Utility of Certain 2-Furanone Derivatives for Synthesis of Different Heterocyclic Compounds and Testing their Anti-cancer Activity

2021 ◽  
Vol 17 ◽  
Author(s):  
Rania Helmy Abd El-Hameed ◽  
Hend Medhat El-Shanbaky ◽  
Mosaad Sayed Mohamed
Keyword(s):  
Cell Lines ◽  
Heterocyclic Compounds ◽  
Development Process ◽  
Biological Activities ◽  
Biologically Active ◽  
Cytotoxic Agents ◽  
Inhibition Activity ◽  
Small Cell Lung ◽  
Anti Cancer ◽  
Hct 116

Background: 2-Furanones attracted great attention due to their biological activities. They also have the ability to convert to several biologically active heterocyclic and non-heterocyclic compounds, especially as anti-cancer agents. Objectives: This research aims to assist in the development process of novel cytotoxic agents through synthesizing certain 2-furanone derivatives, using them as starting materials for the preparation of novel heterocyclic and non-heterocyclic compounds, and then testing the synthesized derivatives for their anti-cancer activities. Methods: All the newly synthesized compounds were fully characterized by elemental analysis, IR, Mass, and 1H-NMR spectroscopy. 18 synthesized compounds were selected by National Cancer Institute (NCI) for testing against 60 cell lines, and the active compound was tested as MAPK14 and VEGFR2-inhibitor using Staurosporine as standard. Results: Compound 3a showed higher activity against several cell lines, including leukemia (SR), Non-Small Cell Lung Cancer (NCI-H460), colon cancer (HCT-116), ovarian cancer (OVCAR-4), renal cancer (786-0, ACHN and UO-31), and finally breast cancer (T-47D). It also had better inhibition activity against MAPK14 than the used reference. Conclusion: Compound 3a has promising anti-cancer activities compared to the used standards and may need further modifications and investigations.

scholarly journals 3′,4′-Dihydro-2′H-spiro[indoline-3,1′-isoquinolin]-2-ones as potential anti-cancer agents: synthesis and preliminary screening

2020 ◽  
Vol 7 (1) ◽  
pp. 191316 ◽  
Author(s):  
Maloba M. M. Lobe ◽  
Simon M. N. Efange
Keyword(s):  
Cell Proliferation ◽  
Cell Lines ◽  
Biological Activities ◽  
Cell Cancer ◽  
Breast Cancer Cell Lines ◽  
Small Cell Lung ◽  
Preliminary Screening ◽  
Anti Cancer ◽  
Molecular Hybrids

Both tetrahydroisoquinolines (THIQs) and oxindoles (OXs) display a broad range of biological activities including anti-cancer activity, and are therefore recognized as two privileged scaffolds in drug discovery. In the present study, 24 3′,4′-dihydro-2′H-spiro[indoline-3,1′-isoquinolin]-2-ones, designed as molecular hybrids of THIQ and OX, were synthesized and screened in vitro against 59 cell lines in the NCI-60 screen. Twenty compounds displayed weak to moderate inhibition of cell proliferation; among them, three compounds displayed at least 50% inhibition of cell proliferation. The compounds appeared to target primarily renal cell cancer lines; however, leukaemia, melanoma, non-small cell lung cancer, prostate, ovarian and even breast cancer cell lines were also affected. Therefore, this class of spirooxindoles may provide useful leads in the search for new anti-cancer agents.

Antioxidant, cytotoxic activity and pharmacokinetic studies by SwissAdme, Molinspiration, Osiris and DFT of PhTAD-substituted dihydropyrrole derivatives

2021 ◽  
Vol 17 ◽  
Author(s):  
Arif Ayar ◽  
Masuk Aksahin ◽  
Seda Mesci ◽  
Burak Yazgan ◽  
Melek Gül ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
Heterocyclic Compounds ◽  
Antioxidant Activities ◽  
Biological Activities ◽  
Molecular Structures ◽  
Biologically Active ◽  
Pharmacokinetic Studies ◽  
Ic50 Values ◽  
Mcf 7

Background: Pyrrole compounds having a heterocyclic structure are the most researched and biological activities such as antioxidant and anticancer. Objective: Herein is a first effort to study the significance of heterocyclic compounds to include pyrrole and triazolidine-3,5-dion moiety, on the pharmacokinetic, antioxidant activity and cytotoxic activity on MCF-7 and MCF-12A cell lines. Method: The molecular structures of compounds I-XIV were simulated by the theoretical B3LYP/DFT method. Pharmacokinetic studies of PhTAD-substituted heterocyclic compounds (I-XIV) were analyzed to show Lipinski's rules via in-silico methods of Swiss-ADME. The drug likeness calculations were carried out Molinspiration analyses. The some toxicity risk parameter can be quantified using Osiris. Antioxidant activities determined by DPPH, Fe+2 ions chelating and reducing. Cytotoxic activity measured by MTT and RTCA. Results: Compared with the DPPH activity, the metal chelating activity exhibited serious similar antioxidant effects by PhTAD substituted pyrrole compounds. The same compounds showed the highest activity among the two antioxidant activities. The IC50 values of the compounds are in the range of 12 and 290 µM in MCF-7 cell line. In the MTT and RTCA assays, All compounds showed cytotoxic activity, but about half of the fourteen compounds showed high cytotoxicity. IC50 values of the compounds are in the range of 5 and 54 µM for MTT and range of 1.5 and 44 µM for RTCA. Conclusion: Data of the antioxidant and cytotoxic activity of PhTAD-substituted dihydropyrrole-derived compounds in MCF-7 and MCF-12A cell lines confirmed that the compounds are a biologically active compound and is notable for anti-cancer researches.

scholarly journals 2-Acetylbenzimidazole: a Valuable Synthon for the Synthesis of Biologically Active Molecules

2020 ◽  
Vol 11 (4) ◽  
pp. 11562-11591
Keyword(s):  
Heterocyclic Compounds ◽  
Heterocyclic System ◽  
Biological Activities ◽  
Biologically Active ◽  
Online Search ◽  
Convenient Synthesis ◽  
Anti Cancer ◽  
Pharmacological Interest ◽  
Main Motive ◽  
Biological Aspects

Benzimidazole is an important moiety from a medicinal chemistry perspective due to its various biological activities such as antimicrobial, anti-cancer, anti-diabetic, anti-Alzheimers, and anti-inflammatory, etc. 2-acetylbenzimidazole is exploited to obtain various heterocyclic compounds of pharmacological interest. This review's main motive is to present the literature on 2-acetylbenzimidazole chemistry and provide valuable and up-to-date information for its applications. The present review is carried out by compiling literature from 1964 to 2020 concerning the synthesis and biological aspects of various heterocyclic compounds derived from 2-acetylbenzimidazole. Literature was collected from various online search engines viz. Google Scholar, PubMed, Science Direct, Core, and Semantic scholar. 2-acetylbenzimidazole has been successfully employed as a synthon to obtain heterocyclic system viz. oxirane, pyrazoline, thiazole, pyrazole, isoxazoline, isoxazole, pyridine, pyrimidine, thiazine, diazepine, and other miscellaneous rings. 2-acetylbenzimidazole has shown promise for the convenient synthesis of various heterocyclic compounds. The reactions can be carried out on various reactive sites of 2-acetylbenzimidazole, which are the carbonyl group and the amino group. This review will help to explore various heterocyclic compounds and particularly in the synthesis of biologically useful compounds.

A Study on Camphor Derivatives and Its Applications: A Mini-Review

2021 ◽  
Vol 25 ◽  
Author(s):  
Bendi Anjaneyulu ◽  
Sangeeta ◽  
Naina Saini
Keyword(s):  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Low Cost ◽  
Starting Material ◽  
Biologically Active ◽  
Camphor Sulfonic Acid ◽  
Anti Cancer ◽  
Camphor Derivatives ◽  
Enantiospecific Synthesis ◽  
Active Substances

: Natural compounds are the prominent sources for the synthesis of abundant biologically active substances in medicinal chemistry. Camphor exists in two enantiomeric forms i.e., R and S, or both, which are readily obtainable. Camphor is a small molecule with chirality property that binds to some active site, together with its low cost and convenience to transform into synthetically useful derivatives and one of the most important monoterpenoids widely spread in plants and has been used as starting material for the various camphor based derivatives which exhibit several biological activities include antimicrobial, antiviral, antioxidant, analgesic and anti-cancer. Many of those simple derivatives are commercially available in the form of camphor sulfonic acid or ketopinic acid that can be easily be produced from camphor. This compound is primarily used as a chiral starting material in the enantiospecific synthesis of natural products is because of its available methods for the direct or indirect introduction of functionality at C-3, C-5, C-8, C-9, and C-10 carbon atoms. In this study, heterocyclic compounds derived from camphor are arranged in different groups as Camphor-Derived Simple Heterocycles, Fused Camphor-Derived Heterocycles, Spiro Camphor-Derived Heterocycles, Ring Expanded Camphor-Derived Heterocycles and Camphor derived metal complexes. This study summarizes the transformations of camphor and its derivatives along with their biological activities.

Biologically Active 2,5-Disubstituted-1,3,4-Oxadiazoles

2009 ◽  
Vol 2 (1) ◽  
pp. 390-406
Author(s):  
Harish Rajak ◽  
Murli Dhar Kharya ◽  
Pradeep Mishra
Keyword(s):  
Heterocyclic Compounds ◽  
Medical Literature ◽  
Biological Activities ◽  
Biologically Active ◽  
Pharmacological Properties ◽  
Clinical Use ◽  
Synthetic Drugs ◽  
Physiologic Activity ◽  
Pharmacologically Active

There are vast numbers of pharmacologically active heterocyclic compounds in regular clinical use. The presence of heterocyclic structures in diverse types of compounds is strongly indicative of the profound effects such structure exerts on physiologic activity, and recognition of this is abundantly reflected in efforts to find useful synthetic drugs. The 1,3,4-oxadiazole nucleus has emerged as one of the potential pharmacophore responsible for diverse pharmacological properties. Medical Literature is flooded with reports of a variety of biological activities of 2,5-Disubstituted-1,3,4-oxadiazoles. The present work is an attempt to summarize and enlist the various reports published on biologically active 2,5-disubstituted-1,3,4-oxadiazoles.

Oxazole-Based Compounds As Anticancer Agents

2020 ◽  
Vol 26 (41) ◽  
pp. 7337-7371 ◽  
Author(s):  
Maria A. Chiacchio ◽  
Giuseppe Lanza ◽  
Ugo Chiacchio ◽  
Salvatore V. Giofrè ◽  
Roberto Romeo ◽  
...  
Keyword(s):  
Cancer Research ◽  
Drug Discovery ◽  
Anticancer Agents ◽  
Heterocyclic Compounds ◽  
Chemical Diversity ◽  
Biologically Active ◽  
New Drugs ◽  
The Core ◽  
Anti Cancer ◽  
Biologically Active Derivatives

: Heterocyclic compounds represent a significant target for anti-cancer research and drug discovery, due to their structural and chemical diversity. Oxazoles, with oxygen and nitrogen atoms present in the core structure, enable various types of interactions with different enzymes and receptors, favoring the discovery of new drugs. Aim of this review is to describe the most recent reports on the use of oxazole-based compounds in anticancer research, with reference to the newly discovered iso/oxazole-based drugs, to their synthesis and to the evaluation of the most biologically active derivatives. The corresponding dehydrogenated derivatives, i.e. iso/oxazolines and iso/oxazolidines, are also reported.

Synthesis of Indolyl Pyrazole Scaffolds as Potential Anti-cancer Agents and their Molecular Modelling Studies

2020 ◽  
Vol 17 (7) ◽  
pp. 828-839
Author(s):  
Ganga Reddy Gaddam ◽  
Pramod Kumar Dubey ◽  
Venkata Ramana Reddy Chittireddy
Keyword(s):  
Cell Lines ◽  
Biological Activities ◽  
Moderate Activity ◽  
Lung Cancer Cell ◽  
Anti Cancer ◽  
A549 Lung Cancer Cell ◽  
New Chemical Entities ◽  
Molecular Modelling Studies ◽  
Modelling Studies ◽  
A549 Lung

Background:: Indole and pyrazoles are one of the prime structural units in the field of medicinal chemistry and have been reported to exhibit a variety of biological activities specifically anti-cancer. In view of their medicinal significance, we synthesized a conjugate of the two moieties to get access to newer and potential anti-cancer agents. Methods: Indolyl pyrazoles [3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-(1-methyl-1H-indole-3-carbon yl)acrylonitriles] (4a-l) were synthesized by adopting simple and greener protocol and all the synthesized derivatives were docked against Bcl-2 protein and the selected chemical moieties were screened for their cytotoxicity by using the MTT assay. Results: : All the synthesized compounds were docked against BCL-2 protein in order to understand their binding pattern. Among the 12 compounds docked, 4d, 4f, 4h, 4j, and 4l compounds exhibited better protein binding interactions and the same were screened for their anti-cancer activity against A549 (lung) cancer cell lines at a concentration of 100 μM using Doxorubicin as standard. Substitutions such as N-benzyl, N-ethyl groups and halogen groups such as Br, Cl on indole ring showed moderate activity against A-549 cell lines. Conclusion:: Among the 5 indolyl pyrazole derivatives screened, compounds 4h and 4j showed significantly better activity with an IC50 of 33.12 and 34.24 μM, respectively. Further, structural tweaking of the synthesized new chemical entities may lead to potential hit/lead-like molecules.

Evaluation of Pyrano[3,2 C] Quinoline Analogues as Anticancer Agents

2019 ◽  
Vol 19 (10) ◽  
pp. 1285-1292 ◽  
Author(s):  
Kuldip D. Upadhyay ◽  
Anamik K. Shah
Keyword(s):  
Anticancer Agents ◽  
Human Cancer ◽  
Biological Activities ◽  
Cytotoxic Agents ◽  
Tumor Growth Inhibition ◽  
Mice Model ◽  
One Pot ◽  
Aryl Ring ◽  
Hct 116

Background: Quinoline analogues exhibited diversified biological activities depending on the structure type. A number of natural products with pyrano[3,2-c]quinolone structural motifs and patented chromenes were reported as promising cytotoxic agents. Objective: The present study is aimed to evaluate a new series of pyrano[3,2-c]quinoline scaffolds derived from the fusion of bioactive quinolone pharmacophore with structurally diverse aryl substituted chromene for its cytotoxicity. Methods: A library of pyrano[3,2-c]quinoline analogues was prepared from one-pot multi component synthesis using various aromatic aldehydes, malononitrile and 2,4-dihydroxy-1-methylquinoline. The new synthetics were primarily screened for its cytotoxicity (IC50) against different human cancer cell lines in vitro. The promising synthetics were further evaluated in vitro for their potency against different kinase activity. The promising compounds were finally tested for their in vivo efficacy in SCID type mice HCT-116 tumor model. Results: The screening results revealed that compounds 4c, 4f, 4i and 4j showed promising activity in in vitro study. However, compound 4c was found to be the most potent candidate with 23% tumor growth inhibition in HCT-116 tumor mice model. Conclusion: The structure activity relationship suggested that 3-substitution on the aryl ring at C4 position of the pyrano[3,2 c]quinolone moiety seems to have an important position for cytotoxicity activity. However, 3- chloro substitution at C4 aryl ring showed a significant alteration of the bioactive conformer of the parent scaffold and outcome with compound 4c as the most potent candidate of the series.

scholarly journals Mangiferin as New Potential Anti-Cancer Agent and Mangiferin-Integrated Polymer Systems—A Novel Research Direction

Biomolecules ◽  
2021 ◽  
Vol 11 (1) ◽  
pp. 79
Author(s):  
Svetlana N. Morozkina ◽  
Thi Hong Nhung Vu ◽  
Yuliya E. Generalova ◽  
Petr P. Snetkov ◽  
Mayya V. Uspenskaya
Keyword(s):  
Molecular Mechanisms ◽  
Biological Activities ◽  
Research Direction ◽  
Biological Action ◽  
The Body ◽  
Biologically Active ◽  
Polymer Systems ◽  
Anti Cancer ◽  
Long Time ◽  
Cancer Agent

For a long time, the pharmaceutical industry focused on natural biologically active molecules due to their unique properties, availability and significantly less side-effects. Mangiferin is a naturally occurring C-glucosylxantone that has substantial potential for the treatment of various diseases thanks to its numerous biological activities. Many research studies have proven that mangiferin possesses antioxidant, anti-infection, anti-cancer, anti-diabetic, cardiovascular, neuroprotective properties and it also increases immunity. It is especially important that it has no toxicity. However, mangiferin is not being currently applied to clinical use because its oral bioavailability as well as its absorption in the body are too low. To improve the solubility, enhance the biological action and bioavailability, mangiferin integrated polymer systems have been developed. In this paper, we review molecular mechanisms of anti-cancer action as well as a number of designed polymer-mangiferin systems. Taking together, mangiferin is a very promising anti-cancer molecule with excellent properties and the absence of toxicity.

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