- Hydroxychalcone dyes that serve as color indicators for pH and fluoride ions
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A chalcone, which is composed of two aromatic rings bridged by an α,β-unsaturated carbonyl group, exhibits a variety of biological activities. With an objective to develop a novel chalcone-based functional dye, we have synthesized a chalcone diol CLN1, bearing two OH groups at the 2-positions on both phenyl rings, as well as reference compounds CLN2-6, and found that it serves as color indicators for pH and fluoride ions. CLN1showed a vivid color change from colorless to yellow (halochromism) in water at pH ≥ 10. Furthermore, it presented a selective color change from colorless to red upon the addition of TBAF in an organic solvent such as CH3CN. CLN1provided a strong red-shifted absorption band in the visible region under alkaline conditions in water and upon the addition of TBAF in CH3CN. The absorption spectral study together with TD-DFT calculations and X-ray crystallographic analysis revealed that the characteristic π-resonant structures of CLN1caused by the ionization or OH-F?interactions and the planar conformation due to its intramolecular hydrogen bonding may provide a strong charge transfer (CT) absorption in the visible region.
- Bu, Ren,Du, Yanqing,Eerdun, Chaolu,Hu, Mixia,Liang, Fengying,Tsuda, Akihiko,Wang, Meiling
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- 2′-Hydroxyflavylium: introducing flavanones into the flavylium network of chemical reactions
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Chalcones possessing a hydroxyl group in position 2 cyclize to form flavylium salts in acidic media, this reaction being reversible under neutral-basic conditions. On the other hand, chalcones possessing a hydroxyl group in position 2′ cyclize to form flavanones in basic media. By synthesizing 2′-hydroxyflavylium tetrafluoroborate, it was possible to obtain trans-2,2′-dihydroxychalcone that in solution can evolve to 2′-hydroxyflavanone or back to 2′-hydroxyflavylium depending on the pH. The several equilibria established in aqueous solution were fully characterized. The importance of including flavanones into the flavylium network of chemical reactions is briefly exploited.
- Petrov, Vesselin,Gomes, Raquel,Parola, A. Jorge,Jesus, Alexandre,Laia, César A.T.,Pina, Fernando
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- Effect of OH substitution in 3-benzylchroman-4-ones: crystallographic, CSD, DFT, FTIR, Hirshfeld surface, and energy framework analysis
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3-Benzylchroman-4-ones (homoisoflavanones) are oxygen-containing heterocycles with a sixteen-carbon skeleton. They belong to the class of naturally occurring polyphenolic flavonoids with limited occurrence in nature and possess anti-inflammatory, antibact
- Abdul Salam, Abdul Ajees,Bankapur, Aseefhali,Chidangil, Santhosh,Kumar S., Madan,Simon, Lalitha,Sinha, Rajeev K.,T., Shilpa
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- Mycobactin Analogues with Excellent Pharmacokinetic Profile Demonstrate Potent Antitubercular Specific Activity and Exceptional Efflux Pump Inhibition
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In this study, we have designed and synthesized pyrazoline analogues that partially mimic the structure of mycobactin, to address the requirement of novel therapeutics to tackle the emerging global challenge of antimicrobial resistance (AMR). Our investigation resulted in the identification of novel lead compounds 44 and 49 as potential mycobactin biosynthesis inhibitors against mycobacteria. Moreover, candidates efficiently eradicated intracellularly surviving mycobacteria. Thermofluorimetric analysis and molecular dynamics simulations suggested that compounds 44 and 49 bind to salicyl-AMP ligase (MbtA), a key enzyme in the mycobactin biosynthetic pathway. To the best of our knowledge, these are the first rationally designed mycobactin inhibitors to demonstrate an excellent in vivo pharmacokinetic profile. In addition, these compounds also exhibited more potent whole-cell efflux pump inhibition than known efflux pump inhibitors verapamil and chlorpromazine. Results from this study pave the way for the development of 3-(2-hydroxyphenyl)-5-(aryl)-pyrazolines as a new weapon against superbug-associated AMR challenges.
- Shyam, Mousumi,Verma, Harshita,Bhattacharje, Gourab,Mukherjee, Piyali,Singh, Samsher,Kamilya, Sujit,Jalani, Pushpendu,Das, Swetarka,Dasgupta, Arunava,Mondal, Abhishake,Das, Amit Kumar,Singh, Amit,Brucoli, Federico,Bagnéris, Claire,Dickman, Rachael,Basavanakatti, Vinay N.,Naresh Babu, Patibandla,Sankaran, Vadivelan,Dev, Abhimanyu,Sinha, Barij Nayan,Bhakta, Sanjib,Jayaprakash, Venkatesan
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p. 234 - 256
(2022/01/20)
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- Differences in antioxidant potential of chalcones in human serum: In vitro study
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Introduction: An imbalance between oxidants and antioxidants in favour of oxidants, potentially leading to damage, is termed oxidative stress. Antioxidants (AO), either enzymatic or non-enzymatic, are the ones that can reduce diverse effects of pro-oxidan
- Ivkovi?, Branka,Jankovi?, Tamara,Kotur-Stevuljevi?, Jelena,Turkovi?, Nemanja,Vuji?, Zorica
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- Novel isoniazid-spirooxindole derivatives: design, synthesis, biological evaluation, in silico ADMET prediction and computational studies
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In the present scenario, the Synthesis of new and desired antimycobacterial agent has an eternal demand to resist Mycobacterium tuberculosis (MTB). The design and identification of new molecules for the treatment of tuberculosis is an important task in organic as well as medicinal chemistry research. In the present study, we have reported the combination of the desired compound using two versatile and significant moieties, isoniazid and spirooxindole derivatives. A series of novel isoniazid-spirooxindole hybrid molecules (6a-6ao) were designed, synthesized, and well-characterized by various spectroscopic methods. We have evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) strain and MDR-TB. Among them, Compound 6ab was found to be the most effective compare to other compounds. ADMET-related descriptors were to be calculated of all the compounds to predict the pharmacokinetic properties for the selection of the effective and bioavailable compounds. In addition, molecular docking and molecular dynamics studies reveal that the binding modes of all the compounds in the active site of isoniazid-resistant enoyl-ACP(COA) reductase, which helped to establish a structural basis of inhibition of Mycobacterium tuberculosis.
- Bhoi, Manoj N.,Borad, Mayuri A.,Jethava, Divya J.,Pandya, Himanshu A.,Patel, Chirag N.,Patel, Hitesh D.
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- Synthesis, Structure, and Anti-Inflammatory Activity of Functionally Substituted Chalcones and Their Derivatives
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Functionally substituted chalcones, pyrazolines, and flavonones have been synthesized. Their structure has been studied by means of 1H and 13C NMR spectroscopy, including COSY and HMQC experiments. Anti-inflammatory activity of the s
- Nurkenov,Ibraev,Schepetkin,Khlebnikov,Seilkhanov,Arinova,Isabaeva
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p. 1360 - 1367
(2019/08/21)
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- Synthesis, in vitro antigiardial activity, SAR analysis and docking study of substituted chalcones
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A series of 15 chalcones-bearing substituents at positions 2, 4, and 5 of rings A and B were synthesized using microwave-assisted Claissen–Smichdt condensation and evaluated for their activity against Giardia lamblia and Green monkey kidney cells. Five co
- Cáceres-Castillo, David,Carballo, Rubén M.,Graniel-Sabido, Manlio,Mena-Rejón, Gonzalo J.,Mirón-López, Gumersindo,Moo-Puc, Rosa E.,Quijano-Qui?ones, Ramiro
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- Phototransformations of some 3-cyclohexenyloxychromenones: Synthesis of Spirocyclic compounds
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The phototransformation of the 3-cyclohexenyloxychromenones by irradiation with a pyrex-filtered light from a 125 W Hg vapor lamp under an inert atmosphere into the spirocyclic fused xanthenones was described. The efficacy of the protocol depended upon th
- Khanna, Radhika,Dalal, Aarti,Berar, Urmila,Singh, Sandeep,Kamboj, Ramesh C.
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p. 668 - 673
(2019/01/05)
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- Metal-free Synthesis of Spiro-2,2′-benzo[b]furan-3,3′-ones via PhI(OAc)2-Mediated Cascade Spirocyclization
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Treating the benzyl protected 3-hydroxy-1,3-bis(2-hydroxyphenyl)prop-2-en-1-ones solely with PhI(OAc)2 (PIDA) in DCE at room temperature readily furnished the seldom studied spiro-2,2′-benzo[b]furan-3,3′-ones in satisfactory to excellent yields. The hypervalent iodine reagent enables the metal-free cascade spirocyclization resulting in the dual oxidative C?O bond formation. (Figure presented.).
- Xing, Qingyu,Liang, Huiyuan,Bao, Mingmai,Li, Xuemin,Zhang, Jingran,Bi, Tianhao,Zhang, Yilin,Xu, Jun,Du, Yunfei,Zhao, Kang
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supporting information
p. 4669 - 4673
(2019/09/17)
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- Synthesis of novel pyrazoline-based bis(1,2,3-triazole) scaffolds via click chemistry
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A series of novel bis(1,2,3-triazoles) derivatives 7a-m were synthesized by the 1,3-dipolar cycloaddition (click-reaction) of 1-methyl-3,5-bis(2-(prop-2-yn-1-yloxy)phenyl)-4,5-dihydro-1H-pyrazole (5) with various aralkyl azides 6a-m in the presence of sod
- Kiran, Kothuri,Ashok, Dongamanti,Rao, Boddu Ananda,Sarasija, Madderla,Rao, Alapati Srinivas
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p. 241 - 251
(2017/05/09)
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- Synthesis and evaluation of hydroxychalcones as multifunctional non-purine xanthine oxidase inhibitors for the treatment of hyperuricemia
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A series of hydroxychalcone derivatives have been designed, synthesized and evaluated for human xanthine oxidase (XO) inhibitory activity. Most of the tested compounds acted moderate XO inhibition with IC50 values in the micromolar rang. Molecular docking and kinetic studies have been performed to explain the binding modes of XO with the selected compounds. In addition, in vitro antioxidant screening results indicated that some of the hydroxychalcones possessed good anti-free radical activities. Furthermore, the preferred compounds 16 and 18 were able to significantly inhibit hepatic xanthine oxidase activity and reduced serum uric acid level of hyperuricemic mice in vivo. In summary, compounds 16 and 18 with balanced activities of antioxidant, XO inhibition and serum uric acid reduction, which are promising candidates for the treatment of hyperuricemia and gout.
- Xie, Zhaodi,Luo, Xiaoting,Zou, Zhuan,Zhang, Xiao,Huang, Feifei,Li, Ruishan,Liao, Shijie,Liu, Yun
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supporting information
p. 3602 - 3606
(2017/07/07)
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- Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives
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A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1–20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1–5, 7–17, 19) were found to be selective towards hMAO-B, while two w
- Badavath, Vishnu Nayak,Nath, Chandrani,Ganta, Narayana Murthy,Ucar, Gulberk,Sinha, Barij Nayan,Jayaprakash, Venkatesan
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p. 1528 - 1532
(2017/07/17)
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- Synthesis and antimicrobial evaluation of tricyclic macrocycles containing a chalcone moiety
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A series of new tricyclic macrocycles containing a chalcone moiety were synthesized from chalcones through alkylation using different dibromoalkanes. All the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass s
- Dongamanti,Aamate,Gundu,Devulapally
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p. 1705 - 1710
(2016/08/26)
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- Design and characterization of highly in vitro antitumor active ternary copper(II) complexes containing 2′-hydroxychalcone ligands
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A series of innovative copper(II) complexes of the general composition [Cu(Ln)(phen)]NO3 (1–8; phen?=?1,10-phenanthroline), involving 2′-hydroxychalcone {(E)-1-(2′-hydroxyphenyl)-3-phenylprop-2-en-1-one} derivatives (HLn)
- K?ikavová, Radka,Van?o, Ján,Trávní?ek, Zdeněk,Hutyra, Jakub,Dvo?ák, Zdeněk
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- QSAR, in silico docking and in vitro evaluation of chalcone derivatives as potential inhibitors for H1N1 virus neuraminidase
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Thirty three chalcones were synthesized and tested on viral H1N1 neuraminidase activity by using MUNANA assay [2′-(4-methylumbelliferyl)-α-d-N-acetylneuraminic acid] assay with DANA (2,3-didehydro-2-deoxy-N-acetylneuraminic acid) was used as standard. 2D and 3D-quantitative structure?activity relationship models have been successfully developed with a good correlative and predictive ability for quantitative structure?activity relationships of these chalcone derivatives. Result from the 2D-quantitative structure?activity relationship model indicates that electrostatic parameter enhanced bioactivity of the chalcones while steric substituents diminished their potency as H1N1 neuraminidase inhibitors. 3D-quantitative structure?activity relationship model showed the importance of the position of the hydroxyl group in chalcone derivatives which can influence on hydrophobicity, hydrogen bond donor and aromatic ring features that enhance the biological activity. Finally, docking studies showed that chalcones MC8 and MC16 with low C docker interaction energies and higher numbers of hydrogen bonding have better inhibitory activity against viral H1N1 neuraminidase.
- Yaeghoobi, Marzieh,Frimayanti, Neni,Chee, Chin Fei,Ikram, Kusaira K.,Najjar, Belal O.,Zain, Sharifuddin M.,Abdullah, Zanariah,Wahab, Habibah A.,Rahman, Noorsaadah Abd.
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p. 2133 - 2142
(2016/10/25)
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- Synthesis and antiviral activity of 2-aryl-4H-chromen-4-one derivatives against Chikungunya virus
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A series of nineteen 2-aryl-4H-chromen-4-one derivatives 2a-2s were synthesized and evaluated for their antiviral activity against Chikungunya virus (LR2006-OPY1) in Vero cell culture by CPE reduction assay. Three compounds 2a, 2b and 2g, were found to be active at concentration of (IC50) 0.44 μM, 0.45 μM and 2.02 μM, respectively. Compounds having heterocyclic ring 2a and 2b at the 2nd position of the chromenone were found to be potent inhibitor of ChikV. Cytotoxicity studies were performed using Vero cell culture, compounds 2a and 2b exhibited SI of ≥100. Molecular docking simulation has been carried out to understand the possible mechanism of action.
- Badavath, Vishnu N.,Jadav, Surender S.,Pastorino, Boris,De Lamballerie, Xavier,Sinha, Barij N.,Jayaprakash, Venkatesan
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p. 1019 - 1024
(2016/11/25)
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- Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones
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A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with Ki value for MAO-B of 0.16 ± 0.01 lM comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 ± 0.01 μM). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO.
- Nayak, Badavath Vishnu,Ciftci-Yabanoglu,Bhakat, Soumendranath,Timiri, Ajay Kumar,Sinha, Barij N.,Ucar,Soliman, Mahmoud E. S.,Jayaprakash, Venkatesan
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- Synthesis, antimicrobial activity and molecular docking of novel tetracyclic scaffolds incorporating a flavonoid framework with medium sized oxygen heterocycles
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A convenient approach for the synthesis of novel tetracyclic scaffolds incorporating a flavonoid framework with medium sized heterocyclic rings (eight-, nine-, ten- and eleven-membered rings) containing two oxygen atoms from flavonols through alkylation using different dibromoalkanes was described. The synthesized compounds were established based on the spectral data and X-ray crystal structure for 6c. The synthesized compounds were evaluated for their in vitro antimicrobial activity. Docking studies were carried out for most active two compounds 6f and 6i.
- Dongamanti, Ashok,Aamate, Vikas Kumar,Devulapally, Mohan Gandhi,Gundu, Srinivas,Kotni, Meena Kumari,Manga, Vijjulatha,Balasubramanian, Sridhar,Ernala, Prasad
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p. 898 - 903
(2015/02/19)
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- Synthesis and biological activity of 2,4-di-p-phenolyl-6-2-furanyl-pyridine as a potent topoisomerase II poison
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Dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives were simply achieved using Claisen-Schmidt condensation reaction and modified Kr?hnke pyridine synthetic method. Total forty-five compounds were designed and synthesized which contain hydroxyl groups
- Karki, Radha,Park, Chanmi,Jun, Kyu-Yeon,Kadayat, Tara Man,Lee, Eung-Seok,Kwon, Youngjoo
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p. 360 - 378
(2015/03/18)
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- Synthesis and biological activity of 2,4-di- p -phenolyl-6- 2 -furanyl-pyridine as a potent topoisomerase II poison
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Dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives were simply achieved using Claisen-Schmidt condensation reaction and modified Kr?hnke pyridine synthetic method. Total forty-five compounds were designed and synthesized which contain hydroxyl groups
- Karki, Radha,Park, Chanmi,Jun, Kyu-Yeon,Kadayat, Tara Man,Lee, Eung-Seok,Kwon, Youngjoo
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p. 360 - 378
(2015/02/19)
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- Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: Synthesis of 2-arylchromans
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Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable.
- Shang, Xuyang,Zhou, Xiaomeng,Zhang, Wei,Wan, Changfeng,Chen, Junmin
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p. 8187 - 8193
(2015/12/30)
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- Chalcones with electron-withdrawing and electron-donating substituents: Anticancer activity against TRAIL resistant cancer cells, structure-activity relationship analysis and regulation of apoptotic proteins
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In the present study, a series of 46 chalcones were synthesised and evaluated for antiproliferative activities against the human TRAIL-resistant breast (MCF-7, MDA-MB-231), cervical (HeLa), ovarian (Caov-3), lung (A549), liver (HepG2), colorectal (HT-29), nasopharyngeal (CNE-1), erythromyeloblastoid (K-562) and T-lymphoblastoid (CEM-SS) cancer cells. The chalcone 38 containing an amino (-NH2) group on ring A was the most potent and selective against cancer cells. The effects of the chalcone 38 on regulation of 43 apoptosis-related markers in HT-29 cells were determined. The results showed that 20 apoptotic markers (Bad, Bax, Bcl-2, Bcl-w, Bid, Bim, CD40, Fas, HSP27, IGF-1, IGFBP-4, IGFBP-5, Livin, p21, Survivin, sTNF-R2, TRAIL-R2, XIAP, caspase-3 and caspase-8) were either up regulated or down regulated.
- Mai, Chun Wai,Yaeghoobi, Marzieh,Abd-Rahman, Noorsaadah,Kang, Yew Beng,Pichika, Mallikarjuna Rao
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supporting information
p. 378 - 387
(2014/04/17)
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- Discovery of dihydroxylated 2,4-diphenyl-6-thiophen-2-yl-pyridine as a non-intercalative DNA-binding topoisomerase II-specific catalytic inhibitor
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We describe our rationale for designing specific catalytic inhibitors of topoisomerase II (topo II) over topoisomerase I (topo I). Based on 3D-QSAR studies of previously published dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives, 9 novel dihydroxyl
- Jun, Kyu-Yeon,Kwon, Hanbyeol,Park, So-Eun,Lee, Eunyoung,Karki, Radha,Thapa, Pritam,Lee, Jun-Ho,Lee, Eung-Seok,Kwon, Youngjoo
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p. 428 - 438
(2014/05/20)
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- Dual inhibition of the α-glucosidase and butyrylcholinesterase studied by Molecular Field Topology Analysis
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A striking dual inhibition of enzymes α-glucosidase and butyrylcholinesterase by small drug-like molecules, including 1,4-disubstituted-1,2,3-triazoles, chalcones, and benzothiazepines, was rationalized with the help of Molecular Field Topology Analysis, a 3D QSAR technique similar to CoMFA. A common pharmacophore supported the concept of a link existing between type-2 diabetes mellitus and Alzheimer's disease. These findings will be instrumental for rational design of drug candidates for both of these conditions.
- Jabeen, Farukh,Oliferenko, Polina V.,Oliferenko, Alexander A.,Pillai, Girinath G.,Ansari, Farzana Latif,Hall, C. Dennis,Katritzky, Alan R.
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p. 228 - 242
(2014/05/20)
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- Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones
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A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with Ki value for MAO-B of 0.16 ± 0.01 μM comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 ± 0.01 μM). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO.
- Badavath, Vishnu Nayak,Ciftci-Yabanoglu,Bhakat, Soumendranath,Timiri, Ajay Kumar,Sinha, Barij N.,Ucar,Soliman, Mahmoud E.S.,Jayaprakash, Venkatesan
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- MW assisted synthesis of some pyrazoles containing benzotriazole moiety: An environmentally benign approach
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MW assisted synthesis of pyrazoles containing benzotriazole moieties 4a-n has been achieved by cyclocondensation of substituted chalcones 3a-n with hydrazide of benzotriazole 2 in presence of glacial acetic acid (GAA). Thus, synthesized compounds 4a-n have been characterized by their spectral data and evaluated for their antibacterial and antifungal activities against various microbes.
- Tiwari, Urvashi,Ameta, Chetna,Rawal, Manish K.,Ameta, Rakshit,Punjabi, Pinki B.
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p. 432 - 439
(2013/05/08)
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- Synthesis and evaluation of novel carbamate-substituted flavanone derivatives as potent acetylcholinesterase inhibitors and anti-amnestic agents
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This study was designed to synthesize and evaluate flavanone derivatives with phenylcarbamate moiety as potent acetylcholinesterase (AChE) inhibitors and anti-amnestic agents for management of AD. The synthesis of carbamate-substituted flavanone derivativ
- Anand, Preet,Singh, Baldev
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p. 1648 - 1659
(2013/07/26)
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- Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics
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A total of 30 chalcone analogues was synthesized via a base catalyzed Claisen Schmidt condensation and screened for their in vitro antibacterial activity against Methicillin-sensitive Staphylococcus aureus (MSSA) and Methicillin-resistant Staphylococcus aureus (MRSA) alone or in combination with non beta-lactam antibiotics namely ciprofloxacin, chloramphenicol, erythromycin, vancomycin, doxycycline and gentamicin. In the checkerboard technique, fractional inhibitory concentration indices (FICI) show that the following combinations like ciprofloxacin with 25 (4′-bromo-2-hydroxychalcone); doxycycline with 21 (4-hydroxychalcone); doxycycline with 25; and doxycycline with 4 (2′,2-dihydroxychalcone) were synergistic against MRSA. In term SAR study, the relationship between chalcone structure and their antibacterial activity against S. aureus and synergy with tested antibiotics were discussed. Possible mechanisms for antibacterial activity of chalcones alone as well as the synergistic effect in combinations were proposed by molecular modeling studies, respectively. Combinations of chalcones with conventional antibiotics could be an effective alternative in the treatment of infection caused by MRSA.
- Tran, Thanh-Dao,Do, Tuong-Ha,Tran, Ngoc-Chau,Ngo, Trieu-Du,Huynh, Thi-Ngoc-Phuong,Tran, Cat-Dong,Thai, Khac-Minh
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experimental part
p. 4555 - 4560
(2012/08/07)
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- On the stereochemistry of the olefinic double bond in 13-membered heterocyclic rings accessible by ring-closing metathesis reaction
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13-Membered heterocyclic ring analogs of the core structure of manzamine alkaloids were synthesized by ring closing metathesis (RCM) reaction. The influence of a remote heteroatom (N, O, S) on E/Z stereochemistry of the olefinic double bond formed in RCM reaction using Grubbs 1st and 2nd generation ruthenium carbene complexes was evaluated. Studies show that RCM reaction is kinetically controlled and the hetero atoms influence the double bond stereochemistry.
- Rao, H. Surya Prakash,Rafi, Shaik,Ratish Kumar,Guravaiah,Muthanna, Nandurka
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supporting information
p. 6877 - 6880
(2013/01/15)
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- Dihydroxylated 2,4,6-triphenyl pyridines: Synthesis, topoisomerase i and II inhibitory activity, cytotoxicity, and structure-activity relationship study
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Twelve dihydroxylated 2,4,6-triphenyl pyridines were designed and synthesized which contain hydroxyl groups at ortho, meta or para position of 2- and 6-phenyl, or 2- and 4-phenyl rings attached to the central pyridine. They were evaluated for topoisomeras
- Karki, Radha,Thapa, Pritam,Yoo, Han Young,Kadayat, Tara Man,Park, Pil-Hoon,Na, Youngwha,Lee, Eunyoung,Jeon, Kyung-Hwa,Cho, Won-Jea,Choi, Heesung,Kwon, Youngjoo,Lee, Eung-Seok
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experimental part
p. 219 - 228
(2012/05/05)
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- An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4
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2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl 4 are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group. 2012 Elsevier Ltd. All rights reserved.
- Maiti, Gourhari,Kayal, Utpal,Karmakar, Rajiv,Bhattacharya, Rudraksha N.
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p. 6321 - 6325,5
(2012/12/12)
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- Synthesis and pharmacological screening of some novel chalconyl derivatives of substituted phenyl semicarbazide
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In the present study, we have synthesized chalcone and semicarbazide-linked chalonyl derivatives and the titled compounds confirmed by MS, IR, and 1H NMR techniques. The anticonvulsant activity was determined by maximal electroshock (MES) induced seizure method. A majority of the compounds exhibited significant anticonvulsant activity after intraperitoneal administration. The results show the importance of hydrogen bonding for activity. In the present study 5e, 5h, 5i, 6e, 6h, and 6i emerged as the most active molecules, showed significant anticonvulsant of activity. Springer Science+Business Media, LLC 2010.
- Singh, Hemendra Pratap,Pandeya,Chauhan,Sharma, Chandra Shekhar
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experimental part
p. 74 - 80
(2012/02/04)
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- Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)
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According to the structural characteristics of isoliquiritigenin from Glycyrrhiza uralensis, a series of hydroxychalcones has been designed, synthesized and evaluated for their in vitro inhibitory activities of β-secretase (BACE1). Structure-activity relationship study suggested that inhibitory activity against BACE1 was governed to a greater extent by the hydroxyl substituent on A-and B-ring of the chalcone, and the most active compound was substituted with four hydroxyl group (17, IC50=0.27 μM).
- Ma, Lei,Yang, Zhengyi,Li, Chenjing,Zhu, Zhiyuan,Shen, Xu,Hu, Lihong
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p. 643 - 648
(2012/04/10)
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- Chalconsemicarbazone: A new scaffold for antiepileptic drug discovery
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During our investigation in the area of epileptic drug discovery, we have identified that the available conventional antiepileptic drugs are effective in 60-80% patients and in specific type of seizures and having various undesirable side effects. But in present time a new class aryl semicarbazone is emerged as new pharmacophore in epileptic drug discovery having broad spectrum activity. On the bases of work done in this area we have applied hybridization of pharmacophore strategy of drug design and developed a new pharmacophore. We have also designed a scheme for synthesizing such pharmacophore and performed their pharmacological screening for the protection of seizures, behavioral study and CNS activity. The compound 1-[1-(2,4-dihydroxyphenyl)-3-(2-hydroxyphenyl) allylidene]-4-(2-fluorophenyl) semicarbazide (8) emerged as the most active prototype molecule in all the models.
- Singh, Hemendra Pratap,Chauhan,Pandeya,Sharma, Chandra Shekhar
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experimental part
p. 103 - 106
(2010/08/06)
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- 1,5-bis (2-hydroxyphenyl)pent-1,4-diene-3-one: A lead compound for the development of broad-spectrum antibacterial agents
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A systematic and comparative study has been made starting from a naturally-occurring chalcone nucleus to design effective antibacterial agents. The present investigation established 1,5-bis(2-hydroxyphenyl)pent-1,4-diene-3- one (1c) as a lead compound with potential against a panel of pathogenic bacterial strains. Staphylococcus (coagulase negative), Escherichia coli, Pseudomonas aeruginosa, Acenetobacter sp. and Klebsiella pneumoniae. Gentamycine and tetracycline were used as reference drugs. The mode of antibacterial action of Ic was also studied by scanning electron microscopy, which showed membrane disruption and cell lysis of the organisms during the exposure of the tested compound. In vitro toxicity tests demonstrated that all the bioactive compounds showed far less toxicity against human erythrocytes.
- Rani,Jain, Sapna,Kumar, Rita,Kumar, Anil
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experimental part
p. 31 - 35
(2011/07/31)
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- Towards development of selective and reversible pyrazoline based MAO-inhibitors: Synthesis, biological evaluation and docking studies
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Ten novel 3,5-diaryl pyrazolines were synthesized and investigated for their monoamine oxidase (MAO) inhibitory property. All the molecules were found to be reversible and selective inhibitor for either one of the isoform (MAO-A or MAO-B). Further insights in the theoretical evaluation of the possible interactions between the compounds and monoamine oxidases (MAO-A or MAO-B) have been developed through docking studies. The theoretical values are in congruence with their experimental values.
- Sahoo, Anasuya,Yabanoglu, Samiye,Sinha, Barij N.,Ucar, Gulberk,Basu, Arijit,Jayaprakash, Venkatesan
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supporting information; experimental part
p. 132 - 136
(2010/04/05)
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- Small molecules with structural similarities to siderophores as novel antimicrobials against Mycobacterium tuberculosis and Yersinia pestis
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Drugs inhibiting the iron scarcity-induced, siderophore-mediated iron-scavenging systems of Mycobacterium tuberculosis (Mtb) and Yersinia pestis (Yp) may provide new therapeutic lines of defense. Compounds with structural similarities to siderophores were synthesized and evaluated as antimicrobials against Mtb and Yp under iron-limiting conditions, which mimic the iron scarcity these pathogens encounter and must adapt to in the host, and under standard iron-rich conditions for comparison. New antimicrobials were identified, some of which warrant exploration as initial leads against potentially novel targets and small-molecule tools to assist in the elucidation of targets specific to iron-scarcity adapted Mtb and Yp.
- Stirrett, Karen L.,Ferreras, Julian A.,Jayaprakash, Venkatesan,Sinha, Barij N.,Ren, Tao,Quadri, Luis E.N.
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p. 2662 - 2668
(2008/12/21)
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- Pyrazoline-based mycobactin analogues as MAO-inhibitors
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3,5-Diaryl carbothioamide pyrazolines designed as mycobactin analogs (mycobacterial siderophore) were reported to be potent antitubercular agents under iron limiting condition in our earlier study. Clinical complications of newly introduced antibiotic Linezolid, due its MAO inhibitory activity, prompted us to evaluate our compounds for their MAO-inhibitory activity against rat liver MAO-A and MAO-B as pyrazolines were reported to be antidepressants and MAO inhibitors. The present study carried out with this pilot library of 32 compounds will provide us with necessary information for designing antitubercular molecules with reduced MAO-inhibitory activity and also help us in identifying a selective MAO-B inhibitor which has potential clinical utility in neurodegenerative disorders. Thirty-two compounds analyzed has shown spectrum of activity from selective to nonselective against two isoforms of rat liver MAO-A and MAO-B and also as competitive, reversible to non-competitive, irreversible. It is also interesting to note that anti-tubercular compound 11, 14 and 16 were also found to be selective inhibitors of rat liver MAO-B. Docking studies with human MAO shows that compound 11 interacts with the catalytic site of both the isoforms, suggesting compound 11 as nonselective inhibitor of human MAO isoforms.
- Jayaprakash, Venkatesan,Sinha, Barij N.,Ucar, Gulberk,Ercan, Ayse
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scheme or table
p. 6362 - 6368
(2009/09/30)
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- Synthesis, biological evaluation and in silico metabolic and toxicity prediction of some flavanone derivatives
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Flavones chemically are anthoxanthins, occur either in the free state or as glycosides associated with tannins (flavanoids). Flavanoids (derivatives of flavone) possess various pharmacological activities and due to its xanthine-oxidase enzyme inhibitory effect it also has superoxide-scavenging activities. A series of 2-phenyl-2,3-dihydrochromon-4-one derivatives (flavanone derivatives) were synthesized from chalcones by cyclization method and their activities were evaluated against some gram positive and gram-negative bacteria. IR, NMR and CHN analysis confirmed the structure of the synthesized compounds. The results of the antibacterial studies shows that compounds 2b, 2e, 2f and 2h possess activity against many bacterial strains. Among that the compound (2h) has remarkable activity against all strains viz. 25 μg/ml inhibitory concentration against S. aureus, S. sonnei, E. coli, S. typhimurium and V. cholerae. Compound 2f possess minimum inhibitory concentration of 200 μg/ml against E. coli and S. typhimurium and 25 μg/ml against S. sonnei, S. dysenteriae and V. cholerae. In silico metabolic and toxicity study of the synthesized compounds were performed and the predicted result showed that the compound having hydroxyl functional group undergo sulfate and O-glucuronide conjugation reaction and methoxy derivatives undergo demethylation reaction. The biologically active compounds are free of toxicity in oncogene, teratogen, sensitivity and immunotoxicity.
- Moorthy, Narayana Subbiah Hari Narayana,Singh, Rahul Jitendra,Singh, Hemendra Pratap,Gupta, Sayan Dutta
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p. 1384 - 1390
(2007/10/03)
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- Preparative monohydroxyflavanone syntheses and a protocol for gas chromatography-mass spectrometry analysis of monohydroxyflavanones
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We describe a facile efficient, and preparative approach for monohydroxyflavanone syntheses. Using this protocol, a hydroxyl is regio-selectively introduced at one carbon of a flavanone A- or B-ring per synthesis. The seven possible isomers were each synthesized from the corresponding monomethoxymethoxylated 2′-hydroxychalcones in acidic solution. These monohydroxyflavanones were characterized using a gas chromatography-mass spectrometry (GC-MS) system that incorporated a DB-5 capillary column. Ours is the first report of a preparative synthetic method during which a single hydroxyl can be selectively added to a flavanone A- or B-ring at any position. We are also the first to develop a procedure that separates the seven isomers by GC and characterizes the mass spectra of the isomers. Both the synthetic method and the GC-MS conditions may become important tools during future flavanone metabolism and oxidation studies.
- Kagawa, Hitoshi,Shigematsu, Asako,Ohta, Shigeru,Harigaya, Yoshihiro
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p. 547 - 554
(2007/10/03)
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- Synthesis of flavanones using nanocrystalline MgO
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The design and development of a truly nano heterogeneous catalyst for the Claisen-Schmidt condensation (CSC) of benzaldehydes with 2-hydroxyacetophenone to yield substituted chalcones followed by isomerization to afford flavanones with excellent yields and selectivity is described.
- Choudary,Ranganath,Yadav, Jagajit,Lakshmi Kantam
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p. 1369 - 1371
(2007/10/03)
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- Differential effects of synthesized 2′-oxygenated chalcone derivatives: Modulation of human cell cycle phase distribution
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Ten structurally related 2′-oxygenated chalcone derivatives, bearing either hydroxy and/or methoxy substituents on the A and B rings, were synthesized through Claisen-Schmidt condensation. The synthesis procedure was relatively easy and had an acceptable yield. The in vitro cytotoxicities of these compounds against the human tumor cells such as Jurkat, U937 cells, and normal cells PHA stimulated PBMCs were investigated. Among those, compounds 1 (IC50=2.5μM), 2 (1.7μM), and 8 (3.2μM) showed potent inhibitory activity toward Jurkat cell line. In parallel, compounds 1 (6.7μM), 2 (1.5μM), and 10 (5.3μM) showed the highest activity against U937 cell line. However, the chalcones also inhibit the PHA stimulated PBMCs cells, but the IC50 values were relatively high when compared to the tumor cell line values. Studies were also on the effect of synthesized chalcones on the cell cycle phase distribution. In Jurkat cell line, compounds 7 and 9 showed the highest activity and the most striking effect in reduction of the percentage of cells in the S phase, which was associated with an increase of cells in G2/M phase. In U937 cell line, compound 3 increased the proportion of cells in the G0/G1 phase and reduced the proportion in S phase. In contrast, compounds 1, 9, and 10 showed a decrease effect on the percentage of cells in S phase and an increase effect on the percentage of cells in the G2/M phase of the cell cycle. Whereas in the case of PHA stimulated PBMCs, compounds 1, 4, 8, and 10 increased the percentage of cells in G2/M phase, which was associated with a decrease effect in the S phase of the cell cycle.
- Rao, Yerra Koteswara,Fang, Shih-Hua,Tzeng, Yew-Min
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p. 2679 - 2686
(2007/10/03)
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- Synthesis and anti-inflammatory effect of chalcones
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The process of degranulation of mast cells and neutrophils contributes to inflammatory disorders. Activation of microglial cells and macrophages is believed to be involved in inflammatory, infectious and degenerative diseases of the CNS. Combining the pot
- Hsieh, Hsin-Kaw,Tsao, Lo-Ti,Wang, Jih-Pyang,Lin, Chun-Nan
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p. 163 - 171
(2007/10/03)
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- SYNTHESIS OF 2'-HYDROXYCHALCONES AND RELATED COMPOUNDS IN INTERFACIAL SOLID-LIQUID CONDITIONS
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A general synthetic method of 2'-hydroxychalcones and 2'-hydroxyphenyl-(2-alkylvinyl)ketones in interfacial solid-liquid conditions, is described.No secondary reactions were observed.The interfacial mechanism is discussed by means of the structure of active sites of solid.
- Alcantara, A. R.,Marinas, J. Ma.,Sinisterra, J. V.
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p. 1515 - 1518
(2007/10/02)
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