Synthetic Methods of Medicinally Important Heterocycles-thiazines: A Review

Sharma, Praveen Kumar; Amin, Andleeb; Kumar, M. Dinesh

doi:10.2174/1874104502014010071

Cited by 7 publications

(3 citation statements)

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“…The increasing need for new antimicrobial and antibiofilm agents has intensified research into potent molecules to combat infections [1]. Many small molecules that contain heterocyclic elements are of pharmaceutical application/potential thanks to their broad biological activity [2]. Heterocyclic compounds are rapidly increasing in number due to extensive synthetic research and their synthetic utility [3] and play diverse roles in pharmacy and medicine, including anti-cancer, antimicrobial (including anti-biofilm), and antiinflammatory actions, and they are a major focus in the organic chemistry literature [4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial and Cytotoxic Activities of Water-Soluble Isoxazole-Linked 1,3,4-Oxadiazole with Delocalized Charge: In Vitro and In Vivo Results

Dudek,

Bąchor,

Drozd-Szczygieł

et al. 2023

IJMS

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The distinct structure of cationic organic compounds plays a pivotal role in enhancing their water solubility, which in turn influences their bioavailability. A representative of these compounds, which contains a delocalized charge, is 5-amino-2-(5-amino-3-methyl-1,2-oxazol-4-yl)-3-methyl-2,3-dihydro-1,3,4-oxadiazol-2-ylium bromide (ED). The high-water solubility of ED obviates the need for potentially harmful solvents during in vitro testing. The antibacterial and antifungal activities of the ED compound were assessed in vitro using the microtiter plate method and a biocellulose-based biofilm model. Additionally, its cytotoxic effects on wound bed fibroblasts and keratinocytes were examined. The antistaphylococcal activity of ED was also evaluated using an in vivo larvae model of Galleria mellonella. Results indicated that ED was more effective against Gram-positive bacteria than Gram-negative ones, exhibiting bactericidal properties. Furthermore, ED demonstrated greater efficacy against biofilms formed by Gram-positive bacteria. At bactericidal concentrations, ED was non-cytotoxic to fibroblasts and keratinocytes. In in vivo tests, ED was non-toxic to the larvae. When co-injected with a high load of S. aureus, it reduced the average larval mortality by approximately 40%. These findings suggest that ED holds promise for further evaluation as a potential treatment for biofilm-based wound infections, especially those caused by Gram-positive pathogens like S. aureus.

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Section: Introductionmentioning

confidence: 99%

Antimicrobial and Cytotoxic Activities of Water-Soluble Isoxazole-Linked 1,3,4-Oxadiazole with Delocalized Charge: In Vitro and In Vivo Results

Dudek,

Bąchor,

Drozd-Szczygieł

et al. 2023

IJMS

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“…Rosuvastatin, containing a sulfonyl functional groups attached to a pyrimidine moiety was used to lower the elevated cholesterol levels [46] (Figure 4). Some other examples of pyrimidine‐based drugs in clinical use include idoxuridine (Antiviral) [47], trimethoprim (Antibacterial) [48], sulphamethiazine (Antibacterial) [49], sulphadiazine (Antibacterial) [50], sulphadoxine (Antimalarial) [51], minoxidil (Antihypertensive) [52] and prazosin (Antihypertensive) [53]. Similarly, barbiturates, such as phenobarbitone, are used as sedatives, hypnotics, and anticonvulsants [54, 55]; propylthiouracil is used as an antithyroid agent [56]; thionzylamine is used as an H1‐antihistamine [57], and toxoflavin and fervennuline are used as antibiotics [58].…”

Section: Introductionmentioning

confidence: 99%

An insight on medicinal attributes of pyrimidine scaffold: An updated review

Vyas

Sahu

Pathania

et al. 2022

Journal of Heterocyclic Chem

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Pyrimidine itself or in different fused forms is an important chemical motif for every step of cell life. Alongside, it exists as a key pharmacophoric part in thiamine, alloxan, orotic acid, and other isoforms of nucleotide bases. It has emerged as a privileged scaffold in medicinal chemistry due to its various possible structural and pharmacological attributes. In a number of clinically used chemical agents, pyrimidine or its fused/clubbed form with other moieties act as a key pharmacophore. Structure activity relationship (SAR) studies of the explored derivatives demonstrated that slight modifications with various substitutions on the pyrimidine rings can deviate biological activity to a large extent. 2-Pyrimidone and 2,4-pyrimidione derivatives are largely explored by a number of research groups for various pharmacological targets and due to their similarity to nucleotide bases, it has a great impact on the biological profile of these molecules. The current review focuses on describing the recent advancements (2015 onward) in the development of pyrimidine-based biologically active molecules along with drug candidates under different clinical trials. The aim of this review is to provide structural features associated with pyrimidine along with their SAR studies, which are believed to be valuable for the scientists working on the development of pyrimidine-based small molecules in the aforementioned disease conditions. We believe that the results of this research will help to provide a structural idea that may be used in the design and development of new pyrimidine-based small molecules that target a variety of receptors or enzymes.

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“…Heterocyclic compounds with a benzothiazine moiety are attractive building blocks in medicinal chemistry. Benzo-1,4-thiazine derivatives possess a wide range of biological and pharmacological properties, such as anticancer and antitumor, antioxidant, antimicrobial, antibacterial, antifungal, antiviral, antimalarial, antidiabetic, antihypertensive, anti-inflammatory, analgesic, anti-rheumatic, or anti-allergic properties [1][2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates

Kisszékelyi¹,

Stankovianska²,

Mečiarová³

et al. 2022

Beilstein J. Org. Chem.

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Herein, we present the synthesis and utilization of derivatives of 4H-benzo[b][1,4]thiazine-3-carboxylic acid. These benzothiazine compounds were assembled via the coupling of aminothiols and bromopyruvates. Oxidative dimerization of these starting materials was also observed and the corresponding benzothiazine dimers were isolated. Moreover, the coupling of benzothiazines with amino acids was realized. In doing so, an enantioselective synthesis of the nonproteinogenic amino acid 2-amino-3-propylhexanoic acid was accomplished.

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Synthetic Methods of Medicinally Important Heterocycles-thiazines: A Review

Cited by 7 publications

References 0 publications

Antimicrobial and Cytotoxic Activities of Water-Soluble Isoxazole-Linked 1,3,4-Oxadiazole with Delocalized Charge: In Vitro and In Vivo Results

Antimicrobial and Cytotoxic Activities of Water-Soluble Isoxazole-Linked 1,3,4-Oxadiazole with Delocalized Charge: In Vitro and In Vivo Results

An insight on medicinal attributes of pyrimidine scaffold: An updated review

Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates

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