Synthesis and biological evaluation of some new 1,3,4-thiadiazole and 1,2,4-triazole derivatives from L-methionine as antituberculosis and antiviral agents

Tatar, Esra; Küçükgüzel, Ş. Güniz; Karakuş, Sevgi; Clercq, Erik De; Andrei, Gracíela; Snoeck, Robert; Pannecouque, Christophe; Oktem-Okullu, Sinem; Unubol, Nihal; Kocagoz, Tanil; Kalaycı, Sadık; Şahın, Fikrettin; Küçükgüzel, İlkay

doi:10.12991/mpj.2015199639

Cited by 26 publications

(27 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As well as other NSAIDs, naproxen was reported to be efficient in the prevention of many cancers [3][4][5]. Hydrazide-hydrazones [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] and 1,2,4-triazole rings [22][23][24][25][26] have diverse biological activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-naproxen as anticancer agents

Han¹,

Bekçi²,

Cumaoğlu³

et al. 2018

jrp

View full text Add to dashboard Cite

How to cite this article: Han M, Bekçi H, Cumaoğlu A, Küçükgüzel ŞG. Synthesis and characterization of 1,2,4-triazole containing hydrazidehydrazones derived from (S)-Naproxen as anticancer agents. Marmara Pharm J. 2018; 22 (4): 559-569. ABSTRACT: A novel series of new naproxen derivativeswere synthesized, in this study. The structures of compounds 5, 6 and 7a-m were defined by spectral ( 1 H-NMR, 13 C-NMR, HR-MS and FT-IR) methods and their purity was proven by elemental analysis, thin layer chromatography and high pressure liquid chromatography. These compounds were evaluated for in vitro anticancer activity by using MTS method against PC-3 and DU-143 (androgen-independent human prostate cancer cell lines) and LNCaP (androgen-sensitive human prostate adenocarcinoma) prostate cancer cell lines. Cisplatin was used as the positive sensitivity reference standard. Compounds (7a-m) exhibited anticancer activity with IC50 values of 87.2-400 µM against prostate cancer cell lines.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-naproxen as anticancer agents

Han¹,

Bekçi²,

Cumaoğlu³

et al. 2018

jrp

View full text Add to dashboard Cite

show abstract

“…No activity was observed at the highest concentration tested or at subtoxic concentration against Influenza B and RSV [49]. Derivatives 47 and 48 exhibited activity against Parainfluenza-3 and Reovirus-1 and probably the thiourea moiety favors antiviral activity on these strains ( Figure 5) [49]. With an EC 50 value of 31.4 µM, the derivative 45 was the most potent among the tested compounds and moderate active compared to standard drug oseltamivir, but a promising scaffold for future developments.…”

Section: Respiratory Virusesmentioning

confidence: 95%

“…An alternative concept has recently emerged and it is based on the idea of designing new molecules targeting host cell factors that are hijacked by the virus during its replication. No activity was observed at the highest concentration tested or at subtoxic concentration against Influenza B and RSV [49]. This type of inhibitors could exhibit a significantly greater barrier for selecting drug-resistant viruses and, in addition, display broad-spectrum antiviral activity when interacting with a cellular target common to several viruses.…”

Section: Respiratory Virusesmentioning

confidence: 95%

“…Host-targeting antivirals are an alternative strategy for addressing host structures involved in the virus life cycle. Derivatives 47 and 48 exhibited activity against Parainfluenza-3 and Reovirus-1 and probably the thiourea moiety favors antiviral activity on these strains ( Figure 5) [49]. The host factor-directed antiviral therapy is recently studied.…”

Section: Respiratory Virusesmentioning

confidence: 99%

“…Antiviral evaluation and in vitro cytotoxicity of compounds 45-48 (adapted from[49]). amine group amide group no activity at subtoxic concentrations loss of activity thiourea group beneficial against HSV, Sindbis virus, Coxsackie virus, Punto Toro virus…”

mentioning

confidence: 99%

See 2 more Smart Citations

Synthetic Compounds with 2-Amino-1,3,4-Thiadiazole Moiety Against Viral Infections

Şerban

2020

Molecules

View full text Add to dashboard Cite

Viral infections have resulted in millions of victims in human history. Although great efforts have been made to find effective medication, there are still no drugs that truly cure viral infections. There are currently approximately 90 drugs approved for the treatment of human viral infections. As resistance toward available antiviral drugs has become a global threat to health, there is an intrinsic need to identify new scaffolds that are useful in discovering innovative, less toxic and highly active antiviral agents. 1,3,4-Thiadiazole derivatives have been extensively studied due to their pharmacological profile, physicochemical and pharmacokinetic properties. This review provides an overview of the various synthetic compounds containing the 2-amino-1,3,4-thiadiazole moiety that has been evaluated for antiviral activity against several viral strains and could be considered possible prototypes for the development of new antiviral drugs.Molecules 2020, 25, 942 2 of 22 due to the ability of viruses to undergo rapid mutations, the mechanisms involved in developing resistance to antiviral drugs are activated in most cases [1,3]. As resistance toward antiviral drugs is becoming a global health threat, there is an intrinsic need to identify new scaffolds that are useful in discovering innovative, less toxic and highly active antiviral agents [3,6,7]. Nitrogen-Containing Heterocycles and Thiadiazole Ring in Biology and Medicinal ChemistryNitrogen-containing heterocycles are widely distributed in nature and are essential in vegetal and animal metabolism. They are found in nucleic acids, vitamins, antibiotics, alkaloids, etc. [8][9][10][11][12][13][14]. In addition, nitrogen-containing heterocycles are important targets for medicinal chemistry, as they are found in more than half of the commercially available drugs and can also act as versatile intermediates in the synthesis of complex products that exhibit outstanding biological activities [15]. Most of the nitrogen-containing heterocyclic compounds exhibit better biological activity than non-nitrogen compounds [12,16,17]. Currently, there are approximately 90 drugs approved for use in the treatment of nine human viral infections caused by human immunodeficiency virus (HIV), hepatitis B virus (HBV), hepatitis C virus (HCV), herpes simplex virus (HSV), Influenza virus, human cytomegalovirus (HCMV), varicella-zoster virus (VZV), respiratory syncytial virus (RSV) and human papillomavirus [18]. Most of these drugs (e.g., acyclovir, cidofovir, idoxuridine, nevirapine, pleconaril, ribavirin, etc.) are nitrogen heterocycle molecules [3,19].Five-membered aromatic systems with three heteroatoms at symmetrical positions, such as the 1,3,4-thiadiazole ring, have been extensively studied due to their pharmacological profile and physicochemical and pharmacokinetic properties. 1,3,4-Thiadiazole derivatives are known as compounds having significant and diverse biological activities such as antibacterial, antifungal, antitubercular [20], analgesic and anti-inflammatory [21,22], antidepr...

show abstract

Significance of Triazole in Medicinal Chemistry: Advancement in Drug Design, Reward and Biological Activity

Ajmal,

Mahato,

Khan

et al. 2024

Chemistry & Biodiversity

View full text Add to dashboard Cite

One of the triazole tautomers, 1,2,4‐triazole derivatives, has a wide range of biological activities that suggest its potential therapeutic utility in medicinal chemistry. These actions include anti‐inflammatory, anti‐cancer, anti‐bacterial, anti‐tuberculosis, and anti‐diabetic effects. The review highlights anti‐inflammatory effect of 1,2,4‐triazoles in relation to their ability to disrupt significant inflammatory mediators and pathways. We present in‐silico data that illuminate the triazoles capacity to inhibit cell division, encourage apoptosis, and stop metastasis in a range of cancer models. This review looks at the bactericidal and bacteriostatic properties of 1,2,4‐triazole derivatives, with a focus on their potential efficacy against multi‐drug resistant bacterial infections and their usage in tuberculosis therapy. In order to better understand these substances' potential anti‐diabetic benefits, this review also looks at how they affect glucose metabolism regulation and insulin responsiveness. Based on information provided, it can be concluded that 1,2,4‐triazole derivatives are a promising class of diverse therapeutic agents with potential utility in a range of disorders. Their development and improvement might herald a new era of medical care that will be immensely advantageous to both patients and medical community as a whole. Additionally, this study encourages more research into these substances and their enhancement for use in pharmaceutical development.

show abstract

Synthesis and biological evaluation of some new 1,3,4-thiadiazole and 1,2,4-triazole derivatives from L-methionine as antituberculosis and antiviral agents

Cited by 26 publications

References 54 publications

Synthesis and characterization of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-naproxen as anticancer agents

Synthesis and characterization of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-naproxen as anticancer agents

Synthetic Compounds with 2-Amino-1,3,4-Thiadiazole Moiety Against Viral Infections

Significance of Triazole in Medicinal Chemistry: Advancement in Drug Design, Reward and Biological Activity

Contact Info

Product

Resources

About