α,α-Dibromoacetophenones mediated synthesis of some new 7H-7-alkoxy-3-alkyl/phenyl-6-aryl-s-triazolo[3,4-b][1,3,4]thiadiazines and their antimicrobial evaluation

Pundeer, Rashmi; Kiran, Vijay; Prakash, Richa; Sushma, .; Bhatia, Subhash C.; Sharma, Chetan; Aneja, K. R.

doi:10.1007/s00044-011-9945-1

Cited by 9 publications

(8 citation statements)

References 25 publications

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“…These class of heterocyclic compounds were found to exhibit considerably better antibacterial and antifungal activity than commercial antibiotics. Similar observation was made by Sharma and his co‐workers as well …”

Section: The Gem‐dihaloketones In the Synthesis Of Heterocyclic Framesupporting

confidence: 88%

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

Sadhukhan

Santhi

Baire

2020

Chemistry A European J

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The α,α‐dihalocarbonyl moiety is a bifunctional system with a gem‐dihalocarbon and a carbonyl carbon in 1,2‐fashion. This is one of the privileged scaffolds in medicinal chemistry due to its chemical and metabolic stability and lipophilicity. They have also been found in numerous structurally divergent natural products and most of their fabricated structures have already been in medicinal use. Apart from their important use in medicinal chemistry, the α,α‐dihalocarbonyl groups have been employed as key building blocks for the development of novel synthetic strategies and utilized as intermediates in total synthesis. In addition to the traditional transformations such as oxidations, reductions, and C−C bond formations, recently several new and non‐classical reactions have also been developed. This review provides short description of existing methods for their synthesis and detailed discussion on the efforts for the discovery and development of new reactions by employing α,α‐dihaloketones as synthetic building blocks. We have presented their use as key functional groups for the synthesis of polycyclic systems of medicinal and material importance and natural products.

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Section: The Gem‐dihaloketones In the Synthesis Of Heterocyclic Framesupporting

confidence: 88%

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

Sadhukhan

Santhi

Baire

2020

Chemistry A European J

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“…The fusion of triazole and thiazole rings can lead to thiazolotriazoles with superior biological properties due to mutual influence of the pharmacophores centers present in the molecule. Thus, literature data indicate that numerous thiazolo [3,2-b] [1,2,4] triazoles derivatives have been reported to possess antibacterial, [3][4][5][6][7][8][9] antifungal, 3,[6][7][8][9] anti-inflammatory, 3,10,11) analgesic, 3,10) antiproliferative, 12) anticonvulsant 13) properties. Also, thiazolo [3,2-b][1,2,4] triazol-ones have been studied for their properties with respect to their biological activities including anti-inflammatory, [14][15][16][17] analgesic, 15,17) anticancer, [18][19][20] antibacterial, 21) antifungal 21) and anticonvulsant.…”

mentioning

confidence: 99%

Design, Synthesis, Characterization and Antimicrobial Evaluation of Some Heterocyclic Condensed Systems with Bridgehead Nitrogen from Thiazolotriazole Class

Bărbuceanu

Drăghici

Bărbuceanu

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Although sulfur-containing heterocyclic compounds were found to have extensive biological applications, 1,3,4-thiadiazines are explored to a much lesser extent in medicinal chemistry, when compared to 1,2,4-triazole and pyrazole motifs. Thiadiazines are themselves showing good biological activities [34][35][36][37][38][39].…”

Section: Introductionmentioning

confidence: 99%

Discovery of ( ±)-3-(1H-pyrazol-1-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazine derivatives with promising in vitro anticoronavirus and antitumoral activity

et al. 2021

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A new series of ( ±)- (3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-phenyl-6,7-dihydro-5H-[1,2,4]triazolo [3,4-b][1,3,4]thiadiazin-7-yl)(phenyl)methanones were efficiently synthesized starting from 4-amino-5-hydrazinyl-4H-1,2,4-triazole-3-thiol 1, acetyl acetone 2, various aromatic and heterocyclic aldehydes 3 and phenacyl bromides 4. All the newly synthesized compounds were tested for their antiviral and antitumoral activity. It was shown that subtle structural variations on the phenyl moiety allowed to tune biological properties toward antiviral or antitumoral activity. Mode-of-action studies revealed that the antitumoral activity was due to inhibition of tubulin polymerization.

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α,α-Dibromoacetophenones mediated synthesis of some new 7H-7-alkoxy-3-alkyl/phenyl-6-aryl-s-triazolo[3,4-b][1,3,4]thiadiazines and their antimicrobial evaluation

Cited by 9 publications

References 25 publications

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

Design, Synthesis, Characterization and Antimicrobial Evaluation of Some Heterocyclic Condensed Systems with Bridgehead Nitrogen from Thiazolotriazole Class

Discovery of ( ±)-3-(1H-pyrazol-1-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazine derivatives with promising in vitro anticoronavirus and antitumoral activity

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