Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives

Okasha, Rawda M.; Albalawi, Fawzia F; Afifi, Tarek H.; Fouda, Ahmed M.; Al-Dies, Al-Anood M.; El‐Agrody, Ahmed M.

doi:10.3390/molecules21111450

Cited by 31 publications

(6 citation statements)

References 31 publications

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“…The optical execution of 4a–z was detected utilising using a Carl Zeiss polarimeter and displayed zero rotation (i.e. optically inactive) due to their occurrence as a racemic (±) mixture 52 , 53 , as shown in Scheme 1 .…”

Section: Resultsmentioning

confidence: 99%

Discovery of benzochromene derivatives first example with dual cytotoxic activity against the resistant cancer cell MCF-7/ADR and inhibitory effect of the P -glycoprotein expression levels

Al‐Harbi¹,

Al-Harbi

Okasha

et al. 2023

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of 1 H -benzo[ f ]chromene moieties ( 4a–z ) were synthesised under Ultrasonic irradiation and confirmed with spectral analyses. Derivative 4i solely possessed an X-ray single crystal. The anti-proliferative efficacy of the desired molecules has been explored against three cancer cells: MCF-7, HCT-116, and HepG-2 with the cytotoxically active derivatives screened against MCF-7/ADR and normal cells HFL-1 and WI-38. Furthermore, compounds 4b–d , 4k , 4n , 4q , and 4w , which possessed good potency against MCF-7/ADR, were tested as permeability glycoprotein ( P- glycoprotein [ P -gp]) expression inhibitors. The attained data confirmed that 4b–d , 4q , and 4w exhibited strong expression inhibition against the P- gp alongside its cytotoxic effect on MCF-7/ADR. The western blot results and Rho123 accumulation assays showed that compounds 4b–d, 4q , and 4w effectively inhibited the P -gp expression and efflux function. Meanwhile, 4b–d , 4q , and 4w induced apoptosis and accumulation of the treated MCF-7/ADR cells in the G1 phase and 4k and 4n in the S phase of the cell cycle.

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Section: Resultsmentioning

confidence: 99%

Discovery of benzochromene derivatives first example with dual cytotoxic activity against the resistant cancer cell MCF-7/ADR and inhibitory effect of the P -glycoprotein expression levels

Al‐Harbi¹,

Al-Harbi

Okasha

et al. 2023

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…The multicomponent reaction between 2,7‐dihydroxynaphthalene, benzaldehyde, and malononitrile in the presence of piperidine afforded the angular enaminonitrile 1 via a convenient and high yielding protocol (Scheme ) . The versatile precursor benzo[ f ]chromeno[2,3‐ d ]pyrimidine derivative 6 was synthesized from the benzochromene derivative 1 through harsh treatment with acetic anhydride under reflux conditions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Computational Analysis of New Antioxidant and Antimicrobial Angular Chromenopyrimidines

Abozeid

El‐Kholany

Abou-Zeid

et al. 2019

Journal of Heterocyclic Chem

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A convenient synthetic protocol for the synthesis of novel chromenopyrimidine derivatives based on angular scaffold has been developed from the readily available enaminonitrile precursor 1. The skeleton of chromenopyrimidines has been decorated with different moieties in order to approach compounds with improved antioxidant and antimicrobial activities. Compound 1 was reacted with Ac2O to yield benzochromenopyrimidine 6 that gave chloropyrimidine 7 via chlorination reaction. The reaction of chloropyrimidine 7 with different amines afforded a series of benzochromenopyrimidines 9–12. The hydrazine 11 and hydrazide 13 derivatives showed excellent antioxidant activity in addition to the potent antimicrobial activity revealed by aminopyrimidines 10 and 16. Computational docking studies indicated the potential recognition of compound 13 towards antioxidant binding site. Dual evaluations of the antimicrobial affinity of compound 16 indicated its promising activity as antimicrobial lead.

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“…For instance, Fig. 1 illustrates how 2 H -benzo[ h ]chromene derivatives ( A ) target AcrB and reverse bacterial multi drug resistance 2 , while 6-methoxy-4 H -benzo[ h ]chromene derivatives ( B-D ) targeted strong antimicrobial activities and had an inhibitory effect against 14 α -demethylase and DNA 3 , 4 . The 3-nitrile and 3-ester derivatives of 9-hydroxyof 1 H -benzo[ f ]chromene (E) have a higher significant potent antibacterial and antifungal activities 5 , 6 .…”

Section: Introductionmentioning

confidence: 99%

“…Derivatives of benzo[ h ]chromene are also a very effective option for treating a variety of human illnesses. For example, 4 H -benzo[ h ]chromene analogues of LY290181 ( H ) acts as potential tumor vascular-disrupting agents 14 , 5,6-dihydro derivative of 4 H -benzo[ h ]chromene ( I ) demonstrated a novel class of cytotoxic agents 15 , 16 , and 4-aryl derivatives of 4 H -benzo[ h ]chromene ( J ) has cytotoxic and apoptotic effects on human cancer cell lines 17 , 2-acetylamino derivative of 6-methoxy-4 H -benzo[ h ]chromene ( K ) induced cell cycle arrest and prompting apoptosis 18 , 3-carbonitrile/carboxylate derivatives of 4 H -benzo[ h ]chromene 4 , 6-chloro/methoxy derivatives of 4 H -benzo[ h ]chromene and 4 H -benzo[ h ]chromene-3-carboxylate ( L ) 20 – 23 , 2,7-diamino derivatives of 4 H -benzo[ h ]chromen-3-carbonitriles and ethyl 4 H -benzo[ h ]chromene-3-carboxylates ( M ) 19 have been reported as active cytotoxic agents against breast adenocarcinoma (MCF-7), human colon carcinoma (HCT-116) and hepatocellular carcinoma (HepG-2), respectively as shown in Fig. 3 .…”

Section: Introductionmentioning

confidence: 99%

Targeted potent antimicrobial and antitumor oxygen-heterocyclic-based pyran analogues: synthesis and computational studies

El-Wahab,

Borik,

Al-Dies

et al. 2024

Sci Rep

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The process of creating a series of 3-amino-1-aryl-8-methoxy-1H-benzo[f]chromene-2-carbonitriles (4a-q) involved reacting 6-methoxynaphthalen-2-ol (1), the appropriate aromatic aldehydes (2a-q), and malononitrile (3) in an absolute ethanol/piperidine solution under Ultrasonic irradiation. However, the attempt to create 3-amino-1-aryl-1H-benzo[f]chromene-2,8-dicarbonitrile (6a, d, e) was unsuccessful when 6-cyanonaphthalen-2-ol (5) was stirred at room temperature, reflux, Microwave irradiation, or Ultrasonic irradiation. In addition, the target molecules were screened against Staphylococcus aureus (MRSA), Staphylococcus aureus, Bacillus subtilis, Bacillus cereus, Escherichia coli and Klebsiella pneumonia, as well as a panel of three human cancer cells lines such as MCF-7, HCT-116, HepG-2 and two normal cell lines HFL-1 and WI-38. The obtained results confirmed that the pyran derivatives (4 m, i, k) which have a double chlorine at 3,4/2,3/2,5-positions, a single halogen atom 3-Cl/4-Br (4c, e) and a double bromine at 3,5-positions with a single methoxy group at 2-position (4n), of phenyl ring, and, to a lesser extent, other pyran derivatives with monoihalogenated (4a, b, d, f), dihalogenated (4 g, h, j, l) or trisubstituent phenyl ring (4o, p, q). Furthermore, compounds 4b-e, g, i, j, m, and n showed negligible activity against the two normal cell lines, HFL-1 and WI-38. Moreover, compound 4 g exhibited the strongest antimicrobial activity among the other pyran derivatives (4a-f, g-q) when compared to Ciprofloxacin. The MIC was assessed and screened for compound 4 g, revealing bactericidal effects. Lastly, SAR and molecular docking were studied.

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Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives

Abstract: Three new series of chromene molecules have been synthesized in order to explore their antimicrobial activity. The series encompass 2-substituted 14-(4-halophenyl)-12-methoxy

Cited by 31 publications

References 31 publications

Discovery of benzochromene derivatives first example with dual cytotoxic activity against the resistant cancer cell MCF-7/ADR and inhibitory effect of the P -glycoprotein expression levels

Discovery of benzochromene derivatives first example with dual cytotoxic activity against the resistant cancer cell MCF-7/ADR and inhibitory effect of the P -glycoprotein expression levels

Synthesis and Computational Analysis of New Antioxidant and Antimicrobial Angular Chromenopyrimidines

Targeted potent antimicrobial and antitumor oxygen-heterocyclic-based pyran analogues: synthesis and computational studies

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