- Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol
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One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.
- Biswal, Priyabrata,Samser, Shaikh,Meher, Sushanta Kumar,Chandrasekhar, Vadapalli,Venkatasubbaiah, Krishnan
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supporting information
p. 413 - 419
(2021/11/01)
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- Cascade Reaction of α, β-Unsaturated Ketones and 2-Aminoaryl Alcohols for the Synthesis of 3-Acylquinolines by a Copper Nanocatalyst
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3-Acylquinolines possess widespread applications in functional chemicals. However, the convenient and selective synthesis of such important substructures has to date remained a challenge. Herein, we report a method to access 3-acylquinolines from α, β-unsaturated ketones and 2-aminoaryl alcohols in one pot with a copper nanocatalyst supported on nitrogen-silica-doped carbon (Cu/N?SiO2?C). Mechanistically, the construction of the product involves a cascade procedure including radical-type oxidation of 2-aminoaryl alcohols, aza-Michael addition and annulation. This developed protocol proceeds with merits of mild reaction conditions, good functional group tolerance, earth-abundant and reusable copper catalyst, easily available stocks and O2 as the sole oxidant, which provides an alternative way for the sustainable synthesis of quinoline derivatives. (Figure presented.).
- Liu, Yuan,Wang, Chen,Tong, Yixin,Ling, Yong,Zhou, Changjian,Xiong, Biao
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supporting information
p. 4422 - 4429
(2021/08/07)
-
- Pharmacophore hybridization approach to discover novel pyrazoline-based hydantoin analogs with anti-tumor efficacy
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In search for new and safer anti-cancer agents, a structurally guided pharmacophore hybridization strategy of two privileged scaffolds, namely diaryl pyrazolines and imidazolidine-2,4-dione (hydantoin), was adopted resulting in a newfangled series of compounds (H1-H22). Herein, a bio-isosteric replacement of “pyrrolidine-2,5-dione” moiety of our recently reported antitumor hybrid incorporating diaryl pyrazoline and pyrrolidine-2,5-dione scaffolds with “imidazoline-2,4-dione” moiety has been incorporated. Complete biological studies revealed the most potent analog among all i.e. compound H13, which was at-least 10-fold more potent compared to the corresponding pyrrolidine-2,5-dione, in colon and breast cancer cells. In-vitro studies showed activation of caspases, arrest of G0/G1 phase of cell cycle, decrease in the expression of anti-apoptotic protein (Bcl-2) and increased DNA damage. In-vivo assay on HT-29 (human colorectal adenocarcinoma) animal xenograft model unveiled the significant anti-tumor efficacy along with oral bioavailability with maximum TGI 36% (i.p.) and 44% (per os) at 50 mg/kg dose. These findings confirm the suitability of hybridized pyrazoline and imidazolidine-2,4-dione analog H13 for its anti-cancer potential and starting-point for the development of more efficacious analogs.
- Upadhyay, Neha,Tilekar, Kalpana,Loiodice, Fulvio,Anisimova, Natalia Yu.,Spirina, Tatiana S.,Sokolova, Darina V.,Smirnova, Galina B.,Choe, Jun-yong,Meyer-Almes, Franz-Josef,Pokrovsky, Vadim S.,Lavecchia, Antonio,Ramaa
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- TBHP/Cu(OAc)2 mediated oxidation of pyrazolines: A convenient method for the preparation of pyrazoles
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An efficient and simple oxidative protocol has been developed for the preparation of pyrazoles from pyrazolines mediated by TBHP/Cu(OAc)2 at room temperature. The present protocol has been successfully applied for the preparation of various pyrazole compounds from heterocyclic pyrazolines.
- Kolla, Sai Teja,Somanaboina, Ramya,Bhimapaka, China Raju
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supporting information
p. 1425 - 1432
(2021/02/27)
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- Rapid umpolung Michael addition of isatin N, N ′-cyclic azomethine imine 1,3-dipoles with chalcones
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The umpolung Michael addition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones is reported. The reaction could be finished within a very short time (0.3-2 min), with 3,3-disubstituted oxindole derivatives obtained in moderate to excellent yields with promising dr values. Unusual Michael adducts were obtained in moderate to high yields (26-98%) with low to high diastereoselectivities (0.8: 1 to 8.5: 1 dr). All the synthesized compounds (3, 3′, 4, 5, 5′, 7, 7′, 9 and 9′) were well characterized by FTIR, NMR, and mass spectral analyses and further confirmed by the single-crystal X-ray diffraction analysis of compounds 3aa and 4n.
- Yue, Guizhou,Jiang, Dan,Dou, Zhengjie,Li, Sicheng,Feng, Juhua,Zhang, Li,Chen, Huabao,Yang, Chunping,Yin, Zhongqiong,Song, Xu,Liang, Xiaoxia,Wang, Xianxiang,Lu, Cuifen
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supporting information
p. 11712 - 11718
(2021/07/12)
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- Pyrazoline derivatives as tubulin polymerization inhibitors with one hit for Vascular Endothelial Growth Factor Receptor 2 inhibition
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In this work, to check the effect of the transposition of the rings in typical patterns, a series of pyrazoline derivatives 3a-3t bearing the characteristic 3,4,5-trimethoxy phenyl and thiophene moieties were synthesized and evaluated as tubulin polymeriz
- Yang, Bing,Zhou, Jiahua,Wang, Fa,Hu, Xiao-Wei,Shi, Yujun
-
-
- Potassium Base-Catalyzed Michael Additions of Allylic Alcohols to α,β-Unsaturated Amides: Scope and Mechanistic Insights
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We report herein the first KHMDS-catalyzed Michael additions of allylic alcohols to α,β-unsaturated amides through allylic isomerization. The reaction proceeds smoothly in the presence of only 5 mol% of KHMDS to afford a variety of 1,5-ketoamides in high yields. Mechanistic investigations, including experimental and computational studies, reveal that the KHMDS-catalyzed in-situ generation of the enolate from the allylic alcohol through a tunneling-assisted 1,2-hydride shift is the key to the success of this transformation. (Figure presented.).
- Kurouchi, Hiroaki,Sai, Masahiro
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supporting information
p. 3585 - 3591
(2021/06/27)
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- Double-edged Swords: Diaryl pyrazoline thiazolidinediones synchronously targeting cancer epigenetics and angiogenesis
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In the present study, two novel series of compounds incorporating naphthyl and pyridyl linker were synthesized and biological assays revealed 5-((6-(2-(5-(2-chlorophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethoxy) naphthalene-2-yl)methylene)thiazolidine-2,4-dione (14b) as the most potent dual inhibitors of vascular endothelial growth factors receptor-2 (VEGFR-2) and histone deacetylase 4 (HDAC4). Compounds 13b, 14b, 17f, and 21f were found to stabilize HDAC4; where, pyridyl linker swords were endowed with higher stabilization effects than naphthyl linker. Also, 13b and 14b showed best inhibitory activity on VEGFR-2 as compared to others. Compound 14b was most potent as evident by in-vitro and in-vivo biological assessments. It displayed anti-angiogenic potential by inhibiting endothelial cell proliferation, migration, tube formation and also suppressed new capillary formation in the growing chick chorioallantoic membranes (CAMs). It showed selectivity and potency towards HDAC4 as compared to other HDAC isoforms. Compound 14b (25 mg/kg, i.p.) also indicated exceptional antitumor efficacy on in-vivo animal xenograft model of human colorectal adenocarcinoma (HT-29). The mechanism of action of 14b was also confirmed by western blot.
- Kumar, Alan P.,Meyer-Almes, Franz-Josef,Ramaa, C. S.,Safuan, Sabreena,Schweipert, Markus,Tilekar, Kalpana,Upadhyay, Neha
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- Unsaturated ketone compound as well as preparation method and application thereof
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The present invention relates to a novel GPR52 antagonist. Specifically, the invention relates to an unsaturated ketone compound, a pharmaceutically acceptable salt, a stereoisomer or a prodrug molecule thereof, and a method for preparing a pharmaceutical composition thereof. The invention further relates to the use of the GPR52 antagonist as an orphan G protein coupled receptor GPR52 antagonist,and further relates to the use of the GPR52 antagonist in the preparation of drugs for preventing and treating Huntington's disease.
- -
-
Paragraph 0219-0222; 0250-0252
(2020/10/30)
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- Synthesis and Biological Evaluation of Pyrazoline and Pyrrolidine-2,5-dione Hybrids as Potential Antitumor Agents
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In search of novel and effective antitumor agents, pyrazoline-substituted pyrrolidine-2,5-dione hybrids were designed, synthesized and evaluated in silico, in vitro and in vivo for anticancer efficacy. All the compounds exhibited remarkable cytotoxic effects in MCF7 and HT29 cells. The excellent antiproliferative activity toward MCF7 (IC50=0.78±0.01 μM), HT29 (IC50=0.92±0.15 μM) and K562 (IC50=47.25±1.24 μM) cell lines, prompted us to further investigate the antitumor effects of the best compound S2 (1-(2-(3-(4-fluorophenyl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethyl)pyrrolidine-2,5-dione). In cell-cycle analysis, S2 was found to disrupt the growth phases with increased cell population in G1/G0 phase and decreased cell population in G2/M phase. The excellent in vitro effects were also supported by inhibition of anti-apoptotic protein Bcl-2. In vivo tumor regression studies of S2 in HT29 xenograft nude mice, exhibited equivalent and promising tumor regression with maximum TGI, 66 % (i. p. route) and 60 % (oral route) at 50 mg kg?1 dose by both the routes, indicating oral bioavailability and antitumor efficacy. These findings advocate that hybridization of pyrazoline and pyrrolidine-2,5-dioes holds promise for the development of more potent and less toxic anticancer agents.
- Anisimova, Natalia Y.,Choe, Jun-yong,Lavecchia, Antonio,Loiodice, Fulvio,Meyer-Almes, Franz-Josef,Pokrovsky, Vadim S.,S Ramaa, C.,Smirnova, Galina B.,Sokolova, Darina V.,Spirina, Tatiana S.,Tilekar, Kalpana,Upadhyay, Neha
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p. 1813 - 1825
(2020/09/07)
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- Tuning the Product Selectivity of the α-Alkylation of Ketones with Primary Alcohols using Oxidized Titanium Nitride Photocatalysts and Visible Light
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The direct α-alkylation of ketones with alcohol to synthesize important α-alkylated ketones and enones is an attractive procedure for C-C bond formation. High reaction temperatures are always needed for heterogeneous catalysis using non-noble metals, and switching product selectivity in one catalysis system remains a great challenge. In the present study, a visible-light-driven procedure for this reaction is proposed, using oxidized TiN photocatalysts under mild conditions, whereby the product selectivity can be well-tuned. Oxidized TiN photocatalysts with tunable surface N/O ratios were successfully synthesized through the facile and flexible thermal oxidation treatment of low-cost TiN nanopowder. The α-alkylation of acetophenone with benzyl alcohol to form the two important compounds chalcone and dihydrochalcone occurred even at room temperature and almost complete conversion was achieved at 100 °C under visible light. The proportion of the two products can be well-tuned by switching the surface N/O ratio of the synthesized photocatalysts. Visible light is demonstrated to affect the surface N/O ratio of the photocatalysts and contribute to tuning the product selectivity. Light intensity and action spectrum study proves that the generation of energetic charge carriers results in the observed activities under visible light, based on interband transitions of TiN or the ligand-to-metal charge transfer (LMCT) effect of the surface complex formed on TiO2. Thermal energy can be coupled with light energy within this photocatalytic system, which will facilitate the full use of solar energy. Different sequential reaction mechanisms on TiN and TiO2 are proposed to be responsible for the tunable product selectivity. The wide reaction scope, the fine conversion at a low light intensity, and the favorable reusability of photocatalysts prove the great application potential of this visible-light-driven procedure for the α-alkylation of ketones with primary alcohols.
- Li, Peifeng,Su, Haijia,Xiao, Gang,Zhao, Yilin
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p. 3640 - 3649
(2020/04/09)
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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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- Preparation method of thiazolyl dihydropyrazole compound and application thereof
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The invention relates to a hydrochloric acid pickling corrosion inhibitor for carbon steel, in particular to a preparation method of a thiazolyl dihydropyrazole compound and application thereof. The thiazolyl dihydropyridine compound is 3-phenyl-1-(4-phen
- -
-
Paragraph 0014-0015
(2019/02/10)
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- Proton-Coupled Electron Transfer: Transition-Metal-Free Selective Reduction of Chalcones and Alkynes Using Xanthate/Formic Acid
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Highly chemoselective reduction of α,β-unsaturated ketones to saturated ketones and stereoselective reduction of alkynes to (E)-alkenes has been developed under a transition-metal-free condition using a xanthate/formic acid mixture through proton-coupled electron transfer (PCET). Mechanistic experiments and DFT calculations support the possibility of a concerted proton electron-transfer (CPET) pathway. This Birch-type reduction demonstrates that a small nucleophilic organic molecule can be used as a single electron-transfer (SET) reducing agent with a proper proton source.
- Prasanna, Ramanathan,Guha, Somraj,Sekar, Govindasamy
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supporting information
p. 2650 - 2653
(2019/04/17)
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- Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones
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(S)-2,15-Br2-DHTP-catalyzed asymmetric conjugate addition of boronic acids to β-trifluoromethyl α,β-unsaturated ketones and enones was studied. The reaction afforded the corresponding Michael addition products in moderate to high yields with excellent enantioselectivities (up to 99:1 er). This catalytic system features mild reaction conditions, high efficiency, and tolerance to heteroarylboronic acids.
- Chai, Guo-Li,Sun, A-Qiang,Zhai, Dong,Wang, Juan,Deng, Wei-Qiao,Wong, Henry N.C.,Chang, Junbiao
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supporting information
p. 5040 - 5045
(2019/07/03)
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- Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols
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The challenge in the C-C cross-coupling of secondary and primary alcohols using acceptorless dehydrogenation coupling (ADC) is the difficulty in accurately controlling product selectivities. Herein, we report a controlled approach to a diverse range of β-alkylated secondary alcohols, α-alkylated ketones and α,β-unsaturated ketones using the ADC methodology employing a Ni(ii) 4,6-dimethylpyrimidine-2-thiolate cluster catalyst under different reaction conditions. This catalyst could tolerate a wide range of substrates and exhibited a high activity for the annulation reaction of secondary alcohols with 2-aminobenzyl alcohols to yield quinolines. This work is an example of precise chemoselectivity control by careful choice of reaction conditions.
- Zhang, Meng-Juan,Li, Hong-Xi,Young, David J.,Li, Hai-Yan,Lang, Jian-Ping
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supporting information
p. 3567 - 3574
(2019/04/14)
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- Straightforward synthesis of quinolines from enones and 2-aminobenzyl alcohols using an iridium-catalyzed transfer hydrogenative strategy
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A new protocol for the direct synthesis of quinolines from enones and 2-aminobenzyl alcohols via iridium-catalyzed transfer hydrogenative reactions has been demonstrated. This method employs easily available [IrCp?Cl2]2/t-BuOK as the efficient catalyst system, proceeding with the merits of high step- and atom efficiency, mild reaction conditions and operational simplicity. The experimental studies suggest that the reactions start with transfer hydrogenation, followed by the Friedl?nder reaction to give the final products.
- Xiong, Biao,Wang, Yingying,Liu, Yuan,Bao, Yandan,Liu, Zhaoguo,Zhang, Yanan,Ling, Yong
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supporting information
p. 5707 - 5711
(2018/08/17)
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- Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols
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A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p
- Paladhi, Sushovan,Hwang, In-Soo,Yoo, Eun Jeong,Ryu, Do Hyun,Song, Choong Eui
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supporting information
p. 2003 - 2006
(2018/04/16)
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- Thienopyridine bis-heterocyclic compound preparation technology
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The invention provides a thienopyridine bis-heterocyclic compound preparation technology which comprises the following steps: 1) putting acetophenone and thiophene-2-formaldehyde in an alcohol solventto react under the alkali action to obtain a compound II; 2) putting the compound II and 2-cyanoethyl thioacetamide in the alcohol solvent to react under the organic alkali action to obtain a compound III; 3) putting the compound III and bromoacetophenone in the alcohol solvent to react under the strong base action to obtain a compound I. A reaction route is shown in the specification. The preparation technology disclosed by the invention has the following advantages that the raw materials and reagents utilized by the reaction are all general synthesized reagents and has cheap price and easiness in obtaining; all the steps have moderate reaction conditions and simple aftertreatment operation; the reaction yield is higher, and the product purity is high; the whole preparation technology has the advantages of convenience in operation, low product cost and ability in meeting an industrial production requirement.
- -
-
Paragraph 0007; 0015-0016
(2018/03/01)
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- Hetero-Diels–Alder reactions of hetaryl thiochalcones with acetylenic dienophiles
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Hetaryl-substituted thiochalcones react with acetylenic mono- and diesters in the THF solution in the presence of LiClO4 at 65°C to give, after 24 h, 4H-thiopyran carboxylates and dicarboxylates, respectively, in moderate to good yields. The same reactions were performed also in the THF solution without a catalyst under microwave irradiation. In that case, the reaction time was reduced to three minutes and, in most cases, an improvement in the yield of the [4+2]-cycloadduct was observed. The reactions with methyl propiolate occurred regioselectively and the 3-carboxylates were formed exclusively.
- Mlostoń, Grzegorz,Grzelak, Paulina,Heimgartner, Heinz
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-
- Chloramphenicol base chemistry. Part 11: chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones
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The first chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones is reported. The Michael adducts were obtained in good to excellent yields (up to 98% yield) and enantioselectivities (up to 94% ee). This reaction has a broad substrate scope to various α,β-unsaturated ketones. With this in mind, this methodology was successfully applied to the synthesis of a chiral piperidone, an advanced building block for dihydropyridinone P2X7 receptor antagonists.
- Yan, Linjie,Wang, Haifeng,Xiong, Fangjun,Tao, Yuan,Wu, Yan,Chen, Fener
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p. 921 - 929
(2017/07/11)
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- Synthesis and carbonic anhydrase inhibitory activities of new thienyl-substituted pyrazoline benzenesulfonamides
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A series of new thienyl-substituted pyrazoline benzenesulfonamides were synthesized and their carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activities were tested on the human (h) isoforms hCA I and hCA II. The inhibition constant (Ki) of thes
- Mete, Ebru,Comez, Birnur,Inci Gul, Halise,Gulcin, Ilhami,Supuran, Claudiu T.
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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 of α,β-unsaturated ketones from alkynes and aldehydes over Hβ zeolite under solvent-free conditions
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A facile Hβ zeolite-catalyzed strategy has been successfully developed for the synthesis of α,β-unsaturated ketones from alkynes and aldehydes under solvent-free conditions. The reaction proceeds via tandem hydration/condensation of alkynes with aldehydes to afford a range of α,β-unsaturated carbonyls in good to excellent yields. This journal is.
- Mameda, Naresh,Peraka, Swamy,Kodumuri, Srujana,Chevella, Durgaiah,Banothu, Rammurthy,Amrutham, Vasu,Nama, Narender
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p. 58137 - 58141
(2016/07/07)
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- Kinetic Resolution of β-Sulfonyl Ketones through Enantioselective β-Elimination using a Cation-Binding Polyether Catalyst
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Reported herein is the first enantioselective β-elimination reaction catalyzed by a chiral cation-binding polyether. By using this catalytic protocol, a wide range of β-sulfonyl ketones could be effectively resolved with high stereoselectivity (S up to >300). Key to the success of this process is the favorable secondary interactions of the catalyst with the Lewis basic groups on the sulfone substrate. The enone product of this process can be easily converted into the racemic starting material, and allows an effective recycling and overall synthesis of chiral β-sulfonyl ketones in high yield and excellent enantioselectivity.
- Li, Liang,Liu, Yidong,Peng, Yang,Yu, Lei,Wu, Xiaoyan,Yan, Hailong
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supporting information
p. 331 - 335
(2016/01/25)
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- A magnetic solid sulfonic acid modified with hydrophobic regulators: An efficient recyclable heterogeneous catalyst for one-pot aza-Michael-type and Mannich-type reactions of aldehydes, ketones, and amines
-
Two convenient green protocols for the synthesis of β-amino ketones have been developed which involve one-pot aza-Michael-type and Mannich-type reactions of a series of aldehydes, ketones, and amines in the presence of a catalytic amount of the magnetic solid sulfonic acid catalyst, Fe3O4@SiO2@Me&Et-PhSO3H, at room temperature. The catalyst can be reused four times without loss of activity.
- Movassagh, Barahman,Tahershamsi, Leili,Mobaraki, Akbar
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p. 1851 - 1854
(2015/03/30)
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- Graphene oxide nanosheets: A highly efficient and reusable carbocatalyst catalyzes the Michael-cyclization reactions of 4-hydroxycoumarins, 4-hydroxypyrone and 4-hydroxy-1-methylquinolinone with chalcone derivatives in aqueous media
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Graphene oxide nanosheets were found to be a highly efficient, reusable and cost-effective carbocatalyst for the facile synthesis of highly diversified 4H-pyrans via a one-pot, two-component condensation reaction between freshly prepared chalcones and 4-hydroxycoumarin in aqueous media offering excellent yields. The new, green and metal free synthetic method also enables the condensation reaction for the formation of a library of pyranoquinolines and pyranopyrans.
- Kausar, Nazia,Ghosh, Partha Pratim,Pal, Gargi,Das, Asish R.
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p. 60199 - 60207
(2015/07/27)
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- A Facile FeCl3/I2-Catalyzed Aerobic Oxidative Coupling Reaction: Synthesis of Tetrasubstituted Imidazoles from Amidines and Chalcones
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A facile and efficient route for the synthesis of tetrasubstituted imidazoles from amidines and chalcones via FeCl3/I2-catalyzed aerobic oxidative coupling has been developed. This new strategy is featured by high regioselectivity an
- Zhu, Yuelu,Li, Cheng,Zhang, Jidong,She, Mengyao,Sun, Wei,Wan, Kerou,Wang, Yaqi,Yin, Bin,Liu, Ping,Li, Jianli
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supporting information
p. 3872 - 3875
(2015/08/18)
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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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- Synthesis and biological evaluation of novel 1,3,5-trisubstituted pyrazolines
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A new series of chalcones (1a-j) was prepared by reacting 2-thiophene carbaldehyde and substituted ketones in alcohol medium in presence of NaOH. The chalcones undergoes selective cyclization with 4-hydroxybenzohydrazide (2) in gl acetic acid medium to yield the title compounds 1,3,5-trisubstituted pyrazolines (3a-j). All the newly synthesized compounds were evaluated for their in-vitro antibacterial and antifungal activities. The structures of the new compounds were assigned on the basis of elemental analysis, 1H NMR, IR and Mass spectral data.
- Revanasiddappa,Jisha,Varghese, Saira Susan,Kalsi, Jasmine,Jose, Neethu
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- An improved iron-mediated synthesis of N-2-aryl substituted 1,2,3-triazoles
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Treatment of various chalcones and sodium azide in the presence of catalytic amounts of commercially available iron oxide nanoparticles, followed by the addition of aryl halides afforded N-2-arylated 1,2,3-triazoles in very good yields. This tandem three-
- Kamal, Ahmed,Swapna, Ponnampalli
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p. 7419 - 7426
(2013/06/27)
-
- Vinylogous organocatalytic triple cascade reaction: Forging six stereocenters in complex spiro-oxindolic cyclohexanes
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We report a triple vinylogous cascade reaction, yielding valuable spiro-oxindolic cyclohexane derivatives. The three-component domino process proceeds by way of a catalyzed Michael/1,6-addition/vinylogous aldol sequence affording the products with six stereogenic centers and very high control over the stereochemistry. The chemistry is based on a rare example of asymmetric 1,6-addition to linear 2,4-dienals proceeding with complete δ-site selectivity. Key to the reaction development was a directing group positioned at the β-dienal position, which was essential for achieving highly predictable reaction outcomes. Copyright
- Chatterjee, Indranil,Bastida, David,Melchiorre, Paolo
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supporting information
p. 3124 - 3130
(2013/12/04)
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- Lithium hydroxide mediated synthesis of 3,4-disubstituted pyrroles
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LiOH·H2O in ethanol was found to be an effective reagent for the synthesis of 3,4-disubstituted pyrrole derivatives by the van Leusen method. In situ formation of chalcones from aromatic aldehydes and enolisable ketones, and their subsequent reaction with tosylmethyl isocyanide resulted in the formation and precipitation of pyrrole derivatives from the reaction medium, in good yields. The solvation effect of the polar medium facilitates the reaction. The Royal Society of Chemistry 2013.
- Sharma, Ratnesh,Kumar, Kapil,Chouhan, Mangilal,Grover, Vikas,Nair, Vipin A.
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p. 14521 - 14527
(2013/09/02)
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- Photodimerization of heteroaryl chalcones: Comparative antimicrobial activities of chalcones and their photoproducts
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The heterocyclic analogues of chalcones were synthesized by Claisen Schmidt reaction of (a) benzaldehyde with 2-acetylfurane, 2-acetylpyrrole and 2-acetylthiophene and (b) acetophenone with furfural, thiophene-2-carbaldehyde and pyrrole-2-carbaldehyde. The photolysis of class (a) and (b) chalcones under UV lamp gave different products. The stereoselective photodimerization of 1-(furane-2-yl)-3-phenylprop-2-en-1-one (1), 3-phenyl-1-(1H-pyrrole-2-yl)-prop- 2-en-1-one (2) gave b-truxinic type dimers, (3,4-diphenylcyclobutane-1,2-diyl) bis (furane-2-yl methanone) (7), (3,4-diphenylcyclobutane-1,2-diyl)bis ((1H-pyrrol-2-yl) methanone) (8) by syn head-to-head coupling whereas 3-phenyl-1-(thiophen-2-yl)-prop-2-en-1-one (3) gave d-truxinic type dimers, (3,4-diphenylcyclobutane-1,2-diyl)bis (thiophen-2-yl methanone) (9) by anti head-to-head coupling. The photolytic products of 3-(furane-2-yl)-1-phenylprop- 2-en-1-one (4), 1-phenyl-3-(thiophen-2-yl)-prop-2-en-1-one (5) and 1-phenyl-3-(1H-pyrrole-2-yl)- prop-2-en-1-one (6) were identified as corresponding 1,6-di(furane-2-yl)-3,4-diphenylhexa-1,5-diene-3,4-diol (10), 3,4-diphenyl-1,6-di(thiophen-2-yl)hexa-1,5-diene-3,4-diol (11) and 3,4-diphenyl-1,6-di (1H-pyrrol-2-yl)hexa-1,5-diene-3,4-diol (12) pinacol dimers. The antibacterial and antifungal activity of the precursor chalcones and the dimeric products showed antimicrobial activities of different extents with respect to individual compounds. In general, photolysis of heteroaryl chalcones causes the depletion of antimicrobial activity. Springer Science+Business Media, LLC 2011.
- Nagwanshi, Rekha,Bakhru, Meena,Jain, Shubha
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p. 1587 - 1596
(2012/11/07)
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- Regioselective synthesis of 3-carbo-5-phosphonylpyrazoles through a one-pot Claisen-Schmidt/1,3-dipolar cycloaddition/oxidation sequence
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A one-pot reaction involving an aldehyde, a methyl ketone, and the Bestmann-Ohira reagent has been developed for the synthesis of variously substituted 3-carbo-5-phosphonylpyrazoles. Our synthetic methodology features a domino Claisen-Schmidt/1,3-dipolar cycloaddition/oxidation sequence, which leads to the target compounds in excellent yields. We further demonstrated that this unprecedented sequence could also be combined with a copper-catalyzed azide-alkyne cycloaddition in a one-pot, four-step cascade process generating five new bonds and two heterocyclic rings. Copyright
- Martin, Anthony R.,Mohanan, Kishor,Toupet, Loic,Vasseur, Jean-Jacques,Smietana, Michael
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experimental part
p. 3184 - 3190
(2011/06/28)
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- Synthesis of thiophene-substituted aza-BODIPYs and their optical and electrochemical properties
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A series of novel thiophene-substituted aza-BODIPY dyes were synthesized by means of a standard procedure and complemented by a Stille-coupling of a brominated species with 2-tributylstannylthiophene. The optical as well as the electrochemical properties of the compounds were investigated and compared to result of density functional theory (DFT) calculations. The influence of the thiophene substituents is discussed in dependence of the position at the aza-BODIPY core regarding the HOMO and LUMO frontier orbitals. The different distributions of the HOMO and LUMO coefficients over the BODIPY core lead to a variable influence of the thiophene substituents on the HOMO and LUMO energies, being the origin of the tunable optical and electrochemical properties.
- Gresser, Roland,Hartmann, Horst,Wrackmeyer, Marion,Leo, Karl,Riede, Moritz
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experimental part
p. 7148 - 7155
(2011/10/08)
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- An improved procedure for the synthesis of 1,5-benzothiazepines using ceric ammonium nitrate (CAN)
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A mild and efficient procedure for the synthesis of various 1,5-benzothiazepines were developed. This method provides an easy access for preparation of 1,5-benzothiazepine derivatives in the presence of 10 mol% catalyst of CAN under ultrasonic irradiation. This method provided clean conversion, mild reaction condition, no use of toxic solvent and shorter reaction time compared to other reported method. Copyright
- Chate, Asha V.,Joshi, Ratnadeep S.,Mandhane, Priyanka G.,Gill, Charansingh H.
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body text
p. 776 - 780
(2012/01/03)
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- Atom-efficient, solvent-free, green synthesis of chalcones by grinding
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An improved Claisen-Schmidt condensation reaction of methyl ketones and aromatic aldehydes can be achieved by grinding at room temperature in the absence of solvents. This process is simple, efficient, economical, and environmentally benign compared to classical reactions.
- Rateb, Nora M.,Zohdi, Hussein F.
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experimental part
p. 2789 - 2794
(2009/12/06)
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- Enantioselective Michael addition of malononitrile to chalcones catalyzed by a simple quinine-Al(OiPr)3 complex: A simple method for the synthesis of a chiral 4H-pyran derivative
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Enantioselective Michael addition of malononitrile to chalcones was catalyzed by a simple quinine and Al(OiPr)3 complex and products were obtained in good ee as well as high yields, which facilitated the asymmetric synthesis of a biologically active 4H-pyran compound. The Royal Society of Chemistry 2009.
- Shi, Jian,Wang, Min,He, Ling,Zheng, Ke,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
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supporting information; experimental part
p. 4711 - 4713
(2010/01/16)
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- Convenient stereoselective synthesis of (Z)-chalcone derivatives from 1,3-diaryl-2-propynyl silyl ethers
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Various (Z)-chalcone derivatives were easily synthesized in a stereoselective manner from 1,3-diaryl-2-propynyl silyl ethers by a catalytic reaction using potassium tert-butoxide under very mild conditions after acid treatment.
- Yoshizawa, Kazuhiro,Shioiri, Takayuki
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p. 4943 - 4945
(2007/10/03)
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- NOVEL PROPENONE DERIVATIVES CONTAINING AROMATIC RINGS, A MAUFACTURING PROCESS THEREOF AND A COMPOSITION CONTAINING THE SAME USING AS AN ANTIINFLAMMATORY AGENT
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The present invention is related to novel propenone derivatives containing aromatic ring, a manufacturing process thereof and a composition containing the same using as an anti? inflammatory agent. The compound of the present invention show potent anti-inflammatory activity confirmed by various experiments for example, the inhibition test of COX and 5-LOX enzyme activity, the inhibition test of LTC reproduction and NO production, MTT assay test, the inhibition test on the iNOS and COX-2 protein expression and PGE reproduction using RAW 264.7 macrophage etc. Accordingly, present compounds can be useful in treating and preventing various inflammatory.
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Page/Page column 15
(2010/02/15)
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- An efficient combination of microwave dielectric heating and the use of solid-supported triphenylphosphine for Wittig reactions
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Figure presented Reaction condition: 150°C, 5 min. Olefins could be formed in an efficient way by the use of stable ylides in just a few minutes using microwave dielectric heating. The drawback with the Wittig reaction in solution phase is the formation of 1 equiv of triphenylphosphine oxide. To avoid this, the corresponding protocol using the efficient combination of solid-supported triphenylphosphine and microwave dielectric heating was developed. An even more efficient one-pot three-step Wittig reaction was also developed.
- Westman, Jacob
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p. 3745 - 3747
(2007/10/03)
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- Synthesis of 3-Cyano-2-methylpyridines Substituted with Heteroaromatics
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A series of title compounds were easily prepared by the sonication of α,β-unsaturated carbonyl compound in acetonitril in the presence of potassium t-butoxide.
- Shibata, Katsuyoshi,Katsuyama, Isamu,Matsui, Masaki,Muramatsu, Hiroshiga
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p. 161 - 165
(2007/10/02)
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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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- 1,4-DIANION OF ACETOPHENONE N-ETHOXYCARBONYLHYDRAZONE AS A SYNTHETIC INTERMEDIATE
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Various β-hydroxyketones and α,β-unsaturated ketones were prepared by the reaction of aldehydes and ketones with 1,4-dianion (2) which is derived from acetophenone N-ethoxycarbonylhydrazone (1) with butyllithium.In the reaction of 2 with carbonyl compounds such as ester, amide, acid anhydride, acyl chloride, and alkyl carbonate, pyrazole derivatives were obtained in good yields.
- Matsumura, Noboru,Kunugihara, Akira,Yoneda, Shigeo
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p. 3239 - 3242
(2007/10/02)
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- Thienyl acrylamides and thienyl pyrazolines as potential schistosomicidal agents
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α Thienyl N substituted acrylamides that possess analogous structures to known schistosomicidal agents were synthesized. Two chalcones were prepared by condensing α thiophenealdehyde and acetophenone or its o hydroxy derivative. Cyclization of the chalcon
- El Kerdawy,Samour,El Agamey
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