Synthesis, anticancer and antimicrobial evaluation of new pyridyl and thiazolyl clubbed hydrazone scaffolds

Muluk, Mahesh B.; Ubale, Akash S.; Dhumal, Sambhaji T.; Rehman, Naziya N. M. A.; Dixit, Prashant P.; Kharat, Kiran; Choudhari, Prafulla B.; Haval, Kishan P.

doi:10.1080/00397911.2019.1692870

Cited by 11 publications

(21 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[42][43][44] Muluk et al reported that new hydrazone derivative compounds containing the pyridyl and thiazolyl ring exhibit stronger cytotoxic effects compared to doxorubicin, the reference cancer drug. [45] In another study, it has been shown that the newly synthesized different hydrazone compounds exhibit varying levels of cytotoxic effect on different cancer cells (HeLa, MCF-7, A-549 and MDA-MB-231). [46] In this study, it was determined that the newly synthesized hydrazone derivative test compound exhibited a strong cytotoxic effect in MCF-7 and PC-3 cells.…”

Section: Cell Viabilitymentioning

confidence: 98%

Biological Effects and Crystal X‐Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies

Hamurcu,

Özmen,

Şentürk

et al. 2023

Chemistry & Biodiversity

View full text Add to dashboard Cite

A novel Schiff base namely 3,5‐di‐tert‐butyl‐6‐((2‐(perfluorophenyl) hydrazono) methyl) phenol was successfully synthesized and characterized using FTIR and 1H‐NMR, 13C‐NMR, and 19F‐NMR. The crystal structure analysis of the Schiff base compound was also characterized with single crystal X‐ray diffraction studies and supported the spectroscopic results. The cytotoxicity, anti‐bacterial properties, and enzyme inhibition of the compound were also investigated. The molecular docking studies were performed in order to explain the interactions of the synthesized compound with target enzymes. The newly synthesized hydrazone derivative Schiff base compound showed high cellular toxicity on MCF‐7 and PC‐3 cells. Also, this compound caused low antibacterial effect on E. coli and S. aureus. Besides, the compound exhibited the inhibitory effect against pancreatic cholesterol esterase and carbonic anhydrase isoenzyme I, II with IC50 values 63, 99, and 188 µM, respectively. Consequently, it has been determined that the prepared Schiff base is an active compound in terms of cytotoxicity, enzyme inhibition, and anti‐bacterial properties. These results provide preliminary information for some biological features of the compound and can play a major role in drug applications of the Schiff base compound.

show abstract

Section: Cell Viabilitymentioning

confidence: 98%

Biological Effects and Crystal X‐Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies

Hamurcu,

Özmen,

Şentürk

et al. 2023

Chemistry & Biodiversity

View full text Add to dashboard Cite

show abstract

“…Six-membered heterocyclic compounds are numerous and versatile in terms of structure and bioactivity. Based on the literature research in recent years, only thiazole clubbed with pyridine antimicrobials were reported [ 76 , 77 , 78 , 79 ]. Thus, we present SAR studies only concerning them.…”

Section: Structure–activity Relationships In Antimicrobial Thiazole-b...mentioning

confidence: 99%

“…Muluk et al and Patil et al designed some 2-(4-pyridyl)-thiazoles as potential DNA gyrase and lumazine synthase inhibitors [ 76 , 77 , 78 ]. These compounds are substituted in the fourth position of the thiazole ring with aryl or hetaryl substituents, linked to the thiazole ring via an acylhydrazonomethylene or α,β-unsaturated carbonyl linker (R 2 ) ( Figure 44 ).…”

Section: Structure–activity Relationships In Antimicrobial Thiazole-b...mentioning

confidence: 99%

“…These compounds are substituted in the fourth position of the thiazole ring with aryl or hetaryl substituents, linked to the thiazole ring via an acylhydrazonomethylene or α,β-unsaturated carbonyl linker (R 2 ) ( Figure 44 ). There is a supplementary substituent in the second position of the pyridine ring, which is ethyl or propyl, depending on the starting thiocarbamide fragment (CN=S) for the Hantzsch synthesis, ethionamide or prothionamide [ 76 , 77 , 78 ].…”

Section: Structure–activity Relationships In Antimicrobial Thiazole-b...mentioning

confidence: 99%

See 1 more Smart Citation

An Overview of the Structure–Activity Relationship in Novel Antimicrobial Thiazoles Clubbed with Various Heterocycles (2017–2023)

Ungureanu,

Tiperciuc,

Nastasă

et al. 2024

Pharmaceutics

View full text Add to dashboard Cite

Antimicrobial resistance is an increasing problem for global public health. One of the strategies to combat this issue is the synthesis of novel antimicrobials through rational drug design based on extensive structure–activity relationship studies. The thiazole nucleus is a prominent feature in the structure of many authorized antimicrobials, being clubbed with different heterocycles. The purpose of this review is to study the structure–activity relationship in antimicrobial thiazoles clubbed with various heterocycles, as reported in the literature between 2017 and 2023, in order to offer an overview of the last years in terms of antimicrobial research and provide a helpful instrument for future research in the field.

show abstract

“…Antibacterial activities of compounds 60-61The design of derivatives 62 and 63 led to products active against M. tuberculosis with MICs varying from 0.39 to 15 μM, 63b being the most active compound of this series (Scheme 13) [57]. Muluk et al reported the synthesis of new pyridyl and thiazolyl clubbed hydrazone derivatives 64 displaying moderate antimicrobial activities and suggesting that the design of new parent derivatives could improve the selectivity and activity encountered (Table22) [58]. …”

mentioning

confidence: 99%

Frontiers in Anti-Infective Drug Discovery: Volume 7

2018

Frontiers in Anti-Infective Drug Discovery

View full text Add to dashboard Cite

Antimicrobial resistance of Gram-negative bacteria is a major concern and no new classes of antibiotics that are effective against this type of bacteria have been discovered since the 1960s. During the last decades, multiple approaches have been developed to combat such a bacterial resistance. However, the combination of antibiotic resistance mechanisms by bacteria and the limited number of effective antibiotics available, decreases the number of the interventions for the treatment of current bacterial infections. The solution to emerging antibiotic resistance will likely involve new therapies or new classes of antibacterial agents. For a few years now, there was a real interest in the design and synthesis of hydrazones possessing an azometine -NHN=CH-proton and constituting an important class of compounds for new drugs development as anticonvulsants, antidepressants, antitumoral agents. In this context, the design and antimicrobial evaluation of hydrazone derivatives has constituted one of the new strategies developed to fight bacterial resistance. As pointed out the range of biological activities is very broad, and this review will deal exclusively with the synthesis and use of hydrazones as antimicrobial agents and will not cover the other biological properties already well depicted in literature. Thus, we will report herein the scope and limitation of such an approach providing numerous examples demonstrating structure-activity relationships and potent interesting antimicrobial activities against both fungi, Gram-positive and/or Gram-negative bacteria.

show abstract

Synthesis, anticancer and antimicrobial evaluation of new pyridyl and thiazolyl clubbed hydrazone scaffolds

Cited by 11 publications

References 29 publications

Biological Effects and Crystal X‐Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies

Biological Effects and Crystal X‐Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies

An Overview of the Structure–Activity Relationship in Novel Antimicrobial Thiazoles Clubbed with Various Heterocycles (2017–2023)

Frontiers in Anti-Infective Drug Discovery: Volume 7

Contact Info

Product

Resources

About