530-53-0Relevant articles and documents
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Oripov et al.
, (1979)
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Insight into the chemical bonding and electrostatic potential: A charge density study on a quinazoline derivative
Tojiboev,Wang,Pan,Englert,Turgunov,Okmanov
, p. 1012 - 1017 (2013)
2,3-Trimethylene-3,4-dihydroquinazoline shares the heterocyclic core with natural compounds and synthetic drugs. The hydrochloride of the compound forms excellent dihydrate crystals which have allowed us to collect high-resolution X-ray diffraction data and obtain the experimental charge density. The solid may be understood as built up from pairs of heterocyclic cations and chloride anions; a direct hydrogen bond links the halide to the formally cationic pyrimidine NH group. The hydrate water molecules interact with the anions, forming an infinite chain along the crystallographic a axis between the stacks of the heterocyclic cations. Based on the experimental charge density, a dipole moment of 16.1 Debye is calculated for a pair of the hydrogen-bonded quinazolinium cation and the chloride anion in the extended crystal structure.
Synthesis, characterization, and antimicrobial activity of novel hydrazone-bearing tricyclic quinazolines
Nasrullaev, Azizbek,Bozorov, Khurshed,Bobakulov, Khayrulla,Zhao, Jiangyu,Nie, Li Fei,Turgunov, Kambarali K.,Elmuradov, Burkhon,Aisa, Haji A.
, p. 2287 - 2300 (2019)
Abstract: A series of novel substituted hydrazone-bearing (unsymmetrical azines, RR1C=N–N=CR2R3) tricyclic quinazoline derivatives are reported. All novel compounds were characterized by 1H, 13C nuclear magnetic resonance (NMR), and Fourier-transform infrared (FT-IR) analyses. An important intermediate (E/Z)-hydrazono-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazoline (8) was synthesized from tricyclic quinazoline-4-thione 7 using 80?% of hydrazine hydrate. In addition, the antimicrobial activity of all synthesized novel compounds against three types of pathogenic microorganism was tested, revealing that some compounds showed satisfactory good activity and could serve as lead compounds for further drug discovery and development. Graphical abstract: [Figure not available: see fulltext.].
Copper-Catalyzed Photoinduced Radical Domino Cyclization of Ynamides and Cyanamides: A Unified Entry to Rosettacin, Luotonin A, and Deoxyvasicinone
Baguia, Hajar,Deldaele, Christopher,Romero, Eugénie,Michelet, Bastien,Evano, Gwilherm
, p. 3022 - 3030 (2018)
A general and efficient procedure for the copper-catalyzed photoinduced radical domino cyclization of ynamides and cyanamides providing an efficient access to complex tri-, tetra- and pentacyclic nitrogen heterocycles is reported. Upon visible light irrad
Deacylation-aided C–H alkylative annulation through C–C cleavage of unstrained ketones
Dong, Guangbin,Xu, Yan,Zhou, Xukai
, p. 703 - 710 (2021/08/09)
Arene- and heteroarene-fused rings are pervasive in biologically active molecules. Direct annulation between a C–H bond on the aromatic core and a tethered alkyl moiety provides a straightforward approach to access these scaffolds; however, such a strategy is often hampered by the need of special reactive groups and/or less compatible cyclization conditions. It would be synthetically appealing if a common native functional group can be used as a handle to enable a general C–H annulation with diverse aromatic rings. Here, we show a deacylative annulation strategy for preparing a large variety of aromatic-fused rings from linear simple ketone precursors. The reaction starts with homolytic cleavage of the ketone α C–C bond via a pre-aromatic intermediate, followed by a radical-mediated dehydrogenative cyclization. Using widely available ketones as the robust radical precursors, this deconstructive approach allows streamlined assembly of complex polycyclic structures with broad functional group tolerance. [Figure not available: see fulltext.]
Dual targeting of acetylcholinesterase and tau aggregation: Design, synthesis and evaluation of multifunctional deoxyvasicinone analogues for Alzheimer's disease
Manzoor, Shoaib,Gabr, Moustafa T.,Rasool, Bisma,Pal, Kavita,Hoda, Nasimul
, (2021/09/28)
Development of multitargeted ligands have demonstrated remarkable efficiency as potential therapeutics for Alzheimer's disease (AD). Herein, we reported a new series of deoxyvasicinone analogues as dual inhibitor of acetylcholinesterase (AChE) and tau aggregation that function as multitargeted ligands for AD. All the multitargeted ligands 11(a-j) and 15(a-g) were designed, synthesized, and validated by 1HNMR, 13CNMR and mass spectrometry. All the synthesized compounds 11(a-j) and 15(a-g) were screened for their ability to inhibit AChE, BACE1, amyloid fibrillation, α-syn aggregation, and tau aggregation. All the screened compounds possessed weak inhibition of BACE-1, Aβ42 and α-syn aggregation. However, several compounds were identified as potential hits in the AChE inhibitory screening assay and cellular tau aggregation screening. Among all compounds, 11f remarkably inhibited AChE activity and cellular tau oligomerization at single-dose screening (10 μM). Moreover, 11f displayed a half-maximal inhibitory concentration (IC50) value of 0.91 ± 0.05 μM and half-maximal effective concentration (EC50) value of 3.83 ± 0.51 μM for the inhibition of AChE and cellular tau oligomerization, respectively. In addition, the neuroprotective effect of 11f was determined in tau-expressing SH-SY5Y cells incubated with Aβ oligomers. These findings highlighted the potential of 11f to function as a multifunctional ligand for the development of promising anti-AD drugs.
Novel deoxyvasicinone and tetrahydro-beta-carboline hybrids as inhibitors of acetylcholinesterase and amyloid beta aggregation
Du, Hongtao,Jiang, Xinyu,Ma, Meng,Xu, Huili,Liu, Shuang,Ma, Fang
, (2020/11/09)
A novel series of deoxyvasicinone-tetrahydro-beta-carboline hybrids were synthesized and evaluated as acetylcholinesterase (AChE) and β-amyloid peptide (Aβ) aggregation inhibitors for the treatment of Alzheimer's disease. The results revealed that the der
