The synthesis of N -acyl-2-hydroxymethyl aziridines of biological interest

Medjahed, W.; Zatla, Amina Tabet; Mulengi, Joseph Kajima; Ahmed, Fátima; Merzouk, Hafida

doi:10.1016/j.tetlet.2003.11.136

Cited by 14 publications

(8 citation statements)

References 24 publications

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“…The conversion of an acyl azide into an aziridine is believed to occur according to mechanism we already suggested in our previous work [27]. After quenching the reaction mixture with an aqueous solution of ammonium chloride and removal of triphenylphosphine oxide, the compound was purified on a silica gel column using petroleum ether (b.p.…”

Section: Synthesesmentioning

confidence: 96%

“…The same approach was successfully applied to generate aziridines from N-phtaloylamino acids 13. Phenylalanine and tyrosine were chosen as a models, since in our initial work in this field [27], aziridine from the former amino acid showed the best biological profile [28], whereas tyrosine is claimed to behave as a residue of utmost importance in many receptors [41]. Derivatives 13 were prepared according to a modified literature procedure [42] and were recrystallized.…”

Section: Diethylphosphonopropionyl-2-tosylmethylaziridine 12mentioning

confidence: 99%

“…The biological activity of aziridines is highly related to the establishment of covalent bond with DNA [26]. In a previous work we reported the synthesis of aziridinyl derivatives [27] that had antitumor activities against breast cancer cells [28]. Such a behaviour was likely due to their capacity to strengthen and modulate the immune system [29].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of a Novel Class of Phosphonoaziridines as Interesting Antibacterial Agents

Keniche¹

2011

TOPROCJ

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Section: Synthesesmentioning

confidence: 96%

Section: Diethylphosphonopropionyl-2-tosylmethylaziridine 12mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of a Novel Class of Phosphonoaziridines as Interesting Antibacterial Agents

Keniche¹

2011

TOPROCJ

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“…As metodologias mais recentes [121][122][123][124][125][126][127][128][129][130][131] de preparação de aziridinas não levam em conta apenas a sua obtenção em altos rendimentos e seletividade, mas também a necessidade de se empregar reagentes mais acessíveis e gerar quantidades reduzidas de sub-produtos tó-xicos. Avanços na síntese assimétrica de aziridinas vêm permitindo um maior entendimento dos parâmetros necessários para a obtenção destes blocos de construção quirais com alta pureza óptica e economia atômica.…”

Section: Conclusãounclassified

Recentes avanços na preparação de aziridinas. Aplicações sintéticas e implicações mecanísticas

Bisol¹,

Sá²

2007

Quím. Nova

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Recebido em 22/8/05; aceito em 3/2/06; publicado na web em 30/8/06RECENT ADVANCES IN THE PREPARATION OF AZIRIDINES AND THEIR APPLICATION IN ORGANIC SYNTHESIS. This article surveys a selection of the most recent advances in aziridine synthesis. Novel synthetic methods and new insights into existing methodologies for the selective construction of the title compounds reported in the past decade are discussed in terms of synthetic applicability and environmentally benign conditions. Mechanisms involving stereoselective preparation of structurally diverse aziridines are also presented in order to highlight the most important issues associated with the synthesis of these versatile building blocks.

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“…8) Using the method of Wang et al, 9) the abromoketones 8a and 8b were prepared in good yields. Oxidation and condensation of compounds 8a and 8b afforded compounds 9a-d using the above method (Chart 2).…”

mentioning

confidence: 99%

Synthesis and Antiviral Activity of Phthiobuzone Analogues

Yang

Jing-hua²,

Pan

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Herpes viruses are a large family of viruses containing eight known human viruses. Amongst them, herpes simplex virus 1 (HSV-1) and herpes simplex virus 2 (HSV-2) cause cold sores and genital infections, respectively. 1) HSV infections are one of the most common contagious diseases in humans. Previous antiviral research on HSVs has primarily focused on the development of nucleoside analogs that target the viral polymerase.2) However, these antiviral agents cannot inhibit resistant viruses and can lead to hemotoxicity. 3)Phthiobuzone (Ftibamzone, Tai Ding An, TDA, Fig. 1), a derivative of thiosemicarzones, has been used in clinical treatment of herpes and trachoma diseases in China and in Egypt. TDA represents a type of molecule that combines 3-phthalimido-2-oxo-n-butyraldehyde and bisthiosemicarbazones in one structure. TDA has a unique mechanism of antiviral action, which is different from those of the antiviral nucleotide analogues. 4) Moreover, recent research has demonstrated that phthiobuzone displays weak inhibitory activity against resistant HSV-1 strains.5) In view of this novel structural template, which differs from those of all reported anti-HSV agents, we are interested in a further study of the structure-activity relationship. In this article, we report the synthesis of a series of TDA analogues, particularly through the modification of the 4Ј,4Љ-N-substituted thiosemicarbazone group and the chain length between the phthalimide and bisthiosemicarbazone moieties. Results and DiscussionThe synthesis of compounds 5a-o (Chart 1) began with potassium phthalimide (1). Treatment of 1 with 3-chloro-2-butanone afforded compound 2, 6) which was brominated by Br 2 in AcOH to give compound 3. We prepared target compounds 5a-o by oxidizing 3 using dimethyl sulfoxide (DMSO) to yield the a-keto aldehyde intermediate 4, followed by direct condensation with 4-substituted-3-thiosemicarbazides.7) Some thiosemicarbazides were purchased from commercial suppliers, and others were prepared from the corresponding isothiocyanate with 85% hydrazine hydrate in ethanol. It should be pointed out that compounds 5a-o were all racemates.Compounds 7a and 7b were obtained by condensation in AcOH of 6 with aminoacetic acid and 4-aminobutyric acid, respectively. 8) Using the method of Wang et al., 9) the abromoketones 8a and 8b were prepared in good yields. Oxidation and condensation of compounds 8a and 8b afforded compounds 9a-d using the above method (Chart 2). Except 5g, other TDA analogues were new compounds.This series of TDA analogues were evaluated for their anti-HSV activity in Vero cells. The cytotoxic activity of the compounds was determined in parallel in the same cell line. A series of phthiobuzone analogs, prepared from potassium phthalimide or phthalandione, have been evaluated for their antiviral activities. Among the candidates, compounds 5j and 5k, which contain the substituted 4-halogenated phenyl ring at N-4 ,4؆ ؆ position, show more potent antiviral activity than phthiobuzone against herpes simplex virus 1 (IC 50 ‫...

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The synthesis of N -acyl-2-hydroxymethyl aziridines of biological interest

Cited by 14 publications

References 24 publications

Synthesis of a Novel Class of Phosphonoaziridines as Interesting Antibacterial Agents

Synthesis of a Novel Class of Phosphonoaziridines as Interesting Antibacterial Agents

Recentes avanços na preparação de aziridinas. Aplicações sintéticas e implicações mecanísticas

Synthesis and Antiviral Activity of Phthiobuzone Analogues

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