- Investigation of 4-amino-5-alkynylpyrimidine-2(1H)-ones as anti-mycobacterial agents
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In vitro anti-mycobacterial activities of novel 4-amino-5-alkynylpyrimidine-2(1H)-ones were investigated. 4-Amino-5-heptynylpyrimidine-2(1H)-one (3) and 4-amino-5-(2-phenylethynyl)pyrimidine-2(1H)-one (7) displayed potent in vitro activity against Mycobac
- Garg, Gaurav,Pande, Milind,Agrawal, Ambika,Li, Jie,Kumar, Rakesh
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- Artificial DNA made exclusively of nonnatural C-nucleosides with four types of nonnatural bases
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We describe a new class of DNA-like oligomers made exclusively of nonnatural, stable C-nucleosides. The nucleosides comprise four types of nonnatural bases attached to a deoxyribose through an acetylene bond with the β-configuration. The artificial DNA fo
- Doi, Yasuhiro,Chiba, Junya,Morikawa, Tomoyuki,Inouye, Masahiko
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- Crystalline supramolecular organic frameworksviahydrogen-bonding between nucleobases
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We report a crystalline supramolecular framework assembled by H-bonding interactions between covalently fused monomers equipped with two guanine-cytosine nucleobase pairs.
- Martín-Arroyo, Miguel,Castells-Gil, Javier,Bilbao, Nerea,Almora-Barrios, Neyvis,Martí-Gastaldo, Carlos,González-Rodríguez, David
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- Nucleobase-guanidiniocarbonyl-pyrrole conjugates as novel fluorimetric sensors for single stranded RNA
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We demonstrate here for the first time that a guanidiniocarbonyl-pyrrole (GCP) unit can be applied for the fine recognition of single stranded RNA sequences-an intuitively unexpected result since so far binding of the GCP unit to ds-DNA or ds-RNA relied s
- Ban, ?eljka,?ini?, Biserka,Vianello, Robert,Schmuck, Carsten,Piantanida, Ivo
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- Synthesis of 5-/8-Halogenated or Ethynylated Lipophilic Nucleobases as Potential Synthetic Intermediates for Supramolecular Chemistry
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A series of lipophilic nucleobases that are substituted at the 5- (pyrimidines) or 8- (purines) position with either a halogen atom or a terminal triple bond have been synthesized. The sequences and reactions studied in this work, which mainly comprise halogenation, alkylation, Sonogashira coupling, and trimethylsilylacetylene deprotection, have been carefully optimized, to reach the final compounds in the most straightforward and convenient way, with the highest possible purity and yield. These compounds include cytosine, isocytosine, and uracil derivatives as pyrimidine heterocycles, and guanine, isoguanine, and 2-aminoadenine derivatives as complementary purine bases. Variability was introduced at the N-1/N-9 positions of these pyrimidine/purine nucleobases, which were functionalized with alkyl or benzyl groups, as well as with protected amine or carboxylic acid substituents. The molecules prepared constitute a useful collection of synthetic intermediates for the field of chemical self-assembly. A series of lipophilic nucleobases substituted at the 5- (pyrimidines) or 8-position (purines) with either a halogen atom or a terminal triple bond have been synthesized. These molecules comprise a useful collection of synthetic intermediates for the field of chemical self-assembly.
- Bilbao, Nerea,Vázquez-González, Violeta,Aranda, M. Teresa,González-Rodríguez, David
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- New Imidazo[1,2-c]pyrimidin-5(6H)-Ones Derived from Cytosine: Synthesis, Structure, and Cytotoxic Activity
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This work describes the synthesis of 8-iodoimidazo[1,2-c]pyrimidin-5(6H)-one 2 from 5-iodocytosine 1. This compound was subjected to Suzuki cross-coupling reaction with aryl and heteroarylboronic acids. After optimization, 10 products 3a-j were
- Jansa, Josef,Ly?ka, Antonín,Padělková, Zdeňka,Grepl, Martin,Kone?ny, Petr,Hajdúch, Marián,D?ubák, Petr
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- X-ray crystal structures of halogen containing nucleobase derivatives in unsolvated and DMSO solvated forms
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A series of halogenated nucleobase derivatives 1-4 is reported to yield solvent-free (2) and DMSO solvated crystals (1, 3, 4) on the crystallization from DMSO with one of them (4) containing an additional molecule of water. The molecular and crystal structures are described and comparatively discussed with reference to previous results on related compounds. The molecule of 1 is planar, molecules of 2 and 3 show syn alignment with reference to the heterocyclic ring and common C2′-endo conformation of the ribose residue, while 4 is also syn aligned but C4′-exo in the sugar conformation. The packing structures reveal typical aggregations created via networks of hydrogen bonds. These involve conventional N-H···N, N-H···O and O-H···O interactions between nucleobase and ribose units as well as solvent molecules, additionally supported by weak C-H···O contacts but excluding the participation of halogen···halogen interactions as well as halogen···heteroatom contacts in the supramolecular structure formation. Springer Science+Business Media, LLC 2009.
- Eissmann, Frank,Schindler, Diana,Weber, Edwin
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- A Simple and Convenient Method for the Synthesis of 1-(2-Deoxy-2-fuoro-β-D-arabinofuranosyl)-5-iodocytosine
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1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodocytosine (FIAC) is a pyrimidine nucleoside analog with activity against various herpes viruses. In this study, FIAC was conveniently synthesized by a substitution reaction between ((2R,3S,4S)-3-(benzoyloxy)-
- Liu, Rong,Wang, Yongsheng,Peng, Weien,Kong, Jianping
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p. 521 - 524
(2021/02/02)
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- Nanostructured Micelle Nanotubes Self-Assembled from Dinucleobase Monomers in Water
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Despite the central importance of aqueous amphiphile assemblies in science and industry, the size and shape of these nano-objects is often difficult to control with accuracy owing to the non-directional nature of the hydrophobic interactions that sustain them. Here, using a bioinspired strategy that consists of programming an amphiphile with shielded directional Watson–Crick hydrogen-bonding functions, its self-assembly in water was guided toward a novel family of chiral micelle nanotubes with partially filled lipophilic pores of about 2 nm in diameter. Moreover, these tailored nanotubes are successfully demonstrated to extract and host molecules that are complementary in size and chemical affinity.
- Aparicio, Fátima,Casado, Santiago,Chamorro, Paula B.,Chamorro, Raquel,González-Rodríguez, David
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supporting information
p. 17091 - 17096
(2020/07/30)
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- Dehalogenation of Halogenated Nucleobases and Nucleosides by Organoselenium Compounds
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Halogenated nucleosides, such as 5-iodo-2′-deoxyuridine and 5-iodo-2′-deoxycytidine, are incorporated into the DNA of replicating cells to facilitate DNA single-strand breaks and intra- or interstrand crosslinks upon UV irradiation. In this work, it is shown that the naphthyl-based organoselenium compounds can mediate the dehalogenation of halogenated pyrimidine-based nucleosides, such as 5-X-2′-deoxyuridine and 5-X-2′-deoxycytidine (X=Br or I). The rate of deiodination was found to be significantly higher than that of the debromination for both nucleosides. Furthermore, the deiodination of iodo-cytidines was found to be faster than that of iodo-uridines. The initial rates of the deiodinations of 5-iodocytosine and 5-iodouracil indicated that the nature of the sugar moiety influences the kinetics of the deiodination. For both the nucleobases and nucleosides, the deiodination and debromination reactions follow a halogen-bond-mediated and addition/elimination pathway, respectively.
- Mondal, Santanu,Mugesh, Govindasamy
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p. 1773 - 1780
(2019/01/10)
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- Synthesis of DNA oligos containing 2′-deoxy-2′-fluoro-d- arabinofuranosyl-5-carboxylcytosine as hTDG inhibitor
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As an important step of the active demethylation of 5-methylcytosine (5mC), human thymine DNA glycosylase (hTDG) efficiently excises 5-carboxylcytosine (5caC) from double-stranded DNA (dsDNA). Here, we present synthesis of DNA oligos containing a 2′-deoxy-2′-fluoro-d-arabinofuranosyl-5- carboxylcytidine (F-5caC) modification that act as hTDG inhibitors. The glycosylase activity assay showed that F-5caC oligos were resistant to excision by the hTDG catalytic domain (hTDGcat, residues 111-308) and they could inhibit the excision of DNA oligos containing 5caC. The electrophoretic mobility shift assay confirmed that DNA oligos containing F-5caC could bind well with unmodified hTDGcat to form a stable complex, which makes it possible to obtain the crystal structure of the complex to reveal details on how hTDGcat recognizes the DNA substrate.
- Dai, Qing,Lu, Xingyu,Zhang, Liang,He, Chuan
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body text
p. 5145 - 5151
(2012/08/13)
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- Non-standard nucleobases implementing the isocytidine and isoguanosine hydrogen bonding patterns
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This invention provides compositions of matter that, when incorporated into an oligonucleotide, present to a complementary strand in a Watson-Crick pairing geometry a pattern of hydrogen bonds that is different from the pattern presented by adenine, guani
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Page/Page column 17
(2010/07/02)
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- Microwave-assisted C-5 iodination of substituted pyrimidinones and pyrimidine nucleosides
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Direct microwave-assisted iodination of several pyrimidinones and pyrimidine nucleosides with N-iodosuccinimide to give the corresponding 5-iodo derivatives is described. Application of this reaction to polymer-bound pyrimidinones was also investigated.
- Paolini, Lisa,Petricci, Elena,Corelli, Federico,Botta, Maurizio
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p. 1039 - 1042
(2007/10/03)
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- Antiviral pyrimidine nucleosides
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Pyrimidine 4'-thionucleosides of the formula I STR1 wherein Y is hydroxy or amino, and X is chloro, bromo, iodo, trifluoromethyl, C2-6 alkyl, C2-6 alkenyl, C2-6 haloalkenyl or C2-6 alkynyl and physiologically functional derivatives thereof. These compounds have utility as anti-vital agents.
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- Nucleoside process
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Process for producing 1-halo-2-deoxy-2-fluoroarabinofuranoside derivatives bearing protective ester groups from 1,3,5-tri-O-acylribofuranose; the 1-halo compounds are intermediates in the synthesis of therapeutically active nucleosidic compounds.
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- Nucleosides. 123. Synthesis of Antiviral Nucleosides: 5-Substituted 1-(2-Deoxy-2-halogeno-β-D-arabinofuranosyl)cytosines and -uracils. Some Structure-Activity Relationships
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The syntheses of several 2'-halogeno-5-substituted-arabinofuranosylcytosines and -uracils are described, and relationships of structure to anti herpes virus activity in vitro were examined.Those arabinonucleosides containing the 2'-fluoro function exhibit
- Watanabe, Kyoichi A.,Su, Tsann-Long,Klein, Robert S.,Chu, Chung K.,Matsuda, Akira,et al.
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p. 152 - 156
(2007/10/02)
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