Antiproliferative effect, cell cycle arrest and apoptosis generation of novel synthesized anticancer heterocyclic derivatives based 4H-benzo[h]chromene

Al-blewi, Fawzia Faleh; Okasha, Rawda M.; Hritani, Zainab M.; Mohamed, Hany M.; El-Nassag, Mohammed A. A.; Halawa, Ahmed H.; Mora, Ahmed; Fouda, Ahmed M.; Assiri, Mohammed A.; Al-Dies, Al-Anood M.; Afifi, Tarek H.; El‐Agrody, Ahmed M.

doi:10.1016/j.bioorg.2019.03.059

Cited by 42 publications

(12 citation statements)

References 45 publications

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“…New 2-substituted 4H-benzo[h]chromenes and 7H-benzo[ h ]chromeno[2,3–d] pyrimidines were prepared by Alblewi et al ( 2019b ) and assessed their in-vitro anticancer activity. As a result, compounds 30 and 31 (IC 50 value 0.45 and 3.8 μg/mL, respectively) showed 13.6 and 1.6 times more cytotoxicity than vinblastine (IC 50 6.1 μg/mL), though compound 30 has the similar activity as doxorubicin, with an IC 50 value of 0.4 μg/mL against MCF-7.…”

Section: Biological Activities Of 2h/4h-chromenesmentioning

confidence: 99%

“…All these compounds showed early and late apoptosis after the exposure under Annexin V/PI double staining. Thus, an in-vitro study showed that compounds 32 , 33 , and 30 had the potency to inhibit cancer, but in the respect of in-vivo study, further investigations are required to clarify the actual potency inside the systemic circulation (Alblewi et al, 2019b ).…”

Section: Biological Activities Of 2h/4h-chromenesmentioning

confidence: 99%

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2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

2020

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2H/4H-chromene (2H/4H-ch) is an important class of heterocyclic compounds with versatile biological profiles, a simple structure, and mild adverse effects. Researchers discovered several routes for the synthesis of a variety of 2H/4H-ch analogs that exhibited unusual activities by multiple mechanisms. The direct assessment of activities with the parent 2H/4H-ch derivative enables an orderly analysis of the structure-activity relationship (SAR) among the series. Additionally, 2H/4H-ch have numerous exciting biological activities, such as anticancer, anticonvulsant, antimicrobial, anticholinesterase, antituberculosis, and antidiabetic activities. This review is consequently an endeavor to highlight the diverse synthetic strategies, synthetic mechanism, various biological profiles, and SARs regarding the bioactive heterocycle, 2H/4H-ch. The presented scaffold work compiled in this article will be helpful to the scientific community for designing and developing potent leads of 2H/4H-ch analogs for their promising biological activities.

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Section: Biological Activities Of 2h/4h-chromenesmentioning

confidence: 99%

Section: Biological Activities Of 2h/4h-chromenesmentioning

confidence: 99%

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

2020

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“…Among the most significant heterocyclics are the substituted chromenes and benzochromenes, owing to their antimicrobial [1-5], antiviral, anti-HIV, antileishmanial, antianaphylactic [6][7][8], anticancer [9][10][11][12][13][14][15][16], anti-inflammatory [17,18] and antioxidant [19] applications. β-enaminonitriles containing 4H-benzo[h]chromene systems have been used in cancer treatment approaches; therefore, they are described as prospective cancer pharmaceuticals' targets.…”

Section: Introductionmentioning

confidence: 99%

“…Meanwhile, fused benzochromenes are also valuable as effective anticancer agents; for instance, the 9amino/benzylideneamino and 8-amino/imino derivatives of benzochromenopyrimidine and benzochromenopyrimidin-8-one, respectively, are found to be effective against caspase 3/7 activators and targets for cell cycle study [5,11]. Furthermore, the cell cycle was arrested in the 9-amino/methyl derivative of 7-(2,4/3,4-dimethoxyphenyl)benzochromenopyrimidine, responsible for apoptosis, caspase 3/7 activation, DNA breakage, cell invasion and migration [13,14]. Overexpression of ABC transporters such as P-glycoprotein (P-gp), multidrug resistance protein 1 (MDR1) and ATP-binding cassette subfamily B member 1 (ABCB1) is the main contributor to MDR [26,27].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 9-Hydroxy-1H-Benzo[f]chromene Derivatives with Effective Cytotoxic Activity on MCF7/ADR, P-Glycoprotein Inhibitors, Cell Cycle Arrest and Apoptosis Effects

Albalawi

El-Nassag

El-Eisawy

et al. 2022

IJMS

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β-Enaminonitriles bearing 9-hydroxy-1H-benzo[f]chromene moiety was synthesized. The targeted compounds were evaluated for their anti-proliferative activity against three human tumor cell lines, PC-3, SKOV-3 and HeLa, and the active cytotoxic compounds were further evaluated against cancer cells, MCF-7/ADR, and two normal cell lines, HFL-1 and WI-38. Few compounds were assigned to be the most potent derivatives against PC-3, SKOV-3 and HeLa cell lines in comparison with Vinblastine and Doxorubicin. Several compounds possessed a relatively good potency against MCF-7/ADR cells as compared with Doxorubicin and were tested as a P-gp inhibitor. Moreover, the halogenated substituents, 2,4-F2, 2,3-Cl2, 2,5-Cl2 and 3,4-Cl2; have good potency against P-gp-mediated MDR in MCF-7/ADR as compared with Doxorubicin. Meanwhile, Rho123 accumulation assays revealed that few compounds effectively inhibited P-pg and efflux function. In addition, certain derivatives induced apoptosis and an accumulation of the treated MCF-7/ADR cells in the G1, S and G1/S phases.

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“…Several other derivatives of I and II were also identi ed as effective antimicrobial agents [8], anticancer agents [9][10][11][12], c-Src kinase inhibitors [13], antioxidants [14], Xanthine oxidase inhibitors [15], etc. In addition, N-substituted as well as 2,3-heterocyclic fused analogs of I were reported to have wide variety of biological applications [16][17][18][19][20]. Structures of the compounds I and II and their derivatives with their pharmacological applications has been given in Fig.…”

Section: Introductionmentioning

confidence: 99%

One-pot Multicomponent Green Chemistry Approach: Sodium Fluoride-Catalysed Highly Efficient Microwave Irradiation-Assisted Synthesis of Substituted Chromene Derivatives in Aqueous Medium

Fabitha

Arya

Chandrakanth

et al. 2022

Preprint

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2-Amino-4H-benzo[h]chromene-3-carbonitrile and 2-amino-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile are two important pharmacophores with extensive applications in medicinal chemistry. The multicomponent Knoevenagel-Michael reaction is one of the most efficient strategies to construct these two scaffolds. Previous efforts have been made in converting the traditional organic solvents to eco-friendly solvents including H2O generally in the presence of complex catalysts. Here we present our work of using sodium fluoride (NaF) as the catalyst to synthesize a wide scope of the two types of substrates starting from α- or β-naphthol or 4-hydroxycoumarin. Using 12 mol% NaF under the microwave irradiation condition, the reactions were completed within 15–25 min with all the yields exceeding 85%. The reaction products were purified simply by washing with H2O and can be further purified by crystallization with MeOH. The analysis of green chemistry-related parameters suggested that the current method was highly environmentally benign, highlighting the potential of this method in the use of drug discovery and development.

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Antiproliferative effect, cell cycle arrest and apoptosis generation of novel synthesized anticancer heterocyclic derivatives based 4H-benzo[h]chromene

Cited by 42 publications

References 45 publications

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

Synthesis of 9-Hydroxy-1H-Benzo[f]chromene Derivatives with Effective Cytotoxic Activity on MCF7/ADR, P-Glycoprotein Inhibitors, Cell Cycle Arrest and Apoptosis Effects

One-pot Multicomponent Green Chemistry Approach: Sodium Fluoride-Catalysed Highly Efficient Microwave Irradiation-Assisted Synthesis of Substituted Chromene Derivatives in Aqueous Medium

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