Synthesis and <i>In Vitro</i> Anticancer Activity of Novel 1,3,4‐Oxadiazole‐Linked 1,2,3‐Triazole/Isoxazole Hybrids

Madhavilatha, B.; Bhattacharjee, Debanjan; Sabitha, Gowravaram; Reddy, B. V. Subba; Yadav, J. S.; Jain, Nishant; Reddy, B. Jagannadha

doi:10.1002/jhet.3110

Cited by 18 publications

(10 citation statements)

References 33 publications

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“…Individually, 1,3,4-oxadiazole and 1,2,3-triazole moieties are of significant biological interest owing to their importance in drugs and pharmaceuticals. A series of new 1,3,4-oxadiazole-linked 1,2,3-triazole derivatives were reported by Madhavilatha et al (2018).Compounds tested, 3-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)-5-phenyl-1,3,4oxadiazol-2(3H)-one (42), 3-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)-5-(p-tolyl)-1,3,4-oxadiazol-2(3H)-one (43), and 3-((1-(2-Fluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-5-(ptolyl)-1,3,4-oxadiazol-2(3H)-one (44) showed utmost anticancer activity against HeLa (cervical), MDA-MB-231 (breast), DU-145 (prostate), and HEPG2 (liver) cancer cell lines (Figure 18). Western blot analysis in the HeLa cell line indicated that these compounds induced cyclin B1 protein level, which is a strong indicator of G2/M cell cycle arrest and disrupted microtubule assembly and increased the amount of insoluble tubulin fractions of cells like other potent tubulin polymerization inhibitors such as nocodazole.…”

Section: 34-oxadiazolesmentioning

confidence: 99%

1,3,4‐oxadiazole and its derivatives: A review on recent progress in anticancer activities

2020

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The 1,3,4-oxadiazole nucleus is a biologically imperative scaffold possesses numerous biological activities. The broad and potent activity of 1,3,4-oxadiazole and their derivatives has established them as important pharmacological scaffolds especially in the treatment of cancer disease. Several di-, tri-, aromatic, and heterocyclic substituted 1,3,4-oxadiazole derivatives have been reported to possess potent anticancer activity. These substituted 1,3,4-oxadiazoles had shown different mechanism of action and participated in anticancer drug discovery and development. This review is complementary to earlier reviews and aims to review the work reported on anticancer activities of 1,3,4-oxadiazole derivatives from year 2000 to the beginning of 2020. K E Y W O R D S 1,3,4-oxadiazole, cancer, histone deacetylase, synthesis, tubulin polymerizations | 573 VAIDYA et Al. anticancer evaluation of 1,3,4-oxadiazole derivatives as inhibitors of Kinesin spindle protein (KSP). KSP inhibitors have been utilized for the treatment of inflammation, hyperplasias, cancer, and immune disorders. Furthermore, Shashikumar and colleagues in year 2015 obtained a WO (World intellectual property organization) patent for 1,3,4-oxadiazoles as therapeutic agents capable of inhibiting the programmed cell death 1 (PD1) signaling pathway. Theses patented compounds having the ability to boost the immunity and were reported as immunomodulators. The growing patent literature of recent years demonstrates that the 1,3,4-oxadiazoles are becoming of great practical significance. The literature clearly reported numerous mechanism for anticancer activities of substituted 1,3,4-oxadiazole derivatives (Zhang et al., 2010, 2011). Recently, Glomb et al. (2018) published a notable review article, describing antiproliferative effects of 1,3,4-oxadiazoles associated with their numerous mechanisms, including inhibition of growth factors, enzymes, kinases and others. Irrespective of Glomb et al. (2018) review in which they were cited numerous anticancer mechanism of 1,3,4-oxadiazoles, herein we had focused on several 1,3,4-oxadiazole derivatives for their anticancer activity. Especially, we focus this review on in vitro and in vivo anticancer activities of 1,3,4-oxadiazoles in the perspective of cancer drug development and refinement.

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Section: 34-oxadiazolesmentioning

confidence: 99%

1,3,4‐oxadiazole and its derivatives: A review on recent progress in anticancer activities

2020

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“…[8][9][10][11][12][13][14][15][16] Among different triazoles, 1,2,3triazoles particularly have a broad range of applications in the field of pharmaceutical and medicinal chemistry, and they are a part of many molecules reported as antidiabetic. [17][18][19][20][21][22][23][24] It has been reported that benzimidazole compounds, that is, 2-aryl benzimidazoles (A) and 2-(2chlorophenyl)-7-methyl-1H-benzo [d]imidazole (B), act as α-glucosidase inhibitors, [25][26][27] but there is still a need to discover some new analogs for improved inhibitory activity. Various studies have reported that by combining a benzimidazole ring with an electron-withdrawing group such as triazole, the biological activity gets enhanced.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antidiabetic evaluation of benzimidazole‐tethered 1,2,3‐triazoles

Deswal

Verma

Kumar

et al. 2020

Archiv der Pharmazie

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Some novel benzimidazole‐tethered 1,2,3‐triazole derivatives (4a–r) were synthesized by a click reaction between 2‐substituted 1‐(prop‐2‐yn‐1‐yl)‐1H‐benzo[d]imidazole and in situ azide. The structures of the synthesized compounds were confirmed by spectroscopic studies (one‐ and two‐dimensional nuclear magnetic resonance, Fourier transform infrared, and high‐resolution mass spectra). The synthesized compounds were evaluated for their antidiabetic activity. Compounds 4a–r exhibited a good‐to‐moderate α‐amylase and α‐glucosidase inhibitory activity, with IC50 values ranging from 0.0410 to 0.0916 µmol/ml and 0.0146 to 0.0732 µmol/ml, respectively. Compounds 4e, 4g, and 4n were found to be most active. Furthermore, the binding conformation of the most active compounds was ascertained by docking studies.

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“…However, 1,3,4‐oxadiazol‐2(3 H )‐one (Fig. ) is a privileged five‐membered heterocycle and has a revitalized interest due to its broad pharmaceutical scope encompassing activities such as anti‐tumor, HCV , anti‐cancer [18a], protoporphyrinogen (PPO) inhibitors as commercial herbicides [18b], hormone‐sensitive lipase , antibacterial , antitubercular , GABA receptor agonists [22a], anti‐microbial [22b], and inhibition of selective monoamine oxidase B . BemPPOX is an oxadiazolone inhibitor slowing down fat digestion, absorption, and targeting selectively gastric lipolysis .…”

Section: Introductionmentioning

confidence: 99%

A Highly Efficient Catalyst for the Suzuki‐Miyaura Cross‐Coupling Reaction of 5‐(5‐chloropyridin‐3‐yl)‐3‐methyl‐1,3,4‐oxadiazol‐2(3H)‐one

Savitha

Reddy

Parthasarathi

et al. 2018

Journal of Heterocyclic Chem

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Synthesis and In Vitro Anticancer Activity of Novel 1,3,4‐Oxadiazole‐Linked 1,2,3‐Triazole/Isoxazole Hybrids

Cited by 18 publications

References 33 publications

1,3,4‐oxadiazole and its derivatives: A review on recent progress in anticancer activities

1,3,4‐oxadiazole and its derivatives: A review on recent progress in anticancer activities

Synthesis and antidiabetic evaluation of benzimidazole‐tethered 1,2,3‐triazoles

A Highly Efficient Catalyst for the Suzuki‐Miyaura Cross‐Coupling Reaction of 5‐(5‐chloropyridin‐3‐yl)‐3‐methyl‐1,3,4‐oxadiazol‐2(3H)‐one

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