Synthesis and hybridization properties of the conjugates of oligonucleotides and stabilization agents—II

Balbi, Alessandro; Sottofattori, Enzo; Grandi, Teresa; Mazzei, Mauro; Pyshnyi, D. V.; Lokhov, S. G.; Lebedev, A. V.

doi:10.1016/s0968-0896(97)00127-2

Cited by 10 publications

(9 citation statements)

References 17 publications

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“…Fluorescent polymerizable metal-chelating lipids and DNA-intercalating coumarin carriers have also been obtained using coumarin as a building block [189,190]. [209]. In addition, it is imperative to point out an elegant synthetic strategy presented by Olson and Slossberg [210], for the synthesis of coumermycin A1, using a commercial 7,4-dihydroxycoumarin derivative.…”

Section: B2 -Synthesis Of Simple Coumarins From Coumarinsmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

883

458

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Coumarins, also known as benzopyrones, are present in remarkable amounts in plants, although their presence has also been detected in microorganisms and animal sources. The structural diversity found in this family of compounds led to the division into different categories, from simple coumarins to many other kinds of policyclic coumarins, such as furocoumarins and pyranocoumarins. Simple coumarins and analogues are a large class of compounds that have attracted their interest for a long time due to their biological activities: they have shown to be useful as antitumoural, anti-HIV agents and as CNS-active compounds. Furthermore, they have been reported to have multiple biological activities (anticoagulant, anti-inflammatory), although all these properties have not been evaluated systematically. In addition, their enzyme inhibition properties, antimicrobial and antioxidant activities are other foremost topics of this field of research. The present work is to survey the information published or abstracted from 1990 till 2003, which is mainly related to the occurrence, synthesis and biological importance of simple coumarins and some analogues, such as biscoumarins and triscoumarins. Data are also highlighted, concerning the development of new synthetic strategies that could help in drug design and in the work on SAR or QSAR.

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Section: B2 -Synthesis Of Simple Coumarins From Coumarinsmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

883

458

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“…Pyranone compounds (Fig. 1 ) and ODNs and their derivatives were synthesized as already described (Balbi et al, 1994(Balbi et al, , 1997Sottofattori et al, 1995).…”

Section: Methodsmentioning

confidence: 99%

Interaction of Oligonucleotides Conjugated to Substituted Chromones and Coumarins with HIV-1 Reverse Transcriptase

Martyanov¹,

Zakharova²,

Sottofattori³

et al. 1999

Antisense and Nucleic Acid Drug Development

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Ten different pyranone-related substituents (chromones or coumarins) were covalently linked to the 5' end of various oligonucleotides (ODN). The interaction of these compounds with human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) was analyzed. A different behavior was found to depend on the structure of the oligonucleotide derivatives. Some compounds activated the enzyme at relatively low concentrations (0.1-0.5 microM), followed by an inhibition of the activity at higher concentrations (5-20 microM), whereas others behave just as inhibitors. Because the presence of some coumarin or chromone derivatives conjugated to ODNs enhanced the interaction with the reverse transcriptase, we analyzed the capacity of such ODN derivatives to be used as primers. The introduction of substituent I, a chromone derivative, the 2-[(3-(aminopropyl)amino]-8-isopropyl-5-methyl-4-oxo-4H-1-benzopyran-3-c arbaldehyde], and II, a coumarin derivative, the 1-(3-aminopropoxy)-2-ethyl-3H-naphto[2,1-b]pyran-3-one, into the 5' end of a noncomplementary ODN allowed these compounds to be used as primers. In the case of complementary primers, the presence of conjugated derivatives enhanced the affinity with Km values that were two to three orders of magnitude lower than that of a complementary primer of the same length. After addition of a ddT-unit to the 3'-terminal end of the ODN, some of these primers became very effective inhibitors of RT with Ki values in the nanomolar range.

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“…Nitrile 3 was prepared by treatment of 7-hydroxycoumarin (2) with 2-chloroacetonitrile in DMF containing K 2 CO 3 [34]. The reactive intermediates 5 were obtained from the α,α'-dichloroazo compounds 4 [35] by treatment with SbCl 5 at -60°C.…”

mentioning

confidence: 99%

Synthesis of new 1H-1,2,4-triazolylcoumarins and their antitumor and anti-HIV activities

Al‐Soud

Al-Masoudi

Saeed

et al. 2006

Chem Heterocycl Compd

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Synthesis and hybridization properties of the conjugates of oligonucleotides and stabilization agents—II

Cited by 10 publications

References 17 publications

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Interaction of Oligonucleotides Conjugated to Substituted Chromones and Coumarins with HIV-1 Reverse Transcriptase

Synthesis of new 1H-1,2,4-triazolylcoumarins and their antitumor and anti-HIV activities

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