Synthesis and biological activity of vicinal diaryl-substituted 1H-imidazoles

Methoden der Organischen Chemie

Synthesis of some novel pyrazolo[3,4-b]pyridine and pyrazolo[3,4-d]pyrimidine derivatives bearing 5,6-diphenyl-1,2,4-triazine moiety as potential antimicrobial agents.

Water-controlled selective preparation of α-mono or α,α′-dihalo ketones via catalytic cascade reaction of unactivated alkynes with 1,3-dihalo-5,5-dimethylhydantoin

A general atom-economical approach for the synthesis of α-halomethyl ketones is demonstrated through hydration of a wide range of haloalkynes. Other outstanding features include excellent yields from both alkyl- and aryl-substituted haloalkynes and wide functional group tolerance. This protocol is an alternative to conventional α-halogenation of ketones.

Gold-Catalyzed Hydration of Haloalkynes to α-Halomethyl Ketones

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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The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

Background Thiazole and thiosemicarbazone derivatives are known to have potential anticancer activity with a mechanism of action related to inhibition of matrix metallo-proteinases, 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, 1H-NMR and 13C-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 IC50 values of 3.80 ± 0.80, 3.65 ± 0.90 and 3.16 ± 0.90 μM, respectively, compared to harmine (IC50 = 2.40 ± 0.12 μM) and cisplatin (IC50 = 5.18 ± 0.94 μM) reference drugs. Also, compounds 8c, 4d and 4c showed promising IC50 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 (IC50 = 4.59 ± 0.67 μM) and cisplatin (IC50 = 11.68 ± 1.54 μM). On the other hand, compounds 4d, 4c, 8c and 11c were the most active (IC50 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 (IC50 = 2.54 ± 0.82 μM) and cisplatin (IC50 = 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.

https://www.dovepress.com/getfile.php?fileID=57237

One-Pot Synthesis of Novel Thiazoles as Potential Anti-Cancer Agents.

The current review presents recent progress in the utility of N,N-dimethyl enaminones as building blocks for a diverse range of acyclic, carbocyclic, five- and six-membered heterocyclic a broad range of heterocyclic and fused heterocyclic derivatives. Most importantly, these N,N-dimethyl analogues have proven to be of biological interest and provide an access to new class of biologically active heterocyclic compounds for biomedical applications. All of these topics are drawn from the recent literature till 2016.

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Recent developments in chemical reactivity of N,N-dimethylenamino ketones as synthons for various heterocycles

http://aether.cmi.ua.ac.be/artikels/MB_12589.pdf

Studies on Enaminonitriles: a New Synthesis of 1,3-Substituted Pyrazole-4-carbonitrile

3-Aminoacrylonitrile derivatives (1d–g) coupled with aromatic and heteroaromatic diazonium salts yielding arylhydrazonals and pyrazolo[5,1-c]triazines. The enaminonitriles 1d–g condensed to form di...

Hatem M. Gaber

Papers

The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

One-Pot Synthesis of Novel Thiazoles as Potential Anti-Cancer Agents.

Recent developments in chemical reactivity of N,N-dimethylenamino ketones as synthons for various heterocycles

Studies on Enaminonitriles: a New Synthesis of 1,3-Substituted Pyrazole-4-carbonitrile

Studies with Functionally Substituted Enamines: Synthesis of New Aminoazolo-Pyrimidines and -1,2,4-Triazines: