scholarly journals Synthesis and in vitro anticancer activities of substituted N -(4′-nitrophenyl)- l -prolinamides

2020 ◽  
Vol 7 (9) ◽  
pp. 200906
Author(s):  
Adejoke Osinubi ◽  
Josephat Izunobi ◽  
Xiaoguang Bao ◽  
Olayinka Asekun ◽  
Jiehong Kong ◽  
...  
Keyword(s):  
Biological Properties ◽  
Lower Percentage ◽  
Cytotoxic Activities ◽  
Anticancer Activities ◽  
One Pot ◽  
Human Carcinoma ◽  
Carcinoma Cell Lines ◽  
Hct 116 ◽  
Cell Inhibition

Prolinamides are present in secondary metabolites and have wide-ranging biological properties as well as antimicrobial and cytotoxic activities. N -(4′-substituted phenyl)- l -prolinamides 4a – 4w were synthesized in two steps, starting from the condensation of p -fluoronitrobenzene 1a – 1b with l -proline 2a – 2b , under aqueous–alcoholic basic conditions to afford N -aryl- l -prolines 3a – 3c , which underwent amidation via a two-stage, one-pot reaction involving SOCl 2 and amines, to furnish l -prolinamides in 20–80% yield. The cytotoxicities of 4a – 4w against four human carcinoma cell lines (SGC7901, HCT-116, HepG2 and A549) were evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay; with good tumour inhibitory activities (79.50 ± 1.24%–50.04 ± 1.45%) against HepG2. 4a exhibited the best anti-tumour activity against A549 with percentage cell inhibition of 95.41 ± 0.67% at 100 µM. Likewise, 4s (70.13 ± 3.41%) and 4u (83.36 ± 1.70%) displayed stronger antineoplastic potencies against A549 than the standard, 5-fluorouracil (64.29 ± 2.09%), whereas 4a (93.33 ± 1.36%) and 4u (81.29 ± 2.32%) outperformed the reference (81.20 ± 0.08%) against HCT-116. SGC7901 showed lower percentage cell viabilities with 4u (8.02 ± 1.54%) and 4w (27.27 ± 2.38%). These results underscore the antiproliferative efficacies of l -prolinamides while exposing 4a and 4u as promising broad-spectrum anti-cancer agents. Structure-activity relationship studies are discussed.

Synthesis and Antitumor Activity Evaluation of New Phenanthrene-Based Tylophorine Derivatives

2019 ◽  
Vol 16 (6) ◽  
pp. 462-467
Author(s):  
Songtao Li ◽  
Hongling Zhao ◽  
Zhifeng Yin ◽  
Shuhua Deng ◽  
Yang Gao ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Cell Lines ◽  
Antitumor Activities ◽  
Human Carcinoma ◽  
Carcinoma Cell Lines ◽  
Structure Activity ◽  
Human Carcinoma Cell ◽  
Ic50 Values ◽  
Relationship Of

A series of new phenanthrene-based tylophorine derivatives (PBTs) were synthesized in good yield and their structures were characterized by 1H-NMR spectroscopy and ESI MS. In vitro antitumor activity of these compounds against five human carcinoma cell lines, including HCT116 (colorectal), BGC-823 (gastric), HepG-2 (hepatic), Hela (cervical) and H460 (lung) cells, was evaluated by MTT assay. Among these PBTs, compound 6b showed the highest antitumor activities against HCT116 and HepG-2 cell lines with IC50 values of 6.1 and 6.4 μM, respectively, which were comparable to that of adriamycin hydrochloride. The structure-activity relationship of these compounds was also discussed based on the results of their antitumor activity.

Synthesis and Anti-Tumor Activity Evaluation of Novel 7-Fluoro-4-(1- Piperazinyl) Quinolines

2019 ◽  
Vol 16 (6) ◽  
pp. 663-669
Author(s):  
Dan Liu ◽  
Aiqi Xue ◽  
Zhixin Liu ◽  
Yi Zhang ◽  
Penghui Peng ◽  
...  
Keyword(s):  
Spectral Analysis ◽  
Cancer Therapy ◽  
Carcinoma Cell ◽  
A549 Cells ◽  
Quinoline Derivatives ◽  
Human Carcinoma ◽  
Carcinoma Cell Lines ◽  
Human Carcinoma Cell ◽  
Anti Tumor Activity

Background: Three series of new 7-fluoro-4-(1-piperazinyl) quinolines (I1~I6, II1~II2 and IV1~IV4) were synthesized. Their anti-tumor activity was evaluated in vitro against three human carcinoma cell lines, namely SGC-7901 cells, BEL-7402 cells and A549 cells expressing high levels of EGFR by Methyl Thiazolyl Terazolium (MTT) assay. Methods: Three series of quinoline derivatives were synthesized, characterized and evaluated for their in vitro anti-tumor activities. Results and Discussion: Structures of the newly synthesized compounds were confirmed by spectral analysis. The preliminary bioassay indicated that compounds I1, I10 and II1 exhibited better anti-tumor activity than the rest of the target compounds and gefitinib against A549 cell based assay, which demonstrated that compounds I1, I10 and II1 are potential agents for cancer therapy. Results suggested that the substitutes on piperazinyl influenced anti-tumor activities remarkably. Conclusion: These results are useful for discovering more potent novel anti-tumor compounds and further studies are ongoing.

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 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.

Suppression of growth in vitro and tumorigenicity in vivo of human carcinoma cell lines by transfectedp16INK4

1996 ◽  
Vol 16 (1) ◽  
pp. 53-60 ◽  
Author(s):  
Elisa A. Spillare ◽  
Aikou Okamoto ◽  
Koichi Hagiwara ◽  
Douglas J. Demetrick ◽  
Manuel Serrano ◽  
...  
Keyword(s):  
Cell Lines ◽  
Carcinoma Cell ◽  
Human Carcinoma ◽  
Carcinoma Cell Lines ◽  
Human Carcinoma Cell

scholarly journals Synthesis and Biological Evaluation of Aminonaphthols Incorporated Indole Derivatives

2014 ◽  
Vol 2014 ◽  
pp. 1-12 ◽  
Author(s):  
Saundane Anand Raghunath ◽  
Kirankumar Nandibeoor Mathada
Keyword(s):  
Radical Scavenging ◽  
Antitubercular Activity ◽  
Antimicrobial Activities ◽  
Biological Evaluation ◽  
Secondary Amines ◽  
Anticancer Activities ◽  
One Pot ◽  
Antioxidant Power ◽  
Mic Value

An efficient one pot condensation of naphthols (1), 2,5-disubstituted indole-3-carboxaldehydes (2), and secondary amines (3) has been achieved using dichloromethane as a solvent, stirring at room temperature. Some of the new [(disubstituted amino)(5-substituted 2-phenyl-1H-indol-3-yl)methyl]naphthalene-ols (4) derivatives were prepared in good yields. The significant features of this method are simple work-up procedure, inexpensive nontoxic solvent, shorter reaction times, and excellent product yields. The structures of newly synthesized compounds (4a–r) are confirmed by their elemental analysis, FTIR, 1H and 13C NMR, and mass spectral data. These compounds were screened for their in vitro antioxidant, antimicrobial, antitubercular, and anticancer activities. Among the synthesized compounds (4a–r), the compound 4e exhibited highest activity for radical scavenging and ferric ions reducing antioxidant power activities; compounds 4b, 4h, and 4k showed good metal chelating activity. Compounds 4n and 4q showed excellent antimicrobial activities with MIC value 08 µg/mL against tested strains. Compounds 4h, 4k, 4n, and 4q exhibited promising antitubercular activity with MIC value 12.5 µg/mL. Compounds 4k and 4q exhibited 100% cell lysis at concentration 10 µg/mL against MDA-MB-231 (human adenocarcinoma mammary gland) cell lines.

scholarly journals Bunias erucago L.: Glucosinolate Profile and In Vitro Biological Potential

Molecules ◽  
2019 ◽  
Vol 24 (4) ◽  
pp. 741 ◽  
Author(s):  
Ivica Blažević ◽  
Azra Đulović ◽  
Vedrana Čikeš Čulić ◽  
Franko Burčul ◽  
Ivica Ljubenkov ◽  
...  
Keyword(s):  
Degradation Products ◽  
Dry Weight ◽  
Mediterranean Area ◽  
Biological Properties ◽  
Glucosinolate Content ◽  
Cytotoxic Activities ◽  
Plant Parts ◽  
Biological Potential ◽  
Glucosinolate Profile

Bunias erucago belongs to the Brassicaceae family, which represents a forgotten crop of the Euro-Mediterranean area. The aim of the present study was to determine the glucosinolate profile in different plant parts and biological properties (antioxidant, anticholinesterase, and cytotoxic activities) of the isolates containing glucosinolate breakdown products. The chemical profiles were determined by using HPLC-PDA-MS/MS of desulfoglucosinolates and GC-MS of glucosinolate degradation products. The analysis of B. erucago showed the presence of seven glucosinolates: gluconapin (1), glucoraphasatin (2), glucoraphenin (3), glucoerucin (4), glucoraphanin (5), glucotropaeolin (6), and glucosinalbin (7). The total glucosinolate content ranged from 7.0 to 14.6 µmol/g of dry weight, with the major glucosinolate glucosinalbin in all parts. The antioxidant activity of all volatile isolates was not notable. At a tested concentration of 227 μg/mL, flower hydro-distillate (FH) showed good AChE inhibition, i.e., 40.9%, while root hydro-distillate (RH) had good activity against BChE, i.e., 54.3%. FH showed the best activity against both tested human bladder cancer cell lines, i.e., against T24 after 72 h, which have IC50 of 16.0 μg/mL, and against TCCSUP after 48 h with IC50 of 7.8 μg/mL, and can be considered as highly active. On the other hand, RH showed weak activity against tested cancer cells.

scholarly journals Composition and in-vitro CytotoxicActivities of the Leaf Essential Oil of Beilschmiedia erythrophloia from Taiwan

2013 ◽  
Vol 8 (1) ◽  
pp. 1934578X1300800
Author(s):  
Yu-Chang Su ◽  
Chen-Lung Ho
Keyword(s):  
Chemical Composition ◽  
Essential Oil ◽  
Cytotoxic Activity ◽  
Cancer Cells ◽  
Cytotoxic Activities ◽  
Anticancer Activities ◽  
Leaf Essential Oil ◽  
Main Components ◽  
Type Apparatus

This study investigated the chemical composition and in-vitro cytotoxic activities of the essential oil isolated from the leaf of Beilschmiedia erythrophloia. The essential oil was isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS. Fifty-five compounds were identified, representing 100% of the oil. The main components identified were β-caryophyllene (22.6%), α-humulene (21.9%), terpinen-4-ol (5.3%), cis-β-ocimene (5.1%), sabinene (5.0%) and limonene (4.5%). The anticancer activities of oil were evaluated. The results showed that the oil exhibited cytotoxic activity against human oral, liver, lung, colon, melanoma, and leukemic cancer cells.

scholarly journals Synthesis, Biological Assessment, and Structure Activity Relationship Studies of New Flavanones Embodying Chromene Moieties

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 544 ◽  
Author(s):  
Eman Assirey ◽  
Azhaar Alsaggaf ◽  
Arshi Naqvi ◽  
Ziad Moussa ◽  
Rawda M. Okasha ◽  
...  
Keyword(s):  
In Silico ◽  
Biological Assessment ◽  
Diffusion Method ◽  
Breast Adenocarcinoma ◽  
Cytotoxic Activities ◽  
Human Pathogens ◽  
Bacterial Strains ◽  
Human Carcinoma ◽  
In Silico Studies

Novel flavanones that incorporate chromene motifs are synthesized via a one-step multicomponent reaction. The structures of the new chromenes are elucidated by using IR, 1H-NMR, 13C-NMR, 1H-1H COSY, HSQC, HMBC, and elemental analysis. The new compounds are screened for their in vitro antimicrobial and cytotoxic activities. The antimicrobial properties are investigated and established against seven human pathogens, employing the agar well diffusion method and the minimum inhibitory concentrations. A majority of the assessed derivatives are found to exhibit significant antimicrobial activities against most bacterial strains, in comparison to standard reference drugs. Moreover, their cytotoxicity is appraised against four different human carcinoma cell lines: human colon carcinoma (HCT-116), human hepatocellular carcinoma (HepG-2), human breast adenocarcinoma (MCF-7), and adenocarcinoma human alveolar basal epithelial cell (A-549). All the desired compounds are subjected to in-silico studies, forecasting their drug likeness, bioactivity, and the absorption, distribution, metabolism, and excretion (ADME) properties prior to their synthetic assembly. The in-silico molecular docking evaluation of all the targeted derivatives is undertaken on gyrase B and the cyclin-dependent kinase. The in-silico predicted outcomes were endorsed by the in vitro studies.

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