9-(cis-3-Hydroxymethyl-2-methylenecyclobutyl)guanine (3b) and 9-(3-methylene-trans-2-hydroxymethylcyclobutyl)guanine (4b) were prepared from N2-isobutyryl-9-[trans-trans-2,3-bis(hydroxymethyl)cyclobutyl]guanine (2f) or 2,3-bis(hydroxymethyl)-1-cyclobutanol (7b). Carbocyclic oxetanocin analogues (A, 1d; G, 2d) and related compounds including 4b were assayed against a broad variety of viruses. It appeared that the activity of 2d against herpes simplex virus (HSV) and varicella-zoster virus (VZV) at least partially depends on phosphorylation by the virus-induced thymidine kinase (TK). Although 1d and 2d are inhibitory to the replication of human immunodeficiency virus (HIV), they are quite toxic to proliferating human T-lymphocytes.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1248/cpb.41.516 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of cyclobutane nucleoside analogues 3: Preparation of carbocyclic derivatives of oxetanocin.
Nucleosides Nucleotides Nucleic Acids
July 2019
a Department of Chemistry , York University, Toronto , Ontario , Canada.
A synthesis of cyclobutene nucleoside analogs in which the nucleobase is tethered by a methylene group is described. The coupling of 6-chloropurine with 3-hydroxymethyl-cyclobutanone proceeds via its triflate to give both N-7 and N-9 regioisomers with relative yields corresponding to the calculated charge distribution of the 6-chloropurinyl anion. The stereoselective reduction of the N-alkylated ketones yielded quantitatively one stereoisomer in each case.
View Article and Find Full Text PDFSynthesis and Evaluation of Novel Cyclopropane Nucleoside as Potential Tube Formation Agents.
Chem Pharm Bull (Tokyo)
June 2017
Department of Pharmaco-Bio-Informatics, Faculty of Medicine, Kagawa University.
Five novel nucleoside analogs with mono or bis-hydroxymethylated cyclopropane rings at the N-position of the 2-chloroadenine moiety (2-chloro-carbocyclic oxetanocin A [COA-Cl] analog) were synthesized and evaluated using human umbilical vein endothelial cells. All the prepared compounds (2a-e) showed good to moderate activity with angiogenic potency. cis-2'-(Hydroxymethyl)cycloprop-1'-yl derivative (2b) at 100 µM had greater angiogenic activity than the other compounds did, with relative tube areas of 2.
View Article and Find Full Text PDFSynthesis and Evaluation of Novel Carbocyclic Oxetanocin A (COA-Cl) Derivatives as Potential Tube Formation Agents.
Chem Pharm Bull (Tokyo)
June 2016
Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University.
Six novel carbocyclic oxetanocin A analogs (2-chloro-C.OXT-A; COA-Cl) with various hydroxymethylated or spiro-conjugated cyclobutane rings at the N(9)-position of the 2-chloropurine moiety were synthesized and evaluated using human umbilical vein endothelial cells. All prepared compounds (2a-f) showed good to moderate activity with angiogenic potency.
View Article and Find Full Text PDF[Synthesis and evaluation of novel nucleic acid derivatives as bioactive substances].
Yakugaku Zasshi
January 2015
Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University.
This review describes the synthesis and evaluation of novel nucleic acid derivatives performed by our research group to date. We developed a new method for the synthesis of 2-alkoxyadenosine analogs via nonaqueous diazotization-dediazoniation reactions. By applying these reactions, we effectively synthesized four types of carbocyclic oxetanocin analogs (2-alkoxy-C.
View Article and Find Full Text PDFStereoselective route to oxetanocin carbocyclic analogues based on a [2 + 2] photocycloaddition to a chiral 2(5H)-furanone.
Org Lett
July 2007
Departament de Química, Universitat Autonoma de Barcelona, 08193 Bellaterra, Spain.
The synthesis of the trisubstituted cyclobutane 7, which is a suitable precursor for the preparation of oxetanocin carbocyclic analogues, is described. The key step involves a regio- and diastereoselective [2 + 2] photochemical reaction of ketene diethyl acetal with (S)-5-pivaloyloxymethyl-2(5H)-furanone, 3. As an application of this methodology, (-)-cyclobut-A has been prepared from the intermediate 7.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!