- Heterocyclic analogs of nucleosides: Synthesis and biological evaluation of some 1-(3-thianyl)uracil and 9-(3-thianyl)adenine derivatives
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The 1-(3-thianyl)uracil (9) and 9-(3-thianyl)adenine (14) nucleoside analogs have been prepared from the key intermediate, (±)-(3β,5β)-3-amino-5-(hydroxymethyl)thinae (6). Analog 9 was converted into a mixture of diastereomeric sulfoxides (10) that afforded, by a Pummerer reaction, a mixture of (±)-1-{(2'β,3'β,5'β)-2'-acetoxy-5'-(acetoxymethyl)thian-3'-yl}2, 4(1H,3H)-pyrimidinedione (11a) and its 6'-β isomer (11b). The EI mass spectra of the nucleoside analogs are discussed. The uracil nucleoside analogs have been evaluated also for their anti-HIV and antitumor activities.
- Hultin,Szarek
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- Heterocyclic analogs of nucleosides: Synthesis and biological evaluation of novel analogs of puromycin
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The diastereomeric 1-(piperidin-3'-yl)uracil compounds 20a, b, and the N6-dimethyl-9-(piperidin-3'-yl)adenine compounds 21a, b, have been prepared as analogs of the naturally occurring aminoacyl nucleoside antibiotic puromycin. The diastereomer
- Hultin,Szarek
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- Synthesis and antiviral evaluation of cyclopentyl nucleoside phosphonates
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The synthesis of both 2?-hydroxy-3?-deoxy and 2?-deoxy-3?-hydroxy cyclopentyl nucleoside phosphonates with the natural nucleobases adenine, thymine, cytosine and guanine from a single precursor has been performed. The guanine containing analogues showed antiviral activity. Especially the 3?-deoxy congener 23 was active, displaying an EC50 of 5.35 μM against TK+ VZV strain and an EC50 of 8.83 μM against TK? VZV strain, besides lacking cytotoxicity. However, the application of phosphonodiamidate prodrug strategy did not lead to a boost in antiviral activity.
- Wang, Mengmeng,Srivastava, Puneet,Liu, Chao,Snoeck, Robert,Andrei, Graciela,De Jonghe, Steven,Herdewijn, Piet
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- Synthesis of Novel Nucleoside Analogues Built on a Bicyclo[4.1.0]heptane Scaffold
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A new class of carbocyclic nucleoside analogues built on a bicyclo[4.1.0]heptane scaffold, a perspective novel pseudosugar pattern, have been conceived as anti-HSV agents on the basis of initial protein-ligand docking studies. The asymmetric synthesis of a series of these compounds incorporating different nucleobases has been efficiently completed starting from 1,4-cyclohexanedione.
- Dom?nguez-Pérez, Beatriz,Ferrer, éric,Figueredo, Marta,Maréchal, Jean-Didier,Balzarini, Jan,Alibés, Ramon,Busqué, Félix
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- Synthesis of new 1′(N)-homocarbanucleosides based on 1-methylcyclopenta[c]pyrazole scaffold
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A series of 1′-homocarbanucleosides was prepared by coupling a purine or pyrimidine to, or constructing it on, a protected 1-methylcyclopenta[c] pyrazole pseudosugar synthesized from (±)-(exo,exo)-1-methyl-4,5,6,7- tetrahydro-4,7-methanoindazole-5,6-diol
- Garcia, Marcos D.,Caamano, Olga,Fernandez, Franco,Abeijon, Paula,Blanco, Jose Manuel
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- Synthesis of nucleosides and related compounds. XXII. Carbocyclic analogues of thymidine and related compounds from 2-azabicyclo[2.2.1]hept-5-en-3-ones
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Reductive amido bond cleavage reaction, previously elaborated by our laboratory for the synthesis of carbocyclic ribothymidine from readily available 2-azabicyclo[2.2.1]hept-5-en-3-one, was successfully applied to the synthesis of carbocyclic analogues of thymidine and related compounds.
- Katagiri,Nomura,Muto,Kaneko
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- A short and novel synthesis of carbocyclic nucleosides and 4′-epi-carbocyclic nucleosides from 2-cyclopenten-1-ones
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Carbocyclic nucleoside analogues remain interesting target molecules having the potential to combine biological activity with greater metabolic stability than their sugar counterparts. This paper describes a rapid and versatile synthetic approach to such
- Gosselin, Gilles,Griffe, Ludovic,Meillon, Jean-Christophe,Storer, Richard
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- Carbocyclic analogues of nucleosides from bis-(Hydroxymethyl)-cyclopentane: synthesis, antiviral and cytostatic activities of adenosine, inosine and uridine analogues.
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Six new carbocyclic nucleosides were prepared by constructing a purine base (in compounds 9-11) or pyrimidine base (in 6-8) on the amino groups of (+/-)-(1 beta,2 alpha,4 beta)-4-amino-1,2-cyclopentanedimethanol (4) and (+/-)-(1 beta,3 alpha,4 beta)-4-amino-1,3-cyclopentanedimethanol (5), and their activities against a variety of viruses and tumour cell lines were determined.
- Blanco, Jose Manuel,Caamano, Olga,Fernandez, Franco,Rodriguez-Borges, Jose Enrique,Balzarini, Jan,de Clercq, Erik
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- Derivatives with uracil-benzothiazole structure, preparation method of derivatives, and application of anti-HCV drugs
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According to the invention, a new series of uracil-benzothiazole NS5B RdRp inhibitors are designed and synthesized; the compounds have the structure shown in a general formula (1), wherein the uracil-benzothiazole NS5B RdRp inhibitor provided by the inven
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Paragraph 0048-0050
(2019/12/02)
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- Six-membered c-n-linked aryl sulfide derivatives and aryl sulfoxide derivatives as pest control agents
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The present application relates to new heterocyclic compounds of formula (I), wherein D stands for a substructure of formula (I-A), a method for the production thereof and the use thereof for combatting animal pests, including arthropods and in particular insects and acarides.
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Paragraph 0683; 0684; 0685; 0686
(2016/10/08)
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- Synthesis, antiviral, cytotoxic and cytostatic evaluation of N1-(Phosphonoalkyl)uracil derivatives
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A series of N1-(phosphonoalkyl)uracils was prepared in a two-step reaction sequence from x- aminoalkylphosphonates and (E)-3-ethoxyacryloyl isocyanate followed by the uracil ring closure. Under standard conditions (NCS; NBS; I2/CAN) all N1-(phosphonoalkyl)uracils were transformed into the respective 5-halogeno derivatives to be later benzoylated at N3. All compounds were evaluated in vitro for activity against a broad variety of DNA and RNA viruses. One compound was slightly active against human cytomegalovirus in HEL cell cultures (EC50 = 45 μM) while another showed weak activity against varicella-zoster virus (TK+ VZV strain OKA and TK- VZV strain 07-1) with EC50 = 43 and 53 μM, respectively. In addition, several compounds exhibited noticeable inhibitory effects on the proliferation of human cervical carcinoma cells (HeLa) at a concentration lower than 200 μM.
- Rygielska-Tokarska, Dorota,Andrei, Graciela,Schols, Dominique,Snoeck, Robert,G?owacka, Iwona E.
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p. 1081 - 1090
(2017/01/11)
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- Synthesis of enantiomerically pure (S)-methanocarbaribo uracil nucleoside derivatives for use as antiviral agents and P2Y receptor ligands
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(Chemical Equation Presented) We have developed an approach toward enantiomerically pure (S)-methanocarba ribonucleosides based on several functional group transformations on a sensitive bicyclo[3.1.0]-hexane system. D-Ribose was transformed into methanocarba alcohol 3 followed by conversion of the OH group to a nitrile with inversion of configuration at C4. The nitrile group was subsequently reduced in two stages to the 5′-hydroxymethyl group. An ester group appended to a tertiary carbon (Cl) was transformed to an amino group as a nucleobase precursor.
- Melman, Artem,Zhong, Minghong,Marquez, Victor E.,Jacobson, Kenneth A.
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p. 8085 - 8088
(2008/12/22)
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- Chemoenzymatic synthesis and synthetic application of enantiopure aminocyclopentenols: Total synthesis of carbocyclic (+)-uracil polyoxin C and its α-epimer
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Carbocyclic uracil polyoxin C (+)-2 and its α-epimer (-)-3 were synthesized in an efficient fashion from cis-4-(N-tert-butylcarbamoyl)cyclopent- 2-en-1-ol (±)-7. The synthesis incorporates a concise, inexpensive chemoenzymatic synthesis of enantiopure ami
- Li, Fangzheng,Brogan, John B.,Gage, Jennifer L.,Zhang, Deyi,Miller, Marvin J.
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p. 4538 - 4540
(2007/10/03)
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- Synthesis of 2′,3′-dideoxy-6′,6′- difluorocarbocyclic nucleosides
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(Chemical Equation Presented) 2′,3′-Dideoxy-6′,6′- difluorouracils, a novel series of gem-difluoromethylenated carbocyclic nucleosides, were synthesized from (Z)-but-2-ene-1,4-diol in 14 steps. A notable step was the construction of the carbocyclic ring v
- Yang, Yan-Yan,Meng, Wei-Dong,Qing, Feng-Ling
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p. 4257 - 4259
(2007/10/03)
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- A short, efficient synthesis of substituted uracil: An indane carbocyclic nucleoside
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(±)-cis-1-(3-Hydroxymethyl-1-indanyl)-1,2,3,4-tetrahy-dropyrimidine-2, 4-dione (1) was synthesised in two steps and with an overall yield of 51percent from (±)-cis-3-amino-1-indanylmethanol (4) and 3-ethoxy-2-propenoyl isocyanate (3). The isocyanate 3 was prepared in 76percent overall yield by reacting silver cyanate with 3-ethoxy-2-propenoyl chloride (2), which was obtained in one pot from ethyl vinyl ether and oxalyl chloride. The aminoalcohol (4) was prepared from phenylsuccinic anhydride in four steps.
- Ferna?ndez,Garci?a-Mera,Morales,Rodri?guez-Borges
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p. 239 - 242
(2007/10/03)
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- Conformationally locked carbocyclic nucleosides built on a bicyclo[3.1.0]hexane template with a fixed Southern conformation. Synthesis and antiviral activity
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The construction of carbocyclic nucleosides with a fixed 3E ring pucker in the Southern hemisphere of the pseudorotational cycle is achieved from a common precursor carbocyclic amine, (1S,3S,4R,5S)-3-benzyloxy-4-benzyloxymethyl-1-aminobicyclo[3
- Ezzitouni, Abdallah,Marquez, Victor E.
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p. 1073 - 1078
(2007/10/03)
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- Nucleosides and nucleotides. 132. Synthesis and biological evaluations of ring-expanded oxetanocin analogues: Purine and pyrimidine analogues of 1,4-anhydro-2-deoxy-D-arabitol and 1,4-anhydro-2-deoxy-3-hydroxymethyl-D-arabitol
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(2R)-2-C-(Adenin-9-yl)- 1,4-anhydro-2-deoxy-D-arabitol (2) and (2R, 3R)-2-C-(adenin-9-yl)- 1,4-anhydro- 2,3-dideoxy-3-C-hydroxymethyl-D-arabitol (3), and their 2,6-diaminopurine analogues 4 and 5 were synthesized from corresponding 1,4-anhydro-D-ribitol derivatives, which were readily obtained from D-glucose. The corresponding guanine isonucleosides 6 and 7 were obtained from 4 and 5 by enzymatic deamination with adenosine deaminase. Pyrimidine counterparts 8 and 9 were synthesized via construction of the pyrimidine moiety from amino derivatives of the 1,4-anhydro-D-arabitol derivatives. Antiviral activity of these ring-expanded derivatives of oxetanocins towards HSV-1, HSV-2, HCMV, and HBV in vitro was examined along with their cytotoxicity against L1210 and KB cells in vitro.
- Kakefuda, Akio,Shuto, Satoshi,Nagahata, Takemitsu,Seki, Jun-Ichi,Sasaki, Takuma,Matsuda, Akira
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p. 10167 - 10182
(2007/10/02)
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- Cyclopentenylcytosine. A Carbocyclic Nucleoside with Antitumor and Antiviral Properties
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Cyclopentenylcytosine (CPE-C, 2), a pyrimidine analogue of the fermentation derived carbocyclic nucleoside neplanocin A, has been synthesized from the optically active cyclopentenylamine 3b by two synthetic routes.CPE-C demonstrates significant antitumor
- Marquez, Victor E.,Lim, Mu-Ill,Treanor, Susan P.,Plowman, Jacqueline,Priest, Matthew A.,et al.
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p. 1687 - 1694
(2007/10/02)
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