Preparation and Properties of the 5,6- and 4,6(5,7)-Dinitro Derivatives of Benzimidazole and their 1-β-D-Ribofuranosides

Kazimierczuk, Zygmunt; Shugar, David

doi:10.1080/07328318908048847

Cited by 13 publications

(7 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In order to expand the group of benzimidazole derivatives, we synthesised several new benzimidazole ring-containing compounds. In addition to the earlier reported 5,6-dinitro-and 4,6-dinitrobenzimidazoles, their nucleosides and 5,6-dinitro-2-trifluoromethylbenzimidazole [17,18], we have undertaken the synthesis of a series of 1-substituted 5,6-dinitrobenzimidazoles (2a-f) by alkylation of 5,6-dinitrobenzimidazole (1) with appropriate halogenoalkylamine in acetonitrile using 1,8-diazabicyclo [5,4,0]undec-7-en (DBU) as a base. Additionally, 5,6-dinitro-1-(2,3-dihydroxyprop-1-yl)benzimidazole (2g) was obtained in the reaction of 1 with glycitole under the same reaction conditions (Scheme 1).…”

Section: Chemical Synthesismentioning

confidence: 59%

Synthesis, antiprotozoal and antibacterial activity of nitro- and halogeno-substituted benzimidazole derivatives.

Kazimierczuk¹,

Upcroft²,

Upcroft³

et al. 2002

Acta Biochim Pol

Self Cite

101

View full text Add to dashboard Cite

Two series of benzimidazole derivatives were sythesised. The first one was based on 5,6-dinitrobenzimidazole, the second one comprises 2-thioalkyl-and thioaryl-substituted modified benzimidazoles. Antibacterial and antiprotozoal activity of the newly obtained compounds was studied. Some thioalkyl derivatives showed remarkable activity against nosocomial strains of Stenotrophomonas malthophilia, and an activity comparable to that of metronidazole against Gram-positive and Gram-negative bacteria. Of the tested compounds, 5,6-dichloro-2-(4-nitrobenzylthio)-benzimidazole showed the most distinct antiprotozoal activity.Benzimidazole derivatives are of wide interest because of their diverse biological activity and clinical applications [1]. This ring system is present in numerous antiparasitic, fungicidal, anithelemintic and anti-inflammatory drugs [2][3][4][5]. Also, some benzimidazole nucleosides, particularly 5,6-dichlorobenzimi-dazole-1-b-D-ribofuranoside (DRB) and its 2-substituted derivatives show activity against human cytomegalovirus [6]. It is also known that 5,6-dinitrobenzimidazole can substitute 5,6-dimethylbenzimidazole in the vitamin B 12 molecule in Corynebacterium diphteriae [7] and 2-trifluorobenzimidazoles are Vol. 49 No.

show abstract

Section: Chemical Synthesismentioning

confidence: 59%

Synthesis, antiprotozoal and antibacterial activity of nitro- and halogeno-substituted benzimidazole derivatives.

Kazimierczuk¹,

Upcroft²,

Upcroft³

et al. 2002

Acta Biochim Pol

Self Cite

101

View full text Add to dashboard Cite

show abstract

“…The benzimidazole nucleobases, when not commercially available, were synthesized according to published procedures (Kazimierczuk & Shugar, 1989). The benzimidazole 1-fl-Dribofuranosides were prepared as described by Vorbruggen et al (1981) and Kazimierczuk et al (1981), then phosphorylated and cyclized by a 'one-pot' method (Genieser et al, 1989).…”

Section: Methodsmentioning

confidence: 99%

Mapping of the epitope/paratope interactions of a monoclonal antibody directed against adenosine 3′,5′-monophosphate

Naß

Colling

Cramer

et al. 1992

Biochemical Journal

View full text Add to dashboard Cite

A series of systematically modified cyclic AMP (cAMP) analogues, including newly synthesized benzimidazole ribofuranosyl 3',5'-monophosphates was used to map the essential molecular interactions between cAMP and the monoclonal antibody 4/2C2 (mab 4/2C2) directed against 2'-O-succinoyl cAMP [Colling, Gilles, Nass, Moka & Jaenicke (1988) Second Messengers Phosphoproteins 12, 123-133]. Its paratope binds the purine base in syn conformation by dipole-dipole interactions and hydrophobic forces and/or stacking interactions. The ribose phosphate moiety is recognized by a combination of charge interactions and H-bonds to the exocyclic and the 5'-oxygen atoms and a hydrophobic interaction at the 2'-position. There is no regioselectivity for the exocyclic oxygen atoms. Compared with the known types of binding, mab 4/2C2 thus shows a new combination of molecular interactions which may be the basis of its strikingly specific recognition and binding of the cyclic adenylates. On this account mab 4/2C2 may become an important tool in studies on cAMP metabolism.

show abstract

“…The derivatives of bis-benzimidazoles are inhibitors of DNA topoisomerase I (Kazimierczuk and Shugar, 1989;Kraut et al, 1991).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel 4-(1H-benzimidazol-2-yl)benzene-1,3-diols and their cytotoxic activity against human cancer cell lines

2011

View full text Add to dashboard Cite

One-pot synthesis of new biologically active 4-(1H-benzimidazol-2-yl)benzene-l,3-diols has been developed. The compounds were prepared by the reaction of aryl-modified sulfinylbis[(2,4-dihydroxyphenyl)methanethione]s with benzene-l,2-diamines. Their structures were identified using elemental, IR, (1)H-NMR, and mass spectra analyses. The developed method offers short reaction times, relatively large-scale synthesis, easy and quick isolation of the products, and good yields. The cytotoxicity in vitro against the 4 human cancer cell lines: SW707 (rectal), HCV29T (bladder), A549 (lung), and T47D (breast) was determined. The antiproliferative properties of some compounds studies were stronger than those of cisplatin, which was used as a comparator drug.

show abstract

Preparation and Properties of the 5,6- and 4,6(5,7)-Dinitro Derivatives of Benzimidazole and their 1-β-D-Ribofuranosides

Cited by 13 publications

References 9 publications

Synthesis, antiprotozoal and antibacterial activity of nitro- and halogeno-substituted benzimidazole derivatives.

Synthesis, antiprotozoal and antibacterial activity of nitro- and halogeno-substituted benzimidazole derivatives.

Mapping of the epitope/paratope interactions of a monoclonal antibody directed against adenosine 3′,5′-monophosphate

Synthesis of novel 4-(1H-benzimidazol-2-yl)benzene-1,3-diols and their cytotoxic activity against human cancer cell lines

Contact Info

Product

Resources

About