- Enantioselective synthesis of coumarin derivatives catalyzed by primary amines
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Cinchona alkaloid-derived primary amines were used as organocatalysts for the preparation of enantioenriched coumarin derivatives. A series of optically active coumarin derivatives was obtained in good yields with excellent enantioselectivities (up to 98%
- Lee, Yen-Te,Das, Utpal,Chen, Yi-Ru,Lee, Chia-Jui,Chen, Chi-Han,Yang, Mei-Chun,Lin, Wenwei
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- Design, synthesis and antibacterial study of new potent and selective coumarin-chalcone derivatives for the treatment of tenacibaculosis
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With the aim of finding new chemical entities selective for fish pathogens to avoid drug resistance in humans, a series of coumarin-chalcone hybrid compounds with different patterns of substitution were designed and synthesized. Their antibacterial activi
- Vazquez-Rodriguez, Saleta,Lama López, Raquel,Matos, Maria Jo?o,Armesto-Quintas, Gabriel,Serra, Silvia,Uriarte, Eugenio,Santana, Lourdes,Borges, Fernanda,Mu?oz Crego, Angeles,Santos, Ysabel
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- Dual Role of Oxoaldehydes: Divergent Synthesis of 3-Aryl- and 3-Aroylcoumarins
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A facile and efficient synthetic approach to various valuable 3-aryl- and 3-aroylcoumarins by the direct arylation and aroylation of coumarins with glyoxals in a metal-free manner is presented. The aryl glyoxal is for the first time recognized to serve as an aryl surrogate in addition to its role as an aroyl transfer reagent via a simple switch in reaction conditions. The approach accommodates a broad substrate scope and high yields of the two types of cross-coupling reactions starting from identical starting materials.
- Ghandi, Mehdi,Jafarpour, Farnaz,Khodadadi, Meysam,Moazzam, Ali
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- An efficient synthesis of some new coumarin hybrids endowed with expected biological activity
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Reactions of 5-bromo-2-hydroxybenzaldehyde with cyanoacetic acid hydrazide derivatives in refluxing ethanol afforded some new chromene-based polyfunctionally substituted heteroaromatics. The antimicrobial activity of some of the obtained products was eval
- Abdel Atty, Hany A.,Dawood, Kamal M.,Hagaggi, Noura Sh.,Nafady, Ayman,Raslan, Mohamed A.
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p. 1579 - 1598
(2020/10/21)
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- Palladium-Catalyzed Carbonylation of Coumarin C(sp 2)-H Bonds: A New Entry to Arylcoumarin Ketones
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A facile and efficient palladium-catalyzed carbonylation of coumarins involving two C-C bond formations has been developed. The C-H bond oxidative functionalization proceeds through aroylation with insertion of carbon monoxide to give arylcoumarin ketones
- Mirzaei, Siyavash,Rajai-Daryasarei, Saideh,Soheilizad, Mehdi,Kabiri, Roya,Ansari, Samira,Shabanian, Meisam,Pashazadeh, Rahim
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p. 1680 - 1688
(2019/03/26)
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- The synthesis of coumarin derivatives using choline chloride/zinc chloride as a deep eutectic solvent
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In this work, choline chloride/zinc chloride was employed as a deep eutectic solvent (DES) in the green synthesis of coumarin derivatives using Knoevenagel condensation. Coumarins are important organic structures with useful application in various fields.
- Keshavarzipour, Fariba,Tavakol, Hossein
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p. 149 - 153
(2016/01/09)
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- The indium(iii) chloride catalyzed synthesis of sulfur incorporated 3-acylcoumarins; Their photochromic and acetate sensing properties
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The synthesis and evaluation of the photochromic properties of 3-acylcoumarins are very important as they exhibit selective sensing properties. We found that InCl3 efficiently catalyzes the condensation of 2-hydroxybenzaldehydes and β-keto este
- Surya Prakash Rao,Desai, Avinash
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p. 63642 - 63649
(2015/02/19)
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- Synthesis of 3-Substituted coumarins: An efficient green approach using l-Proline as catalyst in triethanolamine medium
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3-Substituted coumarins were synthesized very efficiently, using Knoevenagel method from salicylaldehydes 1 and active methylene compounds 2 under green conditions. The effect of catalyst and solvent on this condensation was studied. L-Proline was found t
- Srikrishna, Devulapally,Tasqeeruddin, .Syed,Dubey, Pramod Kumar
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p. 556 - 563
(2014/07/21)
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- DABCO and Bu3P catalyzed [4 + 2] and [3 + 2] cycloadditions of 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate
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DABCO-catalyzed [4 + 2] and Bu3P-catalyzed [3 + 2] cycloadditions between 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate were developed for the synthesis of dihydropyran-fused and cyclopenten-fused chromen-2-ones with high regio- and stereo-
- Wang, Ying,Yu, Zhi-Hua,Zheng, Hu-Fei,Shi, De-Qing
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p. 7739 - 7746
(2013/04/23)
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- Syntheses of furo[3,4-c]coumarins and related furyl coumarin derivatives via intramolecular Wittig reactions
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A new and general strategy for highly functional furo[3,4-c]coumarins and related furyl coumarin derivatives has been developed, which is based on an extraordinarily facile intramolecular Wittig reaction, starting from α,β-unsaturated ketones, tributylpho
- Jang, Yeong-Jiunn,Syu, Siang-En,Chen, Yu-Jhang,Yang, Mei-Chun,Lin, Wenwei
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supporting information; experimental part
p. 843 - 847
(2012/02/02)
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- Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives
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Several 3-carbonyl (1-26), 3-acyl (27-52), and 3-carboxyhydrazido (53-58) coumarins have been synthesized in high yields (72-99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl ester coumarin ring, or the introduction of a hydrazido substituent at C3, were important to obtain highly potent and selective hMAO-B inhibitors with IC50 values in the nanomolar range. Some derivatives were also submitted to a stability test and showed no chemical cleavage in vitro.
- Secci, Daniela,Carradori, Simone,Bolasco, Adriana,Chimenti, Paola,Yá?ez, Matilde,Ortuso, Francesco,Alcaro, Stefano
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experimental part
p. 4846 - 4852
(2011/11/13)
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- α-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives
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Series of 3,4- and 3,6-disubstituted chromenones including new chromenone derivatives were synthesized applying various synthetic strategies including Pechmann condensation, Knoevenagel condensation, Reimer-Tiemann reaction and Suzuki coupling in very good yields. Synthesized compounds (4a-z) were screened for in vitro α-glucosidase inhibitory and 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activities. Majority of compounds displayed varying degrees of α-glucosidase inhibitory and DPPH scavenging activity. Compound 4x emerged as the most potent α-glucosidase inhibitor in present series of compounds owing to the presence of 3-acetyl-6-(6-methoxy-3-pyridyl) group on chromenone; however, it could not display DPPH scavenging activity and was found to be mixed non-competitive type inhibitor of rat intestinal α-glucosidase. When tested in vivo for antihyperglycemic activity in starch loaded Wistar rats, it displayed significant antihyperglycemic property. This is the first report assigning rat intestinal α-glucosidase inhibitory property for this class of new chromenones and presents new family of compounds possessing α-glucosidase inhibitory activities and antihyperglycemic property. Compound 4x may serve as an interesting new compound for the development of therapeutics targeted against diet-induced hyperglycemia in diabetes.
- Raju, B. China,Tiwari, Ashok K.,Kumar, J. Ashok,Ali, A. Zehra,Agawane, Sachin B.,Saidachary,Madhusudana
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experimental part
p. 358 - 365
(2010/04/02)
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