Design, synthesis, biological evaluation and molecular docking studies of novel benzofuran–pyrazole derivatives as anticancer agents

El-Karim, Somaia S. Abd; Anwar, Manal M.; Mohamed, Neama A.; Nasr, Tamer; Elseginy, Samia A.

doi:10.1016/j.bioorg.2015.08.006

Cited by 78 publications

(48 citation statements)

References 25 publications

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“…The most of betulin derivatives exhibited high values of molecular mass (M > 500) and lipophilicity (cLogP > 5). However, the tPSA of all compounds is less than 140 Å, what determines high oral bioavailability (Abd El-Karim et al, 2015). …”

Section: Resultsmentioning

confidence: 99%

New acetylenic derivatives of betulin and betulone, synthesis and cytotoxic activity

et al. 2016

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Betulin 1 and its semisynthetic derivatives exhibit a cytotoxic activity toward various cancer cell lines. These compounds are a promising and potential anticancer candidates. A series of betulin derivatives was prepared and tested for the antiproliferative activity in vitro against T47D breast cancer, CCRF/CEM leukemia, HL-60 promyelocytic leukemia, SW707 colorectal, murine P388 leukemia, as well as BALB3T3 normal fibroblasts cell lines. Cisplatin and betulin 1 were used as a reference compounds. Some derivatives of betulin showed a higher cytotoxic activity than the parent compound 1. Two derivatives (5 and 17) were 24-fold potent than betulin 1 against the human promyelocytic leukemia cell line (HL-60), with an IC 50 value of 0.3 µg/mL.

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Section: Resultsmentioning

confidence: 99%

New acetylenic derivatives of betulin and betulone, synthesis and cytotoxic activity

et al. 2016

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“…It alsod emonstrated that the Oatom of the furan ring forms hydrogen bonds with hydroxy groups,therebysignificantly stabilising the complexes. [85] 2.9. In the case of compound 34,t hey were able to achieve an increasei na nimal life span of up to 262 %attolerable doses in amodel of murine intraperitoneally transplanted P388 leukaemia.…”

Section: Pharmacological Profile Of Furan Derivativesmentioning

confidence: 99%

“…Compound 36 (Figure 8) was assayed further and shown to exhibit remarkable growth inhibitory activity pattern against multiple cell lines. [85]…”

Section: Furanmentioning

confidence: 99%

The Current Status of O‐Heterocycles: A Synthetic and Medicinal Overview

Singh

Silakari

2018

ChemMedChem

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O-Heterocycles have been explored in the field of medicinal chemistry for a long time, but their significance has not been duly recognised and they are often shunned in favour of N-heterocycles. The design of bioactive molecules for nearly every pathophysiological condition is primarily focused on novel N-heterocycles. The main reasons for such bias include the ease of synthesis and possible mimicking of physiological molecules by N-heterocycles. But considering only this criterion rarely provides breakthrough molecules for a given disease condition, and instead the risks of toxicity or side effects are increased with such molecules. On the other hand, owing to improved synthetic feasibility, O-heterocycles have established themselves as equally potent lead molecules for a wide range of pathophysiological conditions. In the last decade there have been hundreds of reports validating the fact that equally potent molecules can be designed and developed by using O-heterocycles, and these are also expected to have comparably low toxicity. Even so, researchers tend to remain biased toward the use of N-heterocycles over O-heterocycles. Thus, this review provides a critical analysis of the synthesis and medicinal attributes of O-heterocycles, such as pyrones, oxazolones, furanones, oxetanes, oxazolidinones, and dioxolonones, and others, reported in the last five years, underlining the need for and the advantages guiding researchers toward them.

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“…The inhibitory activity of ATP-Src with benzofuran linked pyrazole derivatives has been investigated previously [47]. Here we attempted the potentials of benzoxazole linked pyrazoles to impede the role of ATP-Src by aligning with previously reported active compound N-acetyl pyrazoline derivative [47]. The salient features of the present molecular docking studies are alignment, overlap of compounds 9b and 9c ( Fig.…”

Section: Molecular Docking Studiesmentioning

confidence: 90%

“…The validated molecular docking studies against protooncogene tyrosine-protein kinase (ATP-Src, PDB: 2BDF), a putative target for cancer has been carried out. The inhibitory activity of ATP-Src with benzofuran linked pyrazole derivatives has been investigated previously [47]. Here we attempted the potentials of benzoxazole linked pyrazoles to impede the role of ATP-Src by aligning with previously reported active compound N-acetyl pyrazoline derivative [47].…”

Section: Molecular Docking Studiesmentioning

confidence: 99%

Novel Pyrazolyl Benzoxazole Conjugates: Design, Synthesis, Molecular Docking Studies and in vitro Anticancer Activities

Thiriveedhi

Nadh

Srinivasu

et al. 2019

LOC

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Nowadays, hybrid drugs have gained a significant role in the treatment of different health problems. Most of the hybrid molecules with different heterocyclic moieties were proved to be potent anti-tumor agents in cancer chemotherapy. Hence, the present study is aimed at the evaluation of in vitro anticancer activity of novel hybrid molecules (pyrazolyl benzoxazole conjugates) and to investigate their anticancer activity by molecular docking studies. Designed, synthesized and characterized the novel pyrazolyl benzoxazole conjugates. Anticancer activity of these compounds was determined by SRB assay. Then molecular docking studies were carried out against proto-oncogene tyrosine-protein kinase (ATP-Src, PDB: 2BDF), a putative target for cancer. All the synthesized compound derivatives were evaluated against MCF-7, KB, Hop62 and A549 cancer cell lines. Compounds 9b and 9c exhibited excellent anticancer activities with GI50 values of <0.1 µM against MCF-7 and A549 cell lines. Compound 9e exhibited good antitumor activity on MCF-7 and A-549 with GI50 values of 0.12 µM and 0.19 µM respectively. Compound 9g showed better anticancer activity on A-549 cancer cell line with GI50 of 0.34 µM. The two-hybrid molecules 9b and 9c are found to be comparably potent with the standard drug doxorubicin and may act as drug lead compounds in medicinal chemistry aspect. The present docking investigation proved that having benzoxazole of compound 9c at the position of benzofuran of reference compound (N-acetyl pyrazoline derivative) might be valid for contributing to anti-cancer activity.

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Design, synthesis, biological evaluation and molecular docking studies of novel benzofuran–pyrazole derivatives as anticancer agents

Cited by 78 publications

References 25 publications

New acetylenic derivatives of betulin and betulone, synthesis and cytotoxic activity

New acetylenic derivatives of betulin and betulone, synthesis and cytotoxic activity

The Current Status of O‐Heterocycles: A Synthetic and Medicinal Overview

Novel Pyrazolyl Benzoxazole Conjugates: Design, Synthesis, Molecular Docking Studies and in vitro Anticancer Activities

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