Untitled

Iradyan, M. A.; Iradyan, N. S.; Stepanyan, G. M.; Arsenyan, F. G.; Garibdzhanyan, B. T.

doi:10.1023/a:1010467609672

Cited by 11 publications

(28 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[2] The potent antitumor activity shown by dacarbazine led to the development of aryl and heteroaryl triazeno derivatives. [3] Among the derivatives belonging to the latter class of compounds, azole derivatives were the most important. In fact, triazenotriazoles, [4] -pyrazoles, [5] and -imidazoles [6] were active against several types of tumors and, within these series, the heterocyclic moiety seemed to modulate the antitumor activity: the more electron-rich the heterocyclic ring is, the higher is the potency.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Triazenoazaindoles: a New Class of Triazenes with Antitumor Activity

Diana¹,

Stagno²,

Barraja³

et al. 2011

ChemMedChem

View full text Add to dashboard Cite

Despite improvements in the treatment and prevention of cancer, the number of new diagnoses continues to rise; this has fuelled substantial interest in the development of new and effective chemotherapeutic agents. Compounds of the triazene class, such as dacarbazine, have been used in the clinical management of many cancer types including brain, leukemia, and melanoma. A new compound class bearing a triazenoazaindole scaffold was synthesized with the aim of identifying new antiproliferative agents. Compounds 5a-g and 6a-c were screened against a panel of human tumor cell lines, and two of them, 5e and 5f, showed cytotoxicity (GI(50) range: 2.2-8.2 μM) in all cell lines. These two compounds even maintained their cytotoxicity in some multidrug-resistant cell lines. Flow cytometry analysis demonstrated their ability to induce cell death by apoptosis with involvement of lysosomes.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis of Triazenoazaindoles: a New Class of Triazenes with Antitumor Activity

Diana¹,

Stagno²,

Barraja³

et al. 2011

ChemMedChem

View full text Add to dashboard Cite

show abstract

“…The reaction of 5-halo-4-nitroimidazoles 13 with NaOH leads to the sodium salts of 5-hydroxy-4-nitroimidazoles 15 [14], while the reaction with sodium alcoholates leads to 5-alkoxy-4-nitroimidazoles 16 [12][13][14][15][16][17][18].…”

Section: Reactions With O-nucleophilesmentioning

confidence: 99%

“…In [19] it was noted that 5-bromo-1,2-dimethyl-4-nitroimidazole, unlike its 4-bromo-5-nitro isomer, does not react with alcoholates, contradicting the experimental data from other authors [12][13][14][15][16][17][18].…”

Section: Reactions With O-nucleophilesmentioning

confidence: 99%

Reactions of halonitroimidazoles with nucleophiles (review)

Александрова¹,

Кравченко

Кочергин³

2010

Chem Heterocycl Comp

View full text Add to dashboard Cite

On account of their chemical stability, high reactivity, and availability 4(5)-halo-5(4)-nitro-and 2-halo-4(5)-nitroimidazoles have proved useful substrates for the study of reactions with O-, S-, N-, C-, and N,O-nucleophiles. The high reactivity of the halogen atom in the series of 4(5)-halo-5(4)-nitroimidazoles is brought about by the presence of the strong electron-accepting NO 2 group at the "ortho" position. The activating effect of the NO 2 group also extends to the halogen atom at position 2 of the imidazole ring.The products from the reactions of halonitroimidazoles with various nucleophiles have found use in fine organic synthesis, especially in the synthesis of heterocycles with a bridging nitrogen atom, biologically active compounds, and medicinal preparation. Thus, 1-methyl-4-nitro-5-(6-purinyl)mercaptoimidazole has found use under the name azathioprine as a medical preparations in the transplantation of vital organs and the treatment of a series of autoimmune diseases [1][2][3][4].

show abstract

“…Compound XI had activity toward rat tumors similar to that of sarcolysine with slightly lower toxicity [16].…”

mentioning

confidence: 92%

Imidazole derivatives and their antitumor activity (review)

Iradyan

Arsenyan

et al. 2009

Pharm Chem J

Self Cite

View full text Add to dashboard Cite

Bis(2-chloroethyl)amino derivatives of imidazole, 4(5)-aminoimidazol-5(4)-carboxamide, 4-nitro-5-thioimidazole, benzimidazole, and imidazolylpeptides are reviewed. Data are presented for active compounds, some of which have passed the preclinical testing stage. Structures under consideration are interesting with respect to both the search for new antitumor drugs and the synthesis of compounds with different biological properties.Key words: imidazole, 4(5)-aminoimidazol-5(4)-carboxamide, 4-nitro-5-thioimidazole, benzimidazole, imidazolylpeptides, bis(2-chloroethyl)amino derivatives, antitumor activity.Chemotherapy of tumors is one of the most important medical achievements of the 20th century. Chemotherapy of malignant neoplasms was identified as an independent area of oncology in the middle of the 1940s with the advent of alkylating agents.It is currently possible to treat patients with Burkitt's lymphoma, Hodgkin's disease, chorionepithelioma, germinogenic ovarian diseases, Ewing's sarcoma, Kaposi's sarcoma, osteosarcoma, breast and prostate cancer, and certain acute forms of leukemia and lymphosarcoma. However, any treatment method is ineffective at advanced stages of the disease in all instances.The ability to treat cancers with derivatives of bis(2-chloroethyl)amine was discovered serendipitously. The doctor on-board the transport ship John Harvey that was carrying mustard gas (1943) noticed the toxic effect of this compound on the blood of sailors. These and other observations signaled the beginning of studies on the effect of mustard gas and its derivatives on experimental and human tumors. Mustard gas itself is highly toxic and is not used in medical practice. A methyl analog of mustard gas, embichin, which was also one of the first antitumor preparations, was proposed in 1946 as a therapeutic. Searches in the next 20 -30 years in this direction discovered derivatives of bis(2-chloroethyl)-amine with aromatics such as novembichin, chlorambucil, paphencyl; with amino-acids, sarcolysine, asaline, lofenal; with hemi-alcohols, degranol; with phosphorylated amines, cyclophosphane; and with nitrogen-containing heterocycles, dopan and fluorodopan.A distinguishing feature of these preparations is the rather effective action on malignant systemic diseases of blood and hematopoietic organs.The presence of imidazole derivatives in man and their involvement in metabolism has drawn the attention of researchers. For example, a key compound in the biosynthesis of natural purine components of RNA and DNA is the ribotide 4(5)-aminoimidazol-5(4)-carboxamide [1,2]. Involvement of 4,5-aminoimidazolcarboxamide in metabolic processes can be used to synthesize its antimetabolites that can inhibit biosynthesis after biotransformations and thereby suppress tumor growth.The biological activity of bis(2-chloroethyl)amines is due to their interaction with carboxylic, sulfhydryl, and amino groups of proteins. They react with nucleic acids at the phosphoric-acid hydroxyls and DNA guanine at the 7-nitrogen atom [3].A characteristic of 2...

show abstract

Untitled

Cited by 11 publications

References 1 publication

Synthesis of Triazenoazaindoles: a New Class of Triazenes with Antitumor Activity

Synthesis of Triazenoazaindoles: a New Class of Triazenes with Antitumor Activity

Reactions of halonitroimidazoles with nucleophiles (review)

Imidazole derivatives and their antitumor activity (review)

Contact Info

Product

Resources

About