The molecular structures and spectral properties of α-haloketones as well as their syntheses are analyzed and reviewed. Their reactivity towards oxygen, nitrogen, and sulfur nucleophiles, carboxylic acids, carbon nucleophiles, alkenes, and alkynes are discussed.

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Background: Thiazole and thiosemicarbazone derivatives are known to have potential anticancer activity with a mechanism of action related to inhibition of matrix metalloproteinases, kinases and anti-apoptotic BCL2 family proteins. Materials and Methods: A novel three series of 5-(1-(2-(thiazol-2-yl)hydrazono)ethyl) thiazole derivatives were prepared in a one-pot three-component reaction using 2-(2-benzylidene hydrazinyl)-4-methylthiazole as a starting precursor. MS, IR, 1 H-NMR and 13 C-NMR were used to elucidate the structures of the synthesized compounds. Most of the synthesized products were evaluated for their in vitro anticancer screening against HCT-116, HT-29 and HepG2 using the MTT colorimetric assay. Results: The results indicated that compounds 4c, 4d and 8c showed growth inhibition activity against HCT-116 with IC 50 values of 3.80 ± 0.80, 3.65 ± 0.90 and 3.16 ± 0.90 μM, respectively, compared to harmine (IC 50 = 2.40 ± 0.12 μM) and cisplatin (IC 50 = 5.18 ± 0.94 μM) reference drugs. Also, compounds 8c, 4d and 4c showed promising IC 50 values of 3.47 ± 0.79, 4.13 ± 0.51 and 7.24 ± 0.62 μM, respectively, against the more resistant human colorectal cancer (HT-29) cell line compared with harmine (IC 50 = 4.59 ± 0.67 μM) and cisplatin (IC 50 = 11.68 ± 1.54 μM). On the other hand, compounds 4d, 4c, 8c and 11c were the most active (IC 50 values of 2.31± 0.43, 2.94 ± 0.62, 4.57 ± 0.85 and 9.86 ± 0.78 μM, respectively) against the hepatocellular carcinoma (HepG2) cell line compared with harmine (IC 50 = 2.54 ± 0.82 μM) and cisplatin (IC 50 = 41 ± 0.63 μM). The study also suggested that the mechanism of the anticancer action exerted by the most active compounds (4c, 4d and 8c) inside HCT-116 cells was apoptosis through the Bcl-2 family. Conclusion: Thiazole scaffolds 4c, 4d and 8c showed anticancer activities in the micromolar range and are appropriate as a candidate for cancer treatment.

Phosphoramidites of several new twisted intercalating nucleic acid (TINA) monomers and the previously discovered (R)-1-O-[4-(1-pyrenylethynyl)phenylmethyl]glycerol (1) were synthesized and used in DNA synthesis. Stabilization of Hoogsteen-type triplexes was observed in cases of insertion of the novel (R)-1-O-[3-(naphthalen-1-ylethynyl)phenylmethyl]glycerol (2) as a bulge into homopyrimidine oligodeoxynucleotides (ONs), whereas phenylethynyl and 4-(biphenylylethynyl) derivatives of TINAs resulted in destabilization of parallel triplexes relative to the wild-type triplex. It was concluded that TINA monomers should possess at least two fused phenyl rings attached through the triple bond at the 4-position of bulged (R)-1-O-(phenylmethyl)glycerol in homopyrimidine ONs in order to stabilize parallel triplexes.

This review demonstrates the high number of synthetic applications of enaminones in the preparation of acyclic, carbocyclic, heterocyclic and fused heterocyclic compounds.

3-Diethylaminoacrylonitrile (1) reacts with hydrazonyl halides (2a-d) to yield 1,3-disubstituted pyrazole-4-carbonitriles 5a-d. The acetyl 1-p-chlorophenylpyrazole-4-carbonitrile (5a) condensed with hydrazine hydrate to yield the bishydrazone 10 and with dimethylformamide dimethylacetal to yield 1-aryl-3-(3dimethylamino)acryloyl pyrazole-4-carbonitrile (11). This enamine reacts with hydrazine hydrate to yield the pyrazolylpyrazole (12) and with naphthoquinone to yield the 3-naphthofuranoyl pyrazole 13. The pyrazolyl pyridine derivative 14 was obtained upon treatment of 11 with acetylacetone in the presence of ammonium acetate. Compound 11 was coupled with p-chlorobenzene diazonium chloride to yield the hydrazone 16 that was coupled further with p-chlorobenzenediazonium chloride to yield the formazane 18.

The reaction of one equivalents of 5‐acetylthiadiazole with one equivalent of aldehyde in acetic acid and ammonium acetate yielded thiadiazolyl‐pyridine derivatives in a multicomponent reactions. The structures of all the new compounds were elucidated on the basis of elemental analysis and spectral data. The anticancer activities of the synthesized compounds were screened for their activity against human lung carcinoma (A549) and human hepatocellular carcinoma cell lines (HepG2) comparable with cisplatin, and the results showed that most of such compounds exhibit considerable activities. The order of activity against A549 cell line was 4c, 4e, 4a, 6d, 8d, 11, 12, 4b, 4f, and 4d. However, compound 4e exhibited the highest activity against HepG2, followed by 4a, 4c, 6d, 8d, 11, 12, 4f, 4d, and 4b. On the other hand, compounds 11, 12, and 4b showed the highest 2,2‐diphenyl‐1‐picrylhydrazyl free radical scavenging activities. Conclusively, the results of the current study approved the cytotoxic and antioxidant capabilities of the synthesized compounds.

Benzo[b]thiophen-2-yl-hydrazonoesters4 were synthesized by coupling of 2-diazo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (1)