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Journal articles on the topic 'Pyrido[2’,1’ :1,5]pyrazolo[3,4-d]pyrimidine'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Abdelhamid, Abdou O., and Sobhi M. Gomha. "Synthesis of New Pyrazolo[1,5-a]pyrimidine, Triazolo[4,3-a]pyrimidine Derivatives, and Thieno[2,3-b]pyridine Derivatives from Sodium 3-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-3-oxoprop-1-en-1-olate." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/327095.

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Condensation of sodium 3-oxo-3-(1-phenyl-1H-pyrazol-4-yl)prop-1-en-1-olate (2) with several heterocyclic amines, cyanoacetamide, cyanothioacetamide, and 2-cyanoacetohydrazide gives pyrazolo[1,5-a]pyrimidines (5a–d), pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine (9), benzo[4,5]imidazo[1,2-a]pyrimidine (10), [1,2,4]triazolo[1,5-a]pyrimidine (11), and pyridine derivatives (12–14). Also, thieno[2,3-b]pyridines (15–18) were synthesized via pyridinethione (13) withα-halo ketones andα-halo ester. Structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data, alternat

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2

Thokchom, Herojit S., Anita D. Nongmeikapam, and Warjeet S. Laitonjam. "Synthesis of fused pyrazolo-, isoxazolo-, pyrimido-, and pyridopyrimidines." Canadian Journal of Chemistry 83, no. 8 (2005): 1056–62. http://dx.doi.org/10.1139/v05-054.

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A systematic study of the synthesis of the 5,7-diaryl-4-oxo-pyrazolo[3,4-d]pyrimidin-6-thiones (3), 2-phenyl-5,7-bis(2′-methylphenyl)-4-oxo-pyrazolo[3,4-d]pyrimidin-6-thiones (4b), 2(3H)-3-phenyl-5,7-diaryl-4-oxo-pyrazolo[3,4-d]pyrimidin-6-thiones (5), 5,7-diaryl-4-oxo-isoxazolo[5,4-d]pyrimidin-6-thiones (7), 3,5,7-triaryl-2,3-dihydro-4-oxo-isoxazalo[5,4-d]pyrimidin-6-thiones (8), 2-amino-6,8-diaryl-5-oxo-pyrimido[4,5-d]pyrimidin-7-thiones (9), 3,4-dihydro-2-amino-4-phenyl-6,8-diaryl-5-oxo-pyrimido[4,5-d]pyrimidin-7-thiones (10), 3-cyano-6,8-diaryl-2,5-dioxo-pyrido[2,3-d]pyrimidin-7-thiones (1

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3

Ho, Yuh-Wen, and Maw Cherng Suen. "Thioxopyrimidine in Heterocyclic Synthesis I: Synthesis of Some Novel 6-(Heteroatom-substituted)-(thio)pyrimidine Derivatives." Journal of Chemistry 2013 (2013): 1–15. http://dx.doi.org/10.1155/2013/765243.

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A series of novel N-cycloalkanes, morpholine, piperazines, pyrazole, pyrimidine, benzimidazolo[1,2-a]pyrimidine, 1,2,3,4-tetrazolo[1,5-a]pyrimidine, azopyrazolo[1,5- a]pyrimidine, pyrimido[4', 5':3,4]pyrazolo[1,5-a]pyrimidines and pyridine derivatives incorporating a 5-cyano-4-methyl-2-phenyl-(thio)pyrimidine moiety were obtained by the intramolecular cyclization of 6-methylthio-pyrimidine, 6-(benzoylmethyl)thio- pyrimidine and 2-[(5-cyano-4-methyl-2-phenylpyrimidin-6-yl)thio]-3-dimethyl- amino-1-phenyl-prop-2-en-1-one with appropriate amines and enaminone compounds, respectively. The structur

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4

Toplak, Renata, Jurij Svete, Simona Golič Grdadolnik, and Branko Stanovnik. "Methyl (Z)-2-[(Benzyloxycarbonyl)amino]-3-dimethyl- aminopropenoate in the Synthesis of Heterocyclic Systems. Synthesis of (Benzyloxycarbonyl)amino Substituted Fused Pyrimidinones." Collection of Czechoslovak Chemical Communications 64, no. 2 (1999): 177–89. http://dx.doi.org/10.1135/cccc19990177.

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Methyl (Z)-2-[(benzyloxycarbonyl)amino]-3-dimethylaminopropenoate (1) was used as a reagent for preparation of 3-[(benzyloxycarbonyl)amino] substituted 4H-pyrido[1,2-a]pyrimidin-4-ones 17-21, 4H-pyrimido[1,2-b]pyridazin-4-ones 22 and 23, 5H-[1,2,4]triazolo[2,3-a]- pyrimidin-5-one 24, 5H-thiazolo[3,2-a]pyrimidin-5-one 25, and 4H-pyrazino[1,2-a]pyrimidin-4-one 26. Removal of the benzyloxycarbonyl group by catalytical transfer hydrogenation with Pd/C in the presence of cyclohexene is selective to give 3-amino-4H-pyrido[1,2-a]- pyrimidin-4-ones 27-30 in 85-92% yields, or with hydrogen bromide in a

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5

Gad-Elkareem, Mohamed A. M., Azza M. Abdel-Fattah, and Mohamed A. A. Elneairy. "Pyrazolo[3,4-b]pyridine in heterocyclic synthesis: synthesis of new pyrazolo[3,4-b]pyridines, imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines, and pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines." Canadian Journal of Chemistry 85, no. 9 (2007): 592–99. http://dx.doi.org/10.1139/v07-089.

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Pyrazolo[3,4-b]pyridine derivatives 7 and 9 were synthesized via the reaction of 3-amino-1H-pyrazolo-[3,4-b]pyridine derivative 2 with ω-bromoacetophenones. Reaction of 7 and 9 with Ac2O afforded the imidazo[1',2':1,5]py razolo[3,4-b]pyridine derivative 8 and pyrazolo[3,4-b]pyridine derivative 10, respectively. Reaction of 2 with chloroacetonitrile followed by DMF-DMA gave imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines 4 and 5, respectively. Acetyl acetone and 1,1-dicyano-2,2-dimethylthioethene were reacted with 2 to afford the pyrido[2',3':3,4]pyrazolo-[1,5-a]-pyrimidines 11 and 14, respectively.

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6

Youssef, Ahmed Said Ahmed. "Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile and 6-amino-1,4-dihydro-3-methyl-1,4-diphenylpyrano[2,3-c]pyrazole-5-carbonitrile with substituted benzylidenemalononitriles, α,β-acetylenic esters and ketones". Journal of Chemical Research 2009, № 4 (2009): 214–17. http://dx.doi.org/10.3184/030823409x435874.

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Reactions of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3-carbonitrile (1a) with substituted benzylidenemalononitriles gave 4-amino-2-(1-cyano-2-arylvinyl)benzothieno[2,3- d]pyrimidine derivatives (3) as ( E,Z)-mixtures and in one case (2c) as separated ( Z)- and ( E)-isomers. Similar treatment of 6-amino-1,4-dihydro-3-methyl-1,4-diphenyl-pyrano[2,3- c]pyrazole-5-carbonitrile (4) yielded similarly-formed pyrazolopyranopyrimidine derivatives (5a, b) as ( Z)-and ( E)-stereoisomers. Attempted acetylation of the aminobenzothienopyrimidines resulted in degradation of the pyrimidine ring and the fo

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7

Kordian, Marcus, Holger Feist, Willi Kantlehner, Manfred Michalik, and Klaus Peseke. "Nucleoside Analogues from Push-Pull Functionalized Branched-Chain Pyranosides." Zeitschrift für Naturforschung B 61, no. 4 (2006): 406–12. http://dx.doi.org/10.1515/znb-2006-0406.

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The reaction of methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro-hexopyranosid-3-ulose (1) with ethynylmagnesium bromide in tetrahydrofuran and subsequent trimethylsilylation yielded the methyl 4,6-O-benzylidene-2-deoxy-3-C-ethynyl-3-O-trimethylsilyl-α-D-ribo-hexopyranoside (3). Push-pull functionalization of 3 with N,N,N′,N′,N″,N″-hexamethylguanidinium chloride under basic conditions and following deprotection afforded the spiro{2,5-dihydro-3-dimethylamino- furan-2,8’-4’,4’a,6’,7’,8’,8’a-hexahydro-6’-methoxy-2’-phenyl-pyrano[3,2-d][1.3]dioxine}- 5-ylidenemalononitrile (9). Furthermore, compound 1

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8

Tiwari, Sangeeta, Ashok K. Yadav, and A. K. Mishra. "Some New Pyrido[2,3-d]pyridimines and their Nucleoside of Biological Importance." E-Journal of Chemistry 7, s1 (2010): S85—S92. http://dx.doi.org/10.1155/2010/812567.

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Chalcones (I) reacted with malanonitrile and ammonium acetate yielded 2-amino-3-cyano-4,6-disubstituted pyridines (II) in excellent yield. 4-Amino-5,7-disubstituted pyrido [2,3-d]pyrimidine-2(1H)-thiones (III), 4-amino-5,7-disubstituted pyrido[2,3-d]pyrimidines (IV) and 4-imino-3,5,7-trisubstituted pyrido[2,3-d]pyrimidin-2(1H)-ones (V) have been synthesized by the condensation of compound (II) with thiourea, formamide and arylisocynate respectively. The ribofuranosidesviz. 4-amino-5,7-disubstituted-1- [2',3',5'-tri-o-benzoyl-β,D-ribofuranosyl]pyrido[2,3-d]pyrimidine-2-(1H)-thiones (VI) and 4-i

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9

Otero, Iran, Holger Feist, Dirk Michalik, Manfred Michalik, José Quincoces та Klaus Peseke. "Synthesis of Iso-C-nucleoside Analogues from 1-(Methyl 2-O-benzyl-4,6- O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-ones". Zeitschrift für Naturforschung B 60, № 11 (2005): 1175–85. http://dx.doi.org/10.1515/znb-2005-1110.

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1-(Methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-one (3a) reacted with 3-amino-1H-1,2,4-triazole and 5-aminopyrazole-4-carboxylic acid derivatives in the presence of base to furnish the triazolo[1,5-a]pyrimidine (5) and the pyrazolo[1,5- a]pyrimidines (8a - d), respectively. Treatment of 1-(methyl 2-O-benzyl-4,6-O-benzylidene-3- deoxy-α-D-altropyranosid-3-yl)-4-phenyl-but-3-yn-2-one (3b) with cyanacetamide, 2-cyano-N- (4-methoxyphenyl)acetamide und N-aryl-3-oxo-butyramides afforded the substituted nicotinonitriles (11a - d). Furthermore, reaction of 3b with 2-b

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10

Abass, Mohamed, Mostafa Ismail, Wafaa Abdel-Monem, and Aisha Mayas. "Substituted pyridopyrimidinones, Part IV: 2-chloro-4h-pyrido[1,2-a]pyrimidin-4-one as a synthone of some new heterotricycles." Journal of the Serbian Chemical Society 75, no. 1 (2010): 11–17. http://dx.doi.org/10.2298/jsc1001011a.

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2-Chloro-4H-pyrido[1,2-a]pyrimidin-4-one (1) was utilized as a synthone precursor to prepare novel heterotricyclic systems. 2-Azido and 2-hydrazino derivatives (2 and 3) were obtained by nucleophilic replacement evolving compound 1. The hydrazine derivative 3 was transformed into the azido derivative 2 by nitrosation. Treatment of compound 3 with [bis(methylthio)methylene] malononitrile afforded 2-pyrazolylpyridopyrimidine 4. When compound 1 was reacted with 5-amino-3-(methylthio)-1H-pyrazole-4-carbonitrile, the same compound 4 was obtained with no evidence for the production of (pyrazolylamin

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11

Bahashwan, Saleh A. "Pharmacological activities of some triazinopyrazolothieno pyrimidine derivatives." Acta Pharmaceutica 67, no. 3 (2017): 407–14. http://dx.doi.org/10.1515/acph-2017-0022.

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Abstract Triazinopyrazolothieno pyrimidine derivatives 1–5 were evaluated for their anti-inflammatory, analgesic and anticancer activities and acute toxicity. Anti-inflammatory activity of the compounds was studied using the carrageenan test. All tested compounds showed analgesic activity, 3-methoxycarbonyl-4,6-dimethyl-8-[(N-methylindolyl)methyl] pyrimido [5′,4′:4,5]thieno [3′,2′-3,4]pyrazolo [5,1-c]triazine (4) showed activity comparable to that of diclofenac. Compounds 1–5 were also screened for anticancer activity on a human lung cancer cell line (A549) and a human prostate cancer cell lin

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12

Abdelhamid, Abdou O., Zeineb H. Ismail, and Anhar Abdel-Aziem. "Reactions with Hydrazonoyl Halides 601: Synthesis of Thieno[2′,3′:4,5] Pyrimidino[1,2-b][1,2,4,5]tetrazines, [1]benzothieno[2′,3′:4,5]pyrimidino [1,2-b][1,2,4,5]tetrazines, Pyrazolo[3′,4′:4,5]pyrimidino[1,2-b] [1,2,4,5]tetrazines and Pyrazolo[3,4-d]pyridazines." Journal of Chemical Research 2007, no. 10 (2007): 609–16. http://dx.doi.org/10.3184/030823407x256118.

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Thieno[2′,3′:4,5]pyrimidino[1,2- b][1,2,4,5]tetrazine, [1]benzothieno-[2′,3′:4,5]pyrimidino[1,2- b][1,2,4,5]tetrazine, pyrazolo [3′,4′:4,5]pyrimidino[1,2- b][1,2,4,5]tetrazine, triazolo[4,3- a]pyrimidin-5(1 H)-one, 1-{[2-(1-benzofuran-2-yl)-5-phenyl-4,5-dihydro-1 H-pyrazol-1-yl]-4-substituted-1,3-thiazol-5-yl}-2-phenyldiazene, 3-acyl-4-(1-benzofuran-2-ylcarbonyl) pyrazole and pyrazolo[3,4- d]pyridazine derivatives could be obtained via reactions of hydrazonoyl halides with the appropriate pyrimidine-2-thione, 3-amino-5,6-dimethyl-2-sulfanylthieno[2,3- d]pyrimidin-4(3 H)-one, 5-amino-6-mercapto

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13

Hashmi, Imran Ali, Holger Feist, Manfred Michalik, Helmut Reinke та Klaus Peseke. "Dimethylaminomethylene-α-D-xylo-hept-5-ulofuranurononitrile as Building Block in the Synthesis of ‘Reversed’ C-Nucleoside Analogues". Zeitschrift für Naturforschung B 61, № 3 (2006): 292–300. http://dx.doi.org/10.1515/znb-2006-0309.

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Abstract 3-O-Benzyl-6-deoxy-1,2-O-isopropylidene-6-(dimethylaminomethylene)-α-D-xylo-hept-5-ulofuranurononitrile (1) was reacted with amidinium salts, S-methylisothiouronium sulfate, and guanidinium chloride, respectively, in the presence of bases to furnish the 4-(3-O-benzyl-1,2-O-isopropylidene- α-D-xylo-tetrofuranos-4-yl)pyrimidine-5-carbonitriles 2 and the 4-(1,2-O-isopropylidene- α-D-glycero-tetr-3-enofuranos-4-yl)pyrimidine-5-carbonitriles 3, respectively. Treatment of 1 with ethyl 5-aminopyrazole-4-carboxylates yielded the ethyl 7-(3-O-benzyl-1,2-O-isopropylidene- α-D-xylo-tetrofuranos-

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14

Reheim, Mohamed Ahmed Mahmoud Abdel, Ibrahim Saad Abdel Hafiz, and Mohamed Ahmed Elian. "Synthesis and Antimicrobial Evaluation of Some Novel Pyrimidine, Pyrazole, Chromene and Tetrahydrobenzo[b]thiophene Derivatives Bearing Pyrimidinthione Moiety." Current Organic Synthesis 17, no. 7 (2020): 548–57. http://dx.doi.org/10.2174/1570179417666200628021125.

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Aim and Objective: A novel collection of fused pyrimidine, pyridine, pyrazole, chromene and thiophene derivatives 2-30 have been newly synthesized by using the 1a, b as starting material. Fused pyrane exhibits a range of pharmacological activity such as cancer agents [1], antimicrobial [2-4], antioxidant [5], antiproliferative [6], cytotoxic activity [7], anticipated antitumor [8], antiparkinsonian [9] and anti-inflammatory [10]. Moreover, pyrane derivatives are well known for bacterial biofilm disruptor [11], anticonvulsant [12] and inhibitors of mycobacterium bovis [13]. Materials and Method

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15

Dashyan, Sh Sh, E. G. Paronikyan, A. S. Noravyan, and R. G. Paronikyan. "Synthesis and Anticonvulsive Activity of 5-Pyrrolidin-1-Ylpyrano[4″,3″:4′,5′]Pyrido-3′,2′:4,5]Thieno[3,2-D]Pyrimidine Derivatives." Pharmaceutical Chemistry Journal 50, no. 4 (2016): 221–25. http://dx.doi.org/10.1007/s11094-016-1426-x.

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16

Mahmoud, M. R., A. A. Shalaby, T. A. Gad, and A. A. El-Khamry. "A facile synthesis and heteroannulation of pyrido[2,3-d]pyrimidine and related heterocyclic systems." Journal of Chemical Research 2009, no. 10 (2009): 612–15. http://dx.doi.org/10.3184/030823409x12523324765777.

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7-Amino-1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-(3,4,5-trimethoxyphenyl)pyrido[2,3- d]pyrimidine (1) was prepared and reacted with methyl iodide and ethyl chloroacetate to give the S-alkylated products 2 and 3, respectively. The reaction of 1 or 3 with hydrazine hydrate yielded the same 2-hydrazino derivative 4. Treatment of 4 with 2,4-pentanedione, 2-acetylcyclohexanone and ethyl acetoacetate afforded the corresponding pyrazolylpyrido[2,3- d]pyrimidine derivatives (5–7), while phthalic anhydride gave the phthalazinyl compound 8. Ethoxymethylenemalononitrile with the hydrazine 4 formed the fused 1

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17

Ibrahim, Yusria R. "Synthesis of spiro(cyclohexa-diene-pyrazolo[1,5-a]pyrimidine-4-ylidene)-malononitrile derivatives." Journal of Chemical Research 2009, no. 8 (2009): 495–98. http://dx.doi.org/10.3184/030823409x466717.

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The reaction of 4-substituted aryldiazenyl-1 H-pyrazole-3,5-diamines with 7,7′,8,8′-tetra-cyanoquinodimethane gave 2-(2′,7′-diamino-6′-cyano-3′-(aryldiazenyl)-4′ H-spiro(cyclohexa[2,5]-diene-1,5′-pyrazolo[1,5- a]pyrimidine-4-ylidene) malononitriles in 63–79% yield, while, by reaction of 2-aminobenzimidazole with 7,7′,8,8′-tetracyanoquinodimethane, 2-(3′-amino-4′-cyano-6′ H-spiro-(cyclohexa[2′,5′]diene-1,5′-benzo( d)-imidazo[1,2- a]pyrimidine)-4-ylidene)malononitrile was formed in 71% yield. Rationales for these transformations are presented.

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18

El-Sayed, Wael A., Mahmoud M. M. Ramiz та Adel A. H. Abdel-Rahman. "Anti-Hepatitis B Virus Activity of New N4-β-D-Glycoside Pyrazolo[3,4-d]pyrimidine Derivatives". Zeitschrift für Naturforschung C 64, № 5-6 (2009): 323–28. http://dx.doi.org/10.1515/znc-2009-5-603.

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1The reaction of 6-hydrazinyl-1,3-dimethylpyrimidine-2,4-(1H,3H)-dione () with ethoxymethylenemalononitrile afforded 5-amino-1-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin- 6-yl)-1H-pyrazole-4-carbonitrile (2). The latter was reacted with formamide and urea affording the corresponding 4-aminopyrazolo[3,4-d]pyrimidines 3 and 4. The reaction of monosaccharide aldoses with 3 and 4 gave stereoselectively the β-N-glycosides 5a - d and 6a - d which were treated with acetic anhydride in pyridine to afford the corresponding acetylated derivatives 7a - d and 8a - d. The prepared compounds were t

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19

Zhu, Xiao-Tong, Ge Zhang, and Ning Ma. "2-Amino-5,7-bis(4-fluorophenyl)-1′,3′-dimethyl-7,8-dihydrospiro[pyrido[2,3-d]pyrimidine-6(5H),5′-pyrimidine]-2′,4,4′,6′(3H,1′H,3′H,5′H)-tetraone ethanol solvate." Acta Crystallographica Section E Structure Reports Online 65, no. 7 (2009): o1625. http://dx.doi.org/10.1107/s1600536809022946.

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Ebrahimpour, Zahra, Ali Shiri, Mehdi Bakavoli, Seyed Mohammad Seyedi, Masoumeh Bahreini, and Fatemeh Oroojalian. "Microwave-assisted synthesis and antibacterial evaluation of new derivatives of 1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one." Heterocyclic Communications 22, no. 1 (2016): 49–53. http://dx.doi.org/10.1515/hc-2015-0145.

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AbstractSynthesis of new 1,2-dihydro-3H-pyrazolo[3,4-d] pyrimidin-3-ones4–6starting with ethyl 4-hydroxy-2-methylthio-pyrimidine-5-carboxylate (1) under classical heating and microwave-induced conditions is reported. The antibacterial activities of the synthesized compounds were evaluated using chloramphenicol and streptomycin as reference drugs.

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21

Sirakanyan, Samvel N., Domenico Spinelli, Athina Geronikaki, et al. "Synthesis and antimicrobial evaluation of novel polyheterocyclic systems derived from cyclopenta[4',5']pyrido[3',2':4,5]furo[3,2-d]pyrimidine." Chemistry of Heterocyclic Compounds 57, no. 1 (2021): 75–80. http://dx.doi.org/10.1007/s10593-021-02870-1.

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22

Hafez, Hend N., Abdulrahman G. Alshammari, and Abdel-Rhman B. A. El-Gazzar. "Facile heterocyclic synthesis and antimicrobial activity of polysubstituted and condensed pyrazolopyranopyrimidine and pyrazolopyranotriazine derivatives." Acta Pharmaceutica 65, no. 4 (2015): 399–412. http://dx.doi.org/10.1515/acph-2015-0037.

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Abstract Reaction of 6-amino-3-methyl-4-(substituted phenyl)-1,4- dihydropyrano[2,3-c]pyrazole-5-carbonitrile (1) with triethylorthoformate followed by treatment with hydrazine hydrate, formic acid, acetic acid, phenylisocyanate, ammonium thiocyanate and formamide afforded the corresponding pyranopyrimidine derivatives 2-6. Cyclocondensation of 1 with cyclohexanone afforded pyrazolopyranoquinoline 7. One-pot process of diazotation and de-diazochlorination of 1 afforded pyrazolopyranotriazine derivative 8, which upon treatment with secondary amines afforded 9 and 10a- c. Condensation of 2 with

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23

Aleksanyan, M. S., A. A. Karapetyan, A. Sh Oganisyan, and Yu T. Struchkov. "Crystal and molecular structure of the 1:1 solvate of 6,6-dimethyl-4-oxo-2-N-(3-methyl-5-oxo-4H-pyrazolyl)-5,6-dihydro-8H-pyrano[4′,3′:4,5]thieno[2,3-d]pyrimidine with dimethylsulfoxide." Journal of Structural Chemistry 38, no. 6 (1997): 989–92. http://dx.doi.org/10.1007/bf02763824.

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24

Blake, James F., Michael Burkard, Jocelyn Chan, et al. "Discovery of (S)-1-(1-(4-Chloro-3-fluorophenyl)-2-hydroxyethyl)-4-(2-((1-methyl-1H-pyrazol-5-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (GDC-0994), an Extracellular Signal-Regulated Kinase 1/2 (ERK1/2) Inhibitor in Early Clinical Development." Journal of Medicinal Chemistry 59, no. 12 (2016): 5650–60. http://dx.doi.org/10.1021/acs.jmedchem.6b00389.

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Sakamoto, Miho, Takako Moriyasu, Keiko Minowa, et al. "Structure Elucidation of a Novel Analog of Sildenafil Detected as an Adulterant in a Dietary Supplement Using LC-UV and LC/MS." Journal of AOAC INTERNATIONAL 95, no. 4 (2012): 1048–52. http://dx.doi.org/10.5740/jaoacint.11-235.

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Abstract A sildenafil-related compound was detected in a dietary supplement marketed as an aphrodisiac. The compound was detected during analysis of the dietary supplement using LC-UV and LC/electrospray ionization-MS. The structure of the compound was established using high resolution MS, NMR spectrometry, and X-ray crystal structure analysis. The compound was identified as 5-(5-((3,5-dimethylpiperazin-1-yl)sulfonyl)-2-ethoxyphenyl)-1-methyl-7-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-3-propyl-1H-pyrazolo[4,3-d] pyrimidine. Based on this structure, the compound was named nitroprodenafil. The

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Vlotides, George, Yen-Hao Chen, Tamar Eigler, Song-Guang Ren, and Shlomo Melmed. "Fibroblast Growth Factor-2 Autofeedback Regulation in Pituitary Folliculostellate TtT/GF Cells." Endocrinology 150, no. 7 (2009): 3252–58. http://dx.doi.org/10.1210/en.2008-1625.

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To investigate paracrine regulation of pituitary cell growth, we tested fibroblast growth factor (FGF) regulation of TtT/GF folliculostellate (FS) cells. FGF-2, and FGF-4 markedly induced cell proliferation, evidenced by induction of pituitary tumor transforming gene-1 (Pttg1) mRNA expression and percentage of cells in S phase. Signaling for FGF-2-induced FS cell proliferation was explored by specific pharmacological inhibition. A potent inhibitory effect on FGF-2 action was observed by blocking of Src tyrosine kinase with 4-amino-5-(4-chlorophenyl)-7-(t-butyl)pyrazolo[3,4-d] pyrimidine (≥0.1

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Teixeira, Cleber E., Fernanda B. M. Priviero, and R. Clinton Webb. "Molecular Mechanisms Underlying Rat Mesenteric Artery Vasorelaxation Induced by the Nitric Oxide-Independent Soluble Guanylyl Cyclase Stimulators BAY 41-2272 [5-Cyclopropyl-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-4-ylamine] and YC-1 [3-(5′-Hydroxymethyl-2′-furyl)-1-benzyl Indazole]." Journal of Pharmacology and Experimental Therapeutics 317, no. 1 (2005): 258–66. http://dx.doi.org/10.1124/jpet.105.095752.

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Mackay, Kenneth B., Haig Bozigian, Dimitri E. Grigoriadis, Sarah A. Loddick, Gail Verge, and Alan C. Foster. "Neuroprotective Effects of the CRF1 Antagonist R121920 after Permanent Focal Ischemia in the Rat." Journal of Cerebral Blood Flow & Metabolism 21, no. 10 (2001): 1208–14. http://dx.doi.org/10.1097/00004647-200110000-00009.

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The neuroprotective effects of a systemically active, highly selective, corticotropin-releasing factor-1 (CRF1) receptor antagonist, R121920 ((7-(dipropylamino)-2,5-dimethyl-3- [2-(dimethylamino)-5-pyridyl] pyrazolo [1,5-a] pyrimidine), was assessed in two rat models of permanent focal cerebral ischemia, where the middle cerebral artery (MCA) was occluded either through the subtemporal approach or using the intraluminal suture technique. R121920 rapidly crossed the blood–brain barrier after intravenous (IV) bolus administration (10 mg/kg), with peak brain concentrations at 5 minutes (2.26 ± 0.

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Laurenzana, Ilaria, Antonella Caivano, Francesco La Rocca, et al. "A Pyrazolo[3,4-d]Pyrimidine Compound Reduces Fyn Phosphorylation and Induces Apoptosis in Large Granular Lymphocyte Leukemia Cells." Blood 126, no. 23 (2015): 3254. http://dx.doi.org/10.1182/blood.v126.23.3254.3254.

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Abstract Introduction According to WHO classification, large granular lymphocyte leukemia (LGL leukemia) includes three entities: T-cell LGL leukemia, chronic NK lymphoproliferative disorders (NK-CLPD) and aggressive NK cell leukemia. Since no standard therapies for immature NK cell neoplasms have been established so far and the overall outcomes are dismal, new therapeutic options are needed. A pyrazolo[3,4-d]pyrimidine library of compounds have already been studied in a previous work by Tintori et al. It has been demonstrated that one of these compounds proved to be efficient against some mem

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Hayallah, Alaa M. "Design, Molecular Modeling and Synthesis of Some New Purine-diones and Pyridopyrimidine-diones with Anticancer Activity." JOURNAL OF ADVANCES IN CHEMISTRY 13, no. 2 (2017): 5959–76. http://dx.doi.org/10.24297/jac.v13i12.6043.

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An olomoucine analogues of 2-[(1-substituted)-2,6-dioxo-2,3,6,7â€“tetrahydro-1H-purin-8-ylsulfanyl]-N-substituted acetamide 6a-g and 7a-g, 1-substituted-8-[2-(4-substituted phenyl)-2-oxoethylsulphanyl]-3,7-dihydro-1H-purine-2,6-diones 9a-g and 10a-g, 3-(2-substituted benzyl)-6-(4-substituted phenyl)-1H-thiazolo[2,3-f]purine-2,4-dione 11a-g and 12a-g and their isosteres 3-substituted benzyl-5-methyl-7-substituted-1H-pyrido[2,3-d]pyrimidine-2,4-dione 13a-c and 14a-c were designed and synthesized. The target compounds 11a-g and 12a-g were prepared by cyclodehydration of 9a-g and 10a-g in PPA, whi

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Abdel-Rahman, Adel A. H., Amira K. F. Shaban, Ibrahim F. Nassar, et al. "Discovery of New Pyrazolopyridine, Furopyridine, and Pyridine Derivatives as CDK2 Inhibitors: Design, Synthesis, Docking Studies, and Anti-Proliferative Activity." Molecules 26, no. 13 (2021): 3923. http://dx.doi.org/10.3390/molecules26133923.

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New pyridine, pyrazoloyridine, and furopyridine derivatives substituted with naphthyl and thienyl moieties were designed and synthesized starting from 6-(naphthalen-2-yl)-2-oxo-4-(thiophen-2-yl)-1,2-dihydropyridine-3-carbonitrile (1). The chloro, methoxy, cholroacetoxy, imidazolyl, azide, and arylamino derivatives were prepared to obtain the pyridine-‑C2 functionalized derivatives. The derived pyrazolpyridine-N-glycosides were synthesized via heterocyclization of the C2-thioxopyridine derivative followed by glycosylation using glucose and galactose. The furopyridine derivative 14 and the tricy

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Hu, Xiao-Fen, Ya-Qing Feng, Qi Su, and Kang-Jian Qiao. "7′′-Benzyl-9′′-benzylidene-4′-[4-(dimethylamino)phenyl]-1′-methyl-5′′-phenyl- 2′′,3′′,6′′,7′′,8′′,9′′-hexahydro-1H-indole-3(2H)-spiro-2′-pyrrolidine-3′-spiro-2′′-pyrido[4,3-d]thiazolo[3,2-a]pyrimidine-2,2′′-dione acetonitrile disolvate." Acta Crystallographica Section E Structure Reports Online 61, no. 6 (2005): o1830—o1832. http://dx.doi.org/10.1107/s1600536805015485.

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Saberi, Dariush, Mohammad Reza Mohammadizadeh, and Reza Esmaeili. "Diastereoselective and Efficient Synthesis of Indeno[2″,1″: 4′,5′]furo[3′,2′: 5,6]pyrido[2,3-d]pyrimidine-2,4,6(1H,3H)-trione and 6-(2,3-Dihydro-2-hydroxy-1,3-dioxo-1H-inden-2-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-2,4,7(1H,3H,6H)-trione Derivatives." Helvetica Chimica Acta 98, no. 10 (2015): 1411–18. http://dx.doi.org/10.1002/hlca.201500106.

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Ludwig, Lynda M., Dorothee Weihrauch, Judy R. Kersten, Paul S. Pagel, and David C. Warltier. "Protein Kinase C Translocation and Src Protein Tyrosine Kinase Activation Mediate Isoflurane-induced Preconditioning In Vivo." Anesthesiology 100, no. 3 (2004): 532–39. http://dx.doi.org/10.1097/00000542-200403000-00011.

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Background The authors tested the hypotheses that protein kinase C (PKC)-specific isoform translocation and Src protein tyrosine kinase (PTK) activation play important roles in isoflurane-induced preconditioning in vivo. Methods Rats (n = 125) instrumented for measurement of hemodynamics underwent 30 min of coronary artery occlusion followed by 2 h of reperfusion and received 0.9% saline (control); PKC inhibitors chelerythrine (5 mg/kg), rottlerin (0.3 mg/kg), or PKC-epsilonV1-2 peptide (1 mg/kg); PTK inhibitors lavendustin A (1 mg/kg) or 4-amino-5-(4-methylphenyl)-7-(t-butyl)pyrazolo[3,4-d]py

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Liao, Wu-xiang, Lin Feng, Jing Zheng, and Dong-bao Chen. "Deciphering Mechanisms Controlling Placental Artery Endothelial Cell Migration Stimulated by Vascular Endothelial Growth Factor." Endocrinology 151, no. 7 (2010): 3432–44. http://dx.doi.org/10.1210/en.2009-1305.

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Vascular endothelial growth factor (VEGF) stimulated fetoplacental artery endothelial (oFPAE) cell migration and activated multiple signaling pathways including ERK2/1, p38MAPK, Jun N-terminal kinase (JNK1/2), v-Akt murine thymoma viral oncogene homolog 1 (Akt1), and c-Src in oFPAE cells. VEGF-induced cell migration was blocked by specific kinase inhibitors of JNK1/2 (SP600125), c-Src (4-amino-5-(4-chlorophenyl)-7-(t-butyl)pyrazolo[3,4-d] pyrimidine), and phosphatidylinositol 3-kinase/Akt (wortmannin) but not ERK2/1 (U0126) and p38MAPK (SB203580). VEGF-induced cell migration was associated wit

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Tang, Xian-Liang, Eitaro Kodani, Hitoshi Takano, et al. "Protein tyrosine kinase signaling is necessary for NO donor-induced late preconditioning against myocardial stunning." American Journal of Physiology-Heart and Circulatory Physiology 284, no. 4 (2003): H1441—H1448. http://dx.doi.org/10.1152/ajpheart.00789.2002.

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Although protein tyrosine kinases (PTKs) signaling has been implicated in the late phase of ischemic preconditioning (PC), it is unknown whether PTK signaling is necessary for the development of nitric oxide (NO) donor-induced late PC. Thus conscious rabbits underwent a sequence of six 4-min coronary occlusion (O)/4-min reperfusion (R) cycles followed by a 5-h recovery period of reperfusion for 3 consecutive days ( days 1, 2, and 3). On day 0 (24 h before the 6 O/R cycles on day 1), rabbits received no treatment (control), the NO donor diethylenetriamine (DETA)/NO (DETA/NO), the PTK inhibitor

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SHAH, O. Jameel, Scot R. KIMBALL, and Leonard S. JEFFERSON. "The Src-family tyrosine kinase inhibitor PP1 interferes with the activation of ribosomal protein S6 kinases." Biochemical Journal 366, no. 1 (2002): 57–62. http://dx.doi.org/10.1042/bj20020198.

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Considerable biochemical and pharmacological evidence suggests that the activation of ribosomal protein S6 kinases (S6Ks) by activated receptor tyrosine kinases involves multiple co-ordinated input signals. However, the identities of many of these inputs remain poorly described, and their precise involvement in S6K activation has been the subject of great investigative effort. In the present study, we have shown that 4-amino-5-(4-methylphenyl)-7-(t-butyl)pyrazolo[3,4-d]pyrimidine (PP1), a selective inhibitor of the Src family of non-receptor tyrosine kinases, interferes with the activation of

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Gui, Yu, Xi-Long Zheng та Morley D. Hollenberg. "Interleukin-1β, Src- and non-Src tyrosine kinases, and nitric oxide synthase induction in rat aorta in vitro". American Journal of Physiology-Heart and Circulatory Physiology 279, № 2 (2000): H566—H576. http://dx.doi.org/10.1152/ajpheart.2000.279.2.h566.

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We studied the potential roles for endogenous interleukin-1β (IL-1β) and for several signaling pathways in the spontaneous induction in vitro of inducible nitric oxide synthase (iNOS) in endothelium-denuded rat aorta rings. Added IL-1β augmented, whereas the IL-1β receptor antagonist IL-1ra blocked, spontaneous iNOS induction. Furthermore, increases in IL-1β mRNA preceded those of iNOS mRNA. Mitogen-activated protein kinase kinase and phosphatidyl inositol 3′ kinase inhibition did not block iNOS induction, whereas nuclear factor κB inhibition did. The sarcoma virus tyrosine kinase (Src) family

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Tozzi, Alessandro, Ezia Guatteo, Luigi Caputi, Giorgio Bernardi, and Nicola B. Mercuri. "Group I mGluRs Coupled to G Proteins Are Regulated by Tyrosine Kinase in Dopamine Neurons of the Rat Midbrain." Journal of Neurophysiology 85, no. 6 (2001): 2490–97. http://dx.doi.org/10.1152/jn.2001.85.6.2490.

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Metabotropic glutamate receptors (mGluRs) modulate neuronal function via different transduction mechanisms that are either dependent or independent on G-protein function. Here we investigated, using whole cell patch-clamp recordings in combination with fluorimetric measurements of intracellular calcium concentration ([Ca2+]i), the metabolic pathways involved in the responses induced by group I mGluRs in dopamine neurons of the rat midbrain. The inward current and the [Ca2+]i increase caused by the group I mGluR agonist ( S)-3,5-dihydroxyphenylglycine (DHPG, 100 μM) were permanently activated a

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Gao, Ben-Bo, Hans Hansen, Hong-Chi Chen та Edward P. Feener. "Angiotensin II stimulates phosphorylation of an ectodomain-truncated platelet-derived growth factor receptor-β and its binding to class IA PI3K in vascular smooth muscle cells". Biochemical Journal 397, № 2 (2006): 337–44. http://dx.doi.org/10.1042/bj20060095.

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PI3K (phosphoinositide 3-kinase) activity is involved in Ang (angiotensin) II-stimulated VSMC (vascular smooth muscle cell) growth and hypertrophy. In the present study, we demonstrate that the inhibition of PI3K in VSMCs by expression of a dominant-negative p85α mutant lacking the p110-binding domain (Δp85), or by treatment of cells with LY294002, inhibited Ang II-stimulated PAI-1 (plasminogen activator inhibitor-1) mRNA expression. Using a GST (glutathione S-transferase) fusion protein containing the p85 N-terminal SH2 (Src homology 2) domain as ‘bait’ followed by MS/MS (tandem MS), we ident

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Gaben, Anne-Marie, Cécile Saucier, Monique Bedin, Gérard Redeuilh, and Jan Mester. "Mitogenic Activity of Estrogens in Human Breast Cancer Cells Does Not Rely on Direct Induction of Mitogen-Activated Protein Kinase/Extracellularly Regulated Kinase or Phosphatidylinositol 3-Kinase." Molecular Endocrinology 18, no. 11 (2004): 2700–2713. http://dx.doi.org/10.1210/me.2003-0133.

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Abstract We have addressed the question of rapid, nongenomic mechanisms that may be involved in the mitogenic action of estrogens in hormone-dependent breast cancer cells. In quiescent, estrogen-deprived MCF-7 cells, estradiol did not induce a rapid activation of either the MAPK/ERK or phosphatidylinositol-3 kinase (PI-3K)/Akt pathway, whereas the entry into the cell cycle was documented by the successive inductions of cyclin D1 expression, hyperphosphorylation of the retinoblastoma protein (Rb), activity of the promoter of the cyclin A gene, and DNA synthesis. However, pharmacological inhibit

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Bhattacharya, Sujoy, Ramesh M. Ray та Leonard R. Johnson. "Integrin β3-mediated Src activation regulates apoptosis in IEC-6 cells via Akt and STAT3". Biochemical Journal 397, № 3 (2006): 437–47. http://dx.doi.org/10.1042/bj20060256.

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Intestinal epithelial (IEC-6) cells are resistant to apoptosis following the inhibition of ODC (ornithine decarboxylase) and subsequent polyamine depletion. The depletion of polyamines rapidly activates NF-κB (nuclear factor κB) and STAT3 (signal transducer and activator of transcription 3), which is responsible for the observed decrease in apoptosis. Since both NF-κB and STAT3 signalling pathways can be activated by Src kinase, we examined its role in the antiapoptotic response. Inhibition of ODC by DFMO (α-difluoromethylornithine) increased the activity of Src and ERK1/2 (extracellular-signa

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Yano, Naohiro, Daisuke Suzuki, Masayuki Endoh та ін. "β-Adrenergic Receptor Mediated Protection against Doxorubicin-Induced Apoptosis in Cardiomyocytes: The Impact of High Ambient Glucose". Endocrinology 149, № 12 (2008): 6449–61. http://dx.doi.org/10.1210/en.2008-0292.

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Recent studies have demonstrated that the β2-adrenergic receptor (β2AR)-Gαi signaling pathway exerts a cardiac antiapoptotic effect. The goals of this study were to determine the intracellular signaling factors involved in β2AR-mediated protection against doxorubicin-induced apoptosis in H9c2 cardiomyocyte and explore the impact of high ambient glucose on the antiapoptotic effect. Under physiological glucose environment (100 mg/dl), β2AR stimulation prevented doxorubicin-induced apoptosis, which was attenuated by cotreatment with wortmannin, a phosphoinositide 3-kinase (PI3K) inhibitor, or tra

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Kumar, M. Sathish, and M. Vijey Aanandhi. "Design, Molecular docking, Synthesis and Biological evaluation of 5, 7 dimethyl pyrido(2, 3-d)pyrimidin-4-one and 4,5 dihydro pyrazolo (3, 4-d) pyrimidines for cytotoxic activity." Research Journal of Pharmacy and Technology, June 29, 2021, 3029–38. http://dx.doi.org/10.52711/0974-360x.2021.00530.

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The fused pyrimidine derivatives are potent tyrosine kinase and thymidylate synthase inhibitors. The compound 3-(4-sulphonyl amino)-2-methyl thio-6-phenyl azo-5, 7-dimethyl pyrido(2,3-d)pyrimidin-4-one was synthesized from Ethyl 2-amino-4,6-dimethylpyridine-3-carboxylate, benzene diazonium chloride, benzene sulphonyl amino isothiocyanate in subsequent reactions. 1-(1, 3-benzothiazol-2-yl)-3-methyl-4-phenyl-1H-pyrazolo[3,4-d]pyrimidines were synthesized from 1, 3-benzothiazole, 2-thiol, Hydrazine Hydrate, 2-hydrazinyl-1, 3-benzothiazole and aldehydes in subsequent reactions. Twenty-five derivat

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Ashok, D., and K. Pallavi. "SYNTHESIS OF 1-ARYL-5-METHYL-4-[4-ARYL-6-(3-OXO-1,4-BENZOTHIAZIN-6-YL)PYRID-2-YL]PYRAZOLES AND 1-ARYL-5-METHYL-4-[2-AMINO-4-ARYL-PYRIMIDIN-6-YL]PYRAZOLES AS ANTIBACTERIAL AGENTS." Heterocyclic Communications 14, no. 1-2 (2008). http://dx.doi.org/10.1515/hc.2008.14.1-2.33.

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"Orphan designation: 2-(isopropylamino)-3-methyl-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one, Treatment of tenosynovial giant cell tumour, localised and diffuse type." Case Medical Research, February 24, 2020. http://dx.doi.org/10.31525/cmr-2a32a82.

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Kim, Tae Woo, Da-Won Hong та Sung Hee Hong. "CB13, a novel PPARγ ligand, overcomes radio-resistance via ROS generation and ER stress in human non-small cell lung cancer". Cell Death & Disease 11, № 10 (2020). http://dx.doi.org/10.1038/s41419-020-03065-w.

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Abstract Peroxisome proliferator-activated receptor gamma (PPARγ) is a well-known therapeutic target for type 2 diabetes as well as is a potential target for effective anti-cancer drug, since PPARγ ligands such as ciglitazone (Cig) frequently cause cell death in many types of cancer cells and suppress tumor growth. However, many cancer patients acquire chemo-resistance or radio-resistance after chemo or radiotherapy, and it is still unclear. In the difficulty of well-known anti-cancer drugs, we developed a novel PPARγ agonist CB13 (1-benzyl-5-(4-methylphenyl) pyrido [2,3-d]pyrimidine-2,4(1H,3H

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