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Russian Journal of General Chemistry

, Volume 88, Issue 11, pp 2420–2424 | Cite as

Synthesis and Anticancer Evaluation of Some Phenothiazine Derivatives

  • A. H. Ahmed
  • A. Ebead
  • H. Afifi
  • A. A.-H. Abdel-RahmanEmail author
Article

Abstract

10H-Phenothiazine 1 reacts with 2-chloroacetonitrile to give 2-(10H-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-10H-phenothiazin-10-yl)acetimidohydrazide 4 and 2-(2-сhloro-10H-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-10H-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).

Keywords

phenothiazine tetrazole acyclic nucleosides anticancer activity 

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Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • A. H. Ahmed
    • 1
  • A. Ebead
    • 2
  • H. Afifi
    • 3
  • A. A.-H. Abdel-Rahman
    • 4
    Email author
  1. 1.Chemistry Department, Faculty of MedicineUniversity of Science and TechnologyDhamarYemen
  2. 2.Chemistry Department, Faculty of ScienceArish UniversityArishEgypt
  3. 3.Faculty of Industrial EducationBeni Suef UniversityBeni SuefEgypt
  4. 4.Chemistry Department, Faculty of ScienceMenoufia UniversityShebin El-KomEgypt

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