Purines and purine nucleoside analogues as antitumour agents

Robins, Roland K.; Kini, Ganesh D.

doi:10.1007/978-94-009-0397-5_10

Cited by 16 publications

(7 citation statements)

References 78 publications

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“…The chemo‐ and regioselective acylation of amino alcohols, carbohydrates, and nucleosides uses oxime esters as intermediates of importance (Fernández, Menéndez, & Gotor, ; Gotor & Pulido, ; Gotor & Morís, ; Moris & Gotor, ; Pulido & Gotor, ; Pulido, Ortiz, & Gotor, ). These nucleosides thus obtained play an important role in medicine (Isono, ) because they have antiviral and antineoplastic activity (MacCoss & Robins, , Robins & Kini, ; Robins & Revankar, ). Traditional methods for the synthesis of oximes are complex or include the use of corrosive and/or flammable liquids (Houben, Weyl, & Muller, ; Patai & Rappoport, ).…”

Section: Synthesis Of Drugsmentioning

confidence: 99%

Burkholderia cepacia lipase: A versatile catalyst in synthesis reactions

Sánchez

Tonetto

Ferreira

2017

Biotech & Bioengineering

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The lipase from Burkholderia cepacia, formerly known as Pseudomonas cepacia lipase, is a commercial enzyme in both soluble and immobilized forms widely recognized for its thermal resistance and tolerance to a large number of solvents and short-chain alcohols. The main applications of this lipase are in transesterification reactions and in the synthesis of drugs (because of the properties mentioned above). This review intends to show the features of this enzyme and some of the most relevant aspects of its use in different synthesis reactions. Also, different immobilization techniques together with the effect of various compounds on lipase activity are presented. This lipase shows important advantages over other lipases, especially in reaction media including solvents or reactions involving short-chain alcohols.

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Section: Synthesis Of Drugsmentioning

confidence: 99%

Burkholderia cepacia lipase: A versatile catalyst in synthesis reactions

Sánchez

Tonetto

Ferreira

2017

Biotech & Bioengineering

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“…Similar protection levels (83 % and 92%, respectively) were conferred to mice by oral treatment with higher doses.115 Oral protection by 7-dea-zaGuo was also demonstrated against banzi and EMC viral infections. 115 The 7-cyano and 7-carboxylic acid (cadeguomycin) derivatives, 15 and 14, respectively, of 7-dea-zaGuo (13) are less active than the parent compound against SFV infection in mice (Chart III and Table II) although 7-carboxamido and 7-phenyl derivatives, 16 and 17, respectively, are totally inactive (data not shown).…”

Section: Antiviral and Antitumor Inhibition By Various Substituted Gu...mentioning

confidence: 99%

Modulation of leukocyte genetic expression by novel purine nucleoside analogs. A new approach to antitumor and antiviral agents

Bonnet¹,

Robins²

1993

J. Med. Chem.

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“…[1][2][3][4] While several modified nucleosides have clinically verified utility in the treatment of cancer 5 and virus infections, such as HIV, 6 both the demonstration of toxic side effects and the emergence of resistant viral strains stimulate further studies directed toward the synthesis and biology of modified nucleosides.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of exomethylene- and keto-exomethylene-d-glucopyranosyl nucleoside analogs as potential cytotoxic agents

Tzioumaki

Tsoukala

Manta

et al. 2011

Carbohydrate Research

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A novel series of exomethylene- and keto-exomethylene-d-glucopyranonucleosides with thymine, uracil, and 5-fluorouracil as heterocyclic bases have been designed and synthesized. Wittig condensation of the 3-keto glucoside 1 gave the corresponding 1,2:5,6-di-O-isopropylidene-3-deoxy-3-methylene-d-glucofuranose (2), which after hydrolysis and acetylation led to the precursor 1,2,4,6-tetra-O-acetyl-3-deoxy-3-methylene-d-glucopyranose (4). Compound 4 was condensed with silylated thymine, uracil, and 5-fluorouracil, respectively, deacetylated and acetalated to afford 1-(3'-deoxy-4',6'-O-isopropylidene-3'-methylene-β-d-glucopyranosyl)pyrimidines 7a-c. Oxidation of the free hydroxyl group in the 2'-position of the sugar moiety led to the formation of the labile 1-(3'-deoxy-4',6'-O-isopropylidene-3'-methylene-β-d-glucopyranosyl-2'-ulose)pyrimidines 8a-c. Finally, deisopropylidenation of the resulted derivatives 8a-c afforded the diol nucleosides 9a-c. The target keto-exomethylene analogs 9a-c were more cytostatic against a variety of tumor cell lines than the corresponding saturated-hydroxy-exomethylene derivatives 6. In particular, the 5-fluorouracil derivative 9c was highly cytostatic at an IC(50) (50% inhibitory concentration) ranging between 0.56 and 9.4 microg/mL, which was comparable to the free parental 5-fluorouracil base.

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Purines and purine nucleoside analogues as antitumour agents

Cited by 16 publications

References 78 publications

Burkholderia cepacia lipase: A versatile catalyst in synthesis reactions

Burkholderia cepacia lipase: A versatile catalyst in synthesis reactions

Modulation of leukocyte genetic expression by novel purine nucleoside analogs. A new approach to antitumor and antiviral agents

Efficient synthesis of exomethylene- and keto-exomethylene-d-glucopyranosyl nucleoside analogs as potential cytotoxic agents

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