Synthesis, in-vitro cytotoxicity of 1H-benzo[f]chromene derivatives and structure–activity relationships of the 1-aryl group and 9-position

2017 ◽  
Vol 72 (5-6) ◽  
pp. 161-171 ◽  
Author(s):  
Hany M. Mohamed ◽  
Ahmed M. Fouda ◽  
Essam S.A.E.H. Khattab ◽  
Ahmed M. El- Agrody ◽  
Tarek H. Afifi
Keyword(s):  
Phenyl Ring ◽  
In Vitro Cytotoxicity ◽  
Cytotoxic Activities ◽  
Specific Group ◽  
Aryl Group ◽  
Sar Studies ◽  
Structure Activity ◽  
Hct 116 ◽  
Mcf 7

Abstract A series of 1H-benzo[f]chromene-2-carbonitriles was synthesized and evaluated for their cytotoxic activities against MCF-7, HCT-116, and HepG-2 cancer cells. The SAR studies reported that the substitution in the phenyl ring at 1-position of 1H-benzo[f]chromene nucleus with the specific group, H atom, or methoxy group at 9-position increases the ability of the molecule against the different cell lines.

scholarly journals Semi-Synthesis of Harringtonolide Derivatives and Their Antiproliferative Activity

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1380
Author(s):  
Xiutao Wu ◽  
Lijie Gong ◽  
Chen Chen ◽  
Ye Tao ◽  
Wuxi Zhou ◽  
...  
Keyword(s):  
Antiproliferative Activity ◽  
Normal Cell ◽  
Selectivity Index ◽  
Cytotoxic Activities ◽  
Structure Activity ◽  
Growth Inhibitory ◽  
Growth Inhibitory Activity ◽  
Hct 116 ◽  
Systematic Structure

Harringtonolide (HO), a natural product isolated from Cephalotaxus harringtonia, exhibits potent antiproliferative activity. However, little information has been reported on the systematic structure−activity relationship (SAR) of HO derivatives. Modifications on tropone, lactone, and allyl positions of HO (1) were carried out to provide 17 derivatives (2–13, 11a–11f). The in vitro antiproliferative activity against four cancer cell lines (HCT-116, A375, A549, and Huh-7) and one normal cell line (L-02) was tested. Amongst these novel derivatives, compound 6 exhibited comparable cell growth inhibitory activity to HO and displayed better selectivity index (SI = 56.5) between Huh-7 and L-02 cells. The SAR results revealed that the tropone and lactone moieties are essential for the cytotoxic activities, which provided useful suggestions for further structural optimization of HO.

scholarly journals IN-VITRO CYTOTOXICITY AND ANTIOXIDANT EVALUATION OF 7-AMINO-2-STYRYLCHROMONE DERIVATIVES

2017 ◽  
Vol 10 (11) ◽  
pp. 152
Author(s):  
Lalitha Simon
Keyword(s):  
Nitric Oxide ◽  
Cell Lines ◽  
Aromatic Aldehydes ◽  
In Vitro Cytotoxicity ◽  
Hct 116 ◽  
Dpph Scavenging Activity ◽  
Diphenyl Tetrazolium Bromide ◽  
Dpph Scavenging ◽  
Mcf 7

  Objective: The objective of this study was to synthesize 7-amino-2-styrylchromone derivatives and evaluate their in vitro cytotoxic and antioxidant potential.Methods: 7-amino-2-styrylchromones were synthesized from 7-amino-2-methylchromone by condensing it with various substituted aromatic aldehydes. The cytotoxicity of the synthesized molecules was assessed against two cell lines, MCF-7 and HCT-116 by 3-(4,5-dimethyl thiazol-2-yl)-2,5- diphenyl tetrazolium bromide assay. Cell cycle analysis of the most potent molecule ASC-7 was carried out. The antioxidant studies were conducted by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and nitric oxide methods.Result: (E)-7-amino-2-(3,4-methylenedioxystyryl)-4H-chromen-4-one (ASC-7) with inhibitory concentration 50% (IC50) 56.0 μM was found to be the most potent molecule against MCF-7. ASC-7 induced G0/G1 phase arrest of MCF-7. Furthermore, (E)-7-amino-2-(3,4-methylenedioxystyryl)- 4H-chromen-4-one(ASC-7) showed good DPPH scavenging activity (IC50 54.6 μM). However, none of the tested compounds exhibited nitric oxide scavenging property.Conclusion: This study reports the synthesis of 7-amino-2-styrylchromones. Some of the synthesized compounds showed moderate cytotoxicity against the tested cell lines MCF-7 and HCT-116. (E)-7-amino-2-(3,4-methylenedioxystyryl)-4H-chromen-4-one (ASC-7) was found to be the best cytotoxic and antioxidant agent.

Synthesis, in-vitro cytotoxicity of 4H-benzo[h]chromene derivatives and structure–activity relationships of 4-aryl group and 3-, 7-positions

2016 ◽  
Vol 70 (9) ◽  
Author(s):  
Ahmed M. El-Agrody ◽  
Heba K. Abd El-Mawgoud ◽  
Ahmed M. Fouda ◽  
Essam S. A. E. H. Khattab
Keyword(s):  
In Vitro Cytotoxicity ◽  
Aryl Group ◽  
Structure Activity Relationships ◽  
Structure Activity

AbstractA series of 2-amino-4

scholarly journals Design, Synthesis and in vitro Cytotoxicity Evaluation of New Fluorinated Ionic Salt (S)-(+)-2,3-Dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione as Strategies for Improving Anticonvulsant Activity

2020 ◽  
Vol 32 (4) ◽  
pp. 975-980 ◽  
Author(s):  
V. Natchimuthu ◽  
S. Ravi ◽  
Murugan Ramalingam ◽  
V. Renuga
Keyword(s):  
In Vitro Cytotoxicity ◽  
Breast Adenocarcinoma ◽  
Adenocarcinoma Cell Line ◽  
Design Synthesis ◽  
Ionic Salt ◽  
Structure Activity ◽  
Preliminary Study ◽  
Clinical Drugs ◽  
Mcf 7

The reaction of (S)-(+)-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione (1) with 4-(trifluoromethyl)benzoic acid (2, C8H5F3O2) in dimethylformamide leads to the formation of C8H5F3O2 (1) as a classical ionic salt 3. The structure of new compound has been characterized by FTIR, 1H NMR, 13C NMR, HRMS spectroscopy. The new compound was tested for in vitro cytotoxicity evaluation by MTT assay against breast adenocarcinoma cell line of MCF-7 cells. A new compound 3 (IC50:199 μM) emerged as minimal toxic when compared to clinical drugs carbamazepine, topiramate and benzodiazepine. A preliminary study of structure activity relationship revealed that the incorporation of fluoro or trifluoromethyl moiety into the compound, even through ionic bond formation, had a great effect on the biological activity and with less toxicity or side effects.

scholarly journals An Efficient Synthetic Approach Towards Benzo[b]pyrano[2,3-e][1,4]diazepines, and Their Cytotoxic Activity

Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2051
Author(s):  
Islam H. El Azab ◽  
Nadia A.A. Elkanzi
Keyword(s):  
Human Tumor ◽  
Breast Adenocarcinoma ◽  
Cytotoxic Activities ◽  
Synthetic Approach ◽  
Standard Drug ◽  
In Vitro Investigation ◽  
Ic50 Values ◽  
Hct 116 ◽  
Mcf 7

In search of unprecedented tri and/or tetrapod pharmacophoric conjugates, a series of 32 new 4-ethyl-1H-benzo[b][1,4]diazepin-2(3H)-ones were synthesized and properly elucidated using MS, IR, NMR, and elemental analysis. In vitro investigation of 11 compounds of this series, using a panel of two human tumor cell lines namely; human breast adenocarcinoma (MCF-7), and human colorectal carcinoma (HCT-116), revealed promising cytotoxic activities. Among all synthesized compounds, analogue 9 displayed maximum cytotoxicity with IC50 values of 16.19 ± 1.35 and 17.16 ± 1.54 μM against HCT-116 and MCF-7, respectively, compared to standard drug doxorubicin.

scholarly journals Synthesis, Anticancer Evaluation and Structure-Activity Analysis of Novel (E)- 5-(2-Arylvinyl)-1,3,4-oxadiazol-2-yl)benzenesulfonamides

2020 ◽  
Vol 21 (6) ◽  
pp. 2235
Author(s):  
Krzysztof Szafrański ◽  
Jarosław Sławiński ◽  
Łukasz Tomorowicz ◽  
Anna Kawiak
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Human Tumor ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Structure Activity ◽  
Hela Cell Lines ◽  
Hct 116 ◽  
Mcf 7

To learn more about the structure–activity relationships of (E)-3-(5-styryl-1,3,4-oxadiazol-2-yl)benzenesulfonamide derivatives, which in our previous research displayed promising in vitro anticancer activity, we have synthesized a group of novel (E)-5-[(5-(2-arylvinyl)-1,3,4-oxadiazol-2-yl)]-4-chloro-2-R1-benzenesulfonamides 7–36 as well as (E)-4-[5-styryl1,3,4-oxadiazol-2-yl]benzenesulfonamides 47–50 and (E)-2-(2,4-dichlorophenyl)-5-(2-arylvinyl)-1,3,4-oxadiazols 51–55. All target derivatives were evaluated for their anticancer activity on HeLa, HCT-116, and MCF-7 human tumor cell lines. The obtained results were analyzed in order to explain the influence of a structure of the 2-aryl-vinyl substituent and benzenesulfonamide scaffold on the anti-tumor activity. Compound 31, bearing 5-nitrothiophene moiety, exhibited the most potent anticancer activity against the HCT-116, MCF-7, and HeLa cell lines, with IC50 values of 0.5, 4, and 4.5 µM, respectively. Analysis of structure-activity relationship showed significant differences in activity depending on the substituent in position 3 of the benzenesulfonamide ring and indicated as the optimal meta position of the sulfonamide moiety relative to the oxadizole ring. In the next stage, chemometric analysis was performed basing on a set of computed molecular descriptors. Hierarchical cluster analysis was used to examine the internal structure of the obtained data and the quantitative structure–activity relationship (QSAR) analysis with multiple linear regression (MLR) method allowed for finding statistically significant models for predicting activity towards all three cancer cell lines.

scholarly journals New Bioactive Esters and Phosphonates Semisynthesized From (±)-Vasicinone: An Alkaloid Isolated From Peganum harmala

2019 ◽  
Vol 14 (12) ◽  
pp. 1934578X1989354
Author(s):  
Insaf Filali ◽  
Amira Jelassi ◽  
Hichem Ben Jannet
Keyword(s):  
Cell Lines ◽  
Chloroacetic Acid ◽  
Cytotoxic Activities ◽  
Protecting Group ◽  
Peganum Harmala ◽  
Tosyl Chloride ◽  
Trialkyl Phosphites ◽  
Hct 116 ◽  
Mcf 7

A series of N-tosyl α-amino acids 2a-e, prepared using a tosyl chloride protecting group, was condensed with (±)-vasicinone 1, isolated from the seeds of the plant Peganum harmala, to generate the corresponding esters 3a-e and 3b′-e′. (±)-Vasicinone 1 was also reacted with chloroacetic acid chloride to afford a new chlorinated ester 4 which was refluxed with trialkyl phosphites to give 2 new phosphonates 5a,b. All synthesized compounds were characterized with the help of spectroscopic means, including NMR (1H, 13C, and 31P) and ES-HRMS, and then screened for their in vitro anti-acetylcholinesterase (AChE), anti-5-lipoxygenase (5-LOX), and cytotoxic activities (MCF-7, OVCAR-3, and HCT-116 cell lines). Most synthesized derivatives exhibited a cytotoxic activity against 3 cell lines used. The phosphonate derivative 5b was found to be the most active one (IC50 = 63.7 ± 1.4 µM) against AChE enzyme. Only 2 diastereoisomers 3e and 3e′ exhibited activity against 5-LOX enzyme with IC50 values of 63.1 ± 4.2 and 79.2 ± 8.3 µM, respectively.

scholarly journals Synthesis, In Vitro Antimicrobial and Cytotoxic Activities of Some New Pyrazolo[1,5-a]pyrimidine Derivatives

Molecules ◽  
2019 ◽  
Vol 24 (6) ◽  
pp. 1080 ◽  
Author(s):  
Ahmed Fouda ◽  
Hebat-Allah Abbas ◽  
Eman Ahmed ◽  
Ali Shati ◽  
Mohammad Alfaifi ◽  
...  
Keyword(s):  
Antifungal Agents ◽  
Human Cancer ◽  
Cytotoxic Activities ◽  
Antitumor Activities ◽  
Efficient Procedure ◽  
Human Cancer Cell Lines ◽  
Hct 116 ◽  
Antibacterial And Antifungal ◽  
Mcf 7

A new series of pyrazole 4–7 and pyrazolo[1,5-a]pyrimidine 8–13 were synthesized by using a simple, efficient procedure, and screened for their in-vitro antimicrobial and antitumor activities. Symmetrical and asymmetrical 3,6-diarylazo-2,5,7-triaminopyrazolo[1,5-a]pyrimidine were synthesized by the conventional method and also subjected to microwave irradiation and under ultrasound conditions. The biological results revealed that most of the tested compounds proved to be active as antibacterial and antifungal agents. The antitumor activity of the synthesized compounds was evaluated against human cancer cell lines, MCF-7, HCT-116, and HepG-2, as compared with Doxorubicin as a control.

Neurotoxicity of Pesticides: The Roadmap for the Cubic Mode of Action

2020 ◽  
Vol 27 (1) ◽  
pp. 54-77 ◽  
Author(s):  
Bogdan Bumbăcilă ◽  
Mihai V. Putz
Keyword(s):  
Biological Activity ◽  
Wiener Index ◽  
Laboratory Animals ◽  
Covalent Bonds ◽  
Organophosphate Compounds ◽  
Sar Studies ◽  
Structure Activity ◽  
Cubic Structure

Pesticides are used today on a planetary-wide scale. The rising need for substances with this biological activity due to an increasing consumption of agricultural and animal products and to the development of urban areas makes the chemical industry to constantly investigate new molecules or to improve the physicochemical characteristics, increase the biological activities and improve the toxicity profiles of the already known ones. Molecular databases are increasingly accessible for in vitro and in vivo bioavailability studies. In this context, structure-activity studies, by their in silico - in cerebro methods, are used to precede in vitro and in vivo studies in plants and experimental animals because they can indicate trends by statistical methods or biological activity models expressed as mathematical equations or graphical correlations, so a direction of study can be developed or another can be abandoned, saving financial resources, time and laboratory animals. Following this line of research the present paper reviews the Structure-Activity Relationship (SAR) studies and proposes a correlation between a topological connectivity index and the biological activity or toxicity made as a result of a study performed on 11 molecules of organophosphate compounds, randomly chosen, with a basic structure including a Phosphorus atom double bounded to an Oxygen atom or to a Sulfur one and having three other simple covalent bonds with two alkoxy (-methoxy or -ethoxy) groups and to another functional group different from the alkoxy groups. The molecules were packed on a cubic structure consisting of three adjacent cubes, respecting a principle of topological efficiency, that of occupying a minimal space in that cubic structure, a method that was called the Clef Method. The central topological index selected for correlation was the Wiener index, since it was possible this way to discuss different adjacencies between the nodes in the graphs corresponding to the organophosphate compounds molecules packed on the cubic structure; accordingly, "three dimensional" variants of these connectivity indices could be considered and further used for studying the qualitative-quantitative relationships for the specific molecule-enzyme interaction complexes, including correlation between the Wiener weights (nodal specific contributions to the total Wiener index of the molecular graph) and the biochemical reactivity of some of the atoms. Finally, when passing from SAR to Q(uantitative)-SAR studies, especially by the present advanced method of the cubic molecule (Clef Method) and its good assessment of the (neuro)toxicity of the studied molecules and of their inhibitory effect on the target enzyme - acetylcholinesterase, it can be seen that a predictability of the toxicity and activity of different analogue compounds can be ensured, facilitating the in vivo experiments or improving the usage of pesticides.

Evaluation of Cytotoxic and Tyrosinase Inhibitory Activities of 2-phenoxy(thiomethyl) pyridotriazolopyrimidines: In Vitro and Molecular Docking Studies

2020 ◽  
Vol 20 (14) ◽  
pp. 1714-1721
Author(s):  
Hatem A. Abuelizz ◽  
El Hassane Anouar ◽  
Mohamed Marzouk ◽  
Mizaton H. Hasan ◽  
Siti R. Saleh ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Kojic Acid ◽  
Docking Studies ◽  
Breast Adenocarcinoma ◽  
Amino Acid Residues ◽  
New Class ◽  
Structure Activity ◽  
Tyrosinase Inhibitors ◽  
Mcf 7

Background: The use of tyrosinase has confirmed to be the best means of recognizing safe, effective, and potent tyrosinase inhibitors for whitening skin. Twenty-four 2-phenoxy(thiomethyl)pyridotriazolopyrimidines were synthesized and characterized in our previous studies. Objective: The present work aimed to evaluate their cytotoxicity against HepG2 (hepatocellular carcinoma), A549 (pulmonary adenocarcinoma), MCF-7 (breast adenocarcinoma) and WRL 68 (embryonic liver) cell lines. Methods: MTT assay was employed to investigate the cytotoxicity, and a tyrosinase inhibitor screening kit was used to evaluate the Tyrosinase (TYR) inhibitory activity of the targets. Results: The tested compounds exhibited no considerable cytotoxicity, and nine of them were selected for a tyrosinase inhibitory test. Compounds 2b, 2m, and 5a showed good inhibitory percentages against TYR compared to that of kojic acid (reference substance). Molecular docking was performed to rationalize the Structure-Activity Relationship (SAR) of the target pyridotriazolopyrimidines and analyze the binding between the docked-selected compounds and the amino acid residues in the active site of tyrosinase. Conclusion: The target pyridotriazolopyrimidines were identified as a new class of tyrosinase inhibitors.

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