Synthesis and Structures of Novel Multi‐armed Molecules Involving Benzene as a Core and 4‐Phenylthiazole, 4‐Pyrazolylthiazole, or Thiadiazole Units as Arms

Abstract

A synthesis of novel three‐, four‐, and sixfold branched 4‐phenylthiazolylhydrazones, 4‐pyrazolylthiazolyl hydrazones, and thiadiazoles which are linked to a benzene core via phenoxymethyl spacers was reported. The synthetic methodology includes initially formation of poly(aldehyde thiosemicarbazones) 9, 14, and 15 by acid catalyzed condensation of thiosemicarbazide (8) with the appropriate poly(aldehydes) 3, 5, and 7, respectively. Subsequent reaction of 9, 14, and 15 with each of 2‐bromo‐1‐phenylethanone (10a) and 2‐bromo‐1‐(4‐chlorophenyl)ethanone (10b) in refluxing ethanol in the presence of few drops of TEA afforded 11, 16, and 18, respectively, in good yields. On the other hand, the synthesis of the novel poly(4,5‐dihydro‐1,3,4‐thiadiazolyl) derivatives 20, 21a,21b, and 22 was performed by cyclization of 9b, 14a,14b, and 15a, respectively, in refluxing acetic anhydride.

Synthesis of novel bis‐ and poly(benzimidazoles) as well as bis‐ and poly(benzothiazoles) as anticancer agents

“…In connection with these findings and in continuation of our recent interest in the chemistry of bis‐ and poly(heterocycles), we report herein on the synthesis of novel bis‐ and poly(benzimidazoles) as well as bis‐ and poly(benzothiazoles). The anticancer activities of the synthesized compounds were evaluated against human breast adenocarcinoma cell line (MCF‐7), liver cancer cell line (HepG‐2), and epithelial colorectal adenocarcinoma cells (CaCO‐2).…”

Synthesis of novel bis- and poly(hydrazinylthiazole) linked to benzofuran or benzothiazole as new hybrid molecules

“…Mass spectra (EI) were obtained at 70 eV using a type Shimadzu GCMQP 1000 EX Spectrometer. Compounds 3, 74 4, 75 7a-c, 65 10a,b, 76 16, 66 19 66 and 22 66 were prepared according to literature.…”

“…In addition, molecular hybridization have attracted much attention in the last decades in drug design and development as it can lead to compounds with superior efficacy via integration of pharmacophoric moieties from different bioactive substances. [56][57][58][59][60][61][62][63] Motivated by these findings and in conjunction with our ongoing research work on bis-as well as poly(heterocycles) [64][65][66][67][68][69][70][71] we report herein on the synthesis of novel scaffolds based on thiazole linked with benzofuran or benzothiazole moieties as new hybrid molecules with enhanced biological potentials.…”

The Chemistry of Acetylpyrazoles and Its Utility in Heterocyclic Synthesis

“…In analogy, reaction of compounds 168a,b with 2‐bromo‐1‐(5‐methyl‐1‐phenyl‐1 H ‐pyrazol‐4‐yl)ethanone ( 160 ) in refluxing ethanol in the presence of few drops of triethylamine afforded 169a and 169b in 70% and 64% yields, respectively (Scheme ) . Compound 160 was synthesized by the reaction of phenylhydrazine with ((dimethylamino)methylene)pentane‐2,4‐dione, obtained upon treatment of acetylacetone with DMF‐DMA, followed by bromination upon treatment with Br 2 in AcOH .…”