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Cytotoxic and Antioxidant Activity of a Set of Hetero Bicylic Methylthiadiazole Hydrazones: A Structure-Activity Study.

Kodisundaram P, Duraikannu A, Balasankar T, Sundarao Ambure P, Roy K - Int J Mol Cell Med (2015)

Bottom Line: Compounds possessing electron-donor methoxy and methyl substitutions at the para position of the phenyl ring moiety showed a concentration dependent free radical scavenging effects.The free radical-scavenging potential of synthetic compounds 11 and 14 may have significant impact on the prevention of free radical-induced oxidative stress and carcinogenesis.Docking studies revealed interactions of compound 10 with p38α MAP kinase, which may be responsible of its anti-invasive and anti-proliferative effects.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Annamalai University, Annamalai Nagar-608002, Tamilnadu, India.

ABSTRACT
The current study highlights the in vitro antioxidant and antitumor activity of the previously-synthesized hydrazone derivatives against various free radicals and human cancer cell lines, respectively. The anticancer efficacies of the compound were tested by measuring cytotoxicity in cancer cell lines HeLa, A549, and non-cancerous NL20 cells. Compounds possessing electron-donor methoxy and methyl substitutions at the para position of the phenyl ring moiety showed a concentration dependent free radical scavenging effects. The free radical-scavenging potential of synthetic compounds 11 and 14 may have significant impact on the prevention of free radical-induced oxidative stress and carcinogenesis. The results from cytotoxicity and cell migration assay showed that the substitution of electron-withdrawing fluoro, chloro and bromo functional groups induced a significant (P< 0.001) loss of cell viability and inhibited the invasive potential of the human cancer cells. Additionally, these compounds showed significantly (P< 0.05) a less toxicity toward non-cancerous NL20 cells. Docking studies revealed interactions of compound 10 with p38α MAP kinase, which may be responsible of its anti-invasive and anti-proliferative effects.

No MeSH data available.


Related in: MedlinePlus

Numbering of the azabicycle [3.3.1] nonane
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Figure 2: Numbering of the azabicycle [3.3.1] nonane

Mentions: Synthesis of diversely substituted diaryl 3-azabicyclononan-ones 1-7 (22) and their methylthiadiazole hydrazones 9-15 were carried out according to the steps shown in figure 1. The compounds 9-15 were achieved by the reaction of the compounds 1-7 with 4-methyl-1,2,3-thiadiazole-5-carboxylic acid hydrazide 8, respectively (18). Definite structural elucidation has been carried out by exploring IR, H1, C13 NMR and elemental analysis. 2D NMR spectra (1H-1H COSY, HSQC, HMBC and NOESY) recorded for a representative compound 12 confirmed the proposed structures for 9-15 (18). Figure 2 shows the numbering patterns of the compound. The substantial evidence for the proposed structure and twin-chair (CC) conformation of 2r,4c-diaryl-3-azabicyclo [3.3.1] nonan-9-one-4-methyl-1,2,3-thiadazole-5-carbonyl hydrazones 9-15 have been reported (18). The synthesized hydrazones 9-15 were screened for their antioxidant and anticancer effects.


Cytotoxic and Antioxidant Activity of a Set of Hetero Bicylic Methylthiadiazole Hydrazones: A Structure-Activity Study.

Kodisundaram P, Duraikannu A, Balasankar T, Sundarao Ambure P, Roy K - Int J Mol Cell Med (2015)

Numbering of the azabicycle [3.3.1] nonane
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4499575&req=5

Figure 2: Numbering of the azabicycle [3.3.1] nonane
Mentions: Synthesis of diversely substituted diaryl 3-azabicyclononan-ones 1-7 (22) and their methylthiadiazole hydrazones 9-15 were carried out according to the steps shown in figure 1. The compounds 9-15 were achieved by the reaction of the compounds 1-7 with 4-methyl-1,2,3-thiadiazole-5-carboxylic acid hydrazide 8, respectively (18). Definite structural elucidation has been carried out by exploring IR, H1, C13 NMR and elemental analysis. 2D NMR spectra (1H-1H COSY, HSQC, HMBC and NOESY) recorded for a representative compound 12 confirmed the proposed structures for 9-15 (18). Figure 2 shows the numbering patterns of the compound. The substantial evidence for the proposed structure and twin-chair (CC) conformation of 2r,4c-diaryl-3-azabicyclo [3.3.1] nonan-9-one-4-methyl-1,2,3-thiadazole-5-carbonyl hydrazones 9-15 have been reported (18). The synthesized hydrazones 9-15 were screened for their antioxidant and anticancer effects.

Bottom Line: Compounds possessing electron-donor methoxy and methyl substitutions at the para position of the phenyl ring moiety showed a concentration dependent free radical scavenging effects.The free radical-scavenging potential of synthetic compounds 11 and 14 may have significant impact on the prevention of free radical-induced oxidative stress and carcinogenesis.Docking studies revealed interactions of compound 10 with p38α MAP kinase, which may be responsible of its anti-invasive and anti-proliferative effects.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Annamalai University, Annamalai Nagar-608002, Tamilnadu, India.

ABSTRACT
The current study highlights the in vitro antioxidant and antitumor activity of the previously-synthesized hydrazone derivatives against various free radicals and human cancer cell lines, respectively. The anticancer efficacies of the compound were tested by measuring cytotoxicity in cancer cell lines HeLa, A549, and non-cancerous NL20 cells. Compounds possessing electron-donor methoxy and methyl substitutions at the para position of the phenyl ring moiety showed a concentration dependent free radical scavenging effects. The free radical-scavenging potential of synthetic compounds 11 and 14 may have significant impact on the prevention of free radical-induced oxidative stress and carcinogenesis. The results from cytotoxicity and cell migration assay showed that the substitution of electron-withdrawing fluoro, chloro and bromo functional groups induced a significant (P< 0.001) loss of cell viability and inhibited the invasive potential of the human cancer cells. Additionally, these compounds showed significantly (P< 0.05) a less toxicity toward non-cancerous NL20 cells. Docking studies revealed interactions of compound 10 with p38α MAP kinase, which may be responsible of its anti-invasive and anti-proliferative effects.

No MeSH data available.


Related in: MedlinePlus