- Design and synthesis of triazole conjugated novel 2,5-diaryl substituted 1,3,4-oxadiazoles as potential antimicrobial and anti-fungal agents
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A series of triazole conjugated novel 2,5-diaryl 1,3,4-oxadiazole derivatives 8a-q are efficiently synthesized starting from methyl salicylate. All the synthesized compounds were characterized based on their 1H NMR, 13C NMR, Mass and
- Atcha, Krisham Raju,Bhukya, Vijaya Kumar,Birudaraju, Saritha,Bitla, Sampath,Dhanavath, Ramulu,Gayatri, Akkiraju Anjini,Puchakayala, Muralidhar Reddy,Sagurthi, Someswar Rao
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- Design and synthesis, biological evaluation of bis-(1,2,3- and 1,2,4)-triazole derivatives as potential antimicrobial and antifungal agents
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A new series of bis-1,2,3- and 1,2,4-triazoles (10a-m) were designed and efficiently synthesized using methyl salicylate as potential antimicrobial agents. All compounds were characterized by their proton & 13C NMR, IR, Mass spectral data, and
- Bitla, Sampath,Gayatri, Akkiraju Anjini,Puchakayala, Muralidhar Reddy,Kumar Bhukya, Vijaya,Vannada, Jagadeshwar,Dhanavath, Ramulu,Kuthati, Bhaskar,Kothula, Devender,Sagurthi, Someswar Rao,Atcha, Krisham Raju
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supporting information
(2021/04/19)
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- Synthesis, in silico Pharmacokinetic and Antimicrobial Studies of Oxovanadium(V) Complexes with 2-(4-((2-(Carboxy)phenoxy) methyl)-1H-1,2,3-triazol-1-Yl)Benzoic Acid
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New Vanadium(V) complexes with new ligand 2-(4-((2-(carboxy) phenoxy) methyl)-1H-1,2,3triazol-1-yl)benzoic acid (L1) has been synthesized and characterized by different analytical techniques such as elemental analyzer, 1H NMR, UV-Vis
- Abdelbaset, Mohamed,Alghamdi, Hanan,Nazreen, Syed
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p. 645 - 654
(2020/11/25)
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- Synthesis and neuroprotective effects of novel chalcone-triazole hybrids
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The development of novel neuroprotective agents is urgently needed for the treatment of neurodegenerative diseases, affecting aging individuals worldwide. In this study, a new set of chalcone-triazole hybrids (6a-g) was synthesized and evaluated for their
- Sooknual, Pichjira,Pingaew, Ratchanok,Phopin, Kamonrat,Ruankham, Waralee,Prachayasittikul, Supaluk,Ruchirawat, Somsak,Prachayasittikul, Virapong
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- Gold promoted arylative cyclization of alkynoic acids with arenediazonium salts
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Alkynoic acids derived from salicylic acid and analogues undergo arylative cyclization with arenediazonium salts promoted by gold in the absence of external ligands. The reaction is thermally induced and proceeds even in the absence of light. A difference in regioselectivity has been found compared with that observed in the cycloisomerization process of the same type of compounds.
- Carrillo-Arcos, Ulises A.,Porcel, Susana
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supporting information
p. 1837 - 1842
(2018/03/23)
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- Synthesis of Tetrasubstituted α,β-Unsaturated Aldehydes via Radical 1,4-Aryl Migration/Trifluoromethylthiolation Cascade Reaction of Aryl Propynyl Ethers
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A one-pot synthesis of tetrasubstituted acrylaldehydes via difunctionalization of aryl propynyl ethers has been achieved, which involves a trifluoromethylthiolation process and a radical 1,4-aryl migration from oxygen to carbon. The reaction shows excellent conversion of aryl propynyl ethers into trifluoromethyl-containing α,β-unsaturated aldehydes through a radical pathway. (Figure presented.).
- Guo, Chun-Huan,Chen, Dao-Qian,Chen, Si,Liu, Xue-Yuan
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supporting information
p. 2901 - 2906
(2017/09/08)
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- Palladium-catalyzed cyclization of alkynoic acids to form vinyl dioxanones bearing a quaternary allylic carbon
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A palladium-catalyzed intramolecular reaction of carboxylic acids and alkynes in a novel cyclization manner was developed. This unique cyclization efficiently provided a wide range of complex ring systems-vinyl dioxanones bearing a quaternary allylic carbon. Mechanistic studies suggest an allenyl carboxylate as an intermediate.
- Ogiwara, Yohei,Sato, Kazuya,Sakai, Norio
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supporting information
p. 5296 - 5299
(2017/11/06)
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- Natural-Product-Inspired Aminoepoxybenzoquinones Kill Members of the Gram-Negative Pathogen Salmonella by Attenuating Cellular Stress Response
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Gram-negative bacteria represent a challenging task for antibacterial drug discovery owing to their impermeable cell membrane and restricted uptake of small molecules. We herein describe the synthesis of natural-product-derived epoxycyclohexenones and explore their antibiotic activity against several pathogenic bacteria. A compound with activity against Salmonella Typhimurium was identified, and the target enzymes were unraveled by quantitative chemical proteomics. Importantly, two protein hits were linked to bacterial stress response, and corresponding assays revealed an elevated susceptibility to reactive oxygen species upon compound treatment. The consolidated inhibition of these targets provides a rationale for antibacterial activity and highlights epoxycyclohexenones as natural product scaffolds with suitable properties for killing Gram-negative Salmonella.
- Mandl, Franziska A.,Kirsch, Volker C.,Ugur, Ilke,Kunold, Elena,Vomacka, Jan,Fetzer, Christian,Schneider, Sabine,Richter, Klaus,Fuchs, Thilo M.,Antes, Iris,Sieber, Stephan A.
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supporting information
p. 14852 - 14857
(2016/11/23)
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- TRIAZOLOPYRIMIDINE COMPOUNDS AND USES THEREOF
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A compound of Formula (I), or a pharmaceutically acceptable salt thereof, is provided that has been shown to be useful for treating a PRC2-mediated disease or disorder: wherein R1, R2, R3, R4, R5, and n are as defined herein.
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Paragraph 0338; 0339
(2016/07/27)
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- Silver(I) and gold(I)-promoted synthesis of alkylidene lactones and 2H-chromenes from salicylic and anthranilic acid derivatives
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Ag(I) and Au(I) efficiently catalyze the cycloisomerization of terminal alkynoic acids into methylene seven-membered ring lactones. Depending on the metal, divergent reaction pathways were found for non terminal alkynoic acids. While Ag(I) led to lactones, Au(I) led to 2H-chromenes coming from the hydroarylation of the alkyne.
- Nolla-Saltiel, Roberto,Robles-Marín, Elvis,Porcel, Susana
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supporting information
p. 4484 - 4488
(2014/08/05)
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- Synthesis and biological evaluation of 4-(1,2,3-triazol-1-yl)coumarin derivatives as potential antitumor agents
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In this research, a series of 4-(1,2,3-triazol-1-yl)coumarin conjugates were synthesized and their anticancer activities were evaluated in vitro against three human cancer cell lines, including human breast carcinoma MCF-7 cell, colon carcinoma SW480 cell and lung carcinoma A549 cell. To increase the biological potency, structural optimization campaign was conducted focusing on the C-4 position of 1,2,3-triazole and the C-6, C-7 positions of coumarin. In addition, to further evaluate the role of 1,2,3-triazole and coumarin for antiproliferative activity, 9 compounds possessing 4-(piperazin-1-yl)coumarin framework and 3 derivatives baring quinoline core were also synthesized. By MTT assay in vitro, most of the compounds display attractive antitumor activities, especially 23. Further flow cytometry assays demonstrate that compound 23 exerts the antiproliferative role through arresting G2/M cell-cycle and inducing apoptosis.
- Zhang, Wenjuan,Li, Zhi,Zhou, Meng,Wu, Feng,Hou, Xueyan,Luo, Hao,Liu, Hao,Han, Xuan,Yan, Guoyi,Ding, Zhenyu,Li, Rui
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supporting information
p. 799 - 807
(2014/02/14)
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- Design, synthesis and molecular docking studies of novel N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-based triazoles with potential anticancer activity
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A novel series of N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinolines (14-33) containing triazole moiety were designed and synthesized through rational cycloadditions using the modified Pictet-Spengler reaction and the Click chemistry. Antiproliferative act
- Pingaew, Ratchanok,Mandi, Prasit,Nantasenamat, Chanin,Prachayasittikul, Supaluk,Ruchirawat, Somsak,Prachayasittikul, Virapong
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p. 192 - 203
(2014/06/09)
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- Photocycloaddition of arenes and allenes
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In this work, we report on a new intramolecular para cycloaddition of arenes with allenes, yielding attractive rigid scaffolds bearing several reactive functionalities to build in further diversity. Bicyclo[2.2.2]octadiene- type products and benzoxepine acetals are formed in this reaction, in ratios and yields depending on the substitution pattern on the aromatic ring, the nature of the chromophore, and the tether. This unprecedented reaction has remarkable features that distinguish it from many other photochemical transformations: it is particularly robust with respect to substituents, it can be scaled up without a notable loss of efficiency, and it can lead to structures with a high degree of complexity in low to good yields. All photochemical precursors could be synthesized readily in three steps. We confirmed the compatibility of the nitrogen atom in the photocycloaddition step, which gives access to a bicyclo[2.2.2]octadiene scaffold with two points that allow further diversification. This reaction was scaled up to multigram quantities without erosion of the typically high yields in photocycloadducts. Sequential deprotection of the N- or C-terminus of bicyclic amino acids gave access to two conformationally constrained unnatural amino acids with different dispositions of the two anchor points.
- Streit, Ursula,Birbaum, Frederic,Quattropani, Anna,Bochet, Christian G.
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p. 6890 - 6910
(2013/08/23)
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- Ph3PAuNTf2 as a superior catalyst for the selective synthesis of 2H-chromenes: Application to the concise synthesis of benzopyran natural products
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Ph3PAuNTf2 (≈1 mol-%) catalyzes the selective cycloisomerization of substituted aryl propargyl ethers into 2H-chromenes in excellent yields. Benzofuran byproducts are formed only in the case of electron-deficient arenes, in up to 7% relative yield. The Ph 3PAuNTf2-catalyzed cyclization of aryl propargyl ethers was applied as a key step to the concise synthesis of the naturally occurring benzopyrans seselin, xanthyletin, precocenes I and II, 8-(3′,3′- dimethylallyl)wenteria chromene, and 2,2-dimethyl-8-prenylchromene-6-propenoic acid. Ph3PAuNTf2 is a general, highly efficient, and product-selective catalyst for the clean synthesis of 2H-chromenes from the cycloisomerization of aryl propargyl ethers.The Ph3PAuNTf 2-catalyzed cyclization was applied as a key step in the synthesis of several benzopyran-bearing naturally occurring substances. Copyright
- Lykakis, Ioannis N.,Efe, Christina,Gryparis, Charis,Stratakis, Manolis
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supporting information; experimental part
p. 2334 - 2338
(2011/06/20)
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- Intramolecular dipolar cycloaddition reaction of 5H,7H-thiazolo[3,4-c]oxazol-4-ium-l-olates: Synthesis of chiral 1H-pyrrolo[1,2-c]thiazole derivatives
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(2R,4Ae)-Ar-AcyI-2-phenylthiazolidine-4-carboxylic acids were used to generate 5//,7//-thiazolo[3,4-c]oxazol-4-ium1-olates with internal dipolarophiles. The intramolecular 1,3-dipolar cycloaddition of these mesoionic species led to the synthesis of new l/
- Pinho Melo, Teresa M. V.,Barbosa, Dalia M.,Ramos, Paulo J. R. S.,Rocha Gonsalves, Antonio M.,Gilchrist, Thomas L.,Beja, Ana M.,Paixaeo, Jose A.,Silva, Manuela R.,Veiga, Luiz Alte Da
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p. 1219 - 1223
(2007/10/03)
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- A facile synthesis of methyl 5-amino-6-chloro-2h-1-benzopyran-8-carboxylate derivatives
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Methyl 6-chloro-5-pivaloylamino-2H-1-benzopyran-8-carboxylate (4d) was prepared in good yield as a result of the thermal cylcization of methyl 5-chloro-4-pivaloylamino-2-propargyloxybenzoate (3d) using N,N-diethylaniline as a solvent.
- Kakigami, Takuji,Baba, Kunihisa,Usui, Toshinao
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p. 2611 - 2619
(2007/10/03)
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- Cesium Fluoride-Mediated Claisen Rearrangements of Phenyl Propargyl Ethers: Effect of a Substituent on the Phenyl Ring on the Rearrangement
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Methoxy or methoxycarbonyl-substituted phenyl propargyl ethers were subjected to Claisen rearrangement either in the absence or in the presence of CsF.Substituent effect on the cyclization is discussed.
- Ishikawa, Tsutomu,Nagai, Keiko,Ohkubo, Naoko,Ishii, Hisashi
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p. 371 - 380
(2007/10/02)
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