- Design and synthesis of pyrazolo[3,4-d]pyrimidines: Nitric oxide releasing compounds targeting hepatocellular carcinoma
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A new series of pyrazolo[3,4-d]pyrimidines tethered with nitric oxide (NO) producing functionality was designed and synthesized. Sulforhodamine B (SRB) protein assay revealed that NO releasing moiety in the synthesized compounds significantly decreased the cell growth more than the des-NO analogues. Compounds 7C and 7G possessing N-para-substituted phenyl group, released the highest NO concentration of 4.6% and 4.7% respectively. Anti-proliferative activity of synthesized compounds on HepG2 cell line identified compounds 7h, 7p, 14a and 14b as the most cytotoxic compounds in the series of IC50?=?3, 5, 3 and 5?μM, respectively, compared to erlotinib as a reference drug (IC50?=?25?μM). Flow cytometry studies revealed that 7?h arrested the cells in G0/G1 phase of cell cycle while 7p arrested the cells in S phase. Moreover, docking study of the synthesized compounds on EGFR (PDB code: 1M17) and cytotoxicity study indicated that N-1 phenyl para substitution, pyrazole C-3 alkyl substitution and tethering the nitrate moiety through butyl group had a significant impact on the activity.
- Elshaier, Yaseen A.M.M.,Shaaban, Mohamed A.,Abd El Hamid, Mohammed K.,Abdelrahman, Mostafa H.,Abou-Salim, Mahrous A.,Elgazwi, Sara M.,Halaweish, Fathi
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p. 2956 - 2970
(2017/05/24)
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- Synthesis of novel 2-alkyl-4-substituted-amino-pyrazolo[3,4-d]pyrimidines as new leads for anti-bacterial and anti-cancer activity
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Treatment of 6-alkyl-1-phenyl-4-chloro-(1H)-pyrazolo[3,4-d]pyrimidines, with different amines afforded a series of compounds whose identity and purity were confirmed by spectral and analytical means. The compounds were tested for antibacterial activity against four organisms viz. Staphylococcus aureus (Gram positive), S. epidermidis (Gram positive), Bacillus subtilis (Gram positive), Escherichia coli (Gram negative) using amoxicillin as standard control. Compounds 4d, 6b, 6c have shown best antibacterial activity in the series. The antiproliferative activity was tested against human skin cancer cell line G361. The compounds 3d, 4d, 5b, 5d, 5e, 6c, 7a were found to be the best of the series and showed the activity at micromolar concentration.
- Devarakonda, Murty,Doonaboina, Raghava,Vanga, Sreedher,Vemu, Jahnavi,Boni, Sathoshini,Mailavaram, Raghu Prasad
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p. 1090 - 1101
(2013/04/10)
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- Montmorillonite K10 as an efficient and reusable catalyst for the synthesis of substituted pyrazolo[3,4-d]pyrimidin-4-ones under solvent-free conditions
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A green and efficient method for the synthesis of pyrazolo[3,4-d]pyrimidin- 4-ones through heterocyclization reaction of 5-amino-1-phenyl-1H-pyrazole-4- carboxamides with orthoesters using Montmorillonite K10, as an effective and reusable catalyst, under solventfree conditions is described. The present methodology offers several advantages, such as a simple procedure with an easy work-up, short reaction times, high yields and the absence of any volatile and hazardous organic solvents. Furthermore, the products could be separated simply from the catalyst and the catalyst could be recycled and reused with only slight reduction in its catalytic activity.
- Davoodnia,Moloudi,Tavakoli-Hoseini,Shaker
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experimental part
p. 2195 - 2198
(2012/09/07)
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- Synthesis of pyrazolo[3,4-d]pyrimidin-4-ones catalyzed by Bronsted-acidic ionic liquids as highly efficient and reusable catalysts
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A convenient and efficient method for the synthesis of pyrazolo[3,4-d] pyrimidin-4-ones via heterocyclization reaction of 5-amino-1H-pyrazole-4- carboxamides with triethyl orthoesters using two Br?nsted-acidic ionic liquids, 3-methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate [MIM +(CH2)4SO3H][HSO4 -] or N-(4-sulfonic acid)butyl triethylammonium hydrogen sulfate [Et3N+(CH2)4SO3H] [HSO4-], as efficient homogeneous catalysts under solvent-free conditions is described.
- Tavakoli-Hoseini, Niloofar,Moloudi, Raheleh,Davoodnia, Abolghasem,Shaker, Mohammad
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experimental part
p. 2421 - 2426
(2012/03/08)
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- Synthesis of some pyridothienopyrazolopyrimidopyrimidine and mercaptomethylpyrazolopyrimidine derivatives
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Mercaptomethylpyrazolopyrimidine (2) was synthesized and reacted with ethyl chloroacetate to afford ethyl pyrazolpyrimidinylmethylmercapto acetate (3), which in turn was converted into the corresponding carbohydrazide 4. Carbohydrazide 4 reacts with a var
- Kamal El-Dean,Elkhawaga,Radwan, Sh. M.,Ahmed
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experimental part
p. 2034 - 2048
(2010/02/28)
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- Synthesis of some pyrazolopyrimidines
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Some 1-phenyl-1H-6-(un)substituted-5-substituted-arylpyrazolopyrimidine-4(5H)-ones are synthesized by transformation of 6-methyl-1-phenyl-1H-pyrazolooxazin-4-ones and also from 5-amino-4-carbethoxy-1-phenyl pyrazole.
- Pathak, U. S.,Gandhi, Sudha,Rathod, I. S.
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p. 734 - 737
(2007/10/02)
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- Versatile synthesis of 6-alkyl/aryl-1H-pyrazolopyrimidin-4-ones
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Condensation of 5-amino-1H-pyrazole-4-carboxamide (1a) with various aromatic aldehydes furnishes 6-substituted-1H-pyrazolepyrimidin-4(5H)-ones (4a-f) via the intermediates 5-(N-arylideneamino)pyrazole-4-carboxamides (3a-f).Compounds 4a-f have also
- Reddy, K Hemender,Reddy, A Panduranga,Veeranagaiah, V
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p. 163 - 166
(2007/10/02)
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- STUDIES ON PYRAZOLOPYRIMIDINE DERIVATIVES. XVIII. FACILE PREPARATION OF 1H-PYRAZOLOPYRIMIDIN-4(5H)-ONES
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Reaction of 5-amino-1-phenyl-1H-pyrazole-4-carboxamide (4) with the esters (3a-h) in the presence of sodium ethoxide in ethanol gave 1-phenyl-1H-pyrazolopyrimidin-4(5H)-one (1a) and its 6-substituted derivatives (1b-h).Similar treatment of 5-amino-1-methyl-1H-pyrazole-4-carboxamide (5) with 3a-h gave the 1-methyl-1H-pyrazolopyrimidin-4(5H)-ones (2a-h).
- Miyashita, Akira,Iijima, Chihoko,Higashino, Takeo,Matsuda, Hideaki
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p. 1309 - 1314
(2007/10/02)
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