mL) was heated to 100 °C for 10 min. After completion of the reaction, checked by TLC, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (2 × 100 mL) and the organic layer was washed with water, brine solution and dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain 5-nitrofurfural 3. Yield: 5.10 g, 88 %. m.p.: 35-36 °C.(5-Nitrofuran-2-yl)methanol (4): To a stirred solution of 5-nitrofurfural (3) (5 g, 35.44 mmol) in methanol (100 mL), cooled to 0 °C, was added sodium borohydride (1.47 g, 38.98 mmol) portion-wise and continued to stirred for additional 30 min. After completion of the reaction, checked by TLC, the solvent was concentrated under reduced pressure and the residue was quenched with water (2...

show abstract

“…Pyrazoline represents a classical nitrogen‐containing heterocycle that is highly prevalent in a variety of natural and nonnatural products. The five‐membered nitrogen‐containing heterocyclic compound species has demonstrated a wide range of biological activities including antitumor, antibacterial, anti‐inflammatory, antioxidant, antimicrobial, antifungal, and insecticidal activities. In fact, pyrazoline derivatives have attracted significant interest in the scientific community in recent years, particularly in the development of pesticides and pharmaceuticals.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Novel 1,3,4‐Thiadiazolylpyrazolines Compounds Containing Ferrocene

Chen

Duan

Zhang

et al. 2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The synthesis of 1,3,4‐thiadiazole skeleton compounds exhibiting high fungicidal activities has been demonstrated. Thirteen novel 1,3,4‐thiadiazolyl‐pyrazolines compounds containing ferrocene were designed and synthesized from the ferrocenylchalcones intermediates 3a–3m and the 2‐hydrazino‐5‐phenyl‐1,3,4‐thiadiazole intermediate 8. All compounds were characterized by 1H NMR, 13C NMR, FT‐IR spectra, and HR‐MS, and the structure of one of the new compounds N‐(4‐phenyl‐1,3,4‐thiadiazol‐2‐yl)‐3‐ferrocenyl‐5‐phenyl‐pyrazoline 9a was further determined by X‐ray diffraction analysis. The preliminary results of a biological activity assay indicated that all the title compounds exhibited significant fungicidal activities against Pythium solani, Gibberella saubinetii, and Gibberella nicotiancola. Furthermore, compounds 9e and 9h displayed even higher fungicidal activities against the three fungal species compared with the control drug pyraclostrobin.

show abstract

An efficient synthesis of new caffeine-based chalcones, pyrazolines and pyrazolo[3,4-b][1,4]diazepines as potential antimalarial, antitrypanosomal and antileishmanial agents

Cited by 81 publications

References 34 publications

Triclosan-caffeic acid hybrids: Synthesis, leishmanicidal, trypanocidal and cytotoxic activities

Triclosan-caffeic acid hybrids: Synthesis, leishmanicidal, trypanocidal and cytotoxic activities

Synthesis, Characterization and Antiinflammatory Activity of Chalcone Derivatives Linked with Apocynin and 5-Nitrofuran Moiety

Design, Synthesis, and Biological Evaluation of Novel 1,3,4‐Thiadiazolylpyrazolines Compounds Containing Ferrocene

Contact Info

Product

Resources

About