- Water-Tolerant ortho-Acylation of Phenols
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A metal-free, water-tolerant, and one-pot process for ortho-acylation of phenols promoted by the iodine source/hydrogen peroxide system has been developed. This transformation undergoes ether formation, iodocyclization, C-C bond cleavage, and oxidative hydrolysis in a one-step manner, which is supported by control experiments.
- Dong, Shuang-Feng,Gao, Zhi-Yuan,He, Yu,Liu, Xu,Loh, Teck-Peng,Tian, Jie-Sheng,Wu, Peng
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supporting information
p. 6594 - 6598
(2021/09/02)
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- Synthesis, characterization, and antiplasmodial efficacy of sulfonamide-appended [1,2,3]-triazoles
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A series of benzenesulfonamide-appended [1,2,3]-triazole hybrids was synthesized by using [3 + 2] cycloaddition of primary, secondary, and tertiary sulfonamide azides with various phenoxymethylacetylenes under click reaction conditions. After structural c
- Batra, Neha,Dutta, Roshan Kumar,Ghosh, Prahlad C.,Gupta, Rinkoo D.,Lathwal, Ankit,Nath, Mahendra,Rajendran, Vinoth,Wadi, Ishan
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- Iron-Mediated Cyclization of 1,3-Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene-Fused Chromenes
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The synthesis of selenophene-fused chromene derivatives starting from 1,3-diynyl propargyl aryl ethers is reported herein. The method is based on carbon-carbon, carbon-selenium, selenium-carbon and carbon-selenium bonds formation in a one-pot protocol, using iron(III) chloride and dibutyl diselenide as promoters. The same reaction conditions were applied to propargyl anilines leading to the formation of 1-(butylselanyl)-selenophene quinolines. The results showed that the dilution and temperature of substrate addition had a crucial influence in the products obtained. When the substrates were added at room temperature, in the absence of a solvent, a mixture of products was obtained, whereas the slowly addition (15 min) of starting materials, as a dichloromethane solution, at 0 °C led to the product formation in good yields. The mechanistic study indicates that the cooperative action between iron(III) chloride and dibutyl diselenide was essential to promote the cyclization, whereas separately none of them was effective in promoting the cyclization. We proved the synthetic utility of heterocycles obtained in the Suzuki cross coupling reaction, giving the corresponding cross-coupled products in good yields. In addition, the organoselenium moiety was removed from the structures of products by using n-butyllithium. (Figure presented.).
- Back, Davi F.,Lutz, Guilherme,Zeni, Gilson
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p. 1096 - 1105
(2020/01/25)
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- 1,2,3-Triazole-based kojic acid analogs as potent tyrosinase inhibitors: Design, synthesis and biological evaluation
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A series of kojic acid-derived compounds 6a-p bearing aryloxymethyl-1H-1,2,3-triazol-1-yl moiety were designed by modifying primary alcoholic group of kojic acid as tyrosinase inhibitors. The target compounds 6a-p were synthesized via click reaction. All
- Ashooriha, Morteza,Khoshneviszadeh, Mehdi,Khoshneviszadeh, Mahsima,Moradi, Seyed Ershad,Rafiei, Alireza,Kardan, Mostafa,Emami, Saeed
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p. 414 - 422
(2018/11/21)
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- Preparation of novel 1,2,3-triazole furocoumarin derivatives via click chemistry and their anti-vitiligo activity
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The extracts of Psoralea corylifolia?L. were often used for the repigmentation of leukoderma (vitiligo) in traditional Uygur medicine thousands years ago. Nowadays, its active ingredient, furocoumarins, has been clinically applied since it exhibited stron
- Niu, Chao,Lu, Xueying,Aisa, Haji Akber
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p. 1671 - 1678
(2019/01/24)
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- Electrostatic Control of Regioselectivity in Au(I)-Catalyzed Hydroarylation
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Competing pathways in catalytic reactions often involve transition states with very different charge distributions, but this difference is rarely exploited to control selectivity. The proximity of a counterion to a charged catalyst in an ion paired comple
- Lau, Vivian M.,Pfalzgraff, William C.,Markland, Thomas E.,Kanan, Matthew W.
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supporting information
p. 4035 - 4041
(2017/03/31)
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- Synthesis and antibacterial evaluation of novel sulfonamide based [1,2,3]-triazoles
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A new series of sulfonamide based [1,2,3]-triazoles 4a-i, 5 and 6 has been prepared in 65-99% yield through Huisgen [3+2] cycloaddition reaction of 4-azido-N-substitutedbenzenesulfonamides 2a,b with various alkynes (3a-i or phenyl acetylene) in the presence of CuSO4.5H2O and sodium ascorbate in t-butanol and water (1:1) mixture at 40°C. The structures of all the newly synthesized molecules have been established on the basis of IR, 1H and 13C NMR and high resolution mass spectral analysis. Furthermore, these compounds have been evaluated for their preliminary in vitro antibacterial activity against two Gram-negative bacteria viz. Escherichia coli (MTCC 433) and Salmonella enterica ser. typhi (MTCC 733) and a Gram-positive bacterium viz. Streptococcus mutans (MTCC 497) by using MTT assay.
- Batra, Neha,Roy, Basabi,Mazumder, Sibnath,Nath, Mahendra
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p. 650 - 655
(2015/05/27)
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- Synthesis of Potential Bioactive Novel 7-[2-Hydroxy-3-(1,2,3-triazol-1-yl) propyloxy]-3-alkyl-4-methylcoumarins
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A series of 50 novel 7-[2-hydroxy-3-(1,2,3-triazol-1-yl)propyloxy]-3-alkyl-4-methylcoumarins had been designed and synthesized in good to excellent yields via Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction "click chemistry" of 7-(3-azido-2-hydroxypropyloxy)-3-alkyl-4-methylcoumarins with variety of acetylene derivatives. In turn, the precursor compound, that is, 7-(3-azido-2-hydroxypropyloxy)-3-alkyl-4-methylcoumarin, was synthesized by condensation of epichlorohydrin with 7-hydroxy-3-alkyl-4-methylcoumarins followed by opening of the epoxide ring in the resulted 7-epoxymethoxy-3-alkyl-4-methylcoumarins with sodium azide. All the synthesized compounds were unambiguously identified on the basis of their spectral data analyses (IR, 1H-NMR, 13C-NMR spectra, and HRMS).
- Arya, Anu,Kumar, Vinod,Mathur, Divya,Singh, Sukhdev,Brahma, Raju,Singh, Rajpal,Singh, Seema,Sharma,Parmar, Virinder S.,Prasad, Ashok K.
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- Synthesis of new generation triazolyl- and isoxazolyl-containing 6-nitro-2,3-dihydroimidazooxazoles as anti-TB agents: In vitro, structure-activity relationship, pharmacokinetics and in vivo evaluation
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The nitroimidazole scaffold has attracted great interest in the last decade, which ultimately led to the discovery of the successful drug Delamanid for multi-drug resistant tuberculosis (MDR-TB). Herein, we report medicinal chemistry on a 6-nitro-2,3-dihy
- Munagala, Gurunadham,Yempalla, Kushalava Reddy,Singh, Samsher,Sharma, Sumit,Kalia, Nitin Pal,Rajput, Vikrant Singh,Kumar, Sunil,Sawant, Sanghapal D.,Khan, Inshad Ali,Vishwakarma, Ram A.,Singh, Parvinder Pal
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supporting information
p. 3610 - 3624
(2015/03/30)
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- Strategies to reduce hERG K+ channel blockade. Exploring heteroaromaticity and rigidity in novel pyridine analogues of dofetilide
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Drug-induced blockade of the human ether-a-go-go-related gene K+ channel (hERG) represents one of the major antitarget concerns in pharmaceutical industry. SAR studies of this ion channel have shed light on the structural requirements for hERG
- Carvalho, Jo?o F. S.,Louvel, Julien,Doornbos, Maarten L. J.,Klaasse, Elisabeth,Yu, Zhiyi,Brussee, Johannes,Ijzerman, Adriaan P.
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supporting information
p. 2828 - 2840
(2013/05/22)
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- Microwave-assisted copper azide alkyne cycloaddition (CuAAC) reaction using D-glucose as a better alternative reductant
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D-Glucose has been established as a reducing agent for the copper azide alkyne cycloaddition (CuAAC) reactions. Efficacy of this new reductant has been established against various phenyl acetylenes (14 examples) and aryl azides (16 examples). All reaction
- Kumar, Yogesh,Bahadur, Vijay,Singh, Anil K.,Parmar, Virinder S.,Singh, Brajendra K.
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p. 1893 - 1903
(2014/01/17)
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- Silver(I)-organic networks constructed with flexible silver-ethynide supramolecular synthon o-, m-, p-Cl-C6H5OCH 2C≡C?Agn (n = 4, 5)
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A series of five silver coordination polymers [(AgL1)·(AgCF 3COO)5·(H2O)3] (1), [(AgL1)2·(AgCF3COO)11·(H 2O)6] (2), [(AgL2)·(AgCF3COO) 3/su
- Li, Bo,Zang, Shuang-Quan,Ji, Can,Mak, Thomas C.W.
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experimental part
p. 2820 - 2828
(2011/08/09)
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- D-ring substituted 1,2,3-triazolyl 20-keto pregnenanes as potential anticancer agents: Synthesis and biological evaluation
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A facile synthesis of 21-triazolyl derivatives of pregnenolone and their potential antitumour activity is reported. The scheme involves the transformation of the starting pregnenolone acetate into pregnenolone, conversion of pregnenolone to 21-bromo pregnenolone and finally the one-pot, two-step in situ conversion of the bromo derivative to the 21-triazolyl pregnenolone using the 'click chemistry' approach. These derivatives were screened for their anticancer activity against seven human cancer cell lines. The compounds especially 5a, 5b, 5c, 5e, 5g and 5h exhibited significant anticancer activity with compound 5e as the most active in this study.
- Banday, Abid H.,Shameem, Shameem A.,Gupta,Kumar, H.M. Sampath
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experimental part
p. 801 - 804
(2010/10/01)
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- Synthesis of organochalcogen propargyl aryl ethers and their application in the electrophilic cyclization reaction: An efficient preparation of 3-halo-4-chalcogen-2H-benzopyrans
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We herein described the synthesis of various organochalcogen propargyl aryl ethers via reaction of lithium acetylide intermediate with electrophilic chalcogen (sulfur, selenium, tellurium) species. Various aryl and alkyl groups directly bonded to the chal
- Godoi, Benhur,Speranca, Adriane,Back, Davi F.,Brandao, Ricardo,Nogueira, Cristina W.,Zeni, Gilson
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body text
p. 3469 - 3477
(2009/09/06)
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- 1,4-Dihydroindeno[1,2-c]pyrazoles with acetylenic side chains as novel and potent multitargeted receptor tyrosine kinase inhibitors with low affinity for the hERG ion channel
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The synthesis of a novel series of 1,4-dihydroindeno[1,2-c]pyrazoles with acetylene-type side chains is described. Optimization of those compounds as KDR kinase inhibitors identified 8, which displayed an oral activity in an estradiol-induced murine uterine edema model (ED50 = 3 mg/kg) superior to Sutent (ED50 = 9 mg/kg) and showed potent antitumor efficacy in an MX-1 human breast carcinoma xenograft tumor growth model (tumor growth inhibition = 90% at 25 mg/kg·day po). The compound was docked into a homology model of the homo-tetrameric pore domain of the hERG potassium channel to identify strategies to improve its cardiac safety profile. Systematic interruption of key binding interactions between 8 and Phe656, Tyr652, and Ser624 yielded 90, which only showed an IC50 of 11.6 μM in the hERG patch clamp assay. The selectivity profile for 8 and 90 revealed that both compounds are multitargeted receptor tyrosine kinase inhibitors with low nanomolar potencies against the members of the VEGFR and PDGFR kinase subfamilies.
- Dinges, Jürgen,Albert, Daniel H.,Arnold, Lee D.,Ashworth, Kimba L.,Akritopoulou-Zanze, Irini,Bousquet, Peter F.,Bouska, Jennifer J.,Cunha, George A.,Davidsen, Steven K.,Diaz, Gilbert J.,Djuric, Stevan W.,Gasiecki, Alan F.,Gintant, Gary A.,Gracias, Vijaya J.,Harris, Christopher M.,Houseman, Kathryn A.,Hutchins, Charles W.,Johnson, Eric F.,Li, Hu,Marcotte, Patrick A.,Martin, Ruth L.,Michaelides, Michael R.,Nyein, Michelle,Sowin, Thomas J.,Su, Zhi,Tapang, Paul H.,Xia, Zhiren,Zhang, Henry Q.
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p. 2011 - 2029
(2008/02/04)
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- A new series of pyridinyl-alkynes as antagonists of the metabotropic glutamate receptor 5 (mGluR5)
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Synthesis and some structure-activity relationships for a new series of propargyl ethers as mGluR5 antagonists are reported.
- Bach, Peter,Nilsson, Karolina,Wallberg, Andreas,Bauer, Udo,Hammerland, Lance G.,Peterson, Alecia,Svensson, Tor,Oesterlund, Krister,Karis, David,Boije, Maria,Wensbo, David
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p. 4792 - 4795
(2007/10/03)
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- The thermal [3, 3] claisen rearrangement of the 3-substituted phenyl allyl and propargyl ethers. The synthesis of 4-halobenzo[b]furans
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The thermal [3, 3] Claisen rearrangement of the 3-substituted phenyl allyl and propargyl ethers is regioselective. The major product of the reaction incorporates a 1, 2, 3-trisubstituted benzene ring. The 2-allenylphenol intermediates can be manipulated i
- Box, Vernon G. S.,Meleties, Panayiotis C.
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p. 2173 - 2183
(2007/10/03)
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