Synthetic studies of the thieno[3,2-d]pyrimidine C-nucleoside isostere of inosine

Ren, Wu-Yun; Lim, Mu Ill; Otter, Brian A.; Klein, Robert S.

doi:10.1021/jo00145a005

Cited by 33 publications

(3 citation statements)

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“…Compounds containing the thienopyrimidine moiety exhibited moderate activity against tumor cell proliferation in vitro. 3,6 In the ensuing years, various thienopyrimidine analogues attracted additional attention due to the broad spectrum of biological properties they exhibited. 7–20 With a variety of annulations and functional group manipulations possible, many thieno[3,2- d ]pyrimidine derivatives have shown interesting biological activity including as kinase 17–20 and phosphodiesterase 9 inhibitors (Fig.…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative activities of halogenated thieno[3,2-d]pyrimidines

Temburnikar

Zimmermann

Kim

et al. 2014

Bioorganic & Medicinal Chemistry

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The in vitro evaluation of thieno[3,2-d]pyrimidines identified halogenated compounds 1 and 2 with antiproliferative activity against three different cancer cell lines. A structure activity relationship study indicated the necessity of the chlorine at the C4-position for biological activity. The two most active compounds 1 and 2 were found to induce apoptosis in the leukemia L1210 cell line. Additionally, the compounds were screened against a variety of other microbial targets and as a result, selective activity against several fungi was also observed. The synthesis and preliminary biological results are reported herein.

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Section: Introductionmentioning

confidence: 99%

Antiproliferative activities of halogenated thieno[3,2-d]pyrimidines

Temburnikar

Zimmermann

Kim

et al. 2014

Bioorganic & Medicinal Chemistry

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“…5 ). Like other nucleoside coupling approaches (other than the well-known Vorbrüggen coupling reaction [ 66 ], the synthesis of C-nucleosides typically gives a mixture of stereoisomers (α and β) at the anomeric carbon [ 48 – 49 54 , 62 , 67 – 68 ]. Since the naturally occurring nucleosides (and most biologically active nucleosides) are β-anomers, achieving 100% stereospecificity in C–C bond formation is an important goal, but often difficult to attain [ 62 ].…”

Section: Reviewmentioning

confidence: 99%

Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides

Temburnikar¹,

Seley‐Radtke²

2018

Beilstein J. Org. Chem.

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C-nucleosides have intrigued biologists and medicinal chemists since their discovery in 1950's. In that regard, C-nucleosides and their synthetic analogues have resulted in promising leads in drug design. Concurrently, advances in chemical syntheses have contributed to structural diversity and drug discovery efforts. Convergent and modular approaches to synthesis have garnered much attention in this regard. Among them nucleophilic substitution at C1' has seen wide applications providing flexibility in synthesis, good yields, the ability to maneuver stereochemistry as well as to incorporate structural modifications. In this review, we describe recent reports on the modular synthesis of C-nucleosides with a focus on D-ribonolactone and sugar modifications that have resulted in potent lead molecules.

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“…We were also concerned that the need for isolation of 15 might lead to some racemization. Indeed, although the alkene 16 from either route could be reduced catalytically to the alkane 17," material from the Wittig approach displayed a The introduction of an a-formyl (hydroxymethylene) group into 17 could, after some experimentation, be accomplished using ethyl formate and sodium hydride in ether plus a little ethanol; the presumed intermediate 18 was not isolated, but could be trapped by reaction with aminoacetonitrile to give the aminomethylene compound 19 in 45% overall yield. Although obtained as a crystalline solid, 19 was seen by 'H NMR to be a mixture (3: 1) of two isomers about the double bond.…”

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confidence: 99%