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Sapavat Madhavi, Reddymasu Sreenivasulu, Jyothsna Pragathi Yazala, Rudraraju Ramesh Raju
A series of ten novel chalcone incorporated quinazoline derivatives (11a-11j) were designed and synthesized. All the synthesized compounds were evaluated for their anticancer activities against four human cancer cell lines (A549, HT-29, MCF-7 and A375). Among them, four compounds, 11f, 11g, 11i and 11j showed more potent anticancer activity than the control drug, Combretastatin - A4.
February 2017: Saudi Pharmaceutical Journal: SPJ: the Official Publication of the Saudi Pharmaceutical Society
Matthias Zeller, Gabriel Lima Barros de Araujo, Trev Parker, Amrinder Singh Rai, Stephen R Byrn
Afatinib (systematic name: N-{4-(3-chloro-4-fluoro-anilino)-7-[(tetra-hydro-furan-3-yl)-oxy]quinazolin-6-yl}-4-(di-methyl-amino)-but-2-enamide), is a specific in-hibitor of the ErbB family of tyrosine kinases. The free base form crystallizes from aceto-nitrile as a mixed water-aceto-nitrile solvent, C24H25ClFN5O3·0.25C2H3N·2H2O. It crystallizes with two independent mol-ecules (A and B) in the asymmetric unit of the chiral space group P4212, but exhibits close to perfect pseudo-inversion symmetry, emulating P4/ncc that relates the two mol-ecules to each other...
March 1, 2017: Acta Crystallographica. Section E, Crystallographic Communications
Mehboobali Pannipara, Abdullah G Al-Sehemi, Abul Kalam, T N Mohammed Musthafa
Herein, we report the synthesis of two dihydroquinazolinone derivative 2-(2-Hydroxy-naphthalen-1-yl)-2, 3-dihydro-1H-quinazolin-4-one (1) and 2-(3-Methyl-thiophen-2-yl)-2,3-dihydro-1H-quinazolin-4-one (2) by using 2-aminobenzamide, 2-hydroxybenzaldehyde and 3-methyl thiophene-2-carboxaldehyde. The synthesized compounds were characterized by 1H NMR, 13C NMR, FT-IR and its spectral, photophysical, intramolecular charge transfer characteristics were studied by absorption and emission spectroscopy. The synthesized compound exhibits significant changes in their photophysical properties depending on the solvent polarity...
March 17, 2017: Journal of Fluorescence
Hailong Shi, Yan Li, Xiaorong Ren, Yaohong Zhang, Zhen Yang, Chenze Qi
6-amino-4-(4-phenoxyphenylethylamino)quinazoline (QNZ) is an excellent quinazoline-containing NF-κB inhibitor also acting as a novel anticancer agent. Considering both the medicinal significance of quinazoline scaffold and the tunable functionality of Michael acceptor-centric pharmacophores in the electrophilicity-based prooxidant strategy, we designed a novel QNZ-inspired electrophilic molecule QNZ-A by introducing a Michael acceptor unit at position-6 of quinazoline ring in QNZ. Our results identified QNZ-A as a promising selective cytotoxic agent against A549 cells...
March 14, 2017: Biochemical and Biophysical Research Communications
Mostafa M Hamed, Sarah S Darwish, Jennifer Herrmann, Ashraf H Abadi, Matthias Engel
The activation of the NF-κB transcription factor is a major adaptive response induced upon treatment with EGFR kinase inhibitors, leading to the emergence of resistance in nonsmall cell lung cancer and other tumor types. To suppress this survival mechanism, we developed new thiourea quinazoline derivatives that are dual inhibitors of both EGFR kinase and the NF-κB activity. Optimization of the hit compound, identified in a NF-κB reporter gene assay, led to compound 9b, exhibiting a cellular IC50 for NF-κB inhibition of 0...
March 28, 2017: Journal of Medicinal Chemistry
Renee Fleeman, Kurt S Van Horn, Megan M Barber, Whittney N Burda, David L Flanigan, Roman Manetsch, Lindsey N Shaw
We previously reported a series of N(2) ,N(4) -disubstituted quinazoline-2,4-diamine as dihydrofolate reductase inhibitors, with potent in vitro and in vivo antibacterial activity against MRSA strains. In this work we extend our previous study to the Gram-negative pathogen Acinetobacter baumannii We determined that optimized N(2) ,N(4) -disubstituted quinazoline-2,4-diamines are strongly antibacterial against multi-drug resistant A. baumannii strains when the 6-position is substituted with a halide or an alkyl substituent...
March 13, 2017: Antimicrobial Agents and Chemotherapy
Chenzhou Hao, Wanxu Huang, Xiaodong Li, Jing Guo, Meng Chen, Zizheng Yan, Kai Wang, Xiaolin Jiang, Shuai Song, Jian Wang, Dongmei Zhao, Feng Li, Maosheng Cheng
Upon analysis of the reported crystal structure of PAK4 inhibitor KY04031 (PAK4 IC50 = 0.790 μM) in the active site of PAK4, we investigated the possibility of changing the triazine core of KY04031 to a quinazoline. Using KY04031 as a starting compound, a library of 2, 4-diaminoquinazoline derivatives were designed and synthesized. These compounds were evaluated for PAK4 inhibition, leading to the identification of compound 9d (PAK4 IC50 = 0.033 μM). Compound 9d significantly induced the cell cycle in the G1/S phase and inhibited migration and invasion of A549 cells that over-express PAK4 via regulation of the PAK4-LIMK1 signalling pathway...
March 8, 2017: European Journal of Medicinal Chemistry
Tomás Herraiz, Hugo Guillén, Vicente J Arán, Antonio Salgado
Peganum harmala L. is a medicinal plant from the Mediterranean region and Asia currently used for recreative psychoactive purposes (Ayahuasca analogue), and increasingly involved in toxic cases. Its psychopharmacological and toxicological properties are attributed to quinazoline and β-carboline alkaloids. In this work three major quinazoline alkaloids were isolated from P. harmala extracts and characterized as peganine (vasicine), deoxypeganine (deoxyvasicine) and a novel compound identified by HPLC-DAD-MS and NMR as peganine β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside (peganine glycoside)...
March 7, 2017: Food and Chemical Toxicology
K Hęclik, A Szyszkowska, D Trzybiński, K Woźniak, A Klasek, I Zarzyka
1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione reacts with ethyl bromoacetate under mild conditions to give 2-(ethoxycarbonylmethyl)-1-phenyl-6H-imidazo[1,5-c]quinazoline-3,5-dione (MEPIQ) and next 2,6-bis(ethoxycarbonylmethyl)-1-phenylimidazo[1,5-c]quinazoline-3,5-dione (BEPIQ). The products were isolated at high yield and identified on the basis of IR, (1)H- and (13)C-NMR, UV spectroscopy, and X-ray crystallography. Diester (BEPIQ) can be presented by 16 possible pair of enantiomers. Only one pair of them is the most stable and crystallizes which is shown crystallographic research...
April 2017: Journal of Molecular Modeling
Niraj K Vishwakarma, Ajay K Singh, Yoon-Ho Hwang, Dong-Hyeon Ko, Jin-Oh Kim, A Giridhar Babu, Dong-Pyo Kim
Simultaneous capture of carbon dioxide (CO2) and its utilization with subsequent work-up would significantly enhance the competitiveness of CO2-based sustainable chemistry over petroleum-based chemistry. Here we report an interfacial catalytic reaction platform for an integrated autonomous process of simultaneously capturing/fixing CO2 in gas-liquid laminar flow with subsequently providing a work-up step. The continuous-flow microreactor has built-in silicon nanowires (SiNWs) with immobilized ionic liquid catalysts on tips of cone-shaped nanowire bundles...
March 6, 2017: Nature Communications
Mohd Usman Mohd Siddique, Glen J P McCann, Vinay R Sonawane, Neill Horley, Linda Gatchie, Prashant Joshi, Sandip B Bharate, Venkatesan Jayaprakash, Barij N Sinha, Bhabatosh Chaudhuri
CYP1B1 is implicated to have a role in the development of breast, ovarian, renal, skin and lung carcinomas. It has been suggested that identification of potent and specific CYP1B1 inhibitors can lead to a novel treatment of cancer. Flavonoids have a compact rigid skeleton which fit precisely within the binding cavity of CYP1B1. Systematic isosteric replacement of flavonoid 'O' atom with 'N' atom led to the prediction that a 'quinazoline' scaffold could be the basis for designing potential CYP1B1 inhibitors...
April 21, 2017: European Journal of Medicinal Chemistry
Caixia Xie, Zeyuan Zhang, Danyang Li, Jian Gong, Xushuang Han, Xuan Liu, Chen Ma
An efficient, green, and novel method for the synthesis of N-heterocycle-fused quinoxalines is reported herein. Dimethyl sulfoxide was used as both a reactant and a solvent in this reaction. A wide range of products in moderate to excellent yields were obtained, including pyrrolo[1,2-a]quinoxalines, indolo[1,2-a]quinoxalines, 1H-pyrrolo[3,2-c]quinolines, and benzo[4,5]imidazo[1,2-c]quinazolines.
March 13, 2017: Journal of Organic Chemistry
Yaling Zhang, Ying Zhang, Juan Liu, Li Chen, Lijun Zhao, Baolin Li, Wei Wang
A series of novel 4-arylamino-6-(5-substituted furan-2-yl)quinazoline derivatives were designed, synthesized and evaluated on biological activities in vitro. Compound 2a, 3a and 3c exhibited highly anti-proliferation activities on all tested tumor cell lines including SW480, A549, A431 and NCI-H1975 cells. Especially, compound 2a not only exhibited strong anti-proliferation activities against the tumor cell lines which expressed wild type or mutant EGFR(L858R/T790M), but also showed the most potent inhibitory activity toward wild type EGFR (IC50=5...
April 1, 2017: Bioorganic & Medicinal Chemistry Letters
Tarosh S Patel, Satish F Vanparia, Urmila H Patel, Ritu B Dixit, Chaitanya J Chudasama, Bhavesh D Patel, Bharat C Dixit
An optimization of a modified Grimmel's method for N-heterocyclization of Leucine linked sulphonamide leading to 2,3-disustituted-4-quinazolin-(3H)-ones was accomplished. Further, nineteen hybrid quinazolinone motifs (5a-5s) were synthesized by N-heterocyclization reaction under microwave irradiation using TEAA (IL) as green solvent as well as catalyst. The in vitro screening of the hybrid entities against the plasmodium species P. falciparum yielded five antimalarial potent molecules 5g, 5l, 5m, 5n &5p owing comparable activity to the reference drugs...
March 31, 2017: European Journal of Medicinal Chemistry
Zulphikar Ali, Md Jawaid Akhtar, Md Rafi Haider, Ahsan Ahmed Khan, Anees Ahmad Siddiqui, M Shahar Yar
New N3-benzylidene (substituted)-2-phenyl-N4-(thiazol-2-yl)-quinazoline-3,4-(4H)-diamine derivatives were design and synthesized by a sequence of reactions starting from appropriate 6-methyl anthranilic acid. The title compounds were screened for in vitro dipeptidyl peptidase IV (DPP-4) inhibitory activity and diphenyl-2-picryl-hydrazyl (DPPH) assay and results showed significant to good activity in compared to Linagliptin for antidiabetic activity and Ascorbic acid for antioxidant activity. Compound 7g (IC50=0...
February 10, 2017: Bioorganic Chemistry
Young-Won Kwon, So Yeong Cheon, Sung Yun Park, Juhyun Song, Ju-Hee Lee
Microglia are the resident macrophages in the central nervous system (CNS) and play essential roles in neuronal homeostasis and neuroinflammatory pathologies. Recently, microglia have been shown to contribute decisively to neuropathologic processes after ischemic stroke. Furthermore, natural compounds have been reported to attenuate inflammation and pathologies associated with neuroinflammation. Tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione) is a phytoalkaloid with known anti-inflammatory effects in cells...
2017: Frontiers in Cellular Neuroscience
Nada A Noureldin, Hend Kothayer, El-Sayed M Lashine, Mohamed M Baraka, Wafaa El-Eraky, Sally A El Awdan
Series of N-(4-substitutedphenyl)-4-(1-methyl (or 1,2-dimethyl)-4-oxo-1,2-dihydroquinazolin-3(4H)-yl)-alkanamides (5a-j) and 4-chloro-N'-((1-methyl (or 1,2-dimethyl)-4-oxo-1,2-dihydroquinazolin-3(4H)-yl)-alkaloyl)benzohydrazides (6a-f) were designed based on the previously reported essential structural features for anticonvulsant activity. Several amino acids were incorporated within the synthesized quinazolin-4(3H)-ones to improve their bioavailability and the anticonvulsant activity. Synthesis of the target compounds was accomplished in four steps starting from the reaction between N-methyl isatoic anhydride and the appropriate amino acid...
February 2017: Archiv der Pharmazie
Wagdy M Eldehna, Hadia Almahli, Ghada H Al-Ansary, Hazem A Ghabbour, Mohamed H Aly, Omnia E Ismael, Abdullah Al-Dhfyan, Hatem A Abdel-Aziz
Treatment of patients with triple-negative breast cancer (TNBC) is challenging due to the absence of well- defined molecular targets and the heterogeneity of such disease. In our endeavor to develop potent isatin-based anti-proliferative agents, we utilized the hybrid-pharmacophore approach to synthesize three series of novel isatin-based hybrids 5a-h, 10a-h and 13a-c, with the prime goal of developing potent anti-proliferative agents toward TNBC MDA-MB-231 cell line. In particular, compounds 5e and 10g were the most active hybrids against MDA-MB-231 cells (IC50 = 12...
December 2017: Journal of Enzyme Inhibition and Medicinal Chemistry
Xi Liu, Liang-Nian He
Chemical fixation of CO2 into value-added chemicals represents a promising field in view of sustainable development and green synthesis. In this aspect, the construction of heterocyclic compounds from CO2 and readily available starting materials is particularly appealing in both organic and pharmaceutical fields since CO2 can be regarded as carbon and oxygen resource with advantages of abundance, renewability, non-toxicity, and non-flammability. In this chapter, we have summarized elegant protocols with elaborately designed substrates for the direct incorporation of entire CO2 molecule or "CO" or "C" fragments into lactones and other heterocycles such as oxazolidinones, cyclic carbonates, quinazoline-2,4(1H,3H)-diones, etc...
April 2017: Topics in Current Chemistry (Journal)
Ilhem Khelifi, Timothée Naret, Dolor Renko, Abdallah Hamze, Guillaume Bernadat, Jérome Bignon, Christine Lenoir, Joëlle Dubois, Jean-Daniel Brion, Olivier Provot, Mouad Alami
The synthesis and evaluation of a new series of IsoCombretaQuinolines (IsoCoQuines) 2 with a 2-substituted-quinoline in place of the 3,4,5-trimethoxyphenyl ring present in isoCA-4 and CA-4 are described. Most of these compounds displayed a potent cytotoxic activity (IC50 < 10 nM) against a panel of five human cancer cell lines and inhibited tubulin assembly at a micromolar level. The most potent analogue 2b, having a 3-hydroxy-4-methoxyphenyl as B-ring, led to cell cycle arrest in G2/M phase. Docking studies indicate that 2b showed a binding mode comparable to those previously observed with quinazoline analogous (IsoCoQ) and with isoCA-4 at the colchicine binding site of tubulin...
February 15, 2017: European Journal of Medicinal Chemistry
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