Synthesis of novel nicotinohydrazide and (1,3,4-oxadiazol-2-yl)-6-(trifluoromethyl)pyridine derivatives as potential anticancer agents

Kumar, Rakesh; Poornachandra, Y.; Punna, Nagender; Kumar, Gopinatha Suresh; Swaroop, Desireddy Krishna; Kumar, C. Ganesh; Narsaiah, B.

doi:10.1016/j.bmcl.2016.08.020

Cited by 23 publications

(7 citation statements)

References 18 publications

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“…Unfortunately, these two drugs have limited efficacy and exhibit undesirable side effects, such as pruritis, scaling, local irritation, dermatitis, and sexual dysfunction [ 4 , 7 , 8 ]. The other side of the medical spectrum is cancer, which takes the lives of millions of people per year worldwide, and is the second leading cause of death after cardiovascular disease [ 9 ]. No currently available anticancer drugs can eradicate cancer cells without harming normal tissue [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

Hair Growth Promoting and Anticancer Effects of p21-activated kinase 1 (PAK1) Inhibitors Isolated from Different Parts of Alpinia zerumbet

2017

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PAK1 (p21-activated kinase 1) is an emerging target for the treatment of hair loss (alopecia) and cancer; therefore, the search for PAK1 blockers to treat these PAK1-dependent disorders has received much attention. In this study, we evaluated the anti-alopecia and anticancer effects of PAK1 inhibitors isolated from Alpinia zerumbet (alpinia) in cell culture. The bioactive compounds isolated from alpinia were found to markedly promote hair cell growth. Kaempferol-3-O-β-d-glucuronide (KOG) and labdadiene, two of the isolated compounds, increased the proliferation of human follicle dermal papilla cells by approximately 117%–180% and 132%–226%, respectively, at 10–100 μM. MTD (2,5-bis(1E,3E,5E)-6-methoxyhexa-1,3,5-trien-1-yl)-2,5-dihydrofuran) and TMOQ ((E)-2,2,3,3-tetramethyl-8-methylene-7-(oct-6-en-1-yl)octahydro-1H-quinolizine) showed growth-promoting activity around 164% and 139% at 10 μM, respectively. The hair cell proliferation induced by these compounds was significantly higher than that of minoxidil, a commercially available treatment for hair loss. Furthermore, the isolated compounds from alpinia exhibited anticancer activity against A549 lung cancer cells with IC50 in the range of 67–99 μM. Regarding the mechanism underlying their action, we hypothesized that the anti-alopecia and anticancer activities of these compounds could be attributed to the inhibition of the oncogenic/aging kinase PAK1.

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Section: Introductionmentioning

confidence: 99%

Hair Growth Promoting and Anticancer Effects of p21-activated kinase 1 (PAK1) Inhibitors Isolated from Different Parts of Alpinia zerumbet

2017

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“…Introduction of 2-substituted pyridines, as reported by Kumar et al, led to promising results as demonstrated by proving the efficiency of these compounds against HeLa, DU145, HepG2 and MDA-MB-231 cancer cell lines [102]. Among them, 61 ( Figure 11) showed higher toxicity in particular on DU145 cells with an IC50 value of 10.7 µM.…”

Section: Oxadiazoles Derivatives As Anticancer Agents Without a Specimentioning

confidence: 93%

“…Among them, 61 ( Figure 11) showed higher toxicity in particular on DU145 cells with an IC50 value of 10.7 µM. This enhanced activity has been attributed to both the presence of a trifluoromethyl group, that improves lipophilicity, and to the electron-donating effect of methoxy substituent [102].…”

Section: Oxadiazoles Derivatives As Anticancer Agents Without a Specimentioning

confidence: 98%

Groundbreaking Anticancer Activity of Highly Diversified Oxadiazole Scaffolds

Benassi

Doria

Pirota

2020

Preprint

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Nowadays, an increasing number of heterocyclic-based drugs found application in medicinal chemistry and, in particular, as anticancer agents. In this context, oxadiazoles, five-membered aromatic rings, emerged for their interesting biological properties. Modification of oxadiazole scaffolds represents a valid strategy to increase their anticancer activity, especially on 1,2,4 and 1,3,4 regioisomers. In the last years, an increasing number of oxadiazole derivatives, with remarkable cytotoxicity for several tumor lines, were identified. Structural modifications, that ensure higher cytotoxicity towards malignant cells, represent a solid starting point in the development of novel oxadiazoles-based drugs. To increase the specificity of this strategy, outstanding oxadiazole scaffolds have been designed to selectively interact with biological targets, including enzymes, globular proteins and nucleic acids, showing more promising antitumor effects. In the present work, we aim to provide a comprehensive overview of the anticancer activity of these heterocycles, describing their effect on different targets and highlighting how their structural versatility has been exploited to modulate their biological properties.

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“…Introduction of 2-substituted pyridines, as reported by Kumar et al, led to promising results as demonstrated by proving the efficiency of these compounds against HeLa, DU145, HepG2, and MDA-MB-231 cancer cell lines [ 102 ]. Among them, 61 ( Figure 11 ) showed higher toxicity in particular on DU145 cells with an IC 50 value of 10.7 µM.…”

Section: Oxadiazoles Derivatives As Anticancer Agents Without a Spmentioning

confidence: 99%

“…Among them, 61 ( Figure 11 ) showed higher toxicity in particular on DU145 cells with an IC 50 value of 10.7 µM. This enhanced activity has been attributed to both the presence of a trifluoromethyl group, that improves lipophilicity, and to the electron-donating effect of methoxy substituent [ 102 ].…”

Section: Oxadiazoles Derivatives As Anticancer Agents Without a Spmentioning

confidence: 99%

Groundbreaking Anticancer Activity of Highly Diversified Oxadiazole Scaffolds

Benassi

Doria

Pirota

2020

IJMS

View full text Add to dashboard Cite

Nowadays, an increasing number of heterocyclic-based drugs found application in medicinal chemistry and, in particular, as anticancer agents. In this context, oxadiazoles—five-membered aromatic rings—emerged for their interesting biological properties. Modification of oxadiazole scaffolds represents a valid strategy to increase their anticancer activity, especially on 1,2,4 and 1,3,4 regioisomers. In the last years, an increasing number of oxadiazole derivatives, with remarkable cytotoxicity for several tumor lines, were identified. Structural modifications, that ensure higher cytotoxicity towards malignant cells, represent a solid starting point in the development of novel oxadiazole-based drugs. To increase the specificity of this strategy, outstanding oxadiazole scaffolds have been designed to selectively interact with biological targets, including enzymes, globular proteins, and nucleic acids, showing more promising antitumor effects. In the present work, we aim to provide a comprehensive overview of the anticancer activity of these heterocycles, describing their effect on different targets and highlighting how their structural versatility has been exploited to modulate their biological properties.

show abstract

Synthesis of novel nicotinohydrazide and (1,3,4-oxadiazol-2-yl)-6-(trifluoromethyl)pyridine derivatives as potential anticancer agents

Cited by 23 publications

References 18 publications

Hair Growth Promoting and Anticancer Effects of p21-activated kinase 1 (PAK1) Inhibitors Isolated from Different Parts of Alpinia zerumbet

Hair Growth Promoting and Anticancer Effects of p21-activated kinase 1 (PAK1) Inhibitors Isolated from Different Parts of Alpinia zerumbet

Groundbreaking Anticancer Activity of Highly Diversified Oxadiazole Scaffolds

Groundbreaking Anticancer Activity of Highly Diversified Oxadiazole Scaffolds

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