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Benzylidene-isophorone hybrids with strong anticancer activity.
Logeshwari, G; Jeyashri, K R; Rajkumar, M; Manikandan, H; Sivakumar, K; Selvanayagam, S; Rajathi, V.
Afiliación
  • Logeshwari G; Department of Chemistry, Annamalai Univeristy, Annamalainagar 608002, Tamil Nadu, India.
  • Jeyashri KR; Department of Chemistry, Annamalai Univeristy, Annamalainagar 608002, Tamil Nadu, India.
  • Rajkumar M; Department of Chemistry, Annamalai Univeristy, Annamalainagar 608002, Tamil Nadu, India.
  • Manikandan H; Department of Chemistry, Annamalai Univeristy, Annamalainagar 608002, Tamil Nadu, India. Electronic address: profmani.au@gmail.com.
  • Sivakumar K; Department of Chemistry, Faculty of Science, Sri Chandrasekharendra Saraswathi Viswa Mahavidyalaya [SCSVMV] (Deemed to be University), Enathur, Kanchipuram 631 561, Tamil Nadu, India.
  • Selvanayagam S; PG & Research Department of Physics, Govt. Arts College, Melur 625 106, Madurai, Tamil Nadu, India.
  • Rajathi V; Government Arts College, C Mutlur, Chidambaram 608102, Tamil Nadu, India.
Spectrochim Acta A Mol Biomol Spectrosc ; 319: 124577, 2024 Oct 15.
Article en En | MEDLINE | ID: mdl-38850612
ABSTRACT
Isophorone is a cyclic ketone that has gained significant attention in the field of organic chemistry due to its versatile reactivity and structural attributes. Derivatives of isophorone offer a broad spectrum of applications ranging from pharmaceuticals to polymer chemistry. With the aim of developing novel hybrid structures based on benzylidene by combining with isophorone scaffold, we report 3 derivatives of the benzylidene-isophorone hybrids and its potent anticancer activity. In order to optimize the anticancer activity of hybrids di-substitution of -Cl group in C2 and C6 position of phenyl ring (compound1), -OCH3 group in C2 and C5 position of phenyl ring (compound2), and -OCH3 group in C2 and C3 position of phenyl ring (compound3) of benzylidene (PhCH=) moiety were made. The structure of Compounds1,2 and 3 were elucidated using spectral and XRD methods. Compounds1,2 and 3 exhibit space group P c a 21, P-1, and P 1 21/n 1 respectively. Compounds1,2 and 3 were tested for the potent anticancer activity on MDA MB-231 cell line. All the three compounds exhibit good anticancer activity on the breast cancer cells. The parent hybrid with ortho, ortho directing -Cl (1) exhibits strong antiproliferation effect (IC50 = 0.028 µM) on MDA-MB 231 cell line. However, hybrid structures with ortho, meta directing -OCH3 (2) group showed moderate effect (IC50 = 0.061 µM) and hybrid with ortho, meta directing -OCH3 (3) substitution showed the least potent anticancer activity (IC50 = 0.074 µM). The benzylidene-isophorone hybrids exhibit anticancer effects in the following order 1 > 2 > 3.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Compuestos de Bencilideno / Antineoplásicos Límite: Humans Idioma: En Revista: Spectrochim Acta A Mol Biomol Spectrosc Asunto de la revista: BIOLOGIA MOLECULAR Año: 2024 Tipo del documento: Article País de afiliación: India Pais de publicación: Reino Unido
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Compuestos de Bencilideno / Antineoplásicos Límite: Humans Idioma: En Revista: Spectrochim Acta A Mol Biomol Spectrosc Asunto de la revista: BIOLOGIA MOLECULAR Año: 2024 Tipo del documento: Article País de afiliación: India Pais de publicación: Reino Unido