1621-58-5Relevant articles and documents
Coumarin Derivatives Exert Anti-Lung Cancer Activity by Inhibition of Epithelial–Mesenchymal Transition and Migration in A549 Cells
Barreto, Emiliano,Bourguignon, Jean-Jacques,Dos Santos Carmo, Julianderson de Oliveira,Filho, José Maria Barbosa,Mendon?a-Junior, Francisco Jaime Bezerra,Rodarte, Renato Santos,Schmitt, Martine,Silva, Simone Lara de Omena,Souza, Tayhana Priscila Medeiros,da Silva, Camila Radelley Azevedo Costa,de Aquino, Thiago Mendon?a,de Araújo, Rodrigo Santos Aquino,de Mélo, Natália Barbosa,de Moura, Ricardo Olímpio
, (2022/01/24)
A series of coumarin derivatives and isosteres were synthesized from the reaction of triflic intermediates with phenylboronic acids, terminal alkynes, and organozinc compounds through palladium-catalyzed cross-coupling reactions. The in vitro cytotoxic ef
Stille coupling for the synthesis of isoflavones by a reusable palladium catalyst in water
Chang, Ya-Ting,Liu, Ling-Jun,Peng, Wen-Sheng,Lin, Lin-Ting,Chan, Yi-Tsu,Tsai, Fu-Yu
, p. 469 - 475 (2021/02/03)
Isoflavones were synthesized from the reaction of 3-bromochromone derivatives and aryltributylstannanes via Stille coupling catalyzed by a water-soluble and reusable PdCl2(NH3)2/2,2′-cationic bipyridyl system in aqueous solution. For prototype 3-bromochromone, the coupling reaction was performed at 80°C for 24 hr with 2.5 mol% catalyst in water in the presence of tetrabutylammonium fluoride. After the reaction, the aqueous solution could be reused for several runs, indicating that its activity was only slightly decreased. For substituted 3-bromochromones, the addition of NaHCO3 and a higher reaction temperature (120°C) were required to gain satisfactory outcomes. In addition, naturally occurring products, such as daidzein, could be obtained by this protocol via a one-pot reaction.
Pot-economic synthesis of diarylpyrazoles and pyrimidines involving Pd-catalyzed cross-coupling of 3-trifloxychromone and triarylbismuth
Kumar, Abhijeet,Rao, Maddali L N
, (2018/12/10)
Abstract: The present study reveals the formation of 3,4-diarylpyrazole and 4,5-diarylpyrimidine in one-pot operation starting from 3-trifloxychromone and triarylbismuth. The complete process encompasses two steps in the one-pot operation. The first step leads to the formation of isoflavone via cross-coupling reaction of 3-trifloxychromone and triarylbismuth as a threefold arylating reagent. These isoflavones were further converted into 3,4-diarylpyrazole and 4,5-diarylpyrimidine using hydrazine hydrate and guanidinium chloride in the successive step in the same pot. Interestingly the formation of 3,4-diarylpyrazole was achieved in the shortest reaction time i.e., 30 min that too at room temperature. Overall the developed methodology provides easy access to the medicinally important diarylpyrazole and pyrimidine moiety in one-pot operation and in short reaction time. Graphical Abstract: Synopsis The work presented here describes the novel methodology for the formation of medicinally important heterocycles 3,4-diarylpyrazole and 4,5-diarylpyrimidine in one-pot operation starting from 3-trifloxychromone and triarylbismuth.
Scaffold-hopping of bioactive flavonoids: Discovery of aryl-pyridopyrimidinones as potent anticancer agents that inhibit catalytic role of topoisomerase IIα
Priyadarshani, Garima,Amrutkar, Suyog,Nayak, Anmada,Banerjee, Uttam C.,Kundu, Chanakya N.,Guchhait, Sankar K.
, p. 43 - 54 (2016/07/06)
A strategy of scaffold-hopping of bioactive natural products, flavones and isoflavones, leading to target-based discovery of potent anticancer agents has been reported for the first time. Scaffold-hopped flavones, 2-aryl-4H-pyrido[1,2-a]pyrimidin-4-ones and the scaffold-hopped isoflavones, 3-aryl-pyrido[1,2-a]pyrimidin-4-ones were synthesized via Pd-catalyzed activation–arylation methods. Most of the compounds were found to exhibit pronounced human topoisomerase IIα (hTopoIIα) inhibitory activities and several compounds were found to be more potent than etoposide (a hTopoIIα-inhibiting anticancer drug). These classes of compounds were found to be hTopoIIα-selective catalytic inhibitors while not interfering with topoisomerase I and interacted with DNA plausibly in groove domain. Cytotoxicities against various cancer cells, low toxicity in normal cells, and apoptotic effects were observed. Interestingly, compared to parent flavones/isoflavones, their scaffold-hopped analogs bearing alike functionalities showed significant/enhanced hTopoIIα-inhibitory and cytotoxic properties, indicating the importance of a natural product-based scaffold-hopping strategy in the drug discovery.
Synthesis, antimycobacterial evaluation and pharmacophore modeling of analogues of the natural product formononetin
Mutai, Peggoty,Pavadai, Elumalai,Wiid, Ian,Ngwane, Andile,Baker, Bienyameen,Chibale, Kelly
supporting information, p. 2510 - 2513 (2015/06/02)
Abstract The synthesis and antimycobacterial activity of formononetin analogues is hereby reported. Formononetin and its analogue 11E showed 88% and 95% growth inhibition, respectively, against the H37Rv strain of Mycobacterium tuberculosis. Pharmacophore modeling studies indicated that the presence of a hydroxyl group in formononetin and its analogues, is crucial for maintaining activity.
Oxidative regioselective amination of chromones exposes potent inhibitors of the hedgehog signaling pathway
Samanta, Rajarshi,Narayan, Rishikesh,Bauer, Jonathan O.,Strohmann, Carsten,Sievers, Sonja,Antonchick, Andrey P.
supporting information, p. 925 - 928 (2015/01/09)
A transition metal-free, oxidative, regioselective cross-coupling between non-functionalized azoles and chromones at C2-position was developed. A broad reaction scope and further transformation of products were demonstrated. The biological evaluation of products revealed a novel class of hedgehog signaling pathway inhibitors. This journal is
A Concise Synthesis of Pyrazole Analogues of CombretastatinA1 as Potent Anti-Tubulin Agents
Zaninetti, Roberta,Cortese, Salvatore V.,Aprile, Silvio,Massarotti, Alberto,Canonico, Pier Luigi,Sorba, Giovanni,Grosa, Giorgio,Genazzani, Armando A.,Pirali, Tracey
, p. 633 - 643 (2013/08/22)
CombretastatinA1 (CA1) binds to the β-subunit at the colchicine binding site of tubulin and inhibits polymerization. As such, it is both an antitumor agent and a vascular disrupting agent. It has been shown to be at least tenfold more potent than combreta
Novel synthesis of 3-phenyl-chromen-4-ones using n-heterocyclic carbene as organocatalyst: An efficient domino catalysis type approach
Mishra, Priya,Singh, Sarita,Ankit, Preyas,Fatma, Shahin,Singh, Divya,Singh, Jagdamba
, p. 1070 - 1076 (2013/07/28)
Herein is reported a simple and efficient synthesis of isoflavones starting from various substituted phenacyl bromides and salicylaldehydes in presence of NHC. The mechanism involved domino catalysis type approach with consumption and regeneration of catalyst in two catalytic cycles. This method proved to be very lucrative and gives very good yield. The method described here represents an environmentally benign alternative to classical approach.
Oxidative rearrangements of 2'-hydroxychalcones with lh-l-hydroxy-5-methyl- l,2,3-benziodoxathiole 3,3-dioxide
Justik, Michael W.,Zimmerman, Alyssa K.
scheme or table, p. 67 - 71 (2010/03/03)
1H-l-hydroxy-5-methyl-l,2,3-benziodoxathiole 3,3-dioxide (HMBI) has been found to effect the direct conversion of 2'-hydroxychalcones with various B-ring substituents to isoflavones in moderate to good yield (34-83%) in methanol under reflux. The reduced byproduct of HMBI is easily recovered by aqueous extraction and can be recycled and reused with high efficiency. Previous reports of conversions of this type required the use of toxic thallium(III) salts or initial protection of the 2'-hydroxyl group.
Pd-Catalyzed efficient cross-couplings of 3-iodochromones with triarylbismuths as substoichiometric multicoupling organometallic nucleophiles
Rao, Maddali L. N.,Venkatesh, Varadhachari,Jadhav, Deepak N.
experimental part, p. 2597 - 2600 (2010/01/16)
An efficient cross-coupling of 3-iodochromones with triarylbismuths under catalytic palladium conditions is reported. Triarylbismuths were employed as substoichiometric multicoupling nucleophiles for the synthesis of a variety of substituted isoflavones.
