cas 3680-71-5, Pyrrolo[2,3-d]pyrimidin-4-ol

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Preparation method of prodrug intermediate of thymidine phosphorylase inhibitor
The invention relates to the field of preparation of prodrug intermediates of thymidine phosphorylase inhibitors, and discloses a preparation method of a prodrug intermediate of a thymidine phosphorylase inhibitor. The method comprises the following steps: (1) adding ethyl cyanoacetate into a mixed alcoholic-alkaline solution of thiourea, carrying out reflux reaction for 5-6 hours, performing cooling, crystallizing, filtering, and washing with an ethanol/dioxane mixed solution; (2) mixing pyridine with ammonia water, adding Raney nickel, ZnSO4 and the product obtained in the step (1), heating and reacting at 65-75 DEG C for 7-8 hours, performing filtering while the product is hot, and performing cooling and crystallizing, filtering and washing; and (3) adding the product obtained in the step (2) into a mixed alkali solution, slowly adding 2-bromoacetaldehyde at 45-55 DEG C, reacting for 4-5 hours, and performing cooling, crystallizing, filtering, washing and drying. According to the preparation method disclosed by the invention, the total yield of the prodrug intermediate 4-hydroxypyrrolo[2, 3-d] pyrimidine of the thymidine phosphorylase inhibitor is improved.
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Paragraph 0093-0094

(2021/04/14)

Production process 4 -chloropyrrolo [2, 3 - d] pyrimidine
The production process of 4 - chloropyrrolo [2, 3 - d] pyrimidine comprises the following steps: S1, adding the compound I and the compound II to the mixed solvent I, carrying out temperature rise reaction under the catalysis of the base I to obtain the compound III. S2, sodium alkoxide I was added to alcoholic solvent II, compound IV and compound III were added to raise the temperature, and organic solvent III, organic solvent IV and compound V were added to raise the temperature to give 4 - chloropyrrolo [2, 3 - d] pyrimidine crude product. Among them, compound I is. . Compound II was obtained. . Compound III was obtained. . The compound IV is formamidine. Compound V was POCl. 3 To the method, bromoacetaldehyde dimethyl acetal and cyanoethyl acetate are subjected to reflux reaction, and 2 - cyano -4, 4 - methoxybutyric acid ethyl ester and formamidine acetate are subjected to one-pot chlorofluorination reaction, so that the reaction period is greatly shortened.
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Paragraph 0108; 0112

(2021/10/27)

Synthetic method of medical intermediate 4-chloropyrrolopyrimidine
The invention discloses a synthetic method of a medical intermediate, i.e., 4-chloropyrrolopyrimidine. The synthetic method comprises the following steps: with 4-hydroxypyrrolo[2, 3-d]pyrimidine as areaction substrate and a mixed solution of NMP/methylbenzene as a solvent; adding 2.0 to 4.0 equivalents of 1,2,3-trichloropropane into a reaction kettle, carrying out a refluxing and stirring reaction for 4-5 h at 100-120 DEG C in a chlorine environment, carrying out vucummizing at 160-180 DEG C to evaporate excessive solvent so as to obtain an oily substance, starting stirring, adding a sodium hydroxide solution with a concentration of 0.5-1mol/L into the oily substance, and performing filtering and drying to obtain the 4-chloropyrrolopyrimidine product. POCl3 is replaced by using the novelmethod, so the problems of quenching danger and low working efficiency of conventional synthesis methods are solved.
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Paragraph 0020; 0024-0025

(2020/02/14)

Preparation method of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine
The invention discloses a preparation method of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine, wherein the preparation method comprises the steps: carrying out alpha-alkylation reaction on ethyl cyanoacetate and 2-chloromethyl-1,3-dioxolane under the actions of a catalyst and alkali to generate 2-cyano-3-(1,3-dioxolyl)ethyl propionate; carrying out a ring closing reaction on 2-cyano-3-(1,3-dioxolyl)ethyl propionate and formamidine acetate under the action of alkali, and then carrying out hydrolysis ring closing by virtue of hydrochloric acid, so as to obtain 4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine; carrying out a reaction of 4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine under the action of a chlorination reagent, and generating 4-chloro-7H-pyrrolo[2,3-d]pyrimidine. The raw materials adopted in the method arecheap and easy to obtain, and the synthesis method is simple to operate, mild in reaction condition, low in equipment requirement and suitable for industrial large-scale production.
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Paragraph 0052-0054; 0056-0058; 0062-0064; 0066-0068; 0072-

(2020/07/15)

Synthetic method of 4-chloropyrrolopyrimidine
The invention relates to a synthetic method of 4-chloropyrrolopyrimidine. The synthetic method takes ethyl cyanoacetate, bromoacetaldehyde diethyl acetal, thiourea, sodium ethoxide and hydrogen peroxide as raw materials and takes DMF, ethanol, water and phosphorous oxychloride as solvents to obtain the target product 4-chloropyrrolopyrimidine through four steps of reactions. The method improves amethod of removing a mercapto group in a third step. The mercapto group is first oxidized to sulfinic acid by using the hydrogen peroxide and then is removed under acidic conditions. The method is mild in reaction conditions, safe in operation and high in yield, is environmentally friendly, and is suitable for industrial production.
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(2018/12/05)

Synthesis and biological evaluation of some new tricyclic pyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidine derivatives as potential antitubercular agents
A series of new tricyclic pyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidines 8a–l were synthesized and characterized by IR, NMR (1H and 13C), and mass spectral analysis. The newly synthesized compounds 8a–l were inspected for their in vitro antitubercular activity against Mycobacterium tuberculosis (MTB) H37Ra using an established XTT reduction menadione assay (XRMA). The title compounds exhibited minimum inhibitory concentrations (MIC90) ranging from 0.09 to >30 μg/mL. Five compounds (8c, 8i–l) were further confirmed for their dose-dependent effect against MTB. These compounds were evaluated in the THP-1 infection model, where 8i (MIC90 = 0.35 μg/mL), 8j (MIC90 = 1.17 μg/mL), 8k (MIC90 = 2.38 μg/mL), and 8l (MIC90 = 1.17 μg/mL) demonstrated significant antitubercular activity. All the ex vivo active compounds showed insignificant cytotoxicity against the human cancer cell lines, HeLa, MCF-7, and THP-1. Inactivity of all these compounds against Gram positive and Gram negative bacteria indicates their specificity. Molecular docking studies in the active site of the sterol 14alpha-demethylase (CYP51) enzyme revealed a similar binding mode to the native ligand in the crystal structure, thereby helping to understand the ligand–protein interactions and to establish a structural basis for inhibition of MTB. The results suggest novel pharmacophores as selective and specific inhibitors against MTB that can be explored further to synthesize lead compounds against tuberculosis. In summary, the results clearly indicate the identification of some novel, selective, and specific inhibitors against MTB that can be explored further for potential antitubercular drugs.
Patil, Yogesh,Shingare, Ramesh,Choudhari, Amit,Borkute, Rachana,Sarkar, Dhiman,Madje, Balaji R.
(2018/08/07)

METHOD OF MANUFACTURING 4-CHLORO-7H-PYRROLO[2,3-d]PYRIMIDINE
The present invention discloses a method of manufacturing 4-chloro-7H-pyrrolo[2,3-d]pyrimidine comprising the steps: a) Preparing ethyl 2-cyano-4,4-dimethoxybutanoate by coupling ethyl 2- cyanoacetate and 2-bromo-1,1-dimethoxyethane; b) Preparing 6-amino-5-(2,2- dimethoxyethyl)pyrimidin-4-ol by adding formamidine to ethyl 2-cyano-4,4-dimethoxybutanoate; c) Converting 6-amino-5-(2,2-dimethoxyethyl)pyrimidin-4-ol to 7H-pyrrolo[2,3-d]pyrimidin-4-ol; and d) Converting the 7H-pyrrolo[2,3-d]pyrimidin-4-ol to 4-chloro-7H-pyrrolo[2,3-d]pyrimidine. The method offers increased yield, less by-products and a decrease in waste compared to methods known as being state of the art.
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Page/Page column 6

(2018/03/06)

6-methyl 7-position-denitrified purine nucleoside compounds and application thereof
The invention discloses6-methyl 7-position-denitrified purine nucleoside compounds and an application thereof and belongs to the field of medicinal chemistry. The 6-methyl 7-position-denitrified purine nucleoside compounds or pharmaceutically acceptable salts of the compounds having characteristics of a structure shown as formula I are a kind of novel-structured compounds designed and synthesized according to protein structure characteristics of RNA virus polymerase, and the compounds can inhibit RNA viruses, thereby being capable of serving as potential drugs for preventing and treating infection of RNA viruses such as HCV (hepatitis c virus), influenza virus, HRV (rhinovirus), RSV, Ebola virus, DENV (Dengue virus), enterovirus and the like.
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(2017/09/02)

Preparation method of 4-chloropyrrolo[2,3-d]pyrimidine
The invention relates to a preparation method of 4-chloropyrrolo[2,3-d]pyrimidine.The method includes the following steps of obtaining 2-cyano-3-(1,3-dioxolan)ethyl propionate after 2-bromomethyl-1,3-dioxolane and ethyl cyanoacetate which are used as the raw materials react with alkaline matter as the catalyst; conducting cyclization on obtained 2-cyano-3-(1,3-dioxolan)ethyl propionate and formamidine acetate with alkaline matter as the catalyst, and adding hydrochloric acid for hydrolysis cyclization to obtain pyrrolo[2,3-d]pyrimidin-4-ol; making obtained pyrrolo[2,3-d]pyrimidin-4-ol react with phosphorus oxychloride to obtain 4-chloropyrrolo[2,3-d]pyrimidine.The method for preparing 4-chloropyrrolo[2,3-d]pyrimidine is simple in technological process, the requirement for production conditions is low, the product is easy to purify and high in yield, and the production efficiency and product quality of 4-chloropyrrolo[2,3-d]pyrimidine are remarkably improved.
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Paragraph 0044; 0045; 0046

(2016/12/01)

Molecular products from the thermal degradation of glutamic acid
The thermal behavior of glutamic acid was investigated in N2 and 4% O2 in N2 under flow reactor conditions at a constant residence time of 0.2 s, within a total pyrolysis time of 3 min at 1 atm. The identification of the main pyrolysis products has been reported. Accordingly, the principal products for pyrolysis in order of decreasing abundance were succinimide, pyrrole, acetonitrile, and 2-pyrrolidone. For oxidative pyrolysis, the main products were succinimide, propiolactone, ethanol, and hydrogen cyanide. Whereas benzene, toluene, and a few low molecular weight hydrocarbons (propene, propane, 1-butene, and 2-butene) were detected during pyrolysis, no polycyclic aromatic hydrocarbons (PAHs) were detected. Oxidative pyrolysis yielded low molecular weight hydrocarbon products in trace amounts. The mechanistic channels describing the formation of the major product succinimide have been explored. The detection of succinimide (major product) and maleimide (minor product) from the thermal decomposition of glutamic acid has been reported for the first time in this study. Toxicological implications of some reaction products (HCN, acetonitrile, and acyrolnitrile), which are believed to form during heat treatment of food, tobacco burning, and drug processing, have been discussed in relation to the thermal degradation of glutamic acid.
Kibet, Joshua K.,Khachatryan, Lavrent,Dellinger, Barry
p. 7696 - 7704
(2013/09/02)

Pre-steady state kinetic analysis of cyclobutyl derivatives of 2′-deoxyadenosine 5′-triphosphate as inhibitors of HIV-1 reverse transcriptase
Pre-steady state kinetic analysis was utilized for biochemical evaluation of a series of cyclobutyl adenosine nucleotide analogs with HIV-1 RT WT. The phosphonyl-diphosphate form of the cyclobutyl nucleotide, 5, was the most efficiently incorporated of the series. Nucleotide 5 was fourfold more efficiently incorporated than the FDA approved TFV-DP by RTWT. The kinetics of incorporation for 5 using the drug resistant mutant enzyme K65R was also determined. Compound 5 was threefold more efficiently incorporated compared to TFV-DP with RTK65R. These results demonstrate cyclobutyl adenosine analogs can act as substrates for incorporation by HIV-1 RT and be a potential scaffold for HIV inhibitors.
Kim, Jiae,Wang, Ligong,Li, Yongfeng,Becnel, Kimberlynne D.,Frey, Kathleen M.,Garforth, Scott J.,Prasad, Vinayaka R.,Schinazi, Raymond F.,Liotta, Dennis C.,Anderson, Karen S.
supporting information; experimental part
p. 4064 - 4067
(2012/07/14)

Targeting conserved water molecules: Design of 4-aryl-5-cyanopyrrolo[2,3-d] pyrimidine Hsp90 inhibitors using fragment-based screening and structure-based optimization
Inhibitors of the Hsp90 molecular chaperone are showing promise as anti-cancer agents. Here we describe a series of 4-aryl-5-cyanopyrrolo[2,3-d] pyrimidine ATP competitive Hsp90 inhibitors that were identified following structure-driven optimization of purine hits revealed by NMR based screening of a proprietary fragment library. Ligand-Hsp90 X-ray structures combined with molecular modeling led to the rational displacement of a conserved water molecule leading to enhanced affinity for Hsp90 as measured by fluorescence polarization, isothermal titration calorimetry and surface plasmon resonance assays. This displacement was achieved with a nitrile group, presenting an example of efficient gain in binding affinity with minimal increase in molecular weight. Some compounds in this chemical series inhibit the proliferation of human cancer cell lines in vitro and cause depletion of oncogenic Hsp90 client proteins and concomitant elevation of the co-chaperone Hsp70. In addition, one compound was demonstrated to be orally bioavailable in the mouse. This work demonstrates the power of structure-based design for the rapid evolution of potent Hsp90 inhibitors and the importance of considering conserved water molecules in drug design.
Davies, Nicholas G.M.,Browne, Helen,Davis, Ben,Drysdale, Martin J.,Foloppe, Nicolas,Geoffrey, Stephanie,Gibbons, Ben,Hart, Terance,Hubbard, Roderick,Jensen, Michael Rugaard,Mansell, Howard,Massey, Andrew,Matassova, Natalia,Moore, Jonathan D.,Murray, James,Pratt, Robert,Ray, Stuart,Robertson, Alan,Roughley, Stephen D.,Schoepfer, Joseph,Scriven, Kirsten,Simmonite, Heather,Stokes, Stephen,Surgenor, Allan,Webb, Paul,Wood, Mike,Wright, Lisa,Brough, Paul
p. 6770 - 6789
(2013/01/15)

PROCESSES FOR PREPARING JAK INHIBITORS AND RELATED INTERMEDIATE COMPOUNDS
The present invention is related to processes for preparing chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines of Formula III, and related synthetic intermediate compounds. The chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines are useful as inhibitors of the Janus Kinase family of protein tyrosine kinases (JAKs) for treatment of inflammatory diseases, myeloproliferative disorders, and other diseases.
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Page/Page column 100-101

(2010/08/07)

THERAPEUTIC AGENTS
The invention provides a compound of formula (I): wherein R1, and W have any of the values defined in the application; or a salt thereof. The compounds and salts thereof have beneficial therapeutic properties (e.g. immunosuppressant properties).
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Page/Page column 60-61

(2010/04/03)

NOVEL CYCLOBUTYL COMPOUNDS AS KINASE INHIBITORS
The invention relates to compounds of the formula I, to the preparation and use thereof for the preparation of a medicament for the treatment of diseases, in particular tumours and/or diseases in the formation or course of which protein kinases are involved.
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Page/Page column 33

(2010/07/04)

Synthesis and anti-HCV activity of a new 2′-deoxy-2′-fluoro- 2′-C-methyl nucleoside analogue
2′-Deoxy-2′-fluoro-2′-C-methyl nucleoside analogue 4 was designed and synthesized. Initial biological studies indicated that this compound showed promising activity against HCV replication.
Hu, Weidong,Wang, Ping'An,Song, Chuanjun,Pan, Zhenliang,Wang, Qiang,Guo, Xiaohe,Yu, Xuejun,Shen, Zhenhua,Wang, Shuyang,Chang, Junbiao
scheme or table
p. 7297 - 7298
(2011/02/21)

Xanthine oxidase-activated prodrugs of thymidine phosphorylase inhibitors
Thymidine phosphorylase (TP) is over-expressed in various tumour types and plays an important role in tumour angiogenesis, growth, invasion and metastasis. The enzymatic activity of TP is required for the angiogenic effect of TP, therefore, inhibitors of TP are of significant interest in cancer chemotherapy. A series of xanthine oxidase (XO) activated prodrugs of known inhibitors of TP have been designed and synthesized with the ultimate intent of improving tumour selectivity and pharmacokinetic characteristics. These prodrugs were not inhibitors of TP, but were selectively oxidized by XO at C-2 and/or C-4 of the uracil ring moiety to generate the desired TP inhibitor. Molecular modelling of both the TP inhibitors and XO-activated prodrugs rationalized their binding in the active site of the human TP crystal structure.
Reigan, Philip,Gbaj, Abdul,Stratford, Ian J.,Bryce, Richard A.,Freeman, Sally
p. 1248 - 1260
(2008/09/21)

PHARMACEUTICAL COMPOUNDS
The invention provides a compound having the formula (I): or salts, solvates, tautomers or N-oxides thereof, wherein T is N or CR5; J1-J2 is N=C(R6), (R7)C=N, (R8)N-C(O), (R8)2C-C(O), N=N or (R7)C=C(R6); A is an optionally substituted saturated C1-7 hydrocarbon linker group having a maximum chain length of 5 atoms extending between R1 and NR2R3 and a maximum chain length of 4 atoms extending between E and NR2R3, one of the carbon atoms in the linker group being optionally replaced by oxygen or nitrogen; E is a monocyclic or bicyclic carbocyclic or heterocyclic group or an acyclic group X-G wherein X is CH2, O, S or NH and G is a C1-4 alkylene chain wherein one of the carbon atoms is optionally replaced by O, S or NH; R1 is hydrogen or an aryl or heteroaryl group; R2 and R3 are each hydrogen, optionally substituted C1-4 hydrocarbyl or optionally substituted C1-4 acyl; or NR2R3 forms an imidazole group or a saturated monocyclic heterocyclic group having 4-7 ring members; or NR2R3 and A together form a saturated monocyclic heterocyclic group having 4-7 ring members which is optionally substituted by C1-4 alkyl; or NR2R3 and the adjacent carbon atom of linker group A together form a cyano group; or R1, A and NR2R3 together form a cyano group; and R4, R5, R6, R7 and R8 are each independently selected from hydrogen and various substituents as defined in the claims, wherein the compound is for use in: (a) the treatment or prophylaxis of a disease or condition in which the modulation (e.g. inhibition) of ROCK kinase or protein kinase p70S6K is indicated; and/or (b) the treatment of a subject or patient population in which the modulation (e.g. inhibition) of ROCK kinase or protein kinase p70S6K is indicated.
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(2008/06/13)

PYRROLOPYRIMIDINE DERIVATIVES USED AS HSP90 INHIBITORS
Compounds of formula (I) have HSP90 inhibitory activity and are therefore useful in the treatment of, inter alia, cancer: Formula (I) wherein Ri is hydrogen, fluoro, chloro, bromo, or a radical of formula -X-Alk1-(Z)m-(Alk2)n-Q wherein X is -O-, -S- -S(O)-, -SO2-, or -NH-, Z is -O-, -S-, -(C=O)-, -(C=S)-, -S(O)-, -SO2-, -NRA-, or, in either orientation -C(=O)O-, -C(=O)NRA- , -C(=S)NRA-, -SO2NRA-, -NRAC(=O)-, or -NRASO2- wherein RA is hydrogen or C1-C6 alkyl AIk1 and AIk2 are optionally substituted divalent C1-C3 alkylene or C2-C3 alkenylene radicals, m, n and p are independently 0 or 1 , and Q is hydrogen or an optionally substituted carbocyclic or heterocyclic radical; R2 is a radical of formula -(Ar1)p-(Alk1)q-(Z)r-(Alk2)s-Q wherein Ar1 is an optionally substituted aryl or heteroaryl radical, Alk1, Alk2, Z, and Q are as defined above, and p, q, r and s are independently 0 or 1 ; and R3 is cyano (-CN), fluoro, chloro, bromo, methyl in which in which one or more hydrogen atoms are optionally replaced by fluorine atoms, ethyl in which in which one or more hydrogen atoms are optionally replaced by fluorine atoms, cyclopropyl, -OH, -CH2OH, -C(O)NH2, -C(O)CH3, Or -NH2.
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(2008/06/13)

ORTHO- CONDENSED PYRIDINE AND PYRIMIDINE DERIVATIVES (E. G. PURINES) AS PROTEIN KINASES INHIBITORS
The invention provides a compound for use in the prophylaxis or treatment of a disease state or condition mediated by protein kinase B, the compound having the formula (I): or salts, solvates, tautomers or N-oxides thereof, wherein T is N or CR5; J1-J2 is N=C(R6), (R7)C=N, (R8)N-C(O), (R8)2C-C(O), N=N or (R7)C=C(R6); A is an optionally substituted saturated C1-7 hydrocarbon linker group having a maximum chain length of 5 atoms extending between R1 and NR2R3 and a maximum chain length of 4 atoms extending between E and NR2R3, one of the carbon atoms in the linker group being optionally replaced by oxygen or nitrogen; E is a monocyclic or bicyclic carbocyclic or heterocyclic group or an acyclic group X-G wherein X is CH2, O, S or NH and G is a C1-4 alkylene chain wherein one of the carbon atoms is optionally replaced by O, S or NH; R1 is hydrogen or an aryl or heteroaryl group; R2 and R3 are each hydrogen, optionally substituted C1-4 hydrocarbyl or optionally substituted C1-4 acyl; or NR2R3 forms an imidazole group or a saturated monocyclic heterocyclic group having 4-7 ring members; or NR2R3 and A together form a saturated monocyclic heterocyclic group having 4-7 ring members which is optionally substituted by C1-4alkyl; or NR2R3 and the adjacent carbon atom of linker group A together form a cyano group; or R1, A and NR2R3 together form a cyano group; and R4, R5, R6, R7 and R8 are each independently selected from hydrogen and various substituents as defined in the claims.
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Page/Page column 123

(2008/06/13)

ORTHO-CONDENSED PYRIDINE AND PYRIMIDINE DERIVATIVES (E.G. PURINES) AS PROTEIN KINASES INHIBITORS
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Page/Page column 118

(2008/06/13)

Synthesis and enzymatic evaluation of xanthine oxidase-activated prodrugs based on inhibitors of thymidine phosphorylase
A series of xanthine oxidase-activated prodrugs of known inhibitors of thymidine phosphorylase are described. These prodrugs were oxidised by xanthine oxidase at C-2 and/or C-4 of the uracil ring to generate the desired TP inhibitor. The scheme shows the prodrug of TPI. A series of xanthine oxidase-activated prodrugs of known inhibitors of thymidine phosphorylase has been designed and synthesised to introduce tumour selectivity. These prodrugs were oxidised by xanthine oxidase at C-2 and/or C-4 of the uracil ring to generate the desired TP inhibitor.
Reigan, Philip,Gbaj, Abdul,Chinje, Edwin,Stratford, Ian J.,Douglas, Kenneth T.,Freeman, Sally
p. 5247 - 5250
(2007/10/03)

4-substituted 7-aza-indolin-2-ones and their use as protein kinase inhibitors
This invention relates to 4-substituted 7-aza-indolin-2-ones and their use as protein kinase inhibitors. Particular 4-substituted 7-aza-indolin-2-ones disclosed herein are of Formula 1 and pharmaceutically acceptable salts, solvates, clathrates, and prodrugs thereof, wherein R1, R2, R3, R4, X, Y, and Z are defined herein. The invention fuirther relates to pharmaceutical compositions and dosage forms comprising compounds of Formula 1 and to methods of their use for the treatment and/or prevention of diseases such as, but not limited to, cancer.
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(2008/06/13)

β-Homoalanyl-PNA: A Special Case of β-Peptides with β-Sheet-Like Backbone Conformation; Organization in Higher Ordered Structures
Although β-homoalanyl peptide nucleic acid oligomers possess a β-peptide backbone, they contain nucleobases in their side chains and are thus an interesting special case of β-peptides. These nucleobases are mainly responsible for the formation of secondary structures through base pairing and stacking. We have investigated the pairing properties of β-homoalanyl-PNA oligomers using adenine and 7-carbaadenine. Simple model studies indicate the existence of Watson-Crick and Hoogsteen pairing planes as an intrinsic structural feature of purinyl β-PNA. As a consequence, the adeninyl-β-PNA hexamer and pentamer form higher ordered structures and the 7-carbaadenine-β-PNA hexamer, which lacks a Hoogsteen pairing site, pairs as a double strand. The synthesis of adeninyl and carbaadeninyl β-nucleoamino acids and their oligomerization is described. Pairing mode and strand orientation were investigated through experiment and simple model studies. In the context of β-peptides the β-PNA oligomers for the most part tend to exist as double strands and prefer the extended β-sheet-like backbone conformation which provides an interesting structure motif in addition to the 31-helix observed for β-peptides.
Diederichsen, Ulf,Schmitt, Harald W.
p. 827 - 835
(2007/10/03)

Heterocyclic compounds, their production and use
A novel compound of the formula: wherein A is a condensed pyrimidinone or condensed pyridazinone ring; Ar1 and Ar2 are independently a ring; Z is a divalent group, or a salt thereof which have an excellent antitumor activity.
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(2008/06/13)

Acyclic Nucleoside Analogs. II. Acyclic Analogs of Guanosine, 7-Deazaguanosine, and 7-Deazaadenosine with a cis-Hydroxypentene Fragment
Condensations of 5-acetoxy-1-bromo-2-pentene with 2-amino-6-chloropurine, 4-chloropyrrolopyrimidine, and 2-amino-4-chloropyrrolopyrimidine sodium salts gave acyclic analogs of guanosine, 7-deazaguanosine, and 7-deazaadenosine.The subsequent deprotection with 0.1 N NaOH or methanol saturated with ammonium yielded the desired nucleoside analogs containing a cis-hydroxypentene fragment and either natural or modified heterocycle. - Keywords: nucleosides; acyclic analogs; pyrrolopyrimidines.
Tsytovich, A. V.,Shamshin, D. V.,Burkovskii, V. B.,Shvets, V. I.
p. 756 - 761
(2007/10/03)