Synthesis and Anticancer Evaluation of Some Phenothiazine Derivatives

10 H -Phenothiazine 1 reacts with 2-chloroacetonitrile to give 2-(10 H -phenothiazin-10-yl)- acetonitrile 2 , which upon reaction with sodium azide gives the corresponding tetrazole 3 . Treatment of 2 by either hydrazine hydrate or hydroxylamine affords 2-(2-chloro-10 H -phenothiazin-10-yl)acetimido...

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Bibliographic Details
Published in:Russian journal of general chemistry 2018-11, Vol.88 (11), p.2420-2424
Main Authors: Ahmed, A. H., Ebead, A., Afifi, H., Abdel-Rahman, A. A.-H.
Format: Article
Language:English
Subjects:
Acetonitrile
Alkylation
Anhydrides
Cancer
Care and treatment
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Derivatives
Ethanol
Hydrazines
Hydroxides
Infrared spectroscopy
Mass spectrometry
NMR
Nuclear magnetic resonance
Nuclear magnetic resonance spectroscopy
Phenothiazine
Sodium azides
Sodium salts
Synthesis
Tetrazoles
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Summary:10 H -Phenothiazine 1 reacts with 2-chloroacetonitrile to give 2-(10 H -phenothiazin-10-yl)- acetonitrile 2 , which upon reaction with sodium azide gives the corresponding tetrazole 3 . Treatment of 2 by either hydrazine hydrate or hydroxylamine affords 2-(2-chloro-10 H -phenothiazin-10-yl)acetimidohydrazide 4 and 2-(2-сhloro-10 H -phenothiazin-10-yl)- N' -hydroxyacetimidamide 7 , respectively. Reaction of 4 with CS2 leads to the thione derivative 5 . Treatment of 7 with acetic anhydride gives 3-[(2-chloro-10 H -phenothiazin-10- yl)methyl]-4,5-dihydro-1,2,4-oxadiazole 8 . Alkylation of sodium salt of compounds 3 , 5 , 6 , or 8 by 1-chloro-2- methoxyethane and/or 2-(2-chloroethoxy)ethanol leads to the corresponding acyclic derivatives 9–16 . Structures of all newly synthesized compounds are confirmed by IR, NMR and mass spectroscopy. All of the synthesized compounds demonstrate high activity against breast cancer cell line (MCF7).
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363218110269