Design, synthesis, biological evaluation and computational study of novel triazolo [4,3-a]pyrazin analogues

Jethava, Divya J.; Acharya, Prachi T.; Vasava, Mahesh S.; Bhoi, Manoj N.; Bhavsar, Zeel A.; Rathwa, Sanjay K.; Rajani, Dhanji P.; Patel, Hitesh

doi:10.1016/j.molstruc.2019.01.091

Cited by 7 publications

(8 citation statements)

References 92 publications

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“…The synthetic route of 3-(trifluoromethyl)-1,2,4-triazolo [4,3-a]pyrazine as a key scaffold is presented in Scheme 1 [21,26]. The starting material, ethyl trifluoroacetate (I), was dissolved in acetonitrile and reacted with hydrazine hydrate (35%, w/v) for 1 h under almost room-temperature (20 • C) conditions to obtain trifluoroacetohydrazide (II).…”

Section: Chemistrymentioning

confidence: 99%

“…Triazolo [4,3-a]pyrazine is a privileged building block/scaffold used for the synthesis of biologically active molecules and has received significant attention in the field of synthetic organic chemistry. Triazolo [4,3-a]pyrazine derivatives have a wide range of biological activities, such as antidiabetic [19], anti-platelet aggregations [20], anti-fungal [21], anti-bacterial [22], anti-malarial [23], anti-tubercular [24], and anticonvulsant properties [25], which are important in drug discovery programs. 3-(Trifluoromethyl)-1,2,4-triazolo [4,3-a]pyrazine is the key pharmacophore of sitagliptin phosphate, a new drug for the treatment of type II-diabetes mellitus.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Antibacterial Activity of Novel Triazolo[4,3-a]pyrazine Derivatives

Hu,

Dong,

et al. 2023

Molecules

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Infectious diseases pose a major challenge to human health, and there is an urgent need to develop new antimicrobial agents with excellent antibacterial activity. A series of novel triazolo[4,3-a]pyrazine derivatives were synthesized and their structures were characterized using various techniques, such as melting point, 1H and 13C nuclear magnetic resonance spectroscopy, mass spectrometry, and elemental analysis. All the synthesized compounds were evaluated for in vitro antibacterial activity using the microbroth dilution method. Among all the tested compounds, some showed moderate to good antibacterial activities against both Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli strains. In particular, compound 2e exhibited superior antibacterial activities (MICs: 32 μg/mL against Staphylococcus aureus and 16 μg/mL against Escherichia coli), which was comparable to the first-line antibacterial agent ampicillin. In addition, the structure–activity relationship of the triazolo[4,3-a]pyrazine derivatives was preliminarily investigated.

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Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Activity of Novel Triazolo[4,3-a]pyrazine Derivatives

Hu,

Dong,

et al. 2023

Molecules

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“…J. Jethava and co-workers synthesized N -(benzo[ d ]thiazol-2-yl)-2-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo [4,3- a ]pyrazin-7 (8 H )-yl) acetamide derivatives 98a–e after acetylation of benzothiazole 3a–e in presence of base NEt 3 followed by nucleophilic substitution from triazolo-triazine 97 in presence of potassium carbonate in DMF solvent (Scheme 26, Table 21). 64…”

Section: Recent Synthesis Of Benzothiazole Based Anti-tubercular Mole...mentioning

confidence: 99%

“…Molecular docking of the synthesized compounds was done against BTZ043 to evaluate their DprE1 21). 64 Using the well-known Lowenstein-Jensen (L-J) technique, all novel compounds were tested against the M. tuberculosis H 37 Rv strain with Isoniazid as a positive control. A common MIC value of 500 mg mL −1 for the intended pathogenic strain of M. tuberculosis H 37 Rv was observed for compounds 98a, 98d and 98e (Fig.…”

Section: Kavitamentioning

confidence: 99%

Recent advances in the synthesis of new benzothiazole based anti-tubercular compounds

et al. 2023

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“…[59] Meanwhile, when a trifluoromethyl group is at 3-position, different R 1 substituents in the G 2 region afford different activities. [60] Thus, when R 1 is a hydrogen atom, an ethoxy group, or a fluorine atom, the compound has an excellent antimalaria effect against plasmodium falciparum. When R 1 is aminobenzothiazole, good antituberculosis activity against mycobacterium tuberculosis H37Rv strain is obtained.…”

Section: Derivative Activitymentioning

confidence: 99%

Research Progress on the Synthesis and Structure-Activity Relationship of Five Hypoglycemic Active Heterocycles Based on Dipeptidyl Peptidase 4 (DPP-4) Target Design

Kong¹,

Yang²,

Zhou³

et al. 2022

Chinese Journal of Organic Chemistry

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Recently, diabetes has gradually become a main life-threatening disease in China. Drug targets for the treatment of diabetes mainly include dipeptidyl peptidase 4 (DPP-4), adenosine monophosphate-activated protein kinase (AMPK), peroxisome proliferator-activated receptor gamma (PPARγ) receptor and so on, in which targeted drug research targeting DPP-4 is a hot spot in recent years. DPP-4 inhibitor is a drug for the treatment of type 2 diabetes, and its biggest advantage is that it is not easy to induce hypoglycemia and increase weight. It is reported that the currently available DPP-4 targeted drugs can cause adverse reactions, such as pancreatitis and hypersensitivity. Therefore, it is worth further studying to continue to develop new hypoglycemic drugs for DPP-4 inhibitors to avoid adverse reactions. According to the systematic literature review, the potential heterocyclic structures with hypoglycemic activity are summarized and through computer molecular simulation docking, five kinds of heterocyclic structures with high hypoglycemic activity and easy synthesis are finally screened out based on DPP-4 target design. The synthesis routes and structure-activity relationships are summarized and analyzed, which provides a research basis for the development of safe, efficient and novel hypoglycemic drugs for DPP-4 inhibitors in the future. Keywords diabetes; dipeptidyl peptidase 4 (DPP-4) inhibitor; molecular docking; synthesis methods; structure-activity relationship

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Design, synthesis, biological evaluation and computational study of novel triazolo [4,3-a]pyrazin analogues

Cited by 7 publications

References 92 publications

Synthesis and Antibacterial Activity of Novel Triazolo[4,3-a]pyrazine Derivatives

Synthesis and Antibacterial Activity of Novel Triazolo[4,3-a]pyrazine Derivatives

Recent advances in the synthesis of new benzothiazole based anti-tubercular compounds

Research Progress on the Synthesis and Structure-Activity Relationship of Five Hypoglycemic Active Heterocycles Based on Dipeptidyl Peptidase 4 (DPP-4) Target Design

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