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Arabinofuranosyl adenine

In the foregoing procedure, when the temperature of incubation in the two fermentation stages is raised from 25° to 27°C to 36° to 38°C, the same 9-((3-D-arabinofuranosyl)adenine product is obtained in higher yields. [Pg.1577]

The reaction of adenosine with 2-acetoxy-2-methylpropanoyl chloride or the corresponding bromide is less regioselective than that of uridine,400 and gives 9-(2-0-acetyl-3-deoxy-3-halo-/3-D-xylofuranosyl)-and9-(3-0 - acetyl - 2 - deoxy - 2 - halo - /3 - D - arabinofuranosyl) - adenine,... [Pg.84]

Vidarabine [vye DARE a been] arabinofuranosyl adenine, ara-A, adenine arabinoside) is one of the most effective of the nucleoside analogs and is also the least toxic. However, it has been supplanted clinically by acyclovir, which is more efficacious and safe. Although vidarabine is active against herpes simplex virus type 1 (HSV-1), HSV-2, and varicella-zoster virus (VZV), its use is limited to treatment of immunocompromised patients with herpes simplex keratitis or encephalitis, or VZV infections. Vidarabine, an adenosine analog, is converted in the cell to its 5 -triphosphate analog (ara-ATP), which is postulated to inhibit viral DNA synthesis. Some resistant herpes virus... [Pg.378]

The formal charge in 9-fi-D-arabinofuranosyl adenine HCl [ARFUAD01] is on N(l)-H, which is not directly hydrogen-bonded to the three-coordinated chloride ion (Fig. 17.52). [Pg.298]

AMAFAP. 8,2 -Anhydro-8-mercapto-9-/ -D-arabinofuranosyl-adenine 5 -monophosphate trihydrate [C10H12N5PS, 3(H20)]. Thnaka K, Fujii S, Fujiwara T, Ibmita K (1979) Acta Crystallogr, Sect B 35 929... [Pg.548]

ARADEN10. 9-d-D-Arabinofuranosyl-adenine (C10H13N Oa). Bunick G, Voet D (1974) Acta Crystallogr, Sect B 30 1651... [Pg.549]

Several glycosylpurines have been isolated from microorganisms (Table 40) and proved to have substantial biological activity (B-70MI40900). They include substances such as 9-(jS-D-arabinofuranosyl)adenine (Ara A) which is a powerful antiviral and antitumour agent and... [Pg.602]

D-Arabinofuranosyl)adenine 9-[/3-(2 a, 3 a-dihydroxy-4 /3-(hydroxymethyl)cyclopentyl]adenine Spongoadenosine IS. antibioticus) B-70MI40900, p. 128... [Pg.602]

Pankiewicz, K. W., Krzeminski, J., Ciszewski, L. A., et al. (1992) A synthesis of 9-(2-deoxy-2-fluoro-P -D-arabinofuranosyl)adenine and -hypoxanthine. An effect of C3 -endo to C2 -endo conformational shift on the reaction course of 2 -hydroxyl group with DAST. J. Org. Chem., 57, 553-559. [Pg.194]

Maruyama, T., Takamatsu, S., Kozai, S., et al. (1999) Synthesis of 9-(2-deoxy-2-fluoro-P-D-arabinofuranosyl)adenine bearing a selectively removable protecting group. Chem. Pharm. Bull., 47, 966-970. [Pg.194]

The reaction of the chloronucleoside (120) with sodium azide also gave a mixture (121 and 122) preponderating in the product of attack at C-3, that is, 9-(3-azido-3-deoxy-2-(S-ethyl-2-thio-/3-D-arabinofuranosyl)adenine... [Pg.334]

Die Spaltung von O-Benzyl-Schutzgruppen kann auch durch Natrium/fl. Ammoniak und Behandeln mit Ammoniumchlorid durchgefiihrt werden1,2. Z.B. bildet 9-(2,3,5-Tri-0-benzyl-/j-D-arabinofuranosyl)-adenin in 82%iger Ausbeute (9f -D-Arabinofuran-osyI)-adenin (Spongoadenosin) [F 255—256° (Zers.)]1 ... [Pg.658]

Fludarabine phosphate, a fluorinated deamination-resistant nucleotide analog of the antiviral agent vidarabine (9-P-D-arabinofuranosyl-adenine), is active in CLL and low-grade lymphomas. After rapid extracellular dephosphorylation to the nucleoside fludarabine, it is rephosphorylated intracellularly by deoxycytidine kinase to the active triphosphate derivative. This antimetabolite inhibits DNA polymerase, DNA primase DNA ligase, and ribonucleotide reductase, and is incorporated into DNA and RNA. The triphosphate nucleotide is an effective chain terminator when incorporated into DNA, and the incorporation of fludarabine into RNA inhibits RNA function, RNA processing, and mRNA translation. [Pg.277]

S Additional information <3, 7> (<3> enzyme exists in different conformational states with different substrate kinetic properties [9] <3> presumably one common nucleoside acceptor site [15] <3> purine deoxynucleo-side activity inseparably associated with deoxycytidine kinase protein [16] <3> several isozymes cytosolic deoxycytidine kinase I and II, plus mitochondrial isozyme [10] <3> multisubstrate enzyme, that also phos-phorylates purine deoxyribonucleotides [9] <7> enzyme has two separate active sites for deoxycytidine and deoxyadenosine activity [22] <3> reacts with both enantiomers of -deoxycytidine, -deoxyguanidine, -deoxyadenosine, and a-D-deoxycytidine is also substrate [31] <3> reacts with both enantiomers of jS-deoxyadenosine, j3-arabinofuranosyl-adenine and jd-deoxyguanine ]34] <3> remarkably relaxed enantioselectivity with respect to cytidine derivatives in p configuration [36] <3> lack of enantioselectivity for D- and L-analogues of cytidine and adenosine [43]) [9, 10, 15, 16, 22, 31, 34, 43]... [Pg.241]

Numerous nucleoside antibiotics are known. For instance, 9-(p-i)-arabinofuranosyl)adenine 48 possesses antiviral and antitumor activity, puromycin 49 is an inhibitor of protein biosynthesis in bacteria and mammalian cells, tubercidin 50 (as example of a purine isoster, isolated from Streptomyces) possesses anticancer activity. [Pg.416]

ID50 = Concentration of inhibitor giving 50% inhibition of DNA polymerase activity. These inhibitors are the nucleoside 5 -triphosphate derivatives of FNAD. l-(2 -deoxy-2 -fluoro-p-D-arabinoforanosyl)-S-methyluracil FIAC, l-(2 -deoiy-2 -fluoro-p-D-arabinofnranosyl)-S-iodocytosine BVDD. E-5(2-bromovinyl)-2 -deoxynridine Ara-T, l-p-D-arabinofnranosylthymine ACV, 9-(2-hydroxyethoxymethyDguanine Ara-A, 9-p-D-arabinofuranosyl adenine. [Pg.184]

M. J. Robins and S. D. Hawrelak, Nucleic-acid related compounds. 28. 2 -Amino-araA 9-(2-amino-2-deoxy-P-D-arabinofuranosyl)adenine.-synthesis via nucleoside-aziridine or azido intermediates and biological effects. Tetrahedron Lett., 19 (1978) 3653-3656. [Pg.102]

The two most widely investigated nucleosides with unusual sugar residues are 9- -D-arabinofuranosyl adenine (XLV, Ara-A) and l- -D-arabinofm a-nosyl cytosine (XLVI, Ara-C)... [Pg.149]

Treatment of 9-(p-D-arabinofuranosyl)adenine (ara-A) with TPP and DEAD led in high yield to the D-lyxo-epoxide 25, whilst a similar reaction on adenosine gave the 2, 3 -0-triphenylphosphorane The anhydronucleoside 26, in which the furanose ring is restricted to a 2 -endo- (S-type) conformation, has been prepared by cyclization of a T-tosylate, and a 2,r-anhydronucleoside, presumed to be an intermediate, could be isolated at shorter reaction times. The cytosine analogue of 26 was also made, and both products were devoid of anti-HIV activity in MT-4 cells. ... [Pg.251]

Anhydro-8-hydroxyme thyl-9(B D-arabinofuranosyl)adenine (18) was prepared by monotosylation of the 2, 3 -dibutylatannylene... [Pg.198]


See other pages where Arabinofuranosyl adenine is mentioned: [Pg.1577]    [Pg.268]    [Pg.275]    [Pg.77]    [Pg.79]    [Pg.81]    [Pg.536]    [Pg.585]    [Pg.488]    [Pg.536]    [Pg.585]    [Pg.169]    [Pg.178]    [Pg.220]    [Pg.420]    [Pg.332]    [Pg.326]    [Pg.645]    [Pg.328]    [Pg.1577]    [Pg.123]    [Pg.475]    [Pg.1577]    [Pg.195]   


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Arabinofuranosyl

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