2-(Substituted amino)quinolizinium bromides. A new class of anthelmintic agents

Alaimo, Robert J.; Hatton, C. J.; Eckman, Michael K.

doi:10.1021/jm00297a054

Cited by 20 publications

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“…Different pharmacological properties have been described for quinolizinium derivatives. For example, 2-aminoquinolizinium compounds are anthelmintic agents [145], nolinium bromide (203) [150].…”

Section: Relevant Natural And/or Useful Compoundsmentioning

confidence: 99%

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Heterocycles Containing a Ring‐Junction Nitrogen

Vaquero

Alvárez‐Builla

2011

Modern Heterocyclic Chemistry

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Section: Relevant Natural And/or Useful Compoundsmentioning

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“…Nucleophilic substitutions are common reactions on these types of quinolizinium derivatives. One of the most extensive applications of haloquinoliziniums has been their conversion into aminoquinolizinium salts 308 by reaction with primary or secondary amines [145]. Silver acetate or hot water has been used to obtain the .…”

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Heterocycles Containing a Ring‐Junction Nitrogen

Vaquero

Alvárez‐Builla

2011

Modern Heterocyclic Chemistry

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“…The synthetic procedure for the preparation of [1][2][3][4][5][6][7][8][9][10][11][12] is shown in Scheme I.…”

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Book Reviews

1976

J. Med. Chem.

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The synthetic procedure for the preparation of [1][2][3][4][5][6][7][8][9][10][11][12] is shown in Scheme I.Title compounds [1][2][3][4][5][6][7][8][9][10][11][12] are shown in Table I.Anthelmintic Testing. The compounds prepared in this work were tested against the mouse pinworm Syphacia obvelata.1•2 The activity of these compounds, expressed in percent reduction in worm burden, is shown in Table I. The activity of the reference drug, piperazine adipate, is also included for comparison. Test compounds were administered perorally twice a day for 5 days. The most active compounds in reducing worm infestation are those substituted with halogen atoms (1, 3, 4, 7, 10) or a cyano group (8). However, no real structure activity trend is apparent among the cinnamamido-2,4imidazolidinediones.When compared to piperazine adipate for activity against S. obvelata, results indicate a number of compounds (1,3,8, and 10) to be significantly more active, with as much as 97% reduction at 25 mg/kg (8). Experimental SectionMelting points were determined in open capillary tubes using a Mel-Temp melting point apparatus and are uncorrected. The NMR spectra were obtained on a Varían A-60A instrument using tetramethylsilane as an internal standard. The aldehyde intermediates used in the preparation of compounds 3, 6, 10, 11, Book Reviews and 12 were prepared by a general procedure.6 These aldehydes as well as the cinnamic acid derivatives prepared therefrom were not characterized but used directly in the subsequent reactions.l-(3,4-Dichlorocinnamamido)-2,4-imidazolidinedione (1).3,4-Dichlorocinnamic acid (22 g, 0.1 mol) was treated dropwise with thionyl chloride (70 ml, 1 mol). After the addition was complete, the mixture was warmed for 0.5 hr, and then the excess thionyl chloride was removed in vacuo. The residue was stirred with benzene (50 ml) and the benzene removed in vacuo. To the residue was added a suspension of l-amido-2,4-imidazolidinedione hydrochloride (15 g, 0.1 mol) in pyridine (200 ml). The reaction mixture was heated on a steam bath for 3 hr and then treated with charcoal and filtered. The pyridine solution was poured onto ice and the precipitated product (28 g, 89%) recrystallized from methanol to give off-white crystals.Compounds 2-12 in Table I were prepared in a similar manner using the appropriately substituted cinnamic acids.4 6 Biological Method. S. obvelata. The method was described previously2 and compound effectiveness was determined as a percentage reduction in the manner described earlier.1 The results were analyzed for their statistical significance by means of the Mann-Whitney "U" test.7

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“…The general method for the preparation of the amino compounds 6-24 involves displacement of the activated 4-C1 atom in 4-chloro-2-(5-nitro-2-thienyl)quinazolines 5a or 5b by a variety of amines in DMF solution. The synthesis of 5a and 5b involves the reaction of 5-nitro-2-thiophenecarboxaldehyde (1) with an anthranilamide (2a or 2b) in acidic EtOH. The resulting dihydroquinazolinone (3a or 3b) is oxidized to the corresponding quinazolinone (4a or 4b) with p-benzoquinone.…”

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