132364-17-1Relevant articles and documents
Deoxyuridine triphosphate nucleotidohydrolase as a potential antiparasitic drug target
Nguyen, Corinne,Kasinathan, Ganasan,Leal-Cortijo, Isabel,Musso-Buendia, Alexander,Kaiser, Marcel,Brun, Reto,Ruiz-Pérez, Luis M.,Johansson, Nils G.,González-Pacanowska, Dolores,Gilbert, Ian H.
, p. 5942 - 5954 (2007/10/03)
This paper describes a structure-activity study to identify novel, small-molecule inhibitors of the enzyme deoxyuridine 5′-triphosphate nucleotidohydrolase (dUTPase) from parasitic protozoa. The successful synthesis of a variety of analogues of dUMP is de
Synthesis of 2',3'-didehydro-2',3'-dideoxy nucleosides from 2',2'-bis(phenylthio) nucleoside analogs
Niihata,Kuno,Ebata,Matsushita
, p. 2327 - 2329 (2007/10/03)
2',3'-Didehydro-2',3'-dideoxy nucleosides were synthesized from 2',2'-bis(phenylthio) nucleoside analogs via five-step reactions. The sulfonyl group of the intermediate was removed by a treatment with sodium amalgam.
Uracil and Adenine Nucleosides Having a 2',3'-Bromovinyl Structure: Highly Versatile Synthons for the Synthesis of 2'-C- and 3'-C-Branched 2',3'-Unsaturated Derivatives
Haraguchi, Kazuhiro,Itoh, Yoshiharu,Tanaka, Hiromichi,Akita, Mitsuhiro,Miyasaka, Tadashi
, p. 1371 - 1390 (2007/10/02)
Preparation of 2'- and 3'-bromo derivatives of 2',3'-unsaturated uracil and adenine nucleosides has been carried out starting from the corresponding β-hydroxyselenides by way of bromination and successive selenoxide elimination.These compounds have been shown to serve as versatile synthons for the preparation of anti-HIV candidates, 2'-C- and 3'-C-branched 2',3'-unsaturated nucleosides, through palladium-catalyzed cross-coupling and halogen-lithium exchange reactions. Key Words: β-hydroxyselenide; bromovinyl structure; branched-sugar nucleoside; anti-HIV agent; 2',3'-unsaturated nucleoside.
A Highly Stereoselective Synthesis of Anti-HIV 2',3'-Dideoxy- and 2',3'-Didehydro-2',3'-dideoxynucleosides
Beach, J. Warren,Kim, Hea O.,Jeong, Lak S.,Nampalli, Satyanarayana,Islam, Qamrul,et al.
, p. 3887 - 3894 (2007/10/02)
A general total synthesic method for the stereocontrolled synthesis of 2',3'-dideoxy- as well as 2',3'-didehydro-2',3'-dideoxynucleosides is presented.Introduction of an α-phenylselenenyl group at the 2-position of 2,3-dideoxyribosyl acetate directs the glycosyl bond formation to give >/=95percent β-isomer.This 2'-phenylselenenyl nucleoside may be converted to either the 2',3'-dideoxynucleoside by treatment with n-Bu3SnH and Et3B at room temperature or to the unsaturated derivative by treatment with H2O2/cat. pyridine.The application of this method to the syntheses of pyrimidines (ddU, ddT, ddC), 6-substituted purines (ddA, ddI, 6-chloro-ddP, N6-Me-ddA), and 2,6-disubstituted purines (2-F-ddA, 6-chloro-2-amino-ddP) as well as selected 2',3'-didehydro-2',3'-dideoxy derivatives is reported.
SYNTHESIS OF 2',3'-DIDEHYDRO-2',3'-DIDEOXYNUCLEOSIDES UTILIZING COUPLING REACTIONS BETWEEN NUCLEIC BASES AND PHENYLTHIOSUBSTITUTED 2,3-DIDEOXYRIBOSE
Kawakami, Hiroshi,Ebata, Takashi,Koseki, Koshi,Matsumoto, Katsuya,Matsushita, Hajime,et al.
, p. 2451 - 2470 (2007/10/02)
Stereoselectivities in coupling reactions between silylated pyrimidine bases and 3- or 2-α-phenylthio-2,3-dideoxyribose were examined.In the former case, no stereoselectivies were observed when the coupling reactions were performed either with 1-chlorosugar in an SN2 mode or in the presence of Lewis acids as catalyst in an SN1 mode.Coupling reaction with 2-α-phenylthio-2,3-dideoxyribose in the presence of Lewis acids, especially SnCl4, proceeded with good stereoselectivity to give anomeric mixtures of α : β = 1 : 9.All these nucleosides were converted to 2',3'-didehydro-2',3'-dideoxynucleosides by oxidation to sulfoxides followed by thermal elimination of sulfenic acid.
Stereoselectivity in the Coupling Reaction between 2-Phenylthio-2,3-dideoxyribose and Silylated Pyrimidine Bases
Kawakami, Hiroshi,Ebata, Takashi,Koseki, Koshi,Matsushita, Hajime,Naoi, Yoshitake,Itoh, Kazuo
, p. 1459 - 1462 (2007/10/02)
Coupling reaction between 2-α-phenylthio-2,3-dideoxyribose and silylated pyrimidine bases in the presence of SnCl4 proceeded stereoselectively to give the β-anomers.These nucleosides were converted to 2',3'-dideoxy-2',3'-didehydronucleosides by oxidation
