Synthesis of targeted dibenzo[b,f]thiepines and dibenzo[b,f]oxepines as potential lead molecules with promising anti-breast cancer activity

Ansari, Mohd. Imran; Hussain, Mohd Kamil; Arun, Ashutosh; Chakravarti, Bandana; Konwar, Rituraj

doi:10.1016/j.ejmech.2015.05.035

Cited by 35 publications

(17 citation statements)

References 32 publications

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“…Zotepine 1 (Figure ) is a thiepine antipsychotic drug that has been used in clinical practice for the treatment of schizophrenia for several decades . The results published recently have shown that dibenzo[ b , f ]thiepines and pyridobenzothiepines exhibit anticancer and antifungal activity . These results strongly support that thiepines are an important class of biologically active heterocyclic molecules.…”

Section: Methodsmentioning

confidence: 83%

Synthesis and anti‐Candida activity of novel benzothiepino[3,2‐c]pyridine derivatives

et al. 2016

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A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C. parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6 μg/mL and showed no embryotoxicity at 75 μg/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.

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Section: Methodsmentioning

confidence: 83%

Synthesis and anti‐Candida activity of novel benzothiepino[3,2‐c]pyridine derivatives

et al. 2016

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“…3) exhibited potent in vitro antiproliferative activity at 1.33 mM and 5 mM concentration in MCF-7 and MDA-MB-231 cell lines. 96 Meneni et al, 97 synthesized a series of 5-alkynyl-20deoxyuridines tested for antiproliferation properties against MCF-7 and MDA-MB-231 human mammary carcinoma cell lines. Compound 102 (Fig.…”

Section: The Miscellaneous Functional Groups Of Organic Compoundsmentioning

confidence: 99%

Current research on anti-breast cancer synthetic compounds

et al. 2018

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“…Indeed, several examples of dibenzo[b,f]thiepines with antibacterial, anti-psychotic, neuroleptic or anti-proliferative activities have been highlighted in the literature as illustrated in Figure 6 [30][31][32]. Nevertheless, at the best of our knowledge, only one example of MW-assisted synthesis of a dibenzo[b,f]thiepine has been reported in the literature.…”

Section: Oxepanes Thiepanes and Their Derivativesmentioning

confidence: 99%

Microwave-Assisted Syntheses of Bioactive Seven-Membered, Macro-Sized Heterocycles and Their Fused Derivatives

et al. 2016

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This review describes the recent advances in the microwave-assisted synthesis of 7-membered and larger heterocyclic compounds. Several types of reaction for the cyclization step are discussed: Ring Closing Metathesis (RCM), Heck and Sonogashira reactions, Suzuki-Miyaura cross-coupling, dipolar cycloadditions, multi-component reactions (Ugi, Passerini), etc. Green syntheses and solvent-free procedures have been introduced whenever possible. The syntheses discussed herein have been selected to illustrate the huge potential of microwave in the synthesis of highly functionalized molecules with potential therapeutic applications, in high yields, enhanced reaction rates and increased chemoselectivity, compared to conventional methods. More than 100 references from the recent literature are listed in this review.

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Synthesis of targeted dibenzo[b,f]thiepines and dibenzo[b,f]oxepines as potential lead molecules with promising anti-breast cancer activity

Cited by 35 publications

References 32 publications

Synthesis and anti‐Candida activity of novel benzothiepino[3,2‐c]pyridine derivatives

Synthesis and anti‐Candida activity of novel benzothiepino[3,2‐c]pyridine derivatives

Current research on anti-breast cancer synthetic compounds

Microwave-Assisted Syntheses of Bioactive Seven-Membered, Macro-Sized Heterocycles and Their Fused Derivatives

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