A Review on Anticancer Activities of Thiophene and Its Analogs

2020 ◽  
Vol 20 (19) ◽  
pp. 1944-1965
Author(s):  
Raghav Mishra ◽  
Nitin Kumar ◽  
Isha Mishra ◽  
Neetu Sachan

Cancer is the world's second-largest cause of mortality and one of the biggest global health concerns. The prevalence and mortality rates of cancer remain high despite significant progress in cancer therapy. The search for more effective, as well as less toxic treatment methods for cancer, is at the focus of current studies. Thiophene and its derivatives have surged as an influential scaffold, which, because of their appreciable diversity in biological activities, has drawn the concerned interest of the researchers in the field of medicinal chemistry. By the affluent introduction of its derivatives, which have antioxidant, anti-inflammatory, antimicrobial, and anticancer activities, the adaptability of the thiophene moiety has been displayed. The nature and positioning of the substitutions significantly impacted thiophene moiety activity. This decent array in the living response account about this moiety has picked plentiful researcher’s consideration to inquire about it to its peculiar potential across certain activities. In the field of cancer therapy against different cancer cells, the structure-activity relationship for each of the derivatives showed an excellent understanding of thiophene moiety. Information from the various articles revealed the key role of thiophene moiety and its derivatives to develop the vital lead compound. The essential anticancer mechanisms identified include inhibition of the topoisomerase, inhibition of tyrosine kinase, tubulin interaction and apoptosis induction through the activation of reactive oxygen species. This review is an endeavor to promote the anticancer potential of the derivatives, whether having thiophene or condensed thiophene as a core moiety or as a substituent that can lead in the future to synthesize varieties of chemotherapeutic entities in the field of cancer treatment.

2012 ◽  
Vol 84 (6) ◽  
pp. 1369-1378 ◽  
Author(s):  
Mikiko Sodeoka ◽  
Kosuke Dodo ◽  
Yuou Teng ◽  
Katsuya Iuchi ◽  
Yoshitaka Hamashima ◽  
...  

Chaetocin, a natural product isolated from fungi of Chaetomium species, is a member of the epipolythiodiketopiperazines (ETPs), which have various biological activities, including cytostatic and anticancer activities. Recently, the inhibitory activity toward histone methyltransferases (HMTs) was discovered for chaetocin. We previously reported the first total synthesis of chaetocin and various derivatives. During studies on the structure–activity relationship for HMT inhibition, we found that the enantiomer of chaetocin (ent-chaetocin) is a more potent apoptosis inducer than natural chaetocin in human leukemia HL-60 cells. Mechanistic studies showed that ent-chaetocin induces apoptosis through the caspase-8/caspase-3 pathway.


2015 ◽  
Vol 68 (2) ◽  
pp. 178 ◽  
Author(s):  
Paul Waring ◽  
Christina L. L. Chai

The bridged disulfide ring of the fungal metabolite gliotoxin presents both synthetic challenges and confers the molecule with a variety of interesting biological activities. This review summarises recent synthetic strategies used to insert the disulfide and polysulfide bridge across the diketopiperazine ring and briefly describes the limited structure–activity data available for this class of molecule which clearly shows the presence of the disulfide bridge dominates their biological activities. The review also covers possible cellular targets of these toxins, the possible role for the disulfide bridge in toxicity and cellular uptake mechanisms, and the nature of the cell death induced by the epipolythiopiperazinedione toxins. The potential role of this simple molecule as a diagnostic marker for invasive aspergillosis is also discussed.


Proceedings ◽  
2020 ◽  
Vol 41 (1) ◽  
pp. 16
Author(s):  
Afzal Shaik ◽  
Palleapati Kishor ◽  
Venkata Kancharlapalli

A series of isoxazole based (E)-1-(isoxazole-5-yl)-3-(substituted phenyl)-prop-2-en-1-ones (chalcones, 3a-3o) and 3-(isoxazol-5-yl)-5-(substituted phenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide (dihydropyrazoles, 4a-4o) were synthesized, characterized and evaluated for their antimicrobial, antioxidant and anticancer properties. Chalcones exhibited excellent antibacterial and antioxidant activities whereas the dihydropyrazoles shown superior antifungal and anticancer activities. The compound 3l containing 3,4,5-trimethoxy phenyl ring showed the potent antibacterial activity (MIC = 1 µg/mL) as well as the antioxidant activity (IC50 = 5 µg/mL) whereas the dihydropyrazole, 4o (MIC = 0.5 µg/mL) bearing the 2-chloro-3,4-dimethoxyphenyl was the potent antifungal compound identified. The dihydropyrazoles 4n and 4h possessing 2-fluoro-3,4-dimethoxyphenyl and 3,4-dimethoxyphenyl substituents exhibited potent anticancer activity against prostate cancer cell line (DU-145) with MIC 2 and 4 µg/mL respectively. The structure activity relationships had shown that there is a marked influence of both electron withdrawing halogens and electron releasing methoxyl groups on the above biological activities. All the compounds were evaluated for toxicity on normal human cell lines (LO2) and found to be non-toxic. These studies could help to synthesize, explore and identify new isoxazole containing leads for antimicrobial, antioxidant and anticancer properties.


2020 ◽  
Vol 20 (1) ◽  
pp. 12-23 ◽  
Author(s):  
Nandini Pathak ◽  
Ekta Rathi ◽  
Nitesh Kumar ◽  
Suvarna G. Kini ◽  
C. Mallikarjuna Rao

: Benzothiazole is an organic compound bearing a heterocyclic nucleus (thiazole) which imparts a broad spectrum of biological activities to it. The significant and potent activity of benzothiazole moiety influenced distinctively by nature and position of substitutions. This review summarizes the effect of various substituents in recent trends and approaches to design and develop novel benzothiazole derivatives for anticancer potential in different cell lines by interpreting the Structure- Activity Relationship (SAR) and mechanism of action of a wide range of derivatives. The list of derivatives is categorized into different groups and reviewed for their anticancer activity. The structure-activity relationship for the various derivatives revealed an excellent understanding of benzothiazole moiety in the field of cancer therapy against different cancer cell line. Data obtained from the various articles showed the potential effect of benzothiazole moiety and its derivatives to produce the peculiar and significant lead compound. The important anticancer mechanisms found are tyrosine kinase inhibition, topoisomerase inhibition and induction of apoptosis by Reactive Oxygen Species (ROS) activation. Therefore, the design and development of novel benzothiazole have broad scope in cancer chemotherapy.


2020 ◽  
Vol 27 (19) ◽  
pp. 3168-3186 ◽  
Author(s):  
Dan Chen ◽  
Jing-Ru Liu ◽  
Yanjin Cheng ◽  
Hua Cheng ◽  
Ping He ◽  
...  

Rhaponticin is a stilbenoid glucoside compound, found in medicinal plant of rhubarb rhizomes. Rhapontigenin (RHAG), the stilbene aglycone metabolite of rhaponticin, has shown various biological activities including anticancer activities to act a potential human cytochrome P450 inhibitor, antihyperlipidemic effect, anti-allergic action, antioxidant and antibacterial activities. Moreover, it was reported to scavenge intracellular Reactive Oxygen Species (ROS), the 1,1-Diphenyl-2-Picrylliydrazyl (DPPH) radical, and Hydrogen Peroxide (H2O2). Meanwhile, RHAG exhibited the inhibitory activity for the synthesis of DNA, RNA and protein, and also presented the capacity of inducing morphological changes and apoptosis of C. albicans. Here, the structure, pharmacokinetics, pharmacological effects as well as underlying mechanisms of rhaponticin and its metabolite, RHAG, have been extensively reviewed. This review will provide a certain reference value for developing the therapeutic drug of rhaponticin or RHAG.


2017 ◽  
Author(s):  
Salim Abdisalaam ◽  
Souparno Bhattacharya ◽  
Kalayarasan Srinivasan ◽  
Shibani Mukherjee ◽  
Hesham A. Sadek ◽  
...  

MedChemComm ◽  
2015 ◽  
Vol 6 (1) ◽  
pp. 192-201 ◽  
Author(s):  
Manish Singh ◽  
Sandhya Bansal ◽  
Somanath Kundu ◽  
Priyanshu Bhargava ◽  
Ashima Singh ◽  
...  

We report the enhanced anticancer activities of lithocholic acid amphiphiles possessing different charged head group for colon cancer therapy.


Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 899 ◽  
Author(s):  
Chiara Brullo ◽  
Matteo Massa ◽  
Federica Rapetti ◽  
Silvana Alfei ◽  
Maria B. Bertolotto ◽  
...  

Several anti-inflammatory agents based on pyrazole and imidazopyrazole scaffolds and a large library of substituted catechol PDE4D inhibitors were reported by us in the recent past. To obtain new molecules potentially able to act on different targets involved in inflammation onset we designed and synthesized a series of hybrid compounds by linking pyrazole and imidazo-pyrazole scaffolds to differently decorated catechol moieties through an acylhydrazone chain. Some compounds showed antioxidant activity, inhibiting reactive oxygen species (ROS) elevation in neutrophils, and a good inhibition of phosphodiesterases type 4D and, particularly, type 4B, the isoform most involved in inflammation. In addition, most compounds inhibited ROS production also in platelets, confirming their ability to exert an antiinflammatory response by two independent mechanism. Structure–activity relationship (SAR) analyses evidenced that both heterocyclic scaffolds (pyrazole and imidazopyrazole) and the substituted catechol moiety were determinant for the pharmacodynamic properties, even if hybrid molecules bearing to the pyrazole series were more active than the imidazopyrazole ones. In addition, the pivotal role of the catechol substituents has been analyzed. In conclusion the hybridization approach gave a new serie of multitarget antiinflammatory compounds, characterized by a strong antioxidant activity in different biological targets.


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