- Structural, photoluminescence, physical, optical limiting, and hirshfeld surface analysis of polymorphic chlorophenyl organic chalcone derivative for optoelectronic applications
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The polymorphic molecule of (E)-1-(thiophen-2-yl)-3-(4-chlorophenyl) prop-2-en-1-one (2AT4C) was synthesized and grown its single crystals using slow evaporation solution growth technique. The molecular geometry and its structural deviations are studied u
- D, Haleshappa,Bairy, Raghavendra,A, Jayarama,Quah, Ching Kheng,Kwong, Huey Chong,Patil, Parutagouda Shankaragouda
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Read Online
- DNA interaction, in vivo and in vitro cytotoxicity, reactive oxygen species, lipid peroxidation of –N, S donor Re(I) metal complexes
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Abstract: N, S donor ligands (L1–L5){L1–L5 = 1,5-bis(4-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole (L1), 1-(4-bromophenyl)-5-(4-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole (L2), 5-(4-chlorophenyl)-3-(thiophen-2-yl)-1-(p-tolyl)-4,5-dihydro-1H-pyrazole (L3), 5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole (L4), 5-(4-chlorophenyl)-1-(4-nitrophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole (L5)} were synthesized by Claisen–Schmidt condensation and characterized by spectrometric methods. The complexes (I–V) were synthesized by ligand combination followed by metal chelation. The binding of the rhenium complexes to Herrin sperm DNA was monitored by UV spectroscopy and viscosity measurements. The groove binding was suggested as the most possible mode, and the Kb values of the complexes were calculated. The mode of interaction was furthermore confirmed by molecular docking. Brine shrimp lethality and Saccharomyces cerevisiae cytotoxicity against the eukaryotic and prokaryotic cells showed the toxic nature of the synthesized compounds. All compounds were found active against S. cerevisiae, which was confirmed by increased ROS production, and DNA damage as compared to untreated yeast cell culture. The oxidative harm to cell structures was affirmed by lipid peroxidation. An antimicrobial study was carried out by estimating minimum inhibitory concentration against two Gram-positive and three Gram-negative bacteria. All complexes show good antiproliferative activity against the HCT 116 cell line. All synthesized complexes are biologically more active than the corresponding ligands. Graphic abstract: [Figure not available: see fulltext.]
- Varma, Reena R.,Pandya, Juhee G.,Sharma, Jyoti,Pathak, Chandramani,Patel, Mohan N.
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p. 687 - 699
(2020/02/13)
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- Synthesis, Characterization, Biological Evaluation and Molecular Docking Studies of Some Oxazinyl-Thiazolidinone Derivatives
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A series of new 4-thiazolidinone derivatives of 2-(4-chlorophenyl)-3-(6-(thiophen-2-yl)-4-p-tolyl-4H-1,3-oxazin-2-yl)-thiazolidin-4-one (7h-m) are synthesized because of its wide range of biological activities.1H & 13C NMR, IR studie
- Rajalakshmi, Ramarajan,Santhi, Rajavel,Elakkiya, Thangaraj
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p. 2125 - 2129
(2020/09/16)
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- Discovery of Novel Approach for Regioselective Synthesis of Thioxotriaza-Spiro Derivatives via Oxalic Acid
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A vital approach for the synthesis of a range of novel thioxotriaza-spiro derivatives is described. These new heterocyclic systems are obtained via oxalic acid catalyzed reaction of α,β-unsaturated ketones in the presence of 5,6-diamino-2-mercaptopyrimidi
- Gopinatha, Vindya K.,Mantelingu, Kempegowda,Raghavan, Sathees C.,Rangappa, Kanchugarakoppal S.,Swarup, Hassan A.
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supporting information
p. 2004 - 2009
(2019/10/28)
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- Synthesis and anti-proliferative assessment of triazolo-thiadiazepine and triazolo-thiadiazine scaffolds
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A series of triazolo-thiadiazepines 4a-k were synthesized with excellent yields using dehydrated PTSA as a catalyst in toluene. Two triazolo-thiadiazines were obtained; 8a was formed directly by reflux in ethanol, whereas, PTSA promoted the formation of 8
- Boraei, Ahmed T.A.,Ghabbour, Hazem A.,Gomaa, Mohamed S.,El Ashry, El Sayed H.,Barakat, Assem
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- Divergent Synthesis and Evaluation of the in vitro Cytotoxicity Profiles of 3,4-Ethylenedioxythiophenyl-2-propen-1-one Analogues
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A new series of 3,4-ethylenedioxythiophene (EDOT)-appended propenones were prepared by condensation reaction and their in vitro cytotoxicity effects were evaluated against five human cancer cell lines. Preliminary structure–activity relationships of EDOT-
- Karunakaran, Jayachandran,Dhatchana Moorthy, Nachiappan,Chowdhury, Somenath Roy,Iqbal, Saleem,Majumder, Hemanta K.,Gunasekaran, Krishnasamy,Vellaichamy, Elangovan,Mohanakrishnan, Arasambattu K.
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p. 1418 - 1430
(2019/08/07)
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- Studies of NMR Chemical Shifts of Chalcone Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices
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A series of the chalcone derivatives of the five-membered monoheterocyclic compounds, (E)-1-aryl-3-heteroarylpropen-1-ones, were prepared by aldol condensation of the corresponding aldehydes of thiophene, pyrrole, and furan with m- and p-substituted acetophenones. Similar condensation of the acetyl compounds of the heterocycles with m- and p-substituted benzaldehydes gave another series of the chalcone derivatives, (E)-1-heteroaryl-3-arylpropen-1-ones. The 13C chemical shift values (δC) of the chalcone derivatives were determined in order to find if they correlated with the Hammett σ values. A good correlation, especially for the β-C for both series, was found for the 13C chemical shift values (δC) of the chalcone derivatives with the Hammett σ values. The chemical shift values of the β-C of the heterocyclic compounds were plotted against those of the benzene derivatives. The resulting slopes were found to be close to the values of the aromaticity indices.
- Jeong, Eun Jeong,Lee, In-Sook Han
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p. 668 - 673
(2019/07/12)
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- Synthesis, molecular modeling, and biological evaluation of 4-[5-aryl-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes
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In this study, 4-[5-aryl-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl] benzenesulfonamides were synthesized, and inhibition effects on AChE, hCA I, and hCA II were evaluated. Ki values of the compounds toward hCA I were in the range of 24.2?±?4.6-49.8?±?12.8?nm, while they were in the range of 37.3?±?9.0-65.3?±?16.7?nm toward hCA II. Ki values of the acetazolamide were 282.1?±?19.7?nm and 103.60?±?27.6?nm toward both isoenzymes, respectively. The compounds inhibited AChE with Ki in the range of 22.7?±?10.3-109.1?±?27.0?nm, whereas the tacrine had Ki value of 66.5?±?13.8?nm. Electronic structure calculations at M06-L/6-31?+?G(d,p)//AM1 level and molecular docking studies were also performed to enlighten inhibition mechanism and to support experimental findings. Results obtained from calculations of molecular properties showed that the compounds obey drug-likeness properties. The experimental and computational findings obtained in this study might be useful in the design of novel inhibitors against hCA I, hCA II, and AChE.
- Yamali, Cem,Gul, Halise Inci,Ece, Abdulilah,Taslimi, Parham,Gulcin, Ilhami
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p. 854 - 866
(2017/12/13)
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- Fighting against alzheimer’s disease: Synthesis of new pyrazoline and benzothiazole derivatives as new acetylcholinesterase and MAO inhibitors
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Background: Alzheimer’s Disease (AD) is a complicated neurodegenerative disorder with a multifaceted pathogenesis.AD, characterized by gradual memory loss, falling in language ability and other cognitive deterioration, and has been a prominent risk to ageing population. This means that there is an urgent need to find new lead compounds for controlling and fighting against (AD). In this way, a new thiophene-2-pyrazoline derivatives (A1-A5) and benzothiazole derivatives (A6-A13) have been synthesized to give beneficial compounds to controlling and battling against (AD). Results: Compounds A5 and A13 showed the most remarkable activity with an 18.53 μM and 15.26 μM IC50 values against AChE enzyme. In like manner, compound A4 was active with a 20.34 μM IC50 value against MAO-A. These active compounds are in fact non-toxic making them very attractive for additional future studies. Enzyme kinetic was analyzed and the Lineweaver-Burk plot reveals that compound A13 was typically mixed AChE inhibitors, which showed significant similarity to donepezil. In addition, the best docking pose was done by analyzing the docking pattern of the most active compound A13 which was very compatible with the gorge and in interaction with both CAS and PAS. Conclusion: The synthesis of new thiophene-2-pyrazoline and benzothiazole derivatives targeting AChE/(MAO-A)/(MAO-B) enzymes was described. The selection of enzyme-kinetic analysis, molecular docking and toxicity test was led to good understanding to the therapeutic potential for the active derivatives. Therefore, these compounds may be accepted as promising leads for future research efforts in fighting against AD.
- Turan-Zitouni, Gülhan,Hussein, Weiam,Sa?l?k, Begüm Nurpelin,Baysal, Merve,Kaplanc?kl?, Zafer As?m
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p. 414 - 427
(2018/04/20)
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- An improved synthesis of pyrido[2,3-: D] pyrimidin-4(1 H)-ones and their antimicrobial activity
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The screening of a small library of diverse chemical structures resulted in the identification of 2-thioxodihydropyrido[2,3-d]pyrimidine 10a as having broad spectrum antibacterial activity (MIC 0.49-3.9 μg mL-1), and reasonable antifungal activity (MIC 31.25 μg mL-1). An expeditious synthesis of 10a was optimized by varying solvents, catalysts and the use of microwave irradiation with the best conditions using DMF as a solvent, I2 (10 mol%) and a 30 minutes reaction time compared to 15 h for classic conventional heating. The pharmacokinetic properties and calculation of drug likeness of 10a suggested good traditional drug-like properties and led to the synthesis of a small library with seven compounds 10a and 10d-i showing broad antimicrobial activity (MIC = 0.49-7.81 μg mL-1) and selectivity indices of more than 5.6 against the normal colon cell line (CCD-33Co). The antifungal activity of compounds 10d-i was moderate to strong with MIC values of 1.95-15.63 μg mL-1.
- Fares, Mohamed,Abd El Hadi, Soha R.,Eladwy, Radwa A.,Shoun, Aly A.,Abdel-Aziz, Marwa M.,Eldehna, Wagdy M.,Abdel-Aziz, Hatem A.,Keller, Paul A.
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supporting information
p. 3389 - 3395
(2018/05/23)
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- Facile one pot multicomponent synthesis of novel 4-(benzofuran-2-yl)-2-(3-(aryl/heteryl)-5-(aryl/heteryl)-4,5-dihydro-1H-pyrazol-1yl)thiazole derivatives
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An efficient base catalyzed one pot multicomponent reaction of aryl/hetryl chalcones, thiosemicarbazide and 1-(benzofuran-2-yl)-2-bromoethan-1-one was developed to synthesize the novel 4-(benzofuran-2-yl)-2-(3-(aryl/heteryl)-5-(aryl/heteryl)-4,5-dihydro-1H-pyrazol-1yl)thiazole derivatives.
- Arandkar, Varun,Vaarla, Krishnaiah,Vedula, Rajeswar Rao
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p. 1285 - 1290
(2018/05/30)
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- Synthesis, characterization, and antioxidant activity of some new benzodiazepine derivatives
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A series of novel 4-(substituted phenyl)-2-(2-thienyl)-2,3-dihydro-1H-benzo[b] [1,4] diazepines (MB1-MB8) has been synthesized from 3-(substituted phenyl)-1-(2-thienyl)prop-2-en-1ones (MC1-MC8). The latter compo
- Bhat, K. Ishwar,Kumar, Abhishek
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p. 397 - 400
(2018/09/29)
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- Synthesis, characterization and biological applications of some substituted pyrazoline based palladium (II) compounds
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Palladium (II) complexes of the type [PdLCl2] (where L?=?substituted pyrazoline ligands) have been synthesized. The metal complexes (5a-5f) have been characterized by various spectroscopic and analytical techniques like 1H-NMR,
- Thakor, Khyati P.,Lunagariya, Miral V.,Bhatt, Bhupesh S.,Patel, Mohan N.
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- Facile epoxidation of α, β-unsaturated ketones with urea-2,2-dihydroperoxypropane as a new oxidant
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Abstract: Various aromatic α, β-unsaturated ketones were successfully transformed into their corresponding epoxides using urea-2,2-dihydroperoxypropane as the oxygen source for the first time. The reactions were carried out under mild alkaline conditions at room temperature in high yields and short reaction times. Graphical Abstract: [Figure not available: see fulltext.]
- Khosravi, Kaveh,Naserifar, Shirin
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p. 323 - 328
(2017/01/10)
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- Metal-Free and Efficient Epoxidation of α,β-Unsaturated Ketones with 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as a Powerful Solid Oxidant
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1,1,2,2-Tetrahydroperoxy-1,2-diphenylethane was used for the efficient and metal-free epoxidation of various α,β-unsaturated ketones, carried out under mild alkaline conditions at room temperature.
- Khosravi, Kaveh,Naserifar, Shirin,Mahmoudi, Boshra
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p. 683 - 689
(2017/06/19)
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- Aluminum chloride-catalyzed C-alkylation of pyrrole and indole with chalcone and bis-chalcone derivatives
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The AlCl3-catalyzed alkylation of pyrrole (2) with chalcone (1a-i) at a ratio of 8:1 in the presence of 10 mol% AlCl3 gave the solely 2-alkyl pyrroles (3a-i) at room temperature for 12 in good yields. The same reaction was performed with pyrrole (2) and chalcone at a ratio of 1:3 in CH3CN at rt for 3 h to achieve 2,5-dialkyl pyrroles (4a-f). In addition, the reaction of the pyrrole (2) and indole (7) on 1,4-phenylene bis-chalcones (5a-g) at the ratio of 8:1 at rt for 24 h gave the double-addition products 6a-g and 8a-g in good yields, respectively. The structure of the products was confirmed by 1H and 13C NMR spectroscopy and elemental analysis.
- Gürdere, Meliha Burcu,?zbek, Oguz,Ceylan, Mustafa
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p. 322 - 331
(2016/03/23)
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- Triethylamin-mediated addition of 2-aminoethanethiol hydrochloride to chalcones: Synthesis of 3-(2-aminoethylthio)-1-(aryl)-3-(thiophen-2-yl) propan-1-ones and 5,7-diaryl-2,3,6, 7-tetrahydro-1,4-thiazepines
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The triethylamin-mediated addition of 2-aminoethanethiol hydrochloride to chalcone analogs was investigated. This addition, bearing a 2-thienyl group at the 3-position, gave the only addition adduct at room temperature in 3 h, whereas the chalcones bearing the 2-furyl group at the 1-position gave an addition-cyclization product (1, 4-thiazepine) in the same conditions. The effect of the groups to the reaction was investigated by changing the 1- and 3-position groups. The chalcones bearing the 2-thienyl group at the 1-position and the others afforded the mixture of products in different ratio at rt for 0.5-24 h. Moreover, the addition-cyclization products (1,4-thiazepine) were obtained under reflux conditions in 36 h. The structures of the synthesized compounds were elucidated by 1H NMR, 13C NMR, infrared, and elemental analysis.
- Gürdere, Meliha Burcu,Eme?, Ali Cemal,Aslan, Osman Nuri,Budak, Yakup,Ceylan, Mustafa
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p. 536 - 545
(2016/05/02)
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- Design, synthesis and biological evaluation of pyrazoline nucleus based homoleptic Ru(III) compounds
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A series of tri-substituted pyrazoline nucleus based homoleptic Ru(iii) complexes of type [Ru(L1-7)2]·(PF6)3 (L1-7= heterocyclic pyrazoline derivatives) were synthesized and characterized by elemental
- Mehta, Jugal V.,Gajera, Sanjay B.,Patel, Mohan N.
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p. 1367 - 1380
(2016/07/21)
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- Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation, and ulcerogenic liability of new 1,3,5-triarylpyrazoline derivatives possessing a methanesulfonyl pharmacophore
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A new series of 1,3,5-triarylpyrazolines 13a–l was synthesized and all prepared compounds were evaluated for their in vitro COX-1/COX-2 inhibitory activity and in vivo anti-inflammatory activity. All test compounds were more selective for the COX-2 isozyme and showed good in vivo anti-inflammatory activity. Compound 13h was the most COX-2 selective compound (COX-2 selectivity index (SI)=10.23) and the most potent anti-inflammatory derivative (ED50-60.1μmol/kg) in comparison with celecoxib (COX-2 SI=9.29 and ED50=81.4μmol/kg). All screened compounds were less ulcerogenic (ulcer indexes (UI)=0.33–1.33) than aspirin (UI=2.33) and comparable to celecoxib (UI=0.33).
- Abdellatif, Khaled R. A.,Fadaly, Wael A. A.,Azouz, Amany A.
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- D-A-π-D Synthetic approach for thienyl chalcones - NLO - a structure activity study
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With the growing interest for organic molecules in Nonlinear Optical (NLO) applications, we have synthesized nine novel thienyl chalcones based on the D-A-π-D design. In order to establish the identity, these have been characterized in detail. Having followed the design based synthetic route, we have focused on two prime criteria for comparison; namely second harmonic generation (SHG) and non-linear absorption. In this work the role of the electron withdrawing groups, electron donating groups and extended conjugation, have been extensively studied vis-à-vis the NLO properties. The change in these properties by virtue of the molecular structure has been elucidated in this work as the structure activity relationship. Optical nonlinearity is studied using ultrafast (100 fs) laser pulses at 800 nm, employing the open aperture Z-scan technique. The compounds exhibit large effective three-photon absorption (3PA) coefficients, in the order of 10-28 m3/W2. These observations show that these compounds possess potential for application in all-optical limiting and switching devices.
- Tejkiran,Brahma Teja,Sai Siva Kumar,Sankar, Pranitha,Philip, Reji,Naveen,Lokanath,Nageswara Rao
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- Synthesis and selective cytotoxic activities on rhabdomyosarcoma and noncancerous cells of some heterocyclic chalcones
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Chemically diverse heterocyclic chalcones were prepared and evaluated for cytotoxicity, aiming to push forward potency and selectivity. They were tested against rhabdomyosarcoma (RMS) and noncancerous cell line (LLC-PK1). The influence of heteroaryl patte
- Do, Tuong-Ha,Nguyen, Dai-Minh,Truong, Van-Dat,Do, Thi-Hong-Tuoi,Le, Minh-Tri,Pham, Thanh-Quan,Thai, Khac-Minh,Tran, Thanh-Dao
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- Structural identification of pyrazoles and pyrimidines using 2D HMBC NMR and single-crystal X-ray diffraction
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A facile and highly efficient microwave-assisted synthesis of functionalized pyrazoles and pyrimidines based on the regiospecific synthesis is reported. The present work provides unambiguous evidence of the pyrazoles was determined using 2D HMBC NMR. The structure for pyrimidine have been confirmed by single-crystal X-ray diffraction.
- Al-Bogami
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p. 4611 - 4614
(2015/11/28)
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- Synthesis and evaluation of new pyrazoline derivatives as potential anticancer agents
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New pyrazoline derivatives were synthesized and evaluated for their cytotoxic effects on AsPC-1 human pancreatic adenocarcinoma, U87 and U251 human glioblastoma cell lines. 1-[((5-(4-Methylphenyl)-1,3,4-oxadiazol-2-yl)thio)acetyl]-3-(2-thienyl)-5-(4-chlor
- Karabacak, Muhammed,Altintop, Mehlika Dilek,?ift?i, Halil Ibrahim,Koga, Ryoko,Otsuka, Masami,Fujita, Mikako,?zdemir, Ahmet
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p. 19066 - 19084
(2015/11/27)
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- Selected michael additions to thiophene-containing analogues of chalcone
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Using thiophene-containing analogues of chalcone as substrates, a series of Michael additions were investigated. Thia-Michael addition of 4-chlorothiophenol led to 1-(substituted aryl)-3-(4-chlorophenylmercapto)-1-(2-thienyl)-1-propanones, whereas catalyt
- Roman, Gheorghe
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p. 751 - 760
(2015/11/24)
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- Green synthesis of chalcones and microbiological evaluation
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A green method was developed for the synthesis of chalcones using glycerin as solvent. Subsequently, the potential microbiology activity of these molecules was evaluated by testing them against the Gram-positive bacteria Staphylococcus aureus (S. aureus) ATCC 19095 and Enterococcus faecalis (E. faecalis) ATCC 4083, the Gram-negative bacteria Escherichia coli (E. coli) ATCC 29214 and Pseudomonas aeruginosa (P. aeruginosa) ATCC 9027, and the fungus Candida albicans (C. albicans), which includes ATCC 62342 and three clinical strains of C. albicans from human oral cavities. The results showed that some chalcones exhibited moderate inhibitory activity, the most prominent being those acting against the fluconazole-resistant strains of C. albicans.
- Ritter, Marina,Martins, Rosiane M.,Rosa, Silvana A.,Malavolta, Juliana L.,Lund, Rafael G.,Flores, Alex F. C.,Pereira, Claudio M.P.
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p. 1201 - 1210
(2015/06/16)
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- Critical assessment of two classical synthetic methods for preparation of thiophene-substituted isoxazoles
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Formation of thiophene-substituted isoxazoles by reaction of chalcone dibromides and 1,3-diketones with hydroxylamine hydrochloride has been examined under different conditions. Use of KOH as base in the reaction of dibromide chalcone analogs with hydroxy
- Roman, Gheorghe
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p. 2039 - 2057
(2014/05/06)
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- Synthesis, pharmacological, and biological screening of novel derivatives of benzodiazepines
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A series of novel 4-(substituted phenyl)-2-(thiophen-2-yl)-2,3-dihydro-1H- benzo[b][1,4]diazepine have been synthesized from 3-(substituted phenyl)-1-(thiophen-2-yl)prop-2-en-1-one. 3-(Substituted phenyl)-1-(thiophen-2- yl)prop-2-en-1-one was prepared by
- Bhat, K. Ishwar,Chauhan, Manoj Kumar Singh,Kumar, Abhishek,Kumar, Pankaj
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p. 1189 - 1192
(2014/08/05)
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- Synthesis of thiophene-linked pyrimidopyrimidines as pharmaceutical leads
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Thiophene-substituted chalcones were cyclised with guanidine in the presence of potassium hydroxide to get 4-substituted-6-thiophenopyrimidines 2a-e which were then refluxed with acetylacetone to obtain pyrimidopyrimidines 3a-e. Compounds 2a-e were also refluxed with ethylacetoacetate to afford pyirmidopyirimidines 4a-e which on refluxing with POCl3 in presence of DMF produced compounds 5a-e. Nucleophilic substitution reactions on 5a-e were carried out with aniline to obtain 6a-e. The structures of the newly synthesised compounds have been confirmed by elemental analysis and spectral studies. Some selected compounds have been screened for antibacterial and analgesic activities.
- Siddesh,Padmashali, Basavaraj,Thriveni,Sandeep
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p. 821 - 826
(2014/07/07)
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- 1-Acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles: Exhibiting anticancer activity through intracellular ROS scavenging and the mitochondria-dependent death pathway
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A series of 17 analogs of 1-acetyl-4,5-dihydro(1H)pyrazoles (JP-1 to JP-17) bearing two aromatic rings at positions 3 and 5, either of which ought to be heterocyclic, were synthesized and evaluated for their anti-proliferative potential against breast cancer (MCF-7 and T-47D) and lung cancer (H-460 and A-549) cell lines for the first time. JP-1-7, -10, -11, -14, and -15 were observed to exhibit significant anti-proliferative activity against MCF-7 cells. Some notions about structure-activity relationships are reported. The investigated compounds were found to lower the intracellular reactive oxygen species in the H2DCFDA assay and also caused mitochondria-dependent cell death in the MCF-7 cell line, indicating a plausible mechanism of their anticancer effect. Analogs of 1-acetyl-4,5-dihydro(1H)pyrazoles (JP-1-17) were synthesized and evaluated for their anti-proliferative activity in four cancer cell lines and for their intracellular ROS scavenging properties. An attempt was made to determine the mitochondrial membrane potential of MCF-7 cells treated with JP-1 and -14, aiming to elucidate the mechanism by which proliferation was curbed.
- Alex, Jimi M.,Singh, Sandeep,Kumar, Raj
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p. 717 - 727
(2016/02/18)
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- Design and synthesis of spiro derivatives containing a thiophene ring and evaluation of their anti-microbial activity
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Synthesis of a series of novel spiro pyrrolidines has been accomplished by 1, 3-dipolar cycloaddition reaction of azomethine ylide generated from phenylalanine and isatin with dipolarophiles in good yield. The reaction proceeded with high regio and stereoselectivity. The products have been characterized by elemental analyses and spectroscopic techniques, namely IR, 1H NMR and 13C NMR spectroscopies. Single crystal analysis of compounds 4k 2D-NMR analysis of compound 4k confirmed the structures of spiropyrrolidine derivatives. These compounds were evaluated for their antimicrobial activity. Most of the synthetic compounds exhibited good activity against microorganisms.
- Kanagaraju, Geethanjali,Thangamani, Arumugam
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p. 1619 - 1630
(2015/04/22)
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- Design, synthesis, and anti-influenza viral activities of 1,3-diarylprop-2-en-1-ones: A novel class of neuraminidase inhibitors
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A series of 1,3-diarylprop-2-en-1-one derivatives 3a-v have been synthesized and evaluated for their ability to inhibit neuraminidase (NA). Among the prepared compounds, the less lipophilic derivative 3k showed the most potent in vitro inhibitory activity against NA with an IC50 value of 1.5 μM.
- Kinger, Mayank,Park, Yong Dae,Park, Jeong Hoon,Hur, Min Goo,Jeong, Hyung Jae,Park, Su-Jin,Lee, Woo Song,Kim, Sang Wook,Yang, Seung Dae
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experimental part
p. 633 - 638
(2012/09/21)
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- Design, synthesis, preliminary pharmacological evaluation, and docking studies of pyrazoline derivatives
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Ten derivatives of N1 substituted/unsubstituted 5-(4-chlorophenyl)-3-(2- thienyl) pyrazoline were synthesised from chalcone-like intermediate and substituted phenyl hydrazines, hydrazine hydrate, and semi/thiosemicarbazide. The chemical structure of compo
- Das, Nirupam,Dash, Biswajit,Dhanawat, Meenakshi,Shrivastava, Sushant Kumar
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experimental part
p. 67 - 74
(2012/04/18)
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- Synthesis, antitumor and antimicrobial activities of 4-(4-chlorophenyl)-3- cyano-2-(β-O-glycosyloxy)-6-(thien-2-yl)-nicotinonitrile
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4-(4-Chlorophenyl)-3-cyano-6-(thien-2-yl)-1H-pyridin-2-one (2) was obtained by reaction of 2-acetyl thiophene with 4-chlorobenzaldehyde and ethyl cyanoacetate in presence of ammonium acetate or by the reaction of α,β-unsaturated compound 1 with ethyl cyan
- El-Sayed, Hassan A.,Moustafa, Ahmed H.,Haikal, Abd El-Fattah Z.,Abu-El-Halawa, Rajab,El Ashry, El Sayed H.
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scheme or table
p. 2948 - 2954
(2011/07/08)
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- Synthesis of thiophen-2-yl pyrimidines as antitumor, analgesic and antiinflammatory agents
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A series of novel thiophen-2-yl pyrimidine derivatives IV, V(a-e) have beenf synthesized from the intermediate chalcones III(a-h). The structures of these compounds were confirmed by IR, NMR, Mass spectroscopy and elemental analysis. Biological studies of
- James, Jainey P.,Bhat, Ishwar K.
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p. 309 - 312
(2013/09/24)
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- Synthesis, spectral studies and anti-inflammatory activity of 2-acetyl thiophene
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Some new chalcones have been synthesized by the condensation of 2-acetyl thiophene with various aromatic aldehydes in 40% alkali. The synthesized compounds were identified by spectral data and screened for antiinflammatory activity. Some of these compounds showed moderate to considerable anti-inflammatory activity.
- Ramesh,Someswara Rao
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experimental part
p. 433 - 436
(2011/10/18)
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- Antimicrobial activity of new 4, 6-disubstituted pyrimidine, pyrazoline, and pyran derivatives
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A number of new 2, 6-didisubstituted pyrimidine, pyrazoline, and pyran derivatives were synthesized starting from their chalcone derivative. The synthesized compounds displayed different degrees of antimicrobial activity against Bscillus subtilis (Gram-positive), Pseudomonas aeruginosa (Gram-negative), and Streptomyces species (Actinomycetes).
- Ramiz, Mahmoud M. M.,El-Sayed, Wael A.,El-Tantawy, Asmaa I.,Abdel-Rahman, Adel A. -H.
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experimental part
p. 647 - 654
(2011/11/14)
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- New pyrazoline derivatives and their antidepressant activity
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Some triazolo-pyrazoline derivatives were synthesized to investigate their potential antidepressant activities. The chemical structures of the compounds were elucidated by IR, NMR and FAB+-MS spectral data and elemental analyses. Antidepressant-like activities of the test compounds (100 mg/kg) were screened using both modified forced swimming and tail suspension tests. Rota-Rod test was performed for the examination of probable neurological deficits due to the test compounds, which may interfere with the test results. The test compounds in the series exhibited different levels of antidepressant activities when compared to reference drug fluoxetine. None of the test compounds changed motor coordination of animals when assessed in the Rota-Rod test. Therefore, experimental results in this study were not interfered with motor abnormalities. The study supports the antidepressant-like activities of various pyrazoline and/or triazole derivatives and suggests a possible serotonin related mechanism of action for the tested compounds.
- Kaplanckl, Zafer Asm,?zdemir, Ahmet,Turan-Zitouni, Gülhan,Altntop, Mehlika Dilek,Can, ?zgür Devrim
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experimental part
p. 4383 - 4387
(2010/10/02)
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- Regiospecific synthesis and biological evaluation of spirooxindolopyrrolizidines via [3+2] cycloaddition of azomethine ylide
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Reaction of (E)-3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones with azomethine ylide (generated in situ via decarboxylative condensation of isatin with l-proline) in refluxing methanol afforded 1′-(aryl)-2′-(2- thienylcarbonyl)-spiro[3H-indole-3,3′-[3H]pyrrolizin]-2-ones as the sole product in a regiospecific manner. The synthesized compounds have been characterized by their elemental, analytical and spectral studies. The synthesized compounds were screened for their antibacterial and antifungal activities against a spectrum of microbial organisms. These studies proved that compounds 1′-(p-chlorophenyl)-2′-(2-thienylcarbonyl)-spiro[3H- indole-3,3′-[3H]pyrrolizin]-2-one (4b), 1′-(p-fluorophenyl)- 2′-(2-thienylcarbonyl)-spiro[3H-indole-3,3′-[3H]pyrrolizin]-2-one (4d) and 1′-(p-methoxyphenyl)-2′-(2-thienylcarbonyl)-spiro[3H- indole-3,3′-[3H]pyrrolizin]-2-one (4h) against Staphylococcus aureus, 1′-(p-chlorophenyl)-2′-(2-thienylcarbonyl)-spiro[3H-indole-3, 3′-[3H]pyrrolizin]-2-one (4b), 1′-(p-methylphenyl)-2′-(2- thienylcarbonyl)-spiro[3H-indole-3,3′-[3H]pyrrolizin]-2-one (4c) and 1′-(p-fluorophenyl)-2′-(2-thienylcarbonyl)-spiro[3H-indole-3, 3′-[3H]pyrrolizin]-2-one (4d) against Salmonella typhi show maximum inhibition potency at low concentration (6.25 μg/mL) whereas 4d against Candida albicans and 4b and 4d against Rhizopus sp. showed beneficial antifungal activity at minimum concentration.
- Thangamani, Arumugam
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experimental part
p. 6120 - 6126
(2011/01/13)
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- Microwave assisted improved synthesis of 6-carbethoxy-5-aryl-3-(2-thienyl)- 2-cyclohexenones using inorganic solid support and their antibacterial activities
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An efficient one-pot synthesis of 6-carbethoxy-5-aryl-3-(2-thienyl)-2- cyclohexenones (4a-g) has been achieved by the cyclocondensation of (2E)-1-(2-thienyl)-3-aryl-2-propenones (1) with ethyl acetoacetate (EAA) under microwave irradiation (MWI) using ino
- Dulawat, Shiv S.,Chundawat, Jagveer S.,Roy, Ravindra S.,Chundawat, Sumer S.,Verma
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body text
p. 981 - 986
(2011/04/27)
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- Synthesis and antimicrobial activity of some thiazolyl-pyrazoline derivatives
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Some 1-(4-aryl-2-thiazolyl)-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives (TP 1-28) were synthesized by reacting substituted 3-(2-thienyl)-5-aryl-1- thiocarbamoyl-2-pyrazolines (P 1-7) with phenacyl bromides in ethanol. Structures of the synthesized compounds were confirmed by elemental analyses and IR, 1H-NMR and MS-FAB+ spectral data. Their antimicrobial activities against Escherichia coli (NRRL B-3704), Staphylococcus aureus (NRLL B-767), Salmonella typhimurium (NRRL B-4420), Bacillus cereus (NRRL B-3711), Listeria monocytogenes (Ankara University, Faculty of Veterinary, Ankara, Turkey), Aeromonas hydrophila (Ankara University, Faculty of Veterinary, Ankara, Turkey), Candida albicans, and Candida glabrata (isolates obtained from Osmangazi University, Faculty of Medicine, Eskisehir Turkey) were investigated. A significant level of activity was illustrated. Copyright Taylor & Francis Group, LLC.
- Kaplancikli, Zafer Asim,Turan-Zitouni, Guelhan,Oezdemir, Ahmet,Revial, Gilbert,Gueven, Kiymet
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p. 749 - 764
(2007/10/03)
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- Identification of compounds with anti-West Nile virus activity
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The lack of antiviral compounds targeting flaviviruses represents a significant problem in the development of strategies for treating West Nile Virus (WNV), Dengue, and Yellow Fever infections. Using WNV high-throughput screening techniques developed in o
- Goodell, John R.,Puig-Basagoiti, Francesc,Forshey, Brett M.,Shi, Pei-Yong,Ferguson, David M.
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p. 2127 - 2137
(2007/10/03)
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- Synthesis of some 1-[(N,N-disubstituted thiocarbamoylthio)acetyl]-3-(2- thienyl)-5-aryl-2-pyrazoline derivatives and investigation of their antibacterial and antifungal activities
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Fourteen new 1-[(N,N-disubstituted thiocarbamoylthio)acetyl]-3-(2-thienyl)- 5-aryl-2-pyrazoline derivatives (7a-n) were synthesised by reacting 1-(chloroacetyl)-3-(2-thienyl)-5-aryl-2-pyrazolines (5a-g) and appropriate sodium salts of N,N-disubstituted dithiocarbamoic acids (6a, b). The structures of the synthesised compounds were confirmed by elemental analyses, UV, IR, 1H-NMR and FAB+-MS spectral data. Their antibacterial activities against Proteus vulgaris (NRRL B-123), Escherichia coli (NRRL B-3704), Aeromonas hydrophila (Ankara University, Faculty of Veterinary Sciences), Salmonella typhimurium (NRRL B-4420), Streptococcus feacalis (NRRL B-14617), Micrococcus luteus (NRLL B-4375) were investigated and in this investigation, a significant level of activity was illustrated. Antifungal activities of the compounds against Candida albicans and Candida globrata (isolates obtained from Osmangazi Uni. Fac. of Medicine) were found to be inactive. Compounds 7c-n were also evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system and BACTEC 12B medium. The preliminary results indicated that all of the tested compounds were inactive against the test organism.
- Turan-Zitouni, Gulhan,Oezdemir, Ahmet,Gueven, Kiymet
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- Microwave-assisted synthesis and anti-bacterial activity of some 2-Amino-6-aryl-4-(2-thienyl)pyrimidines
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Some novel 2-amino-6-aryl-4-(2-thienyl)pyrimidines were synthesized from 3-aryl-1-thien-2ylprop-2-en-1-ones and guanidine hydrochloride in presence of alkali by conventional heating in alcoholic medium and microwave heating in solvent-free conditions. The compounds were evaluated for in vitro anti-bacterial activity. The anti-bacterial data revealed that compounds 5a-e had better activity against tested Gram-positive organisms than the reference ciprofloxacin and norfloxacin. However, the compounds were nearly inactive against Gram-negative bacteria. Compounds 5c and e were the most active compounds against Gram-positive bacteria.
- Chandrasekaran,Nagarajan
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p. 279 - 282
(2007/10/03)
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- Synthesis, molecular modeling studies, and selective inhibitory activity against monoamine oxidase of 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)- pyrazole derivatives
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A novel series of 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)-pyrazole derivatives have been synthesized and investigated for the ability to inhibit selectively the activity of the A and B isoforms of monoamine oxidase (MAO). All the synthesized compounds show high activity against both the MAO-A and the MAO-B isoforms with Ki values between 27 and 4 nM and between 50 and 1.5 nM, respectively, except for a few derivatives whose inhibitory activity against MAO-B was in the micromolar range. Knowing that stereochemistry may be an important modulator of biological activity, we performed the semipreparative Chromatographic enantioseparation of the most potent, selective, and chiral compounds. The separated enantiomers were then submitted to in vitro biological evaluation. The selectivity of the (-)-(S)-1 enantiomer against MAO-B increases twice and a half, while the selectivity of the (-)-(S)-4 enantiomer against MAO-A triples. Both the MAO-A and MAO-B isoforms respectively of the 1O5W and IGOS models deposited in the Protein Data Bank were considered in the computational study. The docking study was carried out using several computational approaches with the aim of proposing possible binding modes of the MAO enantioselective compounds 1 and 4.
- Chimenti, Franco,Maccioni, Elias,Secci, Daniela,Bolasco, Adriana,Chimenti, Paola,Granese, Arianna,Befani, Olivia,Turini, Paola,Alcaro, Stefane,Ortuso, Francesco,Cirilli, Roberto,La Torre, Francesco,Cardia, Maria C.,Distinto, Simona
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p. 7113 - 7122
(2007/10/03)
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- Stereoselective multicomponent synthesis of [3-(5-substituted 2-methoxyphenyl)-5-aryl-2-phenyltetrahydro-4-isoxazolyl](2-thienyl)methanones via 1,3-dipolar cycloaddition
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Three-component stereoselective synthesis of a set of new tetra substituted isoxazolidines from 5-substituted 2-methoxybenzaldehydes, N-phenylhydroxylamine and 1-(2-thienyl)-3-arylprop-2-en-1-ones has been achieved. The effect of microwave irradiation on the reaction under solvent-free conditions has also been investigated. The stereochemistry of the final products has been confirmed by NMR and single crystal X-ray analysis.
- Sridharan,Pon Saravanakumar,Muthusubramanian
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p. 515 - 518
(2007/10/03)
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- The pyrrole moiety as a template for COX-1/COX-2 inhibitors
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Aroyl- and thiophene-substituted pyrrole derivatives have been synthesized as a new class of COX-1/COX-2 inhibitors. The inhibition of COX-1 was evaluated in a biological system using bovine PMNLs as the enzyme source, whereas LPS-stimulated human monocytes served as the enzyme source for inducible COX-2. The determination of the concentration of arachidonic acid metabolites was performed by HPLC for COX-1 and RIA for COX-2. Variation of the substitution pattern led to a series of active compounds which showed inhibition for COX-1 and COX-2. Structural requirements for the development of COX-1/COX-2 inhibitors are discussed. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
- Dannhardt, Gerd,Kiefer, Werner,Kraemer, Godehard,Maehrlein, Sabine,Nowe, Ulrike,Fiebich, Bernd
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p. 499 - 510
(2007/10/03)
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- Heterocycles. 3. Synthesis and Spectral Data of Some 2-Pyrazolines
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The reaction of 1,3-diaryl-2-propen-1-ones (Ia-o) with hydrazine and methyl- and phenylhydrazine produced different substituted 2-pyrazolines (III).The structures of these products were evident from their chemical and spectroscopic analysis.
- El-Rayyes, Nizar R.,Hovakeemian, George H.,Hmoud, Hayat S.
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p. 225 - 229
(2007/10/02)
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