Design, synthesis, in vitro antimicrobial and anticancer activity of novel methylenebis-isoxazolo[4,5-b]azepines derivatives

Rajanarendar, E.; Reddy, M. Nagi; Krishna, S. Rama; Reddy, K. Govardhan; Reddy, Y. V. R.; Rajam, Manchikatla Venkat

doi:10.1016/j.ejmech.2012.02.013

Cited by 54 publications

(17 citation statements)

References 11 publications

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“…Isoxazoles are potent analgesic, anti‐inflammatory , antimicrobial , COX‐2 inhibitory , antitubercular , anticonvulsant , and anticancer agents . In view of the high degree of bioactivity shown by these heterocyclic systems, and our search for biologically active heterocyclic compounds , it was envisaged to construct a system, which possess these moieties in a single molecular frame and to explore the additive effects towards their biological activities. Hence, we are reporting herein the synthesis of imidazo[1,2‐ b ]isoxazolyl‐ N ‐aryl thiazol amines.…”

Section: Introductionmentioning

confidence: 99%

A Convenient and Facile Hantzsch Synthesis of Aryl Imidazo[1,2‐b]Isoxazolyl‐N‐aryl Thiazol Amines

Rajanarendar

Thirupathaiah

Ramakrishna

et al. 2015

Journal of Heterocyclic Chem

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The Hantzsch synthesis of novel aryl imidazo[1,2‐b]isoxazolyl‐N‐aryl thiazol amines 5 analogues were described. Reaction of 3‐aminoisoxazole 1 with substituted phenacyl bromides 2 in dry ethanol afforded the corresponding 6‐methyl‐3‐arylimidazo[1,2‐b]isoxazoles 3 in good yields. Compounds 3 on reaction with chloroacetyl chloride in 1,4‐dioxane furnished the corresponding 2‐chloro‐1‐(6‐methyl‐3‐arylimidazo[1,2‐b]isoxazol‐2‐yl)ethanones 4. Compounds 4 on heating with N‐aryl thioureas in an oil bath underwent cyclization to afford the title compounds viz., imidazo[1,2‐b]isoxazolyl‐N‐aryl thiazol amines 5 in moderate to good yields by Hantzsch synthesis.

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Section: Introductionmentioning

confidence: 99%

A Convenient and Facile Hantzsch Synthesis of Aryl Imidazo[1,2‐b]Isoxazolyl‐N‐aryl Thiazol Amines

Rajanarendar

Thirupathaiah

Ramakrishna

et al. 2015

Journal of Heterocyclic Chem

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“…In other cases, a variety of heterocyclic cores are connected through linkers of different structural features. For example, bis-azepines [7], bis-isooxazoloazepanes [8], bisindenoquinolines [9] and bis-quinolinium compounds [10] have been described and evaluated.…”

Section: Introductionmentioning

confidence: 99%

New Green Synthesis and Antineoplastic Activity of Bis (3-Arylimidazolidinyl-1) Methanes

Perillo¹,

Villalonga²,

Amiano³

et al. 2013

OJMC

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A new green synthesis and anti-tumor activity of the series of bis (3-arylimidazolidinyl-1) methanes 1 -6 are described. The compounds were synthesized from the corresponding N-arylethylenediamine and trioxane as sources of formaldehyde and the reactions were performed in heterogeneous phase catalyzed by an acidic ion-exchange resin (Amberlyst 15). The compounds were tested with the Sulforhodamine B assay according to the protocol of the National Cancer Institute for several cell lines. The results were expressed as percentage inhibition of growth cell in comparison with the full growth of the cells without treatment. Cytotoxicity on normal cells using the Annexing-PI staining and flow cytometry has been evaluated. The parent compound, bis(3-phenylimidazolidinyl-1)methane 1 and the monohalogenated derivatives 4-chlorophenyl 3 and 3-bromophenyl 5 showed antineoplastic activity, 60%, 82% and 89% inhibition growth cell respectively on the human colon cell line (HCT116). The 4-tolyl derivative 6 presented inhibitory activity (73% inhibition of growth cell) on human lung adenocarcinoma cell line (A549) and 62% on human mammary cell line MCF-7.

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“…The most common form of liver cancer in adults is hepatocellular carcinoma (HCC), which generally starts as a single tumor that grows larger or as many small cancer nodules throughout the liver. There is currently a demand for the discovery and development of new lead compounds of simple structure, exhibiting excellent antitumor property and new mechanisms of action [2]. …”

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confidence: 99%

“…The naturally occurring antimitotic agent colchicine (Figure 1D) and its synthetic analogs have been studied extensively for cancer chemotherapy, however, it lacks in vivo anticancer efficacy at its maximum-tolerated dose [6] because its maximum-tolerated dose is limited to around 1 mg/kg [7]. Azepine analogs such as oxazepine have been subject to much investigation, since they are a class of totally synthetic pharmacological agents with diverse action [2,8]. Recently, pyrrolo-1,5-benzoxazepine, a well-known group of microtubule-targeting agents, was shown to display antitumor effects, mainly inducing cell cycle arrest and apoptosis in several human cancer models [9].…”

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Indole-Fused Benzooxazepines: a New Structural Class of Anticancer Agents

et al. 2017

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Aim:A new series of compounds (1a–16a) bearing indole-fused benzooxazepine was synthesized, characterized and evaluated for anticancer activity.Materials & methods:In this study, all the synthesized compounds were screened via in vitro anticancer testing on Hep-G2 cancer cell line. A computational study was carried out on cancer-related targets including IL-2, IL-6, COX-2 Caspase-3 and Caspase-8.Results:Some of the synthesized compounds effectively controlled the growth of cancerous cells.Conclusion:The most active compounds – 6a, 10a, 13a, 14a and 15a – exemplify notable anticancer profile with GI50 <10 μg/ml. Preliminary structure–activity relationship among the tested compounds can produce an assumption that the electronegative groups at phenyl ring attached with indole-fused benzooxazepine are instrumental for the activity. Molecular docking study showed crucial hydrogen bond and π–π stacking interactions, with good ADMET profiling and molecular dynamic simulation.

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Design, synthesis, in vitro antimicrobial and anticancer activity of novel methylenebis-isoxazolo[4,5-b]azepines derivatives

Cited by 54 publications

References 11 publications

A Convenient and Facile Hantzsch Synthesis of Aryl Imidazo[1,2‐b]Isoxazolyl‐N‐aryl Thiazol Amines

A Convenient and Facile Hantzsch Synthesis of Aryl Imidazo[1,2‐b]Isoxazolyl‐N‐aryl Thiazol Amines

New Green Synthesis and Antineoplastic Activity of Bis (3-Arylimidazolidinyl-1) Methanes

Indole-Fused Benzooxazepines: a New Structural Class of Anticancer Agents

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