- Synthesis, crystal growth, studies on vibrational spectroscopy and nonlinear optical properties of 4-methoxy-4′-chlorochalcone
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Good quality organic non linear optical (NLO) crystals of 4-methoxy-4′-chlorochalcone (4MCC) have been grown by slow evaporation solution growth method. The grown crystals were investigated with various spectroscopy techniques such as the structural confi
- Prabu,Nagalakshmi,Balaji,Srinivasan
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- Design and synthesis of novel pyridopyrimidine derivatives with anchoring non-coplanar aromatic extensions of EGFR inhibitory activity
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The present study describes the synthesis of three series of 4-substituted pyridopyrimidin derivatives 4a-h, 5a-d. 6a-d, starting from 2-amino-6-(4-methoxyphenyl)-4-(4-(substituted) phenyl)nicotinonitrile 2a-d via the reaction with N,N-dimethyl-N-' substi
- Eissa, Amal A.M.,Aljamal, Kholoud F.M.,Ibrahim, Hany S.,Abdelrasheed Allam, Heba
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- Synthesis of chalcone derivatives by phthalhydrazide-functionalized tio2-coated nano-fe3o4 as a new heterogeneous catalyst
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Phthalhydrazide immobilized on TiO2-coated nano Fe3O4 (Fe3O4-P) was synthesized and characterized by FT-IR, XRD, SEM, EDS and VSM analysis. The resulting magnetic nanocatalyst was used as a catalyst for the synthesis of chalcone derivatives which affords the desired products in good to excellent yields. This catalyst can be isolated readily after completion of the reaction by an external magnetite field and reused several times without significant loss of activity.
- Farahi, Mahnaz,Karami, Bahador,Keshavarz, Raziyeh,Nia, Forough Motamedi
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p. 407 - 414
(2021/09/07)
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- Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water
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A variety of chalcones were synthesized in good yields by the activated charcoal-mediated aldol reactions between benzaldehydes and acetophenones catalyzed by NaOH in water. 2,6-Bis((E)-benzylidene)cyclohexan-1-ones were prepared by the aldol reactions between benzaldehydes and cyclohexanone. Activated charcoal could be recycled five times without the significant decrease of yields.
- Tanemura, Kiyoshi,Rohand, Taoufik
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supporting information
(2021/02/27)
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- New nicotinic acid-based 3,5-diphenylpyrazoles: design, synthesis and antihyperlipidemic activity with potential NPC1L1 inhibitory activity
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Nicotinic acid hydrazide was incorporated into new 4,5-dihydro-5-hydroxy-3,5-diphenylpyrazol-1-yl derivatives. Compounds 6a–h were synthesized, and their antihyperlipidemic activity was evaluated in high cholesterol diet-fed rat model. Compounds 6e, 6f were found to decrease the levels of serum total cholesterol by 14–19% compared to control group. Total triglycerides were also reduced by 24–28% and LDL cholesterol by 16%. As expected from parent niacin, compounds 6e and 6f caused an elevation of HDL cholesterol by 33–41%. Docking study supported the ability of designed compounds to block NPC1L1 active site in a manner similar to that observed with ezetimibe.
- Shoman, Mai E.,Aboelez, Moustafa O.,Shaykhon, Montaser Sh. A.,Ahmed, Sanaa A.,Abuo-Rahma, Gamal El-Din A.,Elhady, Omar M.
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p. 673 - 686
(2020/02/25)
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- Novel nicotinonitrile-coumarin hybrids as potential acetylcholinesterase inhibitors: design, synthesis, in vitro and in silico studies
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Abstract: Alzheimer’s disease is a degenerative brain condition that is the leading cause of dementia affecting millions of people around the world. Therapeutic development has focused on the problem of the loss of basal forebrain cholinergic function, as it is the only evidence responsible for brain neurodegeneration in patients with Alzheimer’s disease. Several attempts to improve cholinergic neurotransmission have been investigated by minimizing synaptic degradation of acetylcholine using acetylcholinesterase inhibitors. In the current study, we explore the designing of a new series of nicotinonitrile-coumarin hybrids as potential acetylcholinesterase inhibitors. The new hybrids were prepared utilizing pyridine-2(1H)-thiones as starting precursors. The in vitro acetylcholinesterase (AChE) inhibitory activities were examined for the new nicotinonitrile-coumarin hybrid molecules, when compared with donepezil as a standard drug with IC50 of 14?nM. Coumarin derivative, linked to 6-(4-nitrophenyl)-4-phenylnicotinonitrile, showed more effective inhibitory activity than the reference donepezil with IC50 of 13?nM. The free radical-scavenging capabilities against DPPH of the new hybrid derivatives were screened. Additionally, their in vitro cytotoxic activities have been tested against various eukaryotic cells. Furthermore, docking study showed excellent interaction between nicotinonitrile-coumarin hybrids and AChE. Graphic abstract: [Figure not available: see fulltext.]
- Sanad, Sherif M. H.,Mekky, Ahmed E. M.
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p. 213 - 224
(2020/08/05)
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- Boosting the catalytic performance of zinc linked amino acid complex as an eco-friendly for synthesis of novel pyrimidines in aqueous medium
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Zinc linked amino acid complex, Zn(l-proline)2, is considered as a green catalyst for the synthesis of novel series of pyrimidine derivatives 5a–q. The pyrimidines 5a–q were prepared via two pathways: the first is a one-pot reaction of guanidines 3a–c with aromatic aldehyde 1 and acetophenones 2; and the second one is the reaction of guanidines 3a–c with different chalcones 4a–j in aqueous medium. The simplicity of the operation, the short reaction time, and the high efficiency (97%) are the main advantages of this protocol. Furthermore, the green aspects of this synthetic protocol were further investigated by examining the reusability of Zn(l-proline)2 complex throughout five consecutive cycles without a significant loss of catalytic activity. This new procedure has presented remarkable advantages in terms of safety, simplicity, stability, mild conditions, a short reaction time, excellent yields, and high purities without using any organic solvents.
- Ahmed, Eman A.,Soliman, Ahmed M.M.,Ali, Ali M.,Ali El-Remaily, Mahmoud Abd El Aleem Ali
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- Potassium Natural Asphalt Sulfonate (K-NAS): Synthesis and characterization as a new recyclable solid basic nanocatalyst and its application in the formation of carbon–carbon bonds
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In this research, we synthesized and characterized a new heterogeneous basic nanocatalyst and its catalytic application was studied in the Claisen-Schmidt and Knoevenagel condensations. In order to prepare this nanocatalyst, first, the Iranian natural asphalt was sulfonated with the concentrated sulfuric acid and then, converted to the potassium natural asphalt sulfonate (K-NAS). In order to characterization of the nanocatalyst, used of FT-IR spectroscopy, scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), X-ray diffraction (XRD), inductively coupled plasma (ICP) and thermogravimetric analysis (TGA) techniques. This new basic heterogeneous nanocatalyst have advantages such as being eco-friendly, huge specific surface area, high reactivity and recyclability.
- Falah, Saeid,Soleiman-Beigi, Mohammad,Kohzadi, Homa
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- Synthesis and evaluation of novel 4H-pyrazole and thiophene derivatives derived from chalcone as potential anti-proliferative agents, Pim-1 kinase inhibitors, and PAINS
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The chalcone derivatives 3a-d reacted with either malononitrile or ethyl cyanoacetate in ethanol in the presence of catalytic amount of ammonium acetate in an oil bath at 120°C to give the Knowevenagel condensation products 5a-h. The latter compounds reac
- Megally Abdo, Nadia Y.,Mohareb, Rafat M.,Samir, Eman M.
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- Discovery of new fluorescent thiazole–pyrazoline derivatives as autophagy inducers by inhibiting mTOR activity in A549 human lung cancer cells
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A series of fluorescent thiazole–pyrazoline derivatives was synthesized and their structures were characterized by 1H NMR, 13C NMR, and HRMS. Biological evaluation demonstrated that these compounds could effectively inhibit the growt
- Chen, Yuan,Gao, DongFang,Kong, Feng,Lin, YuXing,Lin, ZhaoMin,Miao, JunYing,Wang, Peng,Wang, ZhaoYang,Zhang, Lu,Zhang, Ming,Zhao, BaoXiang,Zhou, XueWen
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- Synthesis and in vitro study of new coumarin derivatives linked to nicotinonitrile moieties as potential acetylcholinesterase inhibitors
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The appropriate pyridine-2(1H)-thiones were reacted with an equivalent amount of 5-(chloromethyl)-2-hydroxybenzaldehyde in ethanol in the presence of potassium hydroxide to give the corresponding 2-hydroxybenzaldehyde derivatives in excellent yields. The latter derivatives were taken as key synthons for the preparation of the target hybrids. Therefore, 2-hydroxybenzaldehydes were reacted with benzoylglycine in acetic anhydride in the presence of fused sodium acetate at 100°C for 6 hours to afford a new series of nicotinonitrile-coumarin hybrids. The in vitro acetylcholinesterase inhibitory activities were estimated for the new coumarins. The results were expressed as the inhibition percentage of the tested hybrids at concentration of 25 nM, compared to donepezil as a reference (inhibition percentage of 70.5). Coumarin hybrids linked to 6-(4-nitrophenyl) or 6-(4-chlorophenyl)-4-phenylnicotinonitrile exhibited more effective inhibitory activities than donepezil with inhibition percentages of 94.1 and 72.3, respectively. The new coumarins were tested for their free radical-scavenging capabilities against DPPH. Furthermore, some new coumarins were tested for in vitro cytotoxic activity against each MCF-10A, MCF-7, Caco2, and HEPG2. The new hybrids showed cytotoxicity in micromolar range (IC50 of 3.5-13.9 μM) against all tested cell lines. These results clearly demonstrated that the hybrids being tested are not cytotoxic at the concentration required to inhibit acetylcholinesterase effectively.
- Mekky, Ahmed E. M.,Sanad, Sherif M. H.
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p. 4278 - 4290
(2020/09/12)
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- Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes
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Formal [5 + 1] cycloadditions between aryl-substituted vinylcyclopropanes and nitrenoid precursors are reported. The method, which employs Rh2(esp)2 as a catalyst, leads to the highly regioselective formation of substituted tetrahydropyridines. Preliminary mechanistic studies support a stepwise, polar mechanism enabled by the previously observed Lewis acidity of Rh-nitrenoids. Overall, this work expands the application of nitrene-transfer cycloaddition, a relatively underexplored approach to heterocycle synthesis, to the formation of six-membered rings.
- Combee, Logan A.,Johnson, Shea L.,Laudenschlager, Julie E.,Hilinski, Michael K.
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supporting information
p. 2307 - 2311
(2019/04/10)
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- Environment Friendly Synthesis of N′-(1,3-Diphenylallylidene)-1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbohydrazides: Crystal Structure and Their Anti-oxidant Potential
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An environment friendly synthesis of novel hybrid pharmacophores derived from synergism of nalidixic acid and 1,3-diphenylprop-2-en-1-ones is described. Percent yield and reaction times of microwave assisted reactions have been compared with the reactions
- Mubarak, Shafaq,Zia-Ur-Rehman, Muhammad,Jamil, Nadia,Zaheer, Muhammad,Arshad, Muhammad Nadeem,Asiri, Abdullah Mohammad
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p. 1191 - 1200
(2019/11/19)
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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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- Catalytic Synthesis of Chalcones and Pyrazolines Using Nanorod Vanadatesulfuric Acid: An Efficient and Reusable Catalyst
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Nanorod vanadatesulfuric acid (VSA NRs), as a recyclable and ecologically benign catalyst, was used for the one-pot synthesis of chalcones and 1,3,5-triaryl-2-pyrazolines (TAPs). Chalcones were prepared via the condensation of substituted acetophenones with aryl-aldehydes under solvent-free conditions. Subsequently, the synthesized chalcones were used for the catalytic synthesis of TAPs via two-component condensation with phenyl hydrazine in refluxing ethanol. VSA is easily prepared by a simple reaction of chlorosulfonic acid and sodium metavanadate of high purity. Compared to conventional procedures, the present protocol offers several advantages such as simplicity of the procedure, appropriate reaction times, high to excellent yields, easily work-up, recoverability, and reusability of the catalyst, and simple purification of the products.
- Nasr-Esfahani, Masoud,Daghaghale, Mona,Taei, Mahbube
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- In situ formed acetals facilitated direct Michael addition of unactivated ketones
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TfOH-promoted synthesis of 1,5-diketones by the Michael reaction of unactivated ketones with chalcones has been described. Acetals formed under HC(OMe)3/TfOH conditions generate the required enol-equivalents for a smooth Michael reaction. A wide array of symmetrical and unsymmetrical 1,5-diketones has been synthesised.
- Koppolu, Srinivasa Rao,Balamurugan, Rengarajan
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p. 1186 - 1192
(2017/02/10)
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- A regioselective and convenient one-pot multicomponent synthesis of 9-amino-3,5-diaryl-4,9-dihydro-5H-[1,2,4]triazolo[5,1-c][1,2,4]triazepine-8-thiol
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An efficient and environment-friendly procedure for the synthesis of a new series of nitrogen bridge-head [1,2,4]triazolo[5,1-c][1,2,4]triazepine derivatives through one-pot three-component reaction of polyfunctional triazole with aromatic aldehydes and acetophenone derivatives using alcoholic sodium hydroxide solution. The same new products were prepared in classical route through reaction of triazole with the corresponding chalcones under the same conditions.
- Moustafa, Amr Hassan,Amer, Amer Anwar
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p. 1102 - 1109
(2017/05/25)
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- Synthesis and cytotoxicity evaluation of new 3-substituted 4-(4-methyloxy phenyl)-1H-pyrrole derivatives
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A new series of 3-substituted 4-(4-methyloxy phenyl)-1H-pyrrole derivatives were synthesized and biologically evaluated for potential anticancer activity. Fifteen targeted compounds showed high selectivity toward normal cells and cancer cells: that is, al
- Zhan, Xiaoping,Lan, Lan,Zhang, Yuankui,Chen, Jian,Zhao, Kai,Wang, Shuai,Xin, Yuxuan,Mao, Zhenmin
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p. 200 - 206
(2016/02/26)
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- Iron(III) phthalocyanine chloride-catalyzed oxidation-aromatization of α,β-unsaturated ketones with hydrazine hydrate: Synthesis of 3,5-disubstituted 1H-pyrazoles
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We have developed an iron(III) phthalocyanine chloride-catalyzed oxidation-aromatization of α,β-unsaturated ketones with hydrazine hydrate. Various 3,5-disubstituted 1H-pyrazoles were obtained in good to excellent yields. This method offers several advantages, including room-temperature conditions, short reaction time, high yields, simple work-up procedure, and use of air as an oxidant. The catalyst can be recovered and reused five times without loss of activity.
- Zhao, Junlong,Qiu, Jun,Gou, Xiaofeng,Hua, Chengwen,Chen, Bang
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p. 571 - 578
(2016/04/20)
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- Synthesis and cytotoxic activities of some pyrazoline derivatives bearing phenyl pyridazine core as new apoptosis inducers
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The cyclization of chalcones 3a-3u with 3-hydrazinyl-6-phenylpyridazine 7 under basic condition led to the formation of new pyrazoline derivatives 8a-8u. All final compounds were characterized by spectral and elemental analyses. They were screened for their antiproliferative activities against A549 (lung), HepG-2 (liver), CaCo-2 (intestinal) and MCF-7 (breast) cancer cell lines. Some of the synthesized compounds exhibited promising antiproliferative activities especially compound 8k with IC50values of 8.33, 1.67 and 10?μM against HepG-2, MCF-7 and CaCo-2 cancer cell lines, respectively. Moreover, their antiproliferative activity was due to apoptosis rather than necrosis induction except compound 8h which exhibited equal apoptotic and necrotic properties. Compound 8k showed 5 fold increase in caspase-3 activity indicating that the apoptosis proceeds via caspase-3 activation.
- George, Riham F.,Fouad, Marwa A.,Gomaa, Iman E.O.
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- Novel benzothiazole based sulfonylureas/sulfonylthioureas: Design, synthesis and evaluation of their antidiabetic potential
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In the present study, twenty-eight benzothiazole based sulfonylureas/sulfonylthioureas were synthesized and were assessed for their antidiabetic effect in a normoglycemic rat model by the in vivo oral glucose tolerance test (OGTT). All the synthesized com
- Kharbanda, Chetna,Alam, Mohammad Sarwar,Hamid, Hinna,Javed, Kalim,Bano, Sameena,Ali, Yakub,Dhulap, Abhijeet,Alam, Parwez,Pasha
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p. 6777 - 6786
(2016/08/10)
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- Synthesis and Antimicrobial Activity of Racemic 1,5-Diols: 2-(1,3-Diaryl-3-hydroxypropyl)cyclohexan-1-ol Derivatives
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A series of novel racemic 2-(1,3-diaryl-3-hydroxypropyl)cyclohexan-1-ol derivatives were synthesized from 1,5-diketones. All the synthesized compounds were characterized by spectroscopic methods. The antibacterial activities of obtained chiral 1,5-diols were investigated against four Gram-positive and three Gram-negative bacteria by determining of minimum inhibitory concentrations (MICs) in vitro. Compounds 3b, 3c, and 3d were found to be active against Enterococcus faecalis and Escherichia coli. In addition, compound 3j were found to be moderately active against all tested bacterial strains.
- Gezegen, Hayreddin,Tutar, U?ur,Ceylan, Mustafa
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p. 608 - 616
(2016/08/24)
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- Monoamine Oxidase Inhibitory Activity: Methyl- versus Chlorochalcone Derivatives
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Numerous studies have shown that chalcones are promising scaffolds for the development of new monoamine oxidase-B (MAO-B) inhibitors. As a continuation of our ongoing research into the development of reversible human MAO-B (hMAO-B) inhibitors, two series
- Mathew, Bijo,U?ar, Gülberk,Mathew, Githa Elizabeth,Mathew, Sincy,Kalatharakkal Purapurath, Praseedha,Moolayil, Fasil,Mohan, Smrithy,Varghese Gupta, Sheeba
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p. 2649 - 2655
(2016/12/23)
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- Synthesis and antifungal activity of chalcone derivatives
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In the present study, using chalcone as a lead compound, a series of its derivatives (compounds 1-30) were designed and synthesised. Their activity of anti-pathogenic fungi of plants has been evaluated. It is found that these compounds have good antifunga
- Zheng, Yuanyuan,Wang, Xuesong,Gao, Sumei,Ma, Min,Ren, Guiming,Liu, Huabing,Chen, Xiaohong
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p. 1804 - 1810
(2015/03/04)
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- Discovery and Pharmacophore Studies of Novel Pyrazole-Based Anti-Melanoma Agents
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Due to the rising incidence and lack of effective treatments, malignant melanoma is the most dangerous form of skin cancer, so that new treatment strategies are urgently needed. Several recent developments indicate that the V600E mutant BRAF (BRAFV60
- Li, Qing-Shan,Lü, Xian-Hai,Yang, Yang,Ruan, Ban-Feng,Yao, Ri-Sheng,Liao, Chen-Zhong
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p. 116 - 132
(2015/10/19)
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- DNA interaction and cytotoxic activities of square planar platinum(II) complexes with N, S-donor ligands
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The platinum(II) complexes with N, S-donor ligands have been synthesized and characterized by physicochemical methods viz. elemental, electronic, FT-IR, 1H NMR and LC-MS spectra. The binding mode and potency of the complexes with HS DNA (Herrin
- Patel, Mohan N.,Patel, Chintan R.,Joshi, Hardik N.,Thakor, Khyati P.
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supporting information
p. 261 - 267
(2014/04/03)
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- Synthesis and evaluation of pyrazolines bearing benzothiazole as anti-inflammatory agents
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The present study aims at the synthesis of pyrazolines bearing benzothiazole and their evaluation as anti-inflammatory agents. The synthesized compounds were evaluated for their anti-inflammatory potential using carrageenan induced paw edema model. Two co
- Kharbanda, Chetna,Alam, Mohammad Sarwar,Hamid, Hinna,Javed, Kalim,Bano, Sameena,Dhulap, Abhijeet,Ali, Yakub,Nazreen, Syed,Haider, Saqlain
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p. 5804 - 5812
(2015/02/02)
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- Synthesis and anti bacterial and anti-ulcer evaluation of new s-mannich bases of 4,6-diaryl-3,4-dihydropyrimidin-2(1H)-thiones
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The synthesis of title compounds were accomplished by synthetic sequence shown in Scheme 1. Chalcones on cyclocondensation with thiourea in ethanol and potassium hydroxide under reflux yielded the respective dihydropyramidin-2(1H)- thiones. Each of the di
- Kodhati, Venkateshwarlu,Vanga, Malla Reddy,Yellu, Narsimha Reddy
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p. 234 - 240
(2013/07/26)
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- Synthesis and biological evaluation of some new 4-aryl-1-(4,6-diaryl pyrimidine)-2-azetidinone by conventional and microwave methods and their biological activities
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4-Aryl-1-(4,6-diaryl pyrimidine)-2-azetidinone/4-aryl-3-chloro-1-(4,6- diaryl pyrimidine)-2-azetidinone were prepared by reaction of appropriate 2-(methoxy phenylideneamino)-4-diaryl pyrimidine (Schiff base) and acetyl chloride/chloroacetylchloride in dim
- Sharma, Sharda,Jain, Renuka,Sharma, Vikas,Chawla, Chetali
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p. 221 - 229
(2013/06/04)
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- Zinc oxide as a regioselective and heterogeneous catalyst for the synthesis of chalcones at room temperature
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Zinc oxide catalyzed synthesis of chalcones has been carried out under solvent-free conditions at room temperature. Activated as well as unactivated aromatics smoothly underwent Friedel-Crafts acylation with α, β-unsaturated acid chlorides furnishing excellent yields of the corresponding chalcones. The zinc oxide can be recovered and reused at least three times without any appreciable loss in activity.
- More, Parmeshwar E.,Bandgar, Babasaheb P.,Kamble, Vinod T.
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- Chalcones as promising pesticidal agents against diamondback moth (Plutella xylostella): Microwave-assisted synthesis and structure-activity relationship
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A series of chalcones (A-CH=CH-CO-B) were synthesized under microwave irradiation, and for the first time their pesticidal activity against diamondback moth (Plutella xylostella) was evaluated to identify the promising lead structures. The structure-activity relationship (SAR) analysis revealed that electron-withdrawing substituents on ring A of chalcone provided good pesticidal agents, whereas, ring B can bear either electron-withdrawing or electron-releasing substituents. Moreover, compound 22 having para-Cl substitution on ring A as well on ring B showed maximum activity with LC 50 value of 170.24 μg mL-1. Springer Science+Business Media, LLC 2011.
- Kumar, Rakesh,Sharma, Prabha,Shard, Amit,Tewary, Dhananjay Kumar,Nadda, Gireesh,Sinha, Arun Kumar
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p. 922 - 931
(2012/08/14)
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- Silicotungstic acid catalysed Claisen Schmidt condensation reaction: An efficient protocol for synthesis of 1,3-diaryl-2-propenones
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An efficient and clean synthesis of 1,3-diaryl-2-propenones has been carried out by Claisen Schmidt condensation reaction of aryl methyl ketones with a series of aromatic aldehydes at room temperature in the presence of the catalyst silicotungstic acid (STA). This method provides an ecofriendly, chemoselective, efficient and green synthesis of 1,3-diaryl-2-propenones in excellent yields.
- Rajput, Jaspreet Kaur,Kaur, Gagandeep
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experimental part
p. 646 - 649
(2012/02/15)
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- Synthesis and in vitro antimicrobial activity of novel 2-(3-oxo-1,3- diarylpropylthio)acetic acid derivatives
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A series of novel 2-(3-oxo-1,3-diarylpropylthio)acetic acid derivatives (3a-l) were prepared by base catalyzed addition of thioglycolic acid to chalcones (1a-l). The antibacterial activities of synthesized compounds were screened against human pathogenic microorganisms by employing the disk-diffusion technique. For the active compounds, also minimum inhibitory concentrations (MICs) were determined.
- Gezegen, Hayreddin,Karaman, Isa,Ceylan, Mustafa,Dilmac, Merve
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p. 893 - 900
(2012/10/30)
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- Synthesis of polysubstituted pyridines under combined microwave and ultrasound irradiation: K2CO3-promoted tandem addition/cyclization/hydrogen shift process
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A convenient and efficient K2CO3-promoted tandem reaction of chalcone, malononitrile, and methanol for the synthesis of highly functionalized pyridines has been developed. This multi-component reaction employing the weak nucleophilic agent methanol proceeded smoothly under combined microwave and ultrasound irradiation (CMUI). The reaction mechanism was proposed to consist of a Michael addition, a methoxylation of CN bond, a cyclization to a 1,4-dihydropyridine and an intermolecular hydrogen shift between 1,4-dihydropyridine and initial chalcone.
- Feng, Huangdi,Li, Yuan,Van Der Eycken, Erik V.,Peng, Yanqing,Song, Gonghua
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supporting information; experimental part
p. 1160 - 1162
(2012/03/26)
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- Design, synthesis and biological evaluation of pyrazolyl-thiazolinone derivatives as potential EGFR and HER-2 kinase inhibitors
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A series of pyrazolyl-thiazolinone derivatives (E1-E36) have been designed and synthesized and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors. Thirty-four of the 36 compounds were reported for the first time. Among them, compound 2-(5-(4-bromophenyl)-3-p-tolyl-4,5- dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (E28) displayed the most potent inhibitory activity (IC50 = 0.24 μM for EGFR and IC50 = 1.07 μM for HER-2). Antiproliferative assay results indicated that compound E28 owned high antiproliferative activity against MCF-7, B16-F10 and HCT-116 in vitro, with IC50 value of 0.30, 0.54, and 0.70 μM, respectively. Docking simulation was further performed to position compound E28 into the EGFR active site to determine the probable binding model. Based on the preliminary results, compound E28 with potent inhibitory activity in tumor growth would be a potential anticancer agent.
- Qiu, Ke-Ming,Wang, Hai-Hong,Wang, Li-Ming,Luo, Yin,Yang, Xian-Hui,Wang, Xiao-Ming,Zhu, Hai-Liang
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experimental part
p. 2010 - 2018
(2012/05/04)
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- Design, synthesis, and biological evaluation of chalcone oxime derivatives as potential immunosuppressive agents
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A series of deoxybenzoin oximes were recently reported as potent immunosuppressive agents by our group. In order to continue the original research for potential immunosuppressive agents with high efficacy and low toxicity, we synthesized a series of new c
- Luo, Yin,Song, Ran,Li, Yao,Zhang, Shuai,Liu, Zhi-Jun,Fu, Jie,Zhu, Hai-Liang
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supporting information; experimental part
p. 3039 - 3043
(2012/06/04)
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- Synthesis and evaluation of some novel [1,2,4]triazolo[1,5-α] pyrimidine derivatives for anticancer activity
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A series of 7-(4-chlorophenyl)-2-phenyl-1,7-dihydro [1,2,4] triazolo [1,5α] pyrimidine 4a-l have been synthesized and evaluated for anticancer activity. The newly synthesized compounds have been characterized by IR, 1H NMR and elemental analyse
- Pattan, Shashikant,Hole, Mangesh,Pattan, Jayshri,Dengale, Santosh,Shinde, Hemlata,Muluk, Rekha,Nirmal, Sunil,Jadhav, Ravindra
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experimental part
p. 774 - 779
(2012/07/03)
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- Cytotoxic, DNA interaction, SOD mimic, and antimicrobial activities of square pyramidal copper(II) complexes
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The copper(II) complexes with NS donor ligand and ciprofloxacin were synthesized. The synthesized complexes were characterized by physicochemical parameters like elemental and thermal analysis, electronic, FT-IR, and LC-MS spectroscopy. The complexes were
- Patel, Mohan N.,Patel, Chintan R.,Joshi, Hardik N.
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scheme or table
p. 1224 - 1232
(2012/08/13)
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- Synthesis, characterization and pharmacological study of 4,5-dihydropyrazolines carrying pyrimidine moiety
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A series of 5-bromo-2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)pyrimidine were prepared under conventional heating as well as microwave reaction condition. The newly synthesized compounds were characterized on the basis of elemental, spectral and single crystal X-ray studies. These new compounds were screened for their antioxidant, anti-inflammatory and analgesic activities. Some of these compounds exhibited potent biological activities compared to the standard drug.
- Adhikari, Adithya,Kalluraya, Balakrishna,Sujith, Kizhakke Veedu,Gouthamchandra, Kuluvar,Jairam, Ravikumar,Mahmood, Riaz,Sankolli, Ravish
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p. 467 - 474
(2012/11/07)
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- Stereoselective synthesis of γ,δ-unsaturated β-amino sulfones from ellman's N-tert-butylsulfinyl ketimines and methyl Phenyl sulfone
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A practical and straightforward approach for the highly stereoselective synthesis of γ,δ-unsaturated β-amino sulfones by nucleophilic (phenylsulfonyl)methylation of N-tert-butylsulfinyl ketimines with methyl phenyl sulfone was achieved. With lithium bis(trimethylsilyl)amide as the base, the corresponding sulfone-stabilized carbanion derived from methyl phenyl sulfone can be transferred to (S)-α,β-unsaturated N-tert-butylsulfinyl ketimines in very good yields and with high diastereoselectivities. Electron-withdrawing or electron-donating substituents on the aryl rings of (S)-α,β-unsaturated N-tert-butylsulfinyl ketimines did not exert a significant effect on the outcome of the diastereoselective nucleophilic (phenylsulfonyl) methylation.
- Zhang, Hua,Li, Ya,Xu, Fanghui,Ren, Xinfeng,Wang, Le,Sun, Zhihua,Zhou, Pei
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p. 2485 - 2490,6
(2012/12/12)
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- Activated fly ash catalyzed facile synthesis of novel spiro imidazolidine derivatives as potential antibacterial and antifungal agents
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An array of novel spiro imidazolidine derivatives was synthesized in dry media and was screened for their anti-microbial activities. Structure-activity relationship results revealed that compounds 22, 23 against P.aeruginosa, 24 against S.aureus, 24, 25 against K.pneumonia, 27 against S.aureus, β-H.streptococcus, 29 against M.luteus, K.pneumonia, 29, 30 against P.vulgaris exhibited excellent antibacterial activity at a minimum inhibitory concentration (MIC) value of 6.25 μg/mL. Compound 23 against M.gypseum, 25, 29 against Candida 6 and 29, 30 against C.albicans revealed excellent antifungal activity at a MIC value of 6.25 μg/mL.
- Kanagarajan,Thanusu,Gopalakrishnan
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scheme or table
p. 280 - 287
(2011/10/18)
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- Design and synthesis of 1,3-biarylsulfanyl derivatives as new anti-breast cancer agents
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A new series of 1,3-biarylsulfanyl derivatives (homodibenzyl core motif) have been designed and synthesized as new estrogen receptor ligands by chopping benzothiophene core of raloxifene to engender seco-raloxifene scaffold. All the synthesized compounds were screened for anti-proliferative, anti-osteoporotic, and anti-implantation activity. Compounds (35, 36) having basic amino anti-estrogenic side chain were exhibiting potential anti-proliferative activity in MCF-7, MDA-MB-231 and ishikawa cell lines. Some of the synthesized compounds having homodibenzyl motif (5, 8, 10) have shown moderate anti-osteoporotic activity.
- Kumar, Atul,Tripathi, Vishwa Deepak,Kumar, Promod,Gupta, Lalit Prakash,Akanksha,Trivedi, Ritu,Bid, Hemant,Nayak,Siddiqui, Jawed A.,Chakravarti, Bandana,Saxena, Ruchi,Dwivedi, Anila,Siddiquee,Siddiqui,Konwar, Rituraj,Chattopadhyay, Naibedya
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experimental part
p. 5409 - 5419
(2011/10/31)
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- Synthesis, spectral analysis, and in vitro microbiological evaluation of ethyl 7,9-diaryl-1, 4-diazaspiro[4.5]dec-9-ene-6-carboxylates as a new class of antibacterial and antifungal agents
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A series of novel ethyl 7,9-diaryl-1,4-diazaspiro[4.5]dec-9-ene-6- carboxylates was synthesized by the reaction of ethyl 4,6-diaryl-2-oxocyclohex- 3-ene-1-carboxylates with ethylenediamine in the presence of p-toluenesulfonic acid without a solvent under focused microwave irradiation. The title compounds were screened for their antimicrobial activities against a spectrum of clinically isolated microorganisms.
- Thanusu,Kanagarajan,Gopalakrishnan
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body text
p. 575 - 583
(2012/01/19)
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- Highly selective claisen-schmidt condensation catalyzed by silica chloride under solvent-free reaction conditions
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Silica chloride serves as a useful catalyst in the cross-aldol condensation, leading to the synthesis of a wide variety of bisarylidene cycloalkanones and chalcones. The catalyst showed high selectivity; self-condensation of ketones was not observed.
- Hazarkhani, Hassan,Kumar, Pradeep,Kondiram, Kadam Sachin,Shafi Gadwal, Ikhlas M.
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experimental part
p. 2887 - 2896
(2010/10/20)
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- Reinvestigation of structure-activity relationship of methoxylated chalcones as antimalarials: Synthesis and evaluation of 2,4,5-trimethoxy substituted patterns as lead candidates derived from abundantly available natural β-asarone
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We have examined the antimalarial structure-activity relationship of a series of methoxylated chalcones (A-CHCH-CO-B) against Plasmodium falciparum (3D7 strain) using fluorescence-based SYBR Green assay. Our study has revealed that electron releasing methoxy groups on ring A and electron withdrawing groups on ring B increases antimalarial potency while the positional interchange of these groups causes a decrease. In particular, 2,4,5-trimethoxy substitution pattern at ring A provided potent analogues which were easily derived from abundantly available natural β-asarone rich Acorus calamus oil. Cytotoxic evaluation indicated that the most active compounds 27 (IC50: 1.8 μM) and 26 (IC50: 2 μM) were also relatively non-toxic. Furthermore, compound 12 showed excellent resistance index of 1.1 against chloroquine resistant Dd2 strain of P. falciparum.
- Kumar, Rakesh,Mohanakrishnan, Dinesh,Sharma, Abhishek,Kaushik, Naveen Kumar,Kalia, Kalpana,Sinha, Arun Kumar,Sahal, Dinkar
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experimental part
p. 5292 - 5301
(2011/02/23)
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- Microwave assisted synthesis of some novel 2-pyrazoline derivatives as possible antimicrobial agents
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Some new [3-(4-phenyl)-5-phenyl-4,5-dihydropyrazol-1-yl](pyridine-4-yl) methanones and 3-substituted phenyl-5-substituted phenyl-4,5-dihydro-pyrazole-1- carbothioamides have been synthesized employing microwave techniques and evaluated for antimicrobial activity. Substituted acetophenones (1) were reacted with appropriately substituted benzaldehydes (2) in the presence of ethanol to furnish substituted chalcones (3a-f). These chalcones were further treated with isonicotinic acid hydrazide (INH) to afford substituted [3-(4-phenyl)-5-phenyl- 4,5-dihydropyrazol-1-yl](pyridine-4-yl)methanones (4a-f). Reaction of these chalcones with thiosemicarbazide yielded substituted 3,5-diphenyl-4,5-dihydro- 1H-pyrazole-1-carbothioamides (5a-f). The structures of newly synthesized compounds (4a-f) and (5a-f) have been confirmed by suitable spectroscopic techniques such as IR and 1H NMR. All the compounds were screened for their antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa and for antifungal activity against Candida albicans and Aspergillus niger. The compounds exhibited moderate antibacterial and good antifungal activities. Compound 4b and 4d showed significant antifungal activity against A. niger and C. albicans, respectively.
- Chawla, Rakesh,Sahoo, Ujjwal,Arora, Anshu,Sharma, Prabodh Chander,Radhakrishnan, Vijayaraj
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experimental part
p. 55 - 61
(2010/06/12)
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- Design, synthesis, and structure-activity relationships of pyrazole derivatives as potential FabH inhibitors
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Fatty acid biosynthesis is essential for bacterial survival. FabH, β-ketoacyl-acyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and -negative bacteria. Fifty-six 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives were synthesized and developed as potent inhibitors of FabH. This inhibitor class demonstrates strong antibacterial activity. Escherichia coli FabH inhibitory assay and docking simulation indicated that the compounds 1-(5-(4-fluorophenyl)- 3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone (12) and 1-(5-(4-chlorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone (13) were potent inhibitors of E. coli FabH.
- Lv, Peng-Cheng,Sun, Juan,Luo, Yin,Yang, Ying,Zhu, Hai-Liang
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scheme or table
p. 4657 - 4660
(2010/09/16)
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- Synthesis and biological evaluation of some novel 1, 3, 5-trisubstituted pyrazolines
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A new series of chalcones (3a-j) were synthesized by condensation of simple aldehydes with substituted acetophenones in presence of alkali. The resulted chalcones upon cyclization in presence of glacial acetic acid with isoniazid (INH) will yields the title compounds (4a-j). The newly synthesized compounds were assigned on the basis of IR, 1H NMR, and Mass spectral data. All the final compounds were evaluated for their in vitro antimicrobial activity.
- Revanasiddappa,Rao, R Nagendra,Subrahmanyam,Satyanarayana
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experimental part
p. 295 - 298
(2011/01/03)
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- Syntheses of potentially bioactive [1,2,4]oxadiazolo[5,4-d]benzothiazepines by 1,3-dipolar cycloaddition
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The chalcones, 2a-2l reacted with o-aminobenzenthiol to give a series of 1,5-benzothiazepines, 3a-3l. The [3+2] 1, 3-dipolar cycloaddition reactions of 3a-3l with ethyl chlorooximidoacetate in the presence of Et3N afforded the target compounds, 4a-4l possessing an additional 1,2,4-oxadiazole ring fused to the heptaatomic nucleus. The structures have been elucidated by spectral methods and X-ray crystallographic analysis.
- Wu, Xiao-Long,Liu, Fang-Ming,Shen, Song-Wei
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scheme or table
p. 1350 - 1355
(2011/01/05)
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- Synthesis and characterization of some new 2-amino-4-(4′-substituted) -6-(4″-substituted)diphenyl pyrimidines
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Synthesis and characterization of some novel 2-amino-4-(4′- substituted)-6-(4″-substituted)diphenyl pyrimidines has been carried out by the conversion of variably substituted acetophenones and benzaldehydes into corresponding chalcones followed by cyclization with guanidine hydrochloride in the presence of an oxidizing agent.
- Hasan, Aurangzeb,Khaleeq, Musfirah,Riaz, Uzma
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scheme or table
p. 5581 - 5587
(2012/08/07)
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