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Ibrahim F Nassar, Ahmed F El Farargy, Fathy M Abdelrazek, Nasser S M Ismail
The chalcone derivatives 3a,b were cyclized upon reaction with thiourea to give the pyrazolo[3,4-d]pyrimidine derivatives 5a,b. Condensation of 5a,b and their hydrazide derivatives 8a,b with cyclic and acyclic glucose gave the condensed S- and N-glycosides 7a,b and 9a,b, respectively. Reaction of 3b with ethyl cyanoacetate followed by reaction with cyclic glucose afforded a mixture of the O- and/or N-glycoside isomers 12 and 13, respectively. The pyrazolo[3,4-c]pyrazole derivative 14 was also obtained from the reaction of 3b with hydrazine hydrate...
March 21, 2017: Nucleosides, Nucleotides & Nucleic Acids
Weijie Xu, Ying Pan, Hong Wang, Haiyan Li, Qing Peng, Duncan Wei, Cheng Chen, Jinhong Zheng
Cancer is a major public health concern worldwide. Adverse effects of cancer treatments still compromise patients' quality of life. To identify new potential anticancer agents, a series of novel pyrazoline derivatives were synthesized and evaluated for cytotoxic effects on HepG-2 (human liver hepatocellular carcinoma cell line) and primary hepatocytes. Compound structures were confirmed by ¹H-NMR, mass spectrometry, and infrared imaging. An in vitro assay demonstrated that several compounds exerted cytotoxicity in the micromolar range...
March 16, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Katia S Poça, Thiago E M Parente, Lucas F Chagas, Bruna S Leal, Hellen S Leal, Francisco J R Paumgartten, Ana C A X De-Oliveira
BACKGROUND: Cytochrome P450 2A5 (Cyp2a5), a mouse enzyme orthologous of human CYP2A6, catalyzes a number of toxicologically important reactions, including the metabolism of nicotine, aflatoxin B1, and several other xeno- and endobiotics. Cyp2a5 expression is complex and not yet fully understood. We investigated inter-strain differences in the activity and mRNA expression of hepatic Cyp2a5. Cyp1a1/2 and Cyp2b9/10 activities were evaluated for comparative purposes. Data on the interstrain differences in the expression and activity of Cyp2a5 are important to select a suitable mouse model for studying CYP2A6-mediated metabolism...
March 15, 2017: BMC Research Notes
Balvantsingh M Labana, Gaurangkumar C Brahmbhatt, Tushar R Sutariya, Narsidas J Parmar, José M Padrón, Rajni Kant, Vivek K Gupta
A one-pot method has been described to synthesize benzopyran-annulated pyrano[2,3-c]pyrazoles, effectively by combining O-alkenyloxy/alkynyloxy-acetophenones with various pyrazolones in triethylammonium acetate (TEAA) under microwave irradiation. While combination of O-allyloxy- or O-prenyloxy-acetophenones with pyrazolones occurred efficiently, that of O-propargyloxy-acetophenones was found effective in the presence of ZnO catalyst, via a domino Knoevenagel-hetero-Diels-Alder (DKHDA) reaction. Aminobenzopyran frameworks were also synthesized, after nitro-containing products were reduced in tandem with iron(II) in an acidic medium...
March 14, 2017: Molecular Diversity
Zi-Qi Zhu, Yang Shen, Jin-Xi Liu, Ji-Yu Tao, Feng Shi
The first catalytic asymmetric α-arylation of pyrazol-5-ones has been established by using 2-indolylmethanols as direct electrophilic arylation reagents under the cooperative catalysis of Pd(0) and a chiral phosphoric acid, which afforded the α-arylation products of pyrazol-5-ones in generally high yields and good enantioselectivities (up to 99% yield, >99% ee).
March 14, 2017: Organic Letters
Simon Planken, Douglas Carl Behenna, Sajiv K Nair, Theodore Otto Johnson, Asako Nagata, Chau Almaden, Simon Bailey, T Eric Ballard, Louise Bernier, Hengmiao Cheng, Sujin Cho-Schultz, Deepak Dalvie, Judith G Deal, Dac M Dinh, Martin P Edwards, Rose Ann Ferre, Ketan S Gajiwala, Michelle D Hemkens, Robert S Kania, John C Kath, Jean Matthews, Brion W Murray, Sherry Niessen, Suvi T M Orr, Mason Pairish, Neal W Sach, Hong Shen, Manli Shi, James Solowiej, Khanh Tran, Elaine Tseng, Paolo Vicini, Yuli Wang, Scott L Weinrich, Ru Zhou, Michael Zientek, Longqing Liu, Yiqin Luo, Shuibo Xin, Chengyi Zhang, Jennifer Anne Lafontaine
Mutant epidermal growth factor receptor (EGFR) is a major driver of non-small cell lung cancer (NSCLC). Marketed first generation inhibitors, such as erlotinib, effect a transient beneficial response in EGFR-mutant NSCLC patients before resistance mechanisms render these inhibitors ineffective. Secondary oncogenic EGFR mutations account for approximately 50% of relapses, the most common being the gatekeeper T790M substitution that renders existing therapies ineffective. The discovery of PF-06459988 (1), an irreversible pyrrolopyrimidine inhibitor of EGFR T790M mutants was recently disclosed1...
March 13, 2017: Journal of Medicinal Chemistry
Edith Rodríguez-Venegas, Efrén V García-Báez, Francisco J Martínez-Martínez, Alejandro Cruz, Itzia I Padilla-Martínez
The solventless synthesis of tris(pyrazolyl)phenylmethane ligands of formula C₆H₅C(Pz(R2))₃ (R = H, Me), starting from PhCCl₃ and 3,5-dimethylpyrazole (Pz(Me2)) or pyrazole (Pz) was performed. The sterically crowded C₆H₅C(Pz(Me2))₃ is thermally transformed into the bis(pyrazolyl)(p-pyrazolyl)phenylmethane ligand Pz(Me2)-C₆H₄CH(Pz(Me2))₂. In this compound both Pz(Me2) rings are linked through the N-atom to the methine C-atom. At higher temperatures, the binding mode of Pz(Me2) changes from N1 to C4...
March 11, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Nathalie Bridonneau, Luca Rigamonti, Giordano Poneti, Dawid Pinkowicz, Alessandra Forni, Andrea Cornia
The molecular structures and magnetic properties of homoleptic iron(ii) compounds [Fe(bpp-COOMe)2](ClO4)2 (1) and [Fe(bpp-triolH3)2](ClO4)2 (2) have been investigated to ascertain their spin crossover (SCO) behaviour. In these hexacoordinated complexes, the bpp (2,6-bis(pyrazol-1-yl)pyridine) ligands adopt a mer-mer coordination mode and carry COOMe or C(O)NHC(CH2OH)3para substituents, respectively, on the central pyridyl ring. In spite of the almost equal donor power of the ligands to the iron(ii) centre, the two compounds feature different spin state configurations at room temperature...
March 8, 2017: Dalton Transactions: An International Journal of Inorganic Chemistry
Og Soon Kim, Jin Hyeok Jang, Hyun Tae Kim, Su Jin Han, Gavin Chit Tsui, Jung Min Joo
The synthesis of indazoles from pyrazoles and internal alkynes is described. Instead of complex benzenoid compounds, readily available pyrazoles were used for the preparation of indazoles by reaction of the C-H bonds of the heterocyclic ring. Oxidative benzannulation was also applied to imidazoles, providing benzimidazoles. This convergent strategy enabled alteration of the photochemical properties of benzo-fused diazoles by varying the substituents at the benzene ring, thus leading to the development of tetraarylindazoles as new fluorophores...
March 8, 2017: Organic Letters
Khaled Abdellatif, Rania Bakr, Ahmed Mehany
A new series of hybrid pyrazolo[3,4-d]pyrimidine scaffold with a heteroaryl moiety as pyrazole, oxadiazole, triazole or phthalimide moiety (14a-f, 16, 17, 19, 20) was synthesized and biologically evaluated for the cytotoxicity against human liver cancer cell line (HEPG-2), human breast cancer cell line (MCF-7) and human colon cancer cell line (HCT-116). While the pyrazolo hybrid compounds (14a-f) showed good activity against HEPG-2, MCF-7 and HCT-116 cell lines (IC50 = 3.65 - 39.98, 1.45 - 54.19 and 2.00 - 50...
February 12, 2017: Anti-cancer Agents in Medicinal Chemistry
T V Baiju, Irishi N N Namboothiri
1,3-Dipolar cycloaddition of diazo compounds with olefinic substrates is a promising atom-economic strategy for the construction of functionalized pyrazoles. Over the last few years, our group has been engaged in the synthesis of phosphonyl/sulfonylpyrazoles and pyrazole esters by employing Bestmann-Ohira Reagent (BOR) and its sulfur and ester analogs as 1,3-dipole precursors with various dipolarophiles. This account describes the novel synthetic methods developed in our laboratory, in the perspective of closely related work by others, for the synthesis of phosphonyl/sulfonylpyrazoles, pyrazole esters and the total synthesis of Withasomnine, a natural product, by using 1,3-dipolar cycloaddition as the key step...
March 7, 2017: Chemical Record: An Official Publication of the Chemical Society of Japan ... [et Al.]
Joseph P A Harrity, Andrew Brown, Julia Comas-Barcelo
Alkynylboranes show unprecedented reactivity in their [4 + 2] cycloaddition of sydnones offering access to fully substituted pyrazoles within a few hours at room temperature. This method delivers synthetically valuable pyrazoleboranes with complete control of regioselectivity, and these intermediates can be further elaborated through functionalization of the C-B bond.
March 6, 2017: Chemistry: a European Journal
Michiel Van Gool, Sergio Alvar Alonso De Diego, Oscar Delgado, Andrés A Trabanco, Fabrice Jourdan, Gregor J Macdonald, Marijke Somers, Luc Ver Donck
The metabotropic glutamate subtype 2 (mGlu2) receptor is a presynaptic membrane receptor distributed widely in brain that provides feedback inhibitory control of glutamate release. Inhibition of the mGlu2 receptor function with a negative allosteric modulator (NAM) enhances activity dependent glutamate release which may be of therapeutic benefit for treatment of neurological and psychiatric disorders. An attractive pyrazole hit was identified after a high throughput screening (HTS) campaign. The evolution of this hit is described by structure-activity relationship (SAR) study on specific parts of the molecule...
March 6, 2017: ChemMedChem
Halise Inci Gul, Cem Yamali, Fatma Yesilyurt, Hiroshi Sakagami, Kaan Kucukoglu, Ilhami Gulcin, Mustafa Gul, Claudiu T Supuran
In this study, 4-[5-(4-hydroxyphenyl)-3-aryl-4,5-dihydro-1H-pyrazol-1-yl]benzenesulfonamide derivatives (8-14) were synthesized for the first time by microwave irradiation and their chemical structures were confirmed by (1)H NMR, (13)C NMR and HRMS. Cytotoxic activities and inhibitory effects on carbonic anhydrase I and II isoenzymes of the compounds were investigated. The compounds 9 (PSE = 4.2), 12 (PSE = 4.1) and 13 (PSE = 3.9) with the highest potency selectivity expression (PSE) values in cytotoxicity experiments and the compounds 13 (Ki = 3...
December 2017: Journal of Enzyme Inhibition and Medicinal Chemistry
Faryal Chaudhry, Abdul Qayuum Ather, Mohammad Javaid Akhtar, Ayesha Shaukat, Mohammad Ashraf, Mariya Al-Rashida, Munawar Ali Munawar, Misbahul Ain Khan
An efficient and environmentally benign simple fusion reaction of 3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)pyridazine (1a) or 3-chloro-6-(3,5-dimethyl-4-nitro-1H-pyrazol-1-yl)pyridazine (2a) with different aliphatic/aromatic amines have produced a series of novel pyrazolylpyridazine amines (4a-4c &5a-5m). All compounds exhibited moderate in vitro yeast α-glucosidase inhibition except m-chloro derivative 5g, which was found potent inhibitor of this enzyme with IC50 value of 19.27±0.005µM. The molecular docking further helped in understanding the structure activity relationship of these compounds including 5g...
February 9, 2017: Bioorganic Chemistry
Xi Yuan, Jian-Fei Yao, Zhen-Yu Tang
A transition-metal-free decarboxylative fluorination of electron-rich five-membered heteroaromatics, including furan-, pyrazole-, isoxazole-, thiophene-, indole-, benzofuran- and indazolecarboxylic acids, with Selectfluor is reported. Fluorinated dimer products were observed for nitrogen-containing heteroaromatic carboxylic acids, such as indole and pyrazole. An effective method has been developed to synthesize the monomer of 2- and 3-fluoroindoles with Li2CO3 as base at low temperature.
March 3, 2017: Organic Letters
Gabriella Cavallini, Alessio Donati, Michele Taddei, Ettore Bergamini
Like mitochondria, peroxisomes produce reactive oxygen species (ROS), compounds which have been implicated to play an important role in many degenerative diseases and aging itself, and an exaggerated ROS production might occur in altered or older organelles. Growing evidence shows that autophagy, a required function in cell housekeeping during fasting, can remove damaged macromolecules, organelles, and membranes selectively. Proliferation of peroxisomes can be enhanced in liver cells by perfluorooctanoic acid (PFOA), which causes a marked increase of the Acyl-CoA oxidase (ACOX) activity and no significant change in urate oxidase (UOX) activity...
March 2, 2017: Molecular and Cellular Biochemistry
Jitender Dev G, Y Poornachandra, K Ratnakar Reddy, R Naresh Kumar, N Ravikumar, D Krishna Swaroop, P Ranjithreddy, G Shravan Kumar, Jagadeesh B Nanubolu, C Ganesh Kumar, B Narsaiah
A series of novel alkyl amide functionalized 2,3-pyrazole fused quinoline derivatives 5, 6 and 7 have been prepared starting from quinoline-2(1H)one 1 in a series of steps. All the final products were screened for antibacterial activity, the promising lead compound 5r was identified with MIC values ranging between 3.9 and 7.8 μg/mL against different bacterial strains. Compound 5r also showed good antifungal and anti-biofilm activities against the tested panel of various fungal and bacterial strains. Compound 5r when treated on mature biofilms of S...
April 21, 2017: European Journal of Medicinal Chemistry
Subramani Kandhasamy, Giriprasath Ramanathan, Thangavelu Muthukumar, SitaLakshmi Thyagarajan, Narayanan Umamaheshwari, V P Santhanakrishnan, Uma Tiruchirapalli Sivagnanam, Paramasivan Thirumalai Perumal
The nanomaterial with the novel biologically active compounds has been actively investigated for application in cancer research. Substantial use of nanofibrous scaffold for cancer research with potentially bioactive compounds through electrospinning has not been fully explored. Here, we describe the series of fabrication of nanofibrous scaffold loaded with novel potential biologically active hydroxybenzo[a]phenazine pyrazol-5(4H)-one derivatives were designed, synthesized by a simple one-pot, two step four component condensation based on Michael type addition reaction of lawsone, benzene-1,2-diamine, aromatic aldehydes and 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one as the substrates...
May 1, 2017: Materials Science & Engineering. C, Materials for Biological Applications
Yang-Yang Zang, Yuan-Mei Li, Yue Yin, Shan-Shan Chen, Zhen-Peng Kai
BACKGROUND: In the previous study, we have demonstrated that insect 3-hydroxy-3-methylglutaryl-CoA reductase (HMGR) can be a potential selective insecticide target. Three series of inhibitors were designed based on the difference of HMGR structures from Homo sapiens and Manduca sexta with the aim for discovering potent selective insecticide candidate. RESULTS: Bioassay in vitro showed that gem-difluoromethylenated statin analogs have potent effects on JH biosynthesis of M...
March 1, 2017: Pest Management Science
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