16617-46-2Relevant articles and documents
Preparation of 8-Aza-7-deazaaristeromycin and -neplanocin A and Their 5′-Homologs
Wang, Haisheng,Zhang, Yan,Ye, Wei,Schneller, Stewart W.
, p. 1132 - 1135 (2015)
The synthesis of new members of the aristeromycin and neplaoncin A families of carbocyclic nucleosides possessing the 1H-pyrazolo[3,4-d]pyrimidine ring is reported. For this purpose, an adapted route to 4-amino-1H-pyrazolo[3,4-d]pyrimidine is described.
Synthesis of triazenopyrazole derivatives as potential inhibitors of HIV-1
Larsen, Janus S.,Zahran, Magdy A.,Pedersen, Erik B.,Nielsen, Claus
, p. 1167 - 1173 (1999)
Ethoxymethylenemalononitrile and bis(methylthio)methylenemalononitrile were condensed with hydrazine hydrate to yield 5-aminopyrazole-4-carbonitrile (3a) and 5-amino-3-methylthiopyrazole-4-carbonitrile (3b), respectively. These compounds were treated with nitrous acid and coupled with different secondary amines to yield the triazenopyrazoles 4a-j. 5-(3,3-Diethyl-1-triazeno)pyrazole-4-carbonitrile (4c) was transferred into its two regioisomeric 2-deoxyribose nucleosides 5a,b which were subsequently hydrolyzed with H2O2/OH- to give the corresponding carboxamides 6a,b. All synthesized compounds were tested for biological activity against HIV-1 and herpes simplex virus, but only 4c showed moderate activity against HIV-1 with ED50 = 32μM.
Synthesis, anticancer evaluation, and molecular docking studies of some novel 4,6-disubstituted pyrazolo[3,4-d]pyrimidines as cyclin-dependent kinase 2 (CDK2) inhibitors
Cherukupalli, Srinivasulu,Chandrasekaran, Balakumar,Kry?tof, Vladimír,Aleti, Rajeshwar Reddy,Sayyad, Nisar,Merugu, Srinivas Reddy,Kushwaha, Narva Deshwar,Karpoormath, Rajshekhar
, p. 46 - 59 (2018)
A novel series of 4,6-disubstituted pyrazolo[3,4-d]pyrimidines (7–43) bearing various anilines at C-4 position and thiophenethyl or thiopentane moieties at C-6 position have been designed and synthesized by molecular hybridization approach. All the synthesized compounds were evaluated for in vitro CDK2/cyclin E and Abl kinase inhibitory activity as well as anti-proliferative activity against K-562 (chronic myelogeneous leukemia), and MCF-7 (breast adenocarcinoma) cell lines. The structure–activity relationship (SAR) studies revealed that compounds with thiophenethyl group at C-6 with mono-substituted anilines at C-4 exhibited better CDK2 inhibitory activity compared to alkyl group (thiopentane) at C-6 and di-substituted anilines at C-4 of the scaffold. In particular, compounds having 2-chloro, 3-nitro and 4-methylthio aniline groups at C-4 displayed significant enzymatic inhibitory activity against CDK2 with single digit micromolar IC50 values. The in silico molecular docking studies suggested possible binding orientation and the binding energies were in agreement with the observed SAR as well as experimental results. In addition, some of the synthesized compounds showed anti-proliferative effects against K-562 and MCF-7 cancer cell lines with IC50 values in a micromolar range. Thus, the synthesized compounds could be considered as new anticancer hits for further lead optimization.
Design and synthesis of novel heterofused pyrimidine analogues as effective antimicrobial agents
Chandrasekaran, Balakumar,Cherukupalli, Srinivasulu,Karunanidhi, Sivanandhan,Kajee, Afsana,Aleti, Rajeshwar Reddy,Sayyad, Nisar,Kushwaha, Babita,Merugu, Srinivas Reddy,Mlisana, Koleka P.,Karpoormath, Rajshekhar
, p. 246 - 255 (2019/02/15)
A total of 66 novel heterofused pyrimidine analogues (pyrazolo[3,4-d]pyrimidine (7-43) and pyrido[2,3-d]pyrimidine (51a-l & 52a-h)) were synthesized by employing suitable methods. The desired structures of all the synthesized compounds were confirmed based on FT-IR, 1H NMR, 13C NMR and HRMS experimental data. Further, 19F NMR and 1H-15N HMBC of the representative compound were presented. All the final compounds were screened for their in vitro antitubercular (Mycobacterium tuberculosis; H37 Rv), antibacterial (S. aureus, B. subtilis, E. coli and P. aeruginosa) and antifungal (C. neoformans, C. albicans and A. niger) activities. Compounds 51d, 51j, 51k, 51l, and 51g displayed good antibacterial and antifungal activity (MIC = 12.5 μg/ml) against bacterial and fungal strains, while moderate inhibition (MIC = 59 μM) was observed for 51l against H37 Rv strain.
Thermal Ring-Opening of Pyrazolo[3,4-d][1,2,3]triazin-4-ones: An Experimental and Theoretical Study
Colomer, Juan P.,Sciú, María L.,Ramirez, Cristina L.,Soria-Castro, Silvia M.,Vera, D. Mariano A.,Moyano, Elizabeth L.
, p. 1514 - 1524 (2018/03/30)
Several 3-pyrazolylcarbonyl-pyrazolo[3,4-d][1,2,3]triazin-4-ones have been prepared from 5-amino-1H-pyrazole-4-carbonitriles through a simple sequence. In the first step, diazotization of the corresponding aminopyrazoles afforded pyrazolo[3,4-d][1,2,3]triazin-4-ones. Next, thermal rearrangement of these compounds through nitrogen elimination gave the final products. The proposed mechanism for the ring-opening of the pyrazolotriazinones to give the pyrazolylcarbonyl-pyrazolotriazinones involves the generation of an iminoketene intermediate, which reacts with a second molecule of pyrazolotriazinone. The complete mechanism of product formation involving the iminoketene intermediate, and all other reasonable pathways, have been explored in detail through DFT calculations. Furthermore, additional experiments to corroborate the presence of the iminoketene intermediate were carried out.
