Propylphosphonic anhydride (T3P®): an efficient reagent for the one-pot synthesis of 1,2,4-oxadiazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles

Augustine, John Kallikat; Vairaperumal, Veeramani; Narasimhan, Sharmila; Alagarsamy, Padma; Radhakrishnan, Anbarasi

doi:10.1016/j.tet.2009.09.114

Cited by 95 publications

(37 citation statements)

References 31 publications

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“…One-pot synthesis of 1,3,4-thiadiazoles from acylhydrazine and the sulfur reagents Another type of one-pot synthesis of 1,3,4thiadiazole derivatives (31) from carboxylic acids (Scheme 6) was developed by Augustine et al (2010). 44 According to these authors, propylphosphonic anhydride (T3P) is generally used as a coupling agent and water scavenger with low toxicity and offers several advantages over traditional reagents, such as having broad functional group tolerance, low epimerization tendency and, above all, high yields and purity. So, the main scope of the report was to evaluate the efficiency of propylphosphonic anhydride (T3P) as a reagent in one-pot synthesis.…”

Section: From Acylhydrazinesmentioning

confidence: 99%

Synthesis of 1,3,4-Thiadiazole Derivatives and Microbiological Activities: A Review

Aguiar¹,

Barbosa²

2019

Rev. Virtual Quim

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Síntese de Derivados de 1,3,4-Tiadiazol e Atividades Microbiológicas: Uma Revisão Resumo: A resistência bacteriana associada a diferentes antibióticos é uma limitação para o tratamento de infecções e isto tem estimulado o desenvolvimento de novos agentes antimicrobianos. Neste aspecto, novos derivados de 1,3,4-tiadiazol-2,5-dissubstituídos, os quais apresentam diversificada atividade biológica, têm sido o foco de vários projetos de pesquisa nos anos recentes. Este artigo destaca as principais metodologias para a síntese deste heterociclo utilizando acilidrazinas, ditiocarbazatos, tiossemicarbazidas, 1,3,4oxadiazóis. Adicionalmente, derivados de 1,3,4-tiadizol-2,5-dissubstituídos com ação antimicrobiana são reportados.

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Section: From Acylhydrazinesmentioning

confidence: 99%

Synthesis of 1,3,4-Thiadiazole Derivatives and Microbiological Activities: A Review

Aguiar¹,

Barbosa²

2019

Rev. Virtual Quim

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“…1,3,4-Oxadiazole derivatives 17-22 (series C) have been achieved by means of intramolecular cyclodehydration of series A. Cyclodehydration is attainable under several conditions, for instance, heating in solvents such as pyridine, DMF, or in the presence of additives such as 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC). SOCl2, P2O5, H2SO4, POCl3, Burgess reagent, triphenylphospine, and triflic anhydride are used for the cyclization [18]. In this study, POCl3 was used as a solvent and cyclodehydrating agent.…”

Section: Scheme 2: Different Synthetic Pathways Towards Key Compoundmentioning

confidence: 99%

“…Additionally, the influence of cyclizing the aroyl carbohydrazide moiety of series A to 1,3,4-oxadiazole, which is a native anticonvulsant scaffold [9][10][11]in series C, 2-(5-(benzo [d][1,3]dioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl)-5-(4-bromo phenyl)-1,3,4-oxadiazole derivatives (17)(18)(19)(20)(21)(22), is very intriguing, since it will completely omit the H-bond donors and consequently elaborate its impact on anticonvulsant activity. These designs have followed the pharmacophoric model that has been put forward for antiepileptic activity owing to conformational investigations on prevailing anticonvulsant drugs such as phenytoin, carbamazepine, lamotrigine and phenobarbitone [12,13].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Anticonvulsant Profile of 5-(Benzo [D][1,3]dioxol-5-Yl)-3-Tert-Butyl-4, 5-Dihydropyrazole Derivatives

El-Behairy

Attia

2017

Int J Pharm Pharm Sci

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Objective: Utilisation of the ligand-based design and molecular hybridization to design promising candidates with prospective efficacy and safety. Synthesis of the designed candidates using different synthetic methods. Biological evaluation of the newly synthesised candidates as anticonvulsant agents.Methods: Three novel series of 5-(benzo [d][1,3]dioxol-5-yl)-3-tert-butyl-4,5-dihydropyrazoles have been designed via ligand-based drug discovery and molecular hybridization. Proper synthetic routes have been followed in the preparation of compounds (2-23) which have been characterised by different spectral techniques. Antiepileptic potential was assessed by biological evaluation using 'classical' animal models of epilepsy, in addition to rotarod test for toxicity.Results: 4-Nitrophenyl derivatives (5, 13, and19) displayed the highest potency. Compound 5was the most active substituent in series A (N'-aroyl-3-tert-butyl-4,5-dihydro-1H-pyrazole-1-carbohydrazide). It was 2.7 and 1.3 times more active than reference drug Stiripentol (I) and lead compound III, respectively. Compound13 was the best candidate in series B (N'-arylidene-3-tert-butyl-4,5-dihydro-1H-pyrazole-1-carbohydrazide). It was 3.3, 1.5, and 1.2 times more potent than Stiripentol, lead compound III and new compound 5, respectively. Two members (19 and 21) of series C (1,3,4-oxadiazole derivatives) achieved 100 % protection at lower doses than I and III, being 2.6 and 2.4 times more active than Stiripentol. In scPTZ screen, the most active congeners (5,13,19) exhibited ED50 values of 45, 48, and 81 mg/kg, respectively, which are highly superior as compared to that of reference drug Stiripentol(I) and lead compound III (ED50 115 and 110 mg/kg, respectively). Conclusion:Ligand-based design together with molecular hybridization in drug design succeeded to produce potent and wide spectrum candidates.

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“…In the second step the heterocycle is formed by intramolecular cyclodehydration. Several conditions of cyclodehydration have been reported [27], for instance, heating in solvents such as pyridine, DMF, or in the presence of additives such as 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), while SOCl2, P2O5, H2SO4, POCl3, Burgess reagent, triphenylphospine, and triflic anhydride are used for the cyclization. In the present work, POCl3 acted as solvent and as coupling, and cyclodehydrating agent for the synthesis of aminothiadiazoles 3a-e.…”

Section: Chemistrymentioning

confidence: 99%

Design, synthesis, and biological profile of novel N-(5-aryl-1,3,4-thiadiazol-2-yl) hydrazinecarboxamides

et al. 2014

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KEYWORDSNew series of arylthiadiazole hydrazinecarboxamides (5a-e) have been synthesized by hydrazinolysis of carbamates (4a-e) and spectrally characterized. The new candidates have been screened for their anticonvulsant and immunomodulatory activities. Compound 5e was the most potent anticonvulsant candidate as it showed 100% protection against both maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ) screens without neurotoxicity at 100 mg/kg (0.318 mmol/kg). With respect to immunomodulation, compounds 5a and 5d revealed immunostimulatory activity while compounds 5b, 5c, and 5e had immunosuppressive responses based on ELISA detection of IgM and IgG levels, counting the total mesenteric lymph nodes lymphocytes, and histo-pathological examinations.

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Propylphosphonic anhydride (T3P®): an efficient reagent for the one-pot synthesis of 1,2,4-oxadiazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles

Cited by 95 publications

References 31 publications

Synthesis of 1,3,4-Thiadiazole Derivatives and Microbiological Activities: A Review

Synthesis of 1,3,4-Thiadiazole Derivatives and Microbiological Activities: A Review

Design, Synthesis and Anticonvulsant Profile of 5-(Benzo [D][1,3]dioxol-5-Yl)-3-Tert-Butyl-4, 5-Dihydropyrazole Derivatives

Design, synthesis, and biological profile of novel N-(5-aryl-1,3,4-thiadiazol-2-yl) hydrazinecarboxamides

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