Synthesis and biological evaluation of 1,2,4-oxadiazole linked 1,3,4-oxadiazole derivatives as tubulin binding agents

Polothi, Ravikumar; Raolji, G. S. B.; Kuchibhotla, Venkata Sastry; Sheelam, Kalidasu; Tuniki, Balaaraju; Prashanth, T.

doi:10.1080/00397911.2018.1535076

Cited by 20 publications

(14 citation statements)

References 26 publications

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“…Polothi et al [ 54 ] developed 5-(substituted phenyl)-3-(4-(5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-yl)phenyl)-1,2,4-oxadiazole by using Scheme 12 and evaluated for antitumor activity by MTT assay against MDA MB-231, MCF-7 (breast cell line), A549 ( lung cell line) cancer cell lines using doxorubicin as a reference standard. Among the different derivatives, compounds 19b, 19g, 19h , and 19i showed good cytotoxic activity as compared to the reference standard.…”

Section: Antitumor Activitymentioning

confidence: 99%

Therapeutic potential of oxadiazole or furadiazole containing compounds

Siwach

Verma

2020

BMC Chemistry

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As we know that, Oxadiazole or furadi azole ring containing derivatives are an important class of heterocyclic compounds. A heterocyclic five-membered ring that possesses two carbons, one oxygen atom, two nitrogen atoms, and two double bonds is known as oxadiazole. They are derived from furan by the replacement of two methylene groups (= CH) with two nitrogen (-N =) atoms. The aromaticity was reduced with the replacement of these groups in the furan ring to such an extent that it shows conjugated diene character. Four different known isomers of oxadiazole were existed such as 1,2,4-oxadiazole, 1,2,3-oxadiazole, 1,2,5-oxadiazole & 1,3,4-oxadiazole. Among them, 1,3,4-oxadiazoles & 1,2,4-oxadiazoles are better known and more widely studied by the researchers due to their broad range of chemical and biological properties. 1,3,4-oxadiazoles have become important synthons in the development of new drugs. The derivatives of the oxadiazole nucleus (1,3,4-oxadiazoles) show various biological activities such as antibacterial, anti-mycobacterial, antitumor, anti-viral and antioxidant activity, etc. as reported in the literature. There are different examples of commercially available drugs which consist of 1,3,4-oxadiazole ring such as nitrofuran derivative (Furamizole) which has strong antibacterial activity, Raltegravir as an antiviral drug and Nesapidil drug is used in anti-arrhythmic therapy. This present review summarized some pharmacological activities and various kinds of synthetic routes for 2, 5-disubstituted 1,3,4-oxadiazole, and their derived products.

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Section: Antitumor Activitymentioning

confidence: 99%

Therapeutic potential of oxadiazole or furadiazole containing compounds

Siwach

Verma

2020

BMC Chemistry

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“…However, the most toxic compound was 33 ( Figure 6), which displayed an IC50 value of 0.34 ± 0.025 µM on MCF-7 cells. Docking studies confirmed that 33 was potentially able to ensure strong interaction with the binding site of EGFR [54].…”

Section: Kinase Targetingmentioning

confidence: 81%

“…Polothi et al suggested to combine two oxadiazole units (1,2,4-and 1,3,4-) to enhance their anticancer activity. They synthesized various molecules, differing for the type of substituents introduced on one phenyl ring, and tested these compounds towards MCF-7, A549 and MDA-MB-231 cells [54]. In general, IC50 values resulted to be particularly low (below 10 µM), especially on A459 cells.…”

Section: Kinase Targetingmentioning

confidence: 99%

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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“…Polothi et al suggested to combine two oxadiazole units (1,2,4- and 1,3,4-) to enhance their anticancer activity. They synthesized various molecules, differing for the type of substituents introduced on one phenyl ring, and tested these compounds towards MCF-7, A549, and MDA-MB-231 cells [ 54 ]. In general, IC 50 values resulted to be particularly low (below 10 µM), especially on A459 cells.…”

Section: Enzyme Interactionsmentioning

confidence: 99%

“…However, the most toxic compound was 33 ( Figure 6 ), which displayed an IC 50 value of 0.34 ± 0.025 µM on MCF-7 cells. Docking studies confirmed that 33 was potentially able to ensure strong interaction with the binding site of EGFR [ 54 ].…”

Section: Enzyme Interactionsmentioning

confidence: 99%

Groundbreaking Anticancer Activity of Highly Diversified Oxadiazole Scaffolds

Benassi

Doria

Pirota

2020

IJMS

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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 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 and biological evaluation of 1,2,4-oxadiazole linked 1,3,4-oxadiazole derivatives as tubulin binding agents

Cited by 20 publications

References 26 publications

Therapeutic potential of oxadiazole or furadiazole containing compounds

Therapeutic potential of oxadiazole or furadiazole containing compounds

Groundbreaking Anticancer Activity of Highly Diversified Oxadiazole Scaffolds

Groundbreaking Anticancer Activity of Highly Diversified Oxadiazole Scaffolds

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