Considering the highly important biological and medicinal properties of naphthofurans, the synthesis of these heterocycles has attracted the interest of medicinal and organic chemists. This review aims to describe the different strategies developed so far for the synthesis of naphthofurans and their applications and the literature reports for the period of 2000 to early 2020. After a brief introduction of the types of naphthofurans and their biological activities, the different synthetic approaches such as chemical and photochemical, methods are described and organized on the basis of the catalysts and the other reagents employed in the syntheses. Some of the reactions have been applied successfully to the synthesis of biologically important compounds.

A one-pot, three-component reaction of 6-bromo-2-naphthol (1), p-chlorobenzaldehyde (2) and malononitrile or ethyl cyanoacetate (3) in ethanol/piperidine under reflux was performed to afford 4H-naphtho[2,1-b]pyrano-3-carbonitrile (4a) and ethyl 4H-naphtho[2,1-b]pyrano-3-carboxylate (4b) derivatives, respectively. The structure of these compounds was determined using IR, 1H NMR, 13C NMR, mass spectroscopy and UV-Vis spectra. The molecular geometry of compounds 4a and 4b was determined at the B3LYP/631+G(d) level. The geometric optimization was performed on two tautomers and two conformers. Tautomers were separated by about 7.942 kcal/mol, while rotational conformers were separated by just 0.511 kcal/mol. The global electrophilicity, hardness, softness and local condensed Fukui functions were calculated and considered as molecular reactivity descriptors, moreover the frontier molecular orbitals (HOMO and LUMO) were also calculated.

Introduction: Benzochromenes are heterocyclic compounds of growing interest in medicinal chemistry due to their diverse biological activities, including antioxidant, anticancer, and antimicrobial properties. Methods: A one-pot, three-component synthesis was employed to prepare benzochromene derivatives (4a–f) using 2-naphthol or its derivatives, active methylene compounds, and 2-methoxybenzaldehyde in ethanol with piperidine as a catalyst. The compounds were evaluated for their anticancer activity against MCF-7, HepG-2, and HCT-116 cell lines, as well as for their antimicrobial activity through molecular docking studies targeting cancerrelated and microbial proteins. Results: All synthesized compounds were obtained in moderate to good yields. Compounds 4c, 4e, and 4f demonstrated superior biological activity compared to standard drugs Doxorubicin and Augmentin. Docking studies revealed strong binding affinities to key targets, including the TGF-βI receptor and the choline-binding domain. Discussion: The hydroxyl group at position 9 in compounds 4c and 4f likely contributed to enhanced antimicrobial activity, while the bromo group in 4e correlated with significant anticancer effects. These findings suggest meaningful structure–activity relationships and validate the design strategy. Conclusion: The synthesized benzochromene derivatives exhibit promising anticancer and antimicrobial activities. Supported by molecular docking, these findings lay the groundwork for further pharmacological and in vivo evaluations of this scaffold.

Background: Condensation of 3-acetyl coumarin (1) with 2‐(4-methoxy- benzylidene) malononitrile (2) in ammonium acetate/acetic acid or absolute ethanol/piperidine affords pyridine (3) and chromen-2-one (4) derivatives, respectively. Methods: In this study, the reaction of 3 with an electrophilic reagent, namely, formic acid, acetic anhydride and formamide afforded the pyridopyrimidinone and pyridine derivatives (6- 9). Also, treatment of 3 with different aromatic aldehydes, carbon disulfide, NaN3/NH4Cl, 2- (4-methoxybenzylidene)malononitrile and acetophenone afforded pyridopyrimidinone, carbamodithioic acid, tetrazol-5-yl-chromen-2-one, 2H-chromen-2-one, and pyridine derivatives (10-14), respectively. Results: This study synthesized coumarins with antimicrobial activity and verified the structure and purity of the synthesized compounds using spectral data. Conclusion: The new compounds were evaluated in vitro for their antimicrobial activity against gram-positive bacteria (Staphylococcus aureus, Methicillin-resistant Staphylococcus aureus) and gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), in addition to fungus (Candida albicans). The investigated substances 3 and 14 presented good activity against MRSA, E. coli, P. aeruginosa and C. albicans, while compounds 9, 10a-c, 11, 12 and 13 exhibited good to moderate activity.

: In this work, a series of novel 3-(halophenyl)-1-phenyl-1H-pyrazole moieties have been synthesized. Their structures were characterized by IR, NMR, and MS spectroscopy, and the corresponding antitumor properties were also studied. Objectives: This study aimed to synthesize a series of new 3-(halophenyl)-1-phenyl-1Hpyrazole moieties and survey the antitumor properties of these compounds. Materials and Methods: 3-(halophenyl)-1-phenyl-1H-pyrazoles (4a-j) were prepared by reaction of phenyl hydrazine (3) with different halogen aromatic aldehydes 1a-j and malononitrile (2) in C2H5OH and piperidine. The reaction took place under microwave irradiation settings for two minutes at140°C. Results: Three human cancer cell lines were used as in vitro test subjects for compounds 4a - j. Three cell lines from mammals HeLa (a cell line for human cervical cancer), MCF-7 (a cell line for human breast cancer), and PC-3 (a cell line for human prostate cancer), all with 5- fluorouracil as the standard reference drug were used. Conclusion: A series of novel 3-(halophenyl)-1-phenyl-1H-pyrazoles were synthesized in this work. All substances had their anticancer properties assessed.

A series of novel benzo­[f]­chromene derivatives, 4–14, were successfully synthesized and structurally characterized using spectroscopic techniques, including IR, ¹H-NMR, and ¹³C-NMR. The antiproliferative activities of selected compounds were evaluated against three human cancer cell linesHepG-2 (hepatocellular carcinoma), HCT-116 (colorectal carcinoma), and MCF-7 (breast cancer)using the MTT assay. Cytotoxic effects were compared to standard anticancer agents 5-Fluorouracil and Doxorubicin. Among the tested compounds, 7, 9, and 12 exhibited superior cytotoxicity across all three cell lines, outperforming the reference drugs. Structure–activity relationship (SAR) analysis suggested that fused heterocyclic moieties at the 2,3-position significantly enhanced anticancer activity. Furthermore, in silico molecular docking studies targeting the EGFR tyrosine kinase domain (PDB ID: 4HJO) demonstrated that compound 12 and the reference ligand AQ4 formed stable interactions with key active-site residues, suggesting a potential mechanism of action through EGFR inhibition that warrants further experimental validation. These findings suggest that the synthesized benzo­[f]­chromene derivatives, particularly benzo­[f]­chromenopyrimidine derivative 12, represent promising lead candidates for further development pending validation of their proposed mechanism of action, warranting future biochemical and cellular validation.