- Deaminative chlorination of aminoheterocycles
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Selective modification of heteroatom-containing aromatic structures is in high demand as it permits rapid evaluation of molecular complexity in advanced intermediates. Inspired by the selectivity of deaminases in nature, herein we present a simple methodology that enables the NH2 groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp2)?NH2 can be converted into C(sp2)?Cl bonds. The method is characterized by its wide functional group tolerance and substrate scope, allowing the modification of >20 different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH2 into Cl in a late-stage fashion enables practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents. [Figure not available: see fulltext.]
- Ghiazza, Clément,Faber, Teresa,Gómez-Palomino, Alejandro,Cornella, Josep
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- Synthesis of novel selenotetrazole purine derivatives and their potential chemotherapeutic activities
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The development of novel chemotherapeutic agents is indispensable to improve cancer treatment. One of the conventional approaches toward the synthesis of anticancer agents is the design of a compound whose structure is similar to purines found in DNA. In this study, a series of novel artificial purine nucleosides bearing selenotetrazole pharmacophore, 4a–4h, were synthesized. In order to get preliminary information about their cytotoxic activities, the interaction of compounds with DNA was investigated by UV titration and agarose gel electrophoresis and transcription inhibition studies were performed. The cytotoxic effects of the compounds against B16 melanoma, OV90 ovarian cancer, JM1 lymphoma cell lines, and PHA-induced peripheral blood lymphocytes were also investigated. In cell assay studies, the effects of the compounds on synthesis and mitosis stage of cell cycle were compared by flow cytometry. Although none of the compounds synthesized interacted with DNA and exhibited transcription inhibition, all of them significantly inhibited DNA synthesis phase and showed cytotoxic activity on cancer and proliferating cells. [Figure not available: see fulltext.]
- Dilek, Gulay,Tekin, Ishak Ozel,Coban, Burak,Disli, Ali,Gercek, Zuhal
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- Projected Dose Optimization of Amino- And Hydroxypyrrolidine Purine PI3KδImmunomodulators
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The approvals of idelalisib and duvelisib have validated PI3Kδinhibitors for the treatment for hematological malignancies driven by the PI3K/AKT pathway. Our program led to the identification of structurally distinct heterocycloalkyl purine inhibitors wit
- Methot, Joey L.,Zhou, Hua,McGowan, Meredeth A.,Anthony, Neville John,Christopher, Matthew,Garcia, Yudith,Achab, Abdelghani,Lipford, Kathryn,Trotter, Benjamin Wesley,Altman, Michael D.,Fradera, Xavier,Lesburg, Charles A.,Li, Chaomin,Alves, Stephen,Chappell, Craig P.,Jain, Renu,Mangado, Ruban,Pinheiro, Elaine,Williams, Sybill M. G.,Goldenblatt, Peter,Hill, Armetta,Shaffer, Lynsey,Chen, Dapeng,Tong, Vincent,McLeod, Robbie L.,Lee, Hyun-Hee,Yu, Hongshi,Shah, Sanjiv,Katz, Jason D.
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p. 5137 - 5156
(2021/05/04)
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- Purine-ring-containing benzene sulfonamide chalcone derivative and preparation and application methods thereof
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The invention discloses a purine-ring-containing benzene sulfonamide chalcone derivative and preparation and application methods thereof. The purine-ring-containing benzene sulfonamide chalcone derivative has a formula (I) shown as below, in which R1 is 4-oxymethyl, 4-tert-butyl, 4-methyl, 4-flouride, 4-bromide, 2-methyl, 2-fluoride, 2-chloride, 2-bromide and hydrogen atom and R2 is methyl, ethyland benzyl. The purine-ring-containing benzene sulfonamide chalcone derivative can inhibit tobacco mosaic virus, cucumber mosaic virus, potato Y virus and southern rice black-streaked dwarf virus.
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Paragraph 0028
(2019/01/05)
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- Antiviral properties and interaction of novel chalcone derivatives containing a purine and benzenesulfonamide moiety
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A new concise and facile method was explored to synthesize a series of novel chalcone derivatives containing a purine and benzenesulfonamide moiety and their antiviral properties were evaluated against TMV and CMV. Biological assays indicated that several
- Zhou, Dagui,Xie, Dandan,He, Fangcheng,Song, Baoan,Hu, Deyu
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p. 2091 - 2097
(2018/05/08)
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- PURINE INHIBITORS OF HUMAN PHOSPHATIDYLINOSITOL 3-KINASE DELTA
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The instant invention provides compounds of formula (I) which are PI3K-delta inhibitors, and as such are useful for the treatment of PI3K-delta-mediated diseases such as inflamation, asthma, COPD and cancer.
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Page/Page column 57
(2017/11/01)
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- PURINE INHIBITORS OF HUMAN PHOSPHATIDYLINOSITOL 3-KINASE DELTA
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Provided are compounds of formula I which are PI3K-delta inhibitors, and as such are useful for the treatment of PI3K-delta-mediated diseases such as inflammation, asthma, COPD and cancer.
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Page/Page column 43
(2016/01/01)
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- PURINE INHIBITORS OF HUMAN PHOSPHATIDYLINOSITOL 3-KINASE DELTA
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The instant invention provides compounds of formula I which are PI3K-delta inhibitors, and as such are useful for the treatment of PI3K-delta-mediated diseases such as inflamation, asthma, COPD and cancer.
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Page/Page column 66; 67
(2014/06/11)
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- PURINE INHIBITORS OF HUMAN PHOSPHATIDYLINOSITOL 3-KINASE DELTA
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The instant invention provides compounds of formula I which are PI3K-delta inhibitors, and as such are useful for the treatment of PI3K-delta-mediated diseases such as inflamation, asthma, COPD and cancer.
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Page/Page column 66; 67
(2014/06/11)
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- Synthesis of some novel amino and thiotetrazole purine derivatives and investigation of their antimicrobial activity and DNA interactions
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A series of amino and thiotetrazole purine derivatives introduced with different alkyl groups in position 9 was synthesized. The structures of the synthesized compounds were characterized using spectroscopic methods. All the synthesized compounds were screened for their antibacterial activities against Gram-positive and Gram-negative bacteria and for their antifungal activities against yeast strains. The effect of the compounds on pBR322 plasmid DNA was studied by gel electrophoretic mobility measurements. The results of antimicrobial activity show that attachment of tetrazole group to purine bases results in disappearance of antimicrobial activity The results of the plasmid DNA interaction and the restriction studies suggest that while aminotetrazole purine derivatives cause DNA damages, thiotetrazole purine derivatives are believed to form a range of interstrand GG adducts with duplex DNA that induce global changes in the DNA conformation.
- Dilek Celik, Gulay,Disli, Ali,Oner, Yagmur,Acik, Leyla
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p. 1470 - 1479
(2013/03/29)
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- Regioselective N9 alkylation of purine rings assisted by β-cyclodextrin
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Under the assistance of β-cyclodextrin, purine was effectively alkylated at N9 together with up to 99% conversion and good to excellent yield using water as the solvent. High regioselectivity-N9/N7 selectivity>99:1 was attributed to the β-cyclodextrin cav
- Zhang, Qian,Cheng, Gang,Huang, Yong-Zhen,Qu, Gui-Rong,Niu, Hong-Ying,Guo, Hai-Ming
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experimental part
p. 7822 - 7826
(2012/09/22)
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- 8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands
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Importance of making available selective adenosine receptor antagonists is boosted by recent findings of adenosine involvement in many CNS dysfunctions. In the present work a series of 8-bromo-9-alkyl adenines are prepared and fully characterized in radio
- Lambertucci, Catia,Antonini, Ippolito,Buccioni, Michela,Dal Ben, Diego,Kachare, Dhuldeo D.,Volpini, Rosaria,Klotz, Karl-Norbert,Cristalli, Gloria
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experimental part
p. 2812 - 2822
(2009/09/08)
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- Aryl and heteroaryl purine compounds
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Novel bicyclic condensed pyrimidine compounds having general formula (I) STR1 wherein X is --CH2 --, --NH--(CH2)n --, --O--(CH2)n -- or --S--(CH2)n -- in which n is zero or 1; A is a 4,5-fused imidazole ring N-substituted by R3 which is hydrogen, C1 -C4 alkyl or benzyl, or A is a 2,3-fused pyridine ring C-substituted by R4 which is hydrogen, C1 -C4 alkyl, C1 -C4 alkoxy, halogen or NR5 R6 in which each of R5 and R6 independently is H or C1 -C4 alkyl; B is a bicyclic ring chosen from tetralin, indane and 2-oxindole; each of R1 and R2 independently is hydrogen, C1 -C4 alkyl, halogen, hydroxy, C1 -C4 alkoxy, C1 -C4 alkoxycarbonyl, nitro, cyano or CF3 ; and the pharmaceutically acceptable salts thereof.
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- Mitsunobu reactions for the synthesis of carbocyclic analogues of nucleosides: Examintion of the regioselectivity
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In order to provide a general synthetic method for carbocyclic nucleosides, regioselectivities in Mitsunobu reaction of purine, pyrimidin-2-one and their substituted derivatives with a variety of alcohols with a variety of alcohols were examined and found to depend upon both substituents of the bases and kind of the alcohols.
- Toyota,Katagiri,Kaneko
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p. 1295 - 1305
(2007/10/02)
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- The alkylation of 6-chloropurine with alcohols by Mitsunobu reaction
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A general procedure has been developed for the preparation of 9-alkylated adenines by the Mitsunobu reaction between 6-chloropurine and several alcohols, followed by the replacement of the chlorine with ammonia. A lesser amount of the 7-alkylpurines was also obtained, irrespective of the alcohol used.
- Toyota,Katagiri,Kaneko
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p. 1039 - 1041
(2007/10/02)
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- Utility of Purinyl Radicals in the Synthesis of Base-Modified Nucleosides and Alkylpurines: 6-Amino Group Replacement by H, Cl, Br, and I
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When 9-substituted adenines are treated with n-pentyl nitrite in hydrogen atom donating solvents and the resulting reaction mixtures are warmed and photolyzed with visible light, the corresponding 9-substituted purines are isolated.The conversion apparently involves homolysis of the intermediate 6-diazonium salts or azo compounds to produce purinyl radical intermediates.These purinyl radicals can subsequently abstract hydrogen atoms from solvent molecules.We have utilized our deamination procedure for the direct synthesis of the antitumor antibiotic nebularine from adenosine.When the deaminations of 9-substituted adenines are conducted in dry CCl4, CHBr3, or CH2I2, the corresponding 6-chloro-, 6-bromo-, and 6-iodopurines are isolated in good yields.There appears to be no detectable hydrogen abstraction in competition with halogen abstraction in the cases of CHBr3 and CH2I2 solvents.These transformations provide shortened preparative pathways to intermediates useful in the synthesis of other base-modified purines.Under appropriate reaction conditions, conversions to the 6-6' dimers also may be possible.The type of transformation in this report represents one of the first examples of the use of neutral purinyl radicals in nucleic acid chemistry.
- Nair, Vasu,Richardson, Stephen G.
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p. 3969 - 3974
(2007/10/02)
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