Synthesis and properties of new nitroimidazoles

Mokrushin, V. S.; Selezneva, I. S.; Поспелова, T. А.; Usova, V. K.; Malinskaya, S. M.; Anoshina, G. M.; Zubova, T. E.; Pushkareva, Z. V.

doi:10.1007/bf00777271

Cited by 6 publications

(10 citation statements)

References 6 publications

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“…In contrast to previous findings [1,2,9], the direction of the nitrogen transfer in the case of steroid 2 is independent of the structure of the diazoimidazoles (Scheme 1).…”

Section: ____________________________________________________________contrasting

confidence: 83%

“…Samples of 5-diazoimidazoles 1a-d were prepared according to reported procedures [9,[12][13][14][15], while samples of the 5-aminoimidazoles were prepared according to Allsebrook [16], Mokrushin [17,18], and Gireva [19].…”

Section: Methodsmentioning

confidence: 99%

“…Thus, azidoimidazoles 7a-c were obtained according to our previous procedure [9,10]. The ethyl ester of 5-azidoimidazole-4-carboxylic acid (7d) was obtained for the first time from the reaction of the ethyl ester of 5-diazoimidazole-4-carboxylic acid (1d) with sodium azide in aqueous ethanol.…”

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confidence: 99%

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Reactions of 5-diazoimidazoles with steroid hydrazones

Садчикова¹,

Kureneva²,

Shtokareva³

et al. 2004

Chem Heterocycl Compd

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The reaction of 5-diazoimidazoles with steroid hydrazones was studied. The structure of the steroid derivative was found to have a significant effect on the direction of the nitrogen transfer in the unstable intermediate tetrazene. The presence of a labile proton in the reaction mixture permits stabilization of one of the tetrazene forms such that only direction was found for the nitrogen transfer in all the reactions studied, leading to imidazole azides and iminosteroid derivatives.Keywords: 5-azidoimidazoles, 3-hydrazono-5α-hydrazono-5α-androstan-17β-ol, 17-hydrazonoestra-1,3,5(10)-trien-3-ol, 5-diazoimidazoles, 3-imino-5α-androstan-17β-ol, 17-iminoestra-1,3,5(10)-trien-3-ol, tetrazenes.Nitrogen-transfer reactions between aromatic diazo compounds and aliphatic hydrazine have been studied by Tishler [1,2]. Depending on the nature of the reagents, the reaction product may lead either to a stable tetrazene, which can be isolated as a solid, or products of tetrazene decomposition. In the latter case, nitrogen transfer occurs, leading to the formation either of an aromatic azide and aliphatic amine or of an aromatic amine and aliphatic azide.In the present work, we studied the reaction of 5-diazoimidazoles 1a-d possessing antitumor and antibacterial activity [3][4][5] with steroid hydrazones 2 and 3, which also display antitumor activity [6]. The products, tetrazenes 4 and 5, may hold interest since they display selective penetration into tumors both as diazoimidazoles and steroid hormones.We might have expected the formation of a mixture of multiple products, which would be difficult to separate into individual components, since nitrogen transfer upon decomposition of the tetrazene could occur concurrently in two directions. Furthermore, 5-diazoimidazole-4-carboxamide (1a) and 5-diazoimidazole-4-(Nmethylcarboxamide) (1b) may undergo intramolecular cyclization leading to imidazotriazines 6a and 6b [5,7,8].The reaction course and composition of the reaction mixture were monitored by thin-layer chromatography with reference to known standards. Thus, azidoimidazoles 7a-c were obtained according to our previous procedure [9,10]. The ethyl ester of 5-azidoimidazole-4-carboxylic acid (7d) was obtained for the first time from the reaction of the ethyl ester of 5-diazoimidazole-4-carboxylic acid (1d) with sodium azide in aqueous ethanol. Unfortunately, we were unable to obtain the corresponding steroid references either by reduction with NaBH 4 , LiAlH 4 , Na 2 S 2 O 4 , Ni/Ra, or Pd/C or by diazotization of steroid hydrazones due to the instability of the corresponding amine and azide products.

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“…In contrast to previous findings [1,2,9], the direction of the nitrogen transfer in the case of steroid 2 is independent of the structure of the diazoimidazoles (Scheme 1).…”

Section: ____________________________________________________________contrasting

confidence: 83%

Section: Methodsmentioning

confidence: 99%

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Reactions of 5-diazoimidazoles with steroid hydrazones

Садчикова¹,

Kureneva²,

Shtokareva³

et al. 2004

Chem Heterocycl Compd

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“…Of the monoamine-substituted dacarbazine derivatives, the methyl derivative, which was called methyldacarbazine, was the most active [21].…”

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confidence: 99%

“…However, these compounds were slightly active and highly toxic in test against tumors (sarcoma 37, 180, Ca 755, Lewis tumor) [31].…”

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confidence: 99%

Antitumor activity of imidazole derivatives: dacarbazine and the new alkylating agent imidazene (Review)

Iradyan

Stepanyan

et al. 2010

Pharm Chem J

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The physicochemical properties and antitumor activity of dacarbazine, its analogs, and the new alkylating agent imidazene are reviewed. It is shown that the activity of dacarbazine is superior to most of its analogs. Imidazene exhibits an advantage over dacarbazine with respect to both stability and activity and can be used for the treatment of malignant melanoma and sarcoma of soft tissues and in combined chemotherapy.

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Structure and Physical–Chemical Properties of Nitroazoles

Ларина

Лопырев

2009

Nitroazoles: Synthesis, Structure and Applications

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Synthesis and properties of new nitroimidazoles

Cited by 6 publications

References 6 publications

Reactions of 5-diazoimidazoles with steroid hydrazones

Reactions of 5-diazoimidazoles with steroid hydrazones

Antitumor activity of imidazole derivatives: dacarbazine and the new alkylating agent imidazene (Review)

Structure and Physical–Chemical Properties of Nitroazoles

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