Tetramisole (R 8299), A New, Potent Broad Spectrum Anthelmintic

Thienpont, D; Of, Vanparijs; Ah, Raeymaekers; Vandenberk, J.; Ja, Demoen; Ft, Allewijn; Rp, Marsboom; Cj, Niemegeers; Kh, Schellekens; Pa, Janssen

doi:10.1038/2091084a0

Cited by 267 publications

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“…The reaction of 2-amino-5-cyclohexyl-1,3,4-thiadiazole 10 (1) and 3-bromoacetyl coumarin 11 (2) in boiling ethanol afforded 3-(2-cyclohexylimidazo[2,1-b]- [1,3,4]thiadiazol-6-yl)-2H-chromen-2-one (3) as hydrobromide salt, which was neutralized by sodium carbonate solution to get the free base. It was subjected to Vilsmeir Haack reaction to yield…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…1 In this regard, a large number of IT derivatives have been (1) Department of Studies in Chemistry, Bangalore University, Central College Campus, Bangalore 560001, India. (2) Department of Chemistry, Karnatak University, Dharwad 580003, India.…”

Section: Introductionmentioning

confidence: 99%

“…Imidazo [2,1-b] [1,3,4] thiadiazole (IT) deriva tives with pharmacophoric substituents have promising biological and pharmacological activities. The title compound is one of such derivatives, with a coumarin molecule linked to the IT ring system.…”

Section: Introductionmentioning

confidence: 99%

“…The title compound was synthesized using Vilsmeier-Haack reagent which was made to react with the prepared 3-(2-cyclohexylimidazo[2,1-b] [1,3,4]thiadiazol-6-yl)-2H-chromen-2-one. This was followed by measurement of analytical data relating to the compound.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, spectroscopic and crystal structure analysis of a compound with pharmocophoric substituent: 2-cyclohexyl-6-(2-oxo-2H-chromen-3-yl)- imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde

et al. 2007

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Section: Synthesis and Characterizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis, spectroscopic and crystal structure analysis of a compound with pharmocophoric substituent: 2-cyclohexyl-6-(2-oxo-2H-chromen-3-yl)- imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde

et al. 2007

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“…The title compound is one of the members of this series. Also, 1,3,4-thiadiazole is bioisosteric with thiazole in Tetramizole, 5 which is a novel broad spectrum antihelmintic.…”

mentioning

confidence: 99%

Synthesis, Spectroscopy and Crystal Structure of 2‐Ethyl‐6‐(4‐nitrophenyl)imidazo[2,1‐b] [1,3,4]thiadiazole‐5‐carbaldehyde.

et al. 2006

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The preparation of 2-ethyl-6-(4-nitrophenyl)imidazo [2,1-b] [1,3,4]thiadiazole-5-carbaldehyde (4) is described and its crystal structure is determined and discussed.Keywords: fused imidazoles, fused 1,3,4-thiadiazoles, crystal structure, Vilsmeier-Haack Imidazo [2,1-b] [1,3,4]thiadiazoles are known for their promising biological and pharmacological activities. 1,2 Much interest has also been focused on the chemistry, anticonvulsant, analgesic 3 and antibacterial 4 activities displayed by compounds incorporating this heterocyclic system. In view of the pharmacological significance of the imidazo [2,1-b] [1,3,4]thiadiazole ring system, it was considered worthwhile to synthesise its derivatives with pharmacophoric substituents, which may have equally significant roles to play in biological systems. The title compound is one of the members of this series. Also, 1,3,4-thiadiazole is bioisosteric with thiazole in Tetramizole, 5 which is a novel broad spectrum antihelmintic.The compound was synthesised by Vilsmeier-Haack formylation of an imidazo[2,1-b][1,3,4]thiadiazole containing ethyl and nitrophenyl substituents (Scheme 1). The product was subjected to spectroscopic analysis using IR and 1 H and 13 C NMR techniques to confirm the presence of the ring system, and the site of formylation.A single crystal X-ray diffraction analysis was carried out on compound 4 to investigate its supramolecular structure in terms of C-H … O hydrogen bonding. The analysis revealed certain interesting features such as the planarity of the molecule due to the co-planarity of the carbaldehyde group with the imidazo-thiadiazole ring, the presence of a strong intramolecular hydrogen bond, and the conformational rigidity of the pseudo seven-membered ring which contains it. The stabilisation of the structure due to intramolecular C-H … O and C-H … N interactions was analysed, leading to the conclusion that the supramolecular aggregation in the molecule was chiefly a function of C-H … O tetrameric units and C-H … N interactions. ExperimentalThe melting points were determined in open capillaries. The IR spectra were recorded as KBr discs using a Nicolet FT-IR 410 spectrophotometre. 1 H NMR spectra were recorded on a Varian RXZ-300 MHz spectrometre using TMS as internal reference compound. C, H and N analyses were measured on a Heraus CHN rapid analyser at Karnatak University, Dharwad, India.2- imidazo [2,1-b][1,3,4]thiadiazole-5-carbaldehyde (4): The title compound was prepared in two stages as shown in Scheme 1. 2-Ethyl-6-(4-nitrophenyl)imidazo[2,1-b][1,3,4] thiadiazole (3) was prepared by refluxing a mixture of p-nitrophenacyl bromide (2) 6 (2.44 g, 0.01 mol) and 2-amino-5-ethyl-1,3,4-thiadiazole (1) 7 (1.29 g, 0.01 mol) in absolute ethanol for 8 h. Solvent was distilled off and the solid hydrobromide that separated was collected by filtration, suspended in water and neutralised with aqueous sodium carbonate to get the free base. This was filtered off, washed with water, dried, and recrystallised from ethanol, providing compound 3 as a pale y...

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The Use of Levamisole in Atopic Dermatitis

Alomar¹

1978

Arch Dermatol

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Tetramisole (R 8299), A New, Potent Broad Spectrum Anthelmintic

Cited by 267 publications

References 0 publications

Synthesis, spectroscopic and crystal structure analysis of a compound with pharmocophoric substituent: 2-cyclohexyl-6-(2-oxo-2H-chromen-3-yl)- imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde

Synthesis, spectroscopic and crystal structure analysis of a compound with pharmocophoric substituent: 2-cyclohexyl-6-(2-oxo-2H-chromen-3-yl)- imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde

Synthesis, Spectroscopy and Crystal Structure of 2‐Ethyl‐6‐(4‐nitrophenyl)imidazo[2,1‐b] [1,3,4]thiadiazole‐5‐carbaldehyde.

The Use of Levamisole in Atopic Dermatitis

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