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Quinazoline

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https://www.readbyqxmd.com/read/28513683/a-theoretical-study-of-low-lying-singlet-and-triplet-excited-states-of-quinazoline-quinoxaline-and-phthalazine-insight-into-triplet-formation
#1
Mihajlo Etinski, Christel M Marian
Quinazoline, quinoxaline and phthalazine are nitrogen containing heterocyclic aromatic molecules which belong to the class diazanaphthalenes. These isomers have low-lying nπ* and naphthalene-like ππ* states that interact via spin-orbit coupling. In this contribution, we study their structure and electronic states by means of a coupled-cluster method. The computed properties are compared to those of cinnoline which were obtained in our previous study [Etinski et al., Phys. Chem. Chem. Phys., 2014, 16, 4740]...
May 17, 2017: Physical Chemistry Chemical Physics: PCCP
https://www.readbyqxmd.com/read/28501511/identification-of-quinazoline-based-inhibitors-of-irak4-for-the-treatment-of-inflammation
#2
Graham F Smith, Michael D Altman, Brian Andresen, James Baker, Jason D Brubaker, Hongmin Chen, Yiping Chen, Matthew Childers, Anthony Donofrio, Heidi Ferguson, Christian Fischer, Thierry O Fischmann, Craig Gibeau, Alexander Hicks, Sue Jin, Sam Kattar, Melanie A Kleinschek, Erica Leccese, Charles Lesburg, Chaomin Li, Jongwon Lim, Duan Liu, John K F Maclean, Faruk Mansoor, Lilly Y Moy, Erin F Mulrooney, Antoaneta S Necheva, Jeremy Presland, Larissa Rakhilina, Ruojing Yang, Luis Torres, Jie Zhang-Hoover, Alan Northrup
Interleukin-1 receptor associated kinase 4 (IRAK4) has been implicated in IL-1R and TLR based signaling. Therefore selective inhibition of the kinase activity of this protein represents an attractive target for the treatment of inflammatory diseases. Medicinal chemistry optimization of high throughput screening (HTS) hits with the help of structure based drug design led to the identification of orally-bioavailable quinazoline based IRAK4 inhibitors with excellent pharmacokinetic profile and kinase selectivity...
April 18, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28499189/synthesis-biological-evaluation-and-molecular-modeling-study-of-new-1-2-4-triazole-or-1-3-4-thiadiazole-methylthio-derivatives-of-quinazolin-4-3h-one-as-dhfr-inhibitors
#3
Yomna I El-Gazzar, Hanan H Georgey, Shahenda M El-Messery, Heba A Ewida, Ghada S Hassan, Marwa M Raafat, Menna A Ewida, Hussein I El-Subbagh
A new series of 2-mercapto-quinazolin-4-one analogues was designed, synthesized and evaluated for their in vitro DHFR inhibition, antitumor and antimicrobial activity. Compound 17 proved to be the most active DHFR inhibitor with IC50 value of 0.01μM, eight fold more active than methotrexate (MTX). Compounds 16 and 24 showed antitumor activity against human Caco2 colon and MCF-7 breast tumor cell lines with IC50 values of 25.4 and 9.5μg/ml, respectively. Compounds 15, 20, 21 and 30 showed considerable activity against the Gram-positive bacteria Staphylococcus aureus while 24 and 30 proved active against Bacillus subtilis with a magnitude of potency comparable to the broad spectrum antibiotic Ciprofloxacin...
May 4, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/28499171/quinazoline-based-%C3%AE-1-adrenoreceptor-antagonists-with-potent-antiproliferative-activity-in-human-prostate-cancer-cell-lines
#4
Valentina Maestri, Andrea Tarozzi, Elena Simoni, Antonio Cilia, Elena Poggesi, Marina Naldi, Benedetta Nicolini, Letizia Pruccoli, Michela Rosini, Anna Minarini
New α1-adrenoreceptor (α1-AR) antagonists related to prazosin and doxazosin were synthesized by replacing piperazine ring with (S)- or (R)-3-aminopiperidine. Binding studies indicated that the S configuration at the 3-C position of the piperidine ring is crucial for an optimal interaction of the compounds at all three α1-AR subtypes. Quinazolines 9 and 10, bearing a quinone ring on the lateral chain, exhibited also potent antiproliferative activity in LNCaP androgen-sensitive prostate cancer cell lines, higher than that of doxazosin...
May 4, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28498338/synthesis-biological-activity-and-preliminary-in-silico-admet-screening-of-polyamine-conjugates-with-bicyclic-systems
#5
Marta Szumilak, Malgorzata Galdyszynska, Kamila Dominska, Irena I Bak-Sypien, Anna Merecz-Sadowska, Andrzej Stanczak, Boleslaw T Karwowski, Agnieszka W Piastowska-Ciesielska
Polyamine conjugates with bicyclic terminal groups including quinazoline, naphthalene, quinoline, coumarine and indole have been obtained and their cytotoxic activity against PC-3, DU-145 and MCF-7 cell lines was evaluated in vitro. Their antiproliferative potential differed markedly and depended on both their chemical structure and the type of cancer cell line. Noncovalent DNA-binding properties of the most active compounds have been examined using ds-DNA thermal melting studies and topo I activity assay. The promising biological activity, DNA intercalative binding mode and favorable drug-like properties of bis(naphthalene-2-carboxamides) make them a good lead for further development of potential anticancer drugs...
May 12, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28496359/efficacy-of-cr4056-a-first-in-class-imidazoline-2-analgesic-drug-in-comparison-with-naproxen-in-two-rat-models-of-osteoarthritis
#6
Eleonora Comi, Marco Lanza, Flora Ferrari, Valeria Mauri, Gianfranco Caselli, Lucio Claudio Rovati
PURPOSE: CR4056, (2-phenyl-6-(1H-imidazol-1yl) quinazoline), an imidazoline-2 (I2) receptor ligand, is a promising analgesic drug that has been reported to be effective in several animal models of pain. The aim of this study was to evaluate the effects of CR4056 in two well-established rat models of osteoarthritis (OA), mimicking the painful and structural components of human OA. METHODS: Knee OA was induced either by single intra-articular injection of monoiodoacetate (MIA) or by medial meniscal tear (MMT) in the right knee of male rats...
2017: Journal of Pain Research
https://www.readbyqxmd.com/read/28495556/synthesis-crystal-structure-determination-biological-screening-and-docking-studies-of-n-1-substituted-derivatives-of-2-3-dihydroquinazolin-4-1h-one-as-inhibitors-of-cholinesterases
#7
Nargis Sultana, Muhammad Sarfraz, Saba Tahir Tanoli, Muhammad Safwan Akram, Abdul Sadiq, Umer Rashid, Muhammad Ilyas Tariq
Pursuing the strategy of developing potent AChE inhibitors, we attempted to carry out the N(1)-substitution of 2,3-dihydroquinazolin-4(1H)-one core. A set of 32 N-alkylated/benzylated quinazoline derivatives were synthesized, characterized and evaluated for their inhibition against cholinesterases. N-alkylation of the series of the compounds reported previously (N-unsubstituted) resulted in improved activity. All the compounds showed inhibition of both enzymes in the micromolar to submicromolar range. Structure activity relationship (SAR) of the 32 derivatives showed that N-benzylated compounds possess good activity than N-alkylated compounds...
April 17, 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/28489362/atropisomerism-and-conformational-equilibria-impact-on-pi3k%C3%AE-inhibition-of-2-6-amino-9h-purin-9-yl-methyl-5-methyl-3-o-tolyl-quinazolin-4-3h-one-ic87114-and-its-conformationally-restricted-analogs
#8
Alessio Lodola, Serena Bertolini, Matteo Biagetti, Silvia Capacchi, Fabrizio Facchinetti, Paola Maria Gallo, Alice Pappani, Marco Mor, Daniele Pala, Silvia Rivara, Filippo Visentini, Mauro Corsi, Anna Maria Capelli
IC87114 [compound 1, (2-((6-amino-9H-purin-9-yl)methyl)-5-methyl-3-(o-tolyl)quinazolin-4(3H)-one)] is a potent PI3K inhibitor selective for the δ isoform. As predicted by molecular modelling calculations, rotation around the bond connecting the quinazolin-4(3H)-one nucleus to the o-tolyl is sterically hampered, which leads to separable conformers with axial chirality (i.e. atropisomers). After verifying that the aS and aR isomers of compound 1 do not interconvert in solution, we investigated how biological activity is influenced by axial chirality and conformational equilibrium...
May 10, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28487075/n-1h-pyrazol-3-yl-quinazolin-4-amines-as-a-novel-class-of-casein-kinase-1%C3%AE-%C3%AE%C2%B5-inhibitors-synthesis-biological-evaluation-and-molecular-modeling-studies
#9
Chandrabose Karthikeyan, Pramod Jharia, Digambar Kumar Waiker, Amy Catherine Nusbaum, Haneen Amawi, Erin Marie Kirwen, Ryann Christman, Sri Krishna Chaitanya Arudra, Laurent Meijer, Amit K Tiwari, Piyush Trivedi
Described herein is the design, synthesis and biological evaluation of a series of N-(1H-pyrazol-3-yl)quinazolin-4-amines against a panel of eight disease relevant protein kinases. The kinase inhibition results indicated that two compounds inhibited casein kinase 1δ/ε (CK1δ/ε) with some selectivity over related kinases, namely CDK5/p25, GSK-3α/β, and DYRK1A. Docking studies with 3c and 3d revealed the key interactions with desired amino acids in the ATP binding site of CK1δ. Furthermore, compound 3c also elicited selective cytotoxic activity against the pancreas ductal adenocarcinoma (PANC-1) cell line...
April 27, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28478927/discovery-of-novel-substituted-benzo-anellated-4-benzylamino-pyrrolopyrimidines-as-dual-egfr-and-vegfr2-inhibitors
#10
Tim Fischer, Thomas Krüger, Abdulkarim Najjar, Frank Totzke, Christoph Schächtele, Wolfgang Sippl, Christoph Ritter, Andreas Hilgeroth
The quinazoline scaffold is the main part of many marketed EGFR inhibitors. Resistance developments against those inhibitors enforced the search for novel structural lead compounds. We developed novel benzo-anellated 4-benzylamine pyrrolopyrimidines with varied substitution patterns at both the molecular scaffold and the attached residue in the 4-position. The structure-dependent affinities towards EGFR are discussed and first nanomolar derivatives have been identified. Docking studies were carried out for EGFR in order to explore the potential binding mode of the novel inhibitors...
April 19, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28476569/design-and-synthesis-of-a-fluorinated-quinazoline-based-type-ii-trk-inhibitor-as-a-scaffold-for-pet-radiotracer-development
#11
Vadim Bernard-Gauthier, Anne Mahringer, Matthew Vesnaver, Gert Fricker, Ralf Schirrmacher
NTRK1/2/3 fusions have recently been characterized as low incidence oncogenic alterations across various tumor histologies. Tyrosine kinase inhibitors (TKIs) of the tropomyosin receptor kinase family TrkA/B/C (encoded by NTRK1/2/3) are showing promises in the clinic for the treatment of cancer patients whose diseases harbor NTRK tumor drivers. We describe herein the development of [(18)F]QMICF ([(18)F]-(R)-9), a quinazoline-based type-II pan-Trk radiotracer with nanomolar potencies for TrkA/B/C (IC50=85-650nM) and relevant TrkA fusions including TrkA-TPM3 (IC50=162nM)...
April 21, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28471656/4-anilino-2-pyridylquinazolines-and-pyrimidines-as-highly-potent-and-non-toxic-inhibitors-of-breast-cancer-resistance-protein-abcg2
#12
Michael K Krapf, Jennifer Gallus, Michael Wiese
Multidrug resistance (MDR) mediated by ATP-binding cassette (ABC) transport proteins remains a major problem in the chemotherapeutic treatment of cancer and might be overcome by inhibition of the transporter. Due to the lack of understanding the complex mechanisms involved in the transport process, in particular for breast cancer resistance protein (BCRP/ABCG2), there is a persistent need for studies of inhibitors of ABCG2. In this study we investigated a systematic series of 4-substituted-2-pyridylquinazolines in terms of their inhibitory potency as well as selectivity toward ABCG2...
May 4, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28464778/antileishmanial-drug-discovery-synthetic-methods-chemical-characteristics-and-biological-potential-of-quinazolines-and-its-derivatives
#13
Adarsh Sahu, Deepak Kumar, R K Agrawal
Leishmaniasis is a complex devastating disease that is widespread across the globe with 400 million people in 90 countries at risk of acquiring leishmaniasis. It is caused by intracellular parasites belonging to genus Leishmania. The therapeutic use of commonly available drugs like Pentostam, Glucantime, Amphotericin B, Paramomycin, Miltefosine are declined due to their low efficacy, drug resistance and high toxicity. Therefore, a continuous effort is needed in order to find out less toxic and more successful drugs in future for the handling of leishmaniasis...
May 2, 2017: Anti-inflammatory & Anti-allergy Agents in Medicinal Chemistry
https://www.readbyqxmd.com/read/28463515/rational-design-of-bisubstrate-type-analogs-as-inhibitors-of-dna-methyltransferases-in-cancer-cells
#14
Ludovic Halby, Yoann Menon, Elodie Rilova, Dany Pechalrieu, Veronique Masson, Celine Faux, Mohamed Amine Bouhlel, Marie-Hélène David-Cordonnier, Natacha Novosad, Yannick Aussagues, Arnaud Samson, Laurent Lacroix, Frederic Ausseil, Laurence Fleury, Dominique Guianvarc'h, Clotilde Ferroud, Paola B Arimondo
Aberrant DNA hypermethylation of promoter of tumor suppressor genes is commonly observed in cancer and its inhibition by small molecules is promising for their reactivation. Here we designed bisubstrate analogs-based inhibitors, by mimicking each substrate, - the S-adenosyl-L-methionine and the deoxycytidine -, and linking them together. This approach resulted in quinazoline-quinoline derivatives as potent inhibitors of DNMT3A and DNMT1, some showing certain isoform selectivity. We highlighted the importance of (i) the nature and rigidity of the linker between the two moieties for inhibition, as (ii) the presence of the nitrogen on the quinoline group and (iii) of a hydrophobic group on the quinazoline...
May 2, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28462939/facile-access-to-potent-antiviral-quinazoline-heterocycles-with-fluorescence-properties-via-merging-metal-free-domino-reactions
#15
Felix E Held, Anton A Guryev, Tony Fröhlich, Frank Hampel, Axel Kahnt, Corina Hutterer, Mirjam Steingruber, Hanife Bahsi, Clemens von Bojničić-Kninski, Daniela S Mattes, Tobias C Foertsch, Alexander Nesterov-Mueller, Manfred Marschall, Svetlana B Tsogoeva
Most of the known approved drugs comprise functionalized heterocyclic compounds as subunits. Among them, non-fluorescent quinazolines with four different substitution patterns are found in a variety of clinically used pharmaceuticals, while 4,5,7,8-substituted quinazolines and those displaying their own specific fluorescence, favourable for cellular uptake visualization, have not been described so far. Here we report the development of a one-pot synthetic strategy to access these 4,5,7,8-substituted quinazolines, which are fluorescent and feature strong antiviral properties (EC50 down to 0...
May 2, 2017: Nature Communications
https://www.readbyqxmd.com/read/28452390/benzodiazines-recent-synthetic-advances
#16
REVIEW
Thomas Mathew, Attila Á Papp, Farzaneh Paknia, Santos Fustero, G K Surya Prakash
Benzodiazines (diazonaphthalenes with both nitrogens in the same ring) - cinnolines (1,2-benzodiazine), quinazolines (1,3-benzodiazine), phthalazines (2,3-benzodiazine) and quinoxalines (1,4-benzodiazine) - are important class of compounds with broad biological properties and wide application in pharmaceutical as well as agrochemical arenas. These diazaheterocycles are present in a wide variety of bioactive natural products as well as synthetic molecules that are good drug candidates constituting key structural units responsible for their pronounced therapeutic activities...
April 28, 2017: Chemical Society Reviews
https://www.readbyqxmd.com/read/28448438/antiplatelet-activity-of-a-newly-synthesized-novel-ruthenium-ii-a-potential-role-for-akt-jnk-signaling
#17
Themmila Khamrang, Kuo-Chen Hung, Chih-Hsuan Hsia, Cheng-Ying Hsieh, Marappan Velusamy, Thanasekaran Jayakumar, Joen-Rong Sheu
In oncotherapy, ruthenium complexes are considered as potential alternatives for platinum compounds, and have been proved as promising anticancer drugs with high efficacy and lesser side effects. Platelet activation plays a major role in cancer metastasis and progression. Hence, this study explored the effect of a newly synthesized ruthenium complex, [Ru(η⁶-cymene)(L)Cl]BF₄(TQ5), where L = 4-phenyl-2-pyridin-2-yl-quinazoline), on human platelet activation. TQ5 (3-5 µM) inhibited concentration-dependent collagen-induced platelet aggregation in washed human platelets...
April 27, 2017: International Journal of Molecular Sciences
https://www.readbyqxmd.com/read/28432839/copper-catalyzed-straightforward-synthesis-of-5-arylindazolo-3-2-b-quinazolin-7-5h-ones-from-2-nitrobenzaldehydes
#18
Takahisa Imamura, Yoji Murakami, Hidetoshi Nitta
No abstract available.
April 21, 2017: Biological Chemistry
https://www.readbyqxmd.com/read/28428040/design-synthesis-and-docking-studies-of-quinazoline-analogues-bearing-aryl-semicarbazone-scaffolds-as-potent-egfr-inhibitors
#19
Yuanbiao Tu, Caolin Wang, Shan Xu, Zhou Lan, Wei Li, Jiaqian Han, Yuanzhang Zhou, Pengwu Zheng, Wufu Zhu
Two series of quinazoline derivatives bearing aryl semicarbazone scaffolds (9a-o and 10a-o) were designed, synthesized and evaluated for the IC50 values against four cancer cell lines (A549, HepG2, MCF-7 and PC-3). The selected compound 9o was further evaluated for the inhibitory activity against EGFR kinases. Four of the compounds showed excellent cytotoxicity activity and selectivity with the IC50 values in single-digit μM to nanomole range. Two of them are equal to more active than positive control afatinib against one or more cell lines...
April 6, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28422435/blue-organic-light-emitting-diodes-based-on-fluorene-bridged-quinazoline-and-quinoxaline-derivatives
#20
Dong Young Kim, Jisu Kang, Song Eun Lee, Young Kwan Kim, Seung Soo Yoon
Two blue emitters based on fluorene-bridged quinazoline and quinoxaline derivatives were prepared via the Suzuki reaction. Their photoluminescent properties were investigated. Furthermore, theoretical studies on these materials using the density functional theory calculation were conducted. To explore their electroluminescent properties, multilayered organic light-emitting diodes were fabricated with the following device structure: indium-tin-oxide (180 nm)/4,4'-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (50 nm)/blue emitting materials (1 and 2) (30 nm)/bathophenanthroline (35 nm)/8-hydroxy-quinolinato lithium (2 nm)/Al (100 nm)...
April 19, 2017: Luminescence: the Journal of Biological and Chemical Luminescence
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