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Synthesis of (3-(naphthalen-1-yl)oxiran-2-yl)(5,6,7,8-tetrahydronaphthalen-2-yl)methanone and reaction with some nucleophiles for anticancer evaluation

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Abstract

(3-(Naphthalen-1-yl)oxiran-2-yl)(5,6,7,8-tetrahydronaphthalen-2-yl)methanone was prepared and allowed to react with different nucleophile agents such as hydrazine hydrate, phenyl hydrazine, methyl hydrazine, and hydroxylamine hydrochloride to give hydroxy pyrazole 2 and hydroxy oxazole 3. Also, oxirane 1 reacted with semicarbazide and thiosemicarbazide to give substituted pyrazole 4a,b. Also, oxirane 1 was allowed to react with carbon disulfide, glycine, substituted isothiocyanate, and thiourea to give compounds 5–8, respectively. The thiopyrimidine derivative 8 was cyclized by chloroacetic acid or ethyl bromoacetate to give thiazolidine derivative 9, which condensed with different aldehydes to give compound 10a–c. Some of these newly synthesized compounds were evaluated as anticancer agents.

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Authors and Affiliations

  1. Therapeutic Chemistry Department, National Research Centre, Dokki, Cairo, Egypt

    Rasha S. Gouhar

  2. Pharmacology and Toxicology Department, Faculty of Pharmacy, Helwan University, Cairo, Egypt

    Eman Raafat

Authors
  1. Rasha S. Gouhar
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  2. Eman Raafat
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Correspondence to Rasha S. Gouhar.

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Gouhar, R.S., Raafat, E. Synthesis of (3-(naphthalen-1-yl)oxiran-2-yl)(5,6,7,8-tetrahydronaphthalen-2-yl)methanone and reaction with some nucleophiles for anticancer evaluation. Res Chem Intermed 41, 5529–5543 (2015). https://doi.org/10.1007/s11164-014-1679-5

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  • DOI: https://doi.org/10.1007/s11164-014-1679-5

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