- A new synthetic route for the preparation of 2,2′,5′-trimethyl-7-oxo-4,7-dihydro-[6,7′-bipyrazolo[1,5-a]pyrimidine]-3,3′-dicarbonitrile, structural elucidation, Hirshfeld surface analysis, energy framework, density functional theory and molecular docking investigations
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A new bipyrazolo [1,5-a]pyrimidine derivative, 2,2′,5′-trimethyl-7-oxo-4,7-dihydro-[6,7′-bipyrazolo[1,5-a]pyrimidine]-3,3′-dicarbonitrile dihydrate acetic acid solvate (3) has been synthesized via two different methods and characterized by single-crystal X-ray diffraction (XRD) and spectroscopic techniques. A plausible reaction mechanism in the synthesis of 3 through the two synthetic routes used has been proposed. The XRD analysis reveals that the two bicyclic moieties in 3 are close to perpendicular to one another. Some formal double bonds appear localized while others appear to involve some delocalization. In the crystal structure, a layer structure is formed by O-H-O, O-H-N and N-H-O hydrogen bonds, along with weak C-H-O and π-stacking interactions. The energy framework indicates that the packing of 3 is mainly determined by dispersion interactions between molecules. The frontier molecular orbital analysis shows that 3 may act more as a nucleophile than an electrophile. The analysis of the Hirshfeld surface maps and 2D fingerprint plots of 3 reveal that intermolecular hydrogen bonding and H-H, N-H and O-H contacts are the major ones between the units of 3. The antibacterial activity of 3 is explored by its molecular docking into the binding site of tyrosyl-tRNA synthetase, where it formed a stable complex with the amino acids of tyrosyl-tRNA synthetase mainly through hydrogen bonding.
- Albalwi, Hanan,Alharthi, Abdulrahman I.,Anouar, El Hassane,Boulhaoua, Mohammed,El Ghayati, Lhoussaine,El Hafi, Mohamed,Essassi, El Mokhtar,Lahmidi, Sanae,Lai, Chin-Hung,Mague, Joel T.
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- Practical synthesis of 4H-pyrido[1, 2-a]pyrimidin-4-ones using ethylene glycol as a promoting solvent
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A simple and useful protocol leading to different 4H-pyrido[1, 2-a] pyrimidin-4-ones have been established by cyclization of various 2-amino pyridines with β-oxo ester or alkynoate. The use of ethylene glycol was demonstrated to facilitate this condensati
- Hussain, Mustafa,Liu, Jianhui
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supporting information
(2020/08/13)
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- Pyrido[1,2-a]pyrimidin-4-ones: Ligand-based Design, Synthesis, and Evaluation as an Anti-inflammatory Agent
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In the present study, a series of novel pyrido[1,2-a]pyrimidin-4-one derivatives (1–45) were synthesized, characterized, and evaluated for their anti-inflammatory activity. The structures of all newly synthesized compounds were confirmed by 1H
- Jadhav, Sunil B.,Fatema, Samreen,Patil, Rajesh B.,Sangshetti, Jaiprakash N.,Farooqui, Mazahar
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p. 3299 - 3313
(2017/11/21)
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- Silver-catalyzed highly efficient synthesis of pyrido[1,2-a]pyrimidin-4-ones from 2-aminopyridines and alkynoates
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Pyrimidinone is one of the important nitrogen containing heterocycles due to their wide range of bioactivities. An efficient silver-catalyzed intermolecular cyclization of 2-aminopyridines with various alkynoates has been developed. 2-Substituted 4H-pyrido[1,2-a]pyrimidin-4-ones containing a wide range of functional groups are synthesized in the standard conditions. This transformation is conducted under convenient conditions and affords products in good yields.
- Chen, Zhengwang,Wen, Yuelu,Ding, Hao,Luo, Guotian,Ye, Min,Liu, Liangxian,Xue, Jun
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supporting information
p. 13 - 16
(2016/12/23)
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- Simple and efficient protocol for synthesis of pyrido[1,2-a]pyrimidin-4-one derivatives over solid heteropolyacid catalysts
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Aluminium exchanged tungstophosphoric acid salts with Keggin structure (AlxH3-xPW12O40) were prepared by simple ion exchange method. The prepared heteropolyacid salts were characterized by various techniques suc
- Basahel, Sulaiman N.,Ahmed, Nesreen S.,Narasimharao, Katabathini,Mokhtar, Mohamed
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p. 11921 - 11932
(2016/02/12)
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- Solvent-free synthesis of 4H-Pyrido[1,2-a]pyrimidin-4-ones catalyzed by BiCl3: A green route to a privileged backbone
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An extensive array of 4H-pyrido[1,2-a]pyrimidin-4-ones have been synthesized from commercially available 2-aminopyridines and β-oxo esters with excellent yields under solvent-free conditions. The reaction, catalyzed by cheap and nontoxic BiCl3,
- Roslan, Irwan I.,Lim, Qiu-Xuan,Han, Aijuan,Chuah, Gaik-Khuan,Jaenicke, Stephan
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supporting information
p. 2351 - 2355
(2015/04/22)
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- Synthesis of aryl-heteroaryl ureas (AHUs) based on 4-aminoquinoline and their evaluation against the insulin-like growth factor receptor (IGF-1R)
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The insulin-like growth factor receptor (IGF-1R) is a receptor tyrosine kinase (RTK) involved in all stages of the development and propagation of breast and other cancers. The inhibition of IGF-1R by small molecules remains a promising strategy to treat cancer. Herein, we explore SAR around previously characterized lead compound (1), which is an aryl-heteroaryl urea (AHU) consisting of 4-aminoquinaldine and a substituted aromatic ring system. A library of novel AHU compounds was prepared based on derivatives of the 4-aminoquinoline heterocycle (including various 2-substituted derivatives, and naphthyridines). The compounds were screened for in vitro inhibitory activity against IGF-1R, and several compounds with improved activity (3-5 μM) were identified. Furthermore, a computational docking study was performed, which identifies a fairly consistent lowest energy mode of binding for the more-active set of inhibitors in this series, while the less-active inhibitors do not adopt a consistent mode of binding.
- Engen, William,O'Brien, Terrence E.,Kelly, Brendan,Do, Jacinda,Rillera, Liezel,Stapleton, Lance K.,Youngren, Jack F.,Anderson, Marc O.
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scheme or table
p. 5995 - 6005
(2010/09/30)
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- New efficient approach for the synthesis of 2-alkyl(aryl) substituted 4H-pyrido[1,2-a]pyrimidin-4-ones
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A new, efficient and easy route for the preparation of a series of 2-alkyl(aryl) substituted 4-oxo-4H-pyrido[l,2-a]pyrimidines, where alkyl = CH3; aryl = C6H5, 4-FC6H 4,4-ClC6H4,
- Bonacorso, Helio G.,Righi, Fernando J.,Rodrigues, Isadora R.,Cechinel, Cleber A.,Costa, Michelle B.,Wastowski, Arci D.,Martins, A. P. Marcos,Zanatta, Nilo
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p. 229 - 233
(2007/10/03)
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- N-SUBSTITUTED AZABICYCLOALKANE DERIVATIVES, THEIR PREPARATION AND USE
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Compounds of the formula I STR1 where B, R 1, R 2, n, R. sup.3, A, X, Y and Z have the meanings stated in the description, and their preparation are described. The novel ompounds are suitable for controlling diseases.
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- N-substituted azabicycloheptane derivatives
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Abstract of the Disclosure: Compounds of the formula I STR1 where R1, R2, n , R3, A, X, Y and Z have the meanings stated in the description, and the preparation thereof are described. The novel compounds are suitable for controlling diseases , i.e., as neuroleptics, antidepressants, sedatives, hypnotics, CNS protectives or muscle relaxants.
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- Synthesis and antileishmanial activity of some pyridopyrimidines and phenanthrolines
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Synthesis and in vitro biological evaluation for antileishmanial activity of a series of pyridopyrimidines, phenanthrolines are reported.Amongst pyridopyrimidines, compounds 6,7 and 9 have been found to possess promising activity.However, all the tested phenanthroline derivatives exhibit moderate to good anti-leishmania activity.
- Satti, N. K.,Suri, K. A.,Suri, O. P.,Kapil, A.
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p. 978 - 980
(2007/10/02)
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