- Total Synthesis of Mulberry Diels-Alder-Type Adducts Kuwanons G and H
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Mulberry Diels-Alder-type adducts (MDAAs) are a group of rare natural polyphenols biosynthetically derived from [4 + 2]-cycloaddition of chalcones and dehydroprenylphenols. In this study, kuwanons G (1) and H (2), two bioactive MDAAs with unique dehydroprenylflavonoid dienes, were totally synthesized for the first time in a biomimetic manner. The key features of the convergent route include the use of the Baker-Venkataraman rearrangement, alkylation of β-diketone, intramolecular cyclization, and Suzuki-Miyaura coupling to achieve the subunit diene.
- Luo, Si-Yuan,Tang, Zhuo-Ya,Li, Qingjiang,Weng, Jiang,Yin, Sheng,Tang, Gui-Hua
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p. 4786 - 4793
(2021/04/06)
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- Synthesis and biological evaluation of chalcone, dihydrochalcone, and 1,3-diarylpropane analogs as anti-inflammatory agents
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Twenty-one chalcones were prepared via aldol condensation and subsequent reduction of these compound led to the corresponding dihydrochalcone and 1,3-diphenylpropane derivatives. The synthetic products were examined for their effects on NO inhibition in L
- Vijaya Bhaskar Reddy, Mopur,Hung, Hsin-Yi,Kuo, Ping-Chung,Huang, Guan-Jhong,Chan, Yu-Yi,Huang, Shiow-Chyn,Wu, Shwu-Jen,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung,Wu, Tian-Shung
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supporting information
p. 1547 - 1550
(2017/03/17)
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- Total synthesis of (±)-kuwanol e
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The total synthesis of the Diels-Alder-type adducts (±)-kuwanol E and the heptamethyl ether derivative of (±)-kuwanon Y has been accomplished via a convergent strategy involving 2′-hydroxychalcone 6 or 9 and dehydroprenylstilbene 7, in nine steps. The syn
- Iovine, Valentina,Benni, Irene,Sabia, Rocchina,D'Acquarica, Ilaria,Fabrizi, Giancarlo,Botta, Bruno,Calcaterra, Andrea
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p. 2495 - 2503
(2016/11/09)
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- Synthetic studies towards the mulberry Diels-Alder adducts: H-bond accelerated cycloadditions of chalcones
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The methyl ether derivatives 2, 4 and 6 of the mulberry Diels-Alder adducts chalcomoracin (1) and mulberrofuran C (3) and kuwanon J (5) respectively have been synthesized by a thermal [4 + 2]-cycloaddition reaction between a chalcone and dehydroprenyl die
- Boonsri, Sompong,Gunawan, Christian,Krenske, Elizabeth H.,Rizzacasa, Mark A.
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scheme or table
p. 6010 - 6021
(2012/08/28)
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- Synthesis of 1-(4-aminosulfonylphenyl)-3,5-diarylpyrazoline derivatives as potent antiinflammatory and antimicrobial agents
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A new series of 1-(4-aminosulfonylphenyl)-3, 5-diaryl pyrazolines (5) was synthesized by the reaction of appropriate chalcones 3 with 4- hydrazinobenzenesulfonamide hydrochloride (4) in ethanol in the presence of catalytic amount of acetic acid. All newly
- Sharma, Pawan K.,Kumar, Satish,Kumar, Pawan,Kaushik, Pawan,Sharma, Chetan,Kaushik, Dhirender,Aneja, Kamal R.
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p. 2945 - 2954
(2012/11/07)
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- Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics
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A total of 30 chalcone analogues was synthesized via a base catalyzed Claisen Schmidt condensation and screened for their in vitro antibacterial activity against Methicillin-sensitive Staphylococcus aureus (MSSA) and Methicillin-resistant Staphylococcus aureus (MRSA) alone or in combination with non beta-lactam antibiotics namely ciprofloxacin, chloramphenicol, erythromycin, vancomycin, doxycycline and gentamicin. In the checkerboard technique, fractional inhibitory concentration indices (FICI) show that the following combinations like ciprofloxacin with 25 (4′-bromo-2-hydroxychalcone); doxycycline with 21 (4-hydroxychalcone); doxycycline with 25; and doxycycline with 4 (2′,2-dihydroxychalcone) were synergistic against MRSA. In term SAR study, the relationship between chalcone structure and their antibacterial activity against S. aureus and synergy with tested antibiotics were discussed. Possible mechanisms for antibacterial activity of chalcones alone as well as the synergistic effect in combinations were proposed by molecular modeling studies, respectively. Combinations of chalcones with conventional antibiotics could be an effective alternative in the treatment of infection caused by MRSA.
- Tran, Thanh-Dao,Do, Tuong-Ha,Tran, Ngoc-Chau,Ngo, Trieu-Du,Huynh, Thi-Ngoc-Phuong,Tran, Cat-Dong,Thai, Khac-Minh
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experimental part
p. 4555 - 4560
(2012/08/07)
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- Antimitotic and antiproliferative activities of chalcones: Forward structure-activity relationship
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A series of 59 chalcones was prepared and evaluated for the antimitotic effect against K562 leukemia cells. The most active chalcones were evaluated for their antiproliferative activity against a panel of 11 human and murine cell cancer lines. We found that three chalcones were of great interest as potential antimitotic drugs. In vivo safety studies conducted on one of the most active chalcones revealed that the compound was safe, allowing further in vivo antitumor evaluation.
- Boumendjel, Ahcène,Boccard, Julien,Carrupt, Pierre-Alain,Nicolle, Edwige,Blanc, Madeleine,Geze, Annabelle,Choisnard, Luc,Wouessidjewe, Denis,Matera, Eva-Laure,Dumontet, Charles
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p. 2307 - 2310
(2008/12/22)
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- First total synthesis of two 5-deoxyflavone derivatives from Albizia odoratissima
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The first total synthesis of two unusual 5-deoxyflavone derivatives from Albizia odoratissima, 7,8-dimethoxy-3′,4′-methylenedioxyflavone 1 and 7,2′,4′-trimethoxy-flavone 2, has been accomplished.
- Gao, Jin-Ming,Lu, Jia-Wen,Zhang, An-Ling,Cheng, Yong-Xian,Watchueng, Jean,Konishi, Yasuo
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p. 163 - 164
(2007/10/03)
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- Synthesis of isoflavones containing naturally occurring substitution pattern by oxidative rearrangement of respective flavanones using thallium(III) p-tosylate
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Claisen condensation of substituted 2′-hydroxyacetophenones 1a-c with aromatic aldehydes affords respective substituted 2′-hydroxychalcones 2a-n which on base catalyzed cyclization in pyridine:methanol:water (1:1:1) give respective flavanones 3a-n. The oxidative rearrangement of flavanones with thallium(III) p-tosylate furnishes respective isoflavones 4a-n in overall 62-72% yields starting from 1. The present methodology has been successfully applied for the synthesis of naturally occurring isoflavones such as di-O-methyldaidzein 4a, cabruvin 4b, pseudobabtigenin methylether 4d, 5,7-dimethoxyisoflavone 4f, 5,7,4′-trimethoxyisoflavone 4g, derrustone 4i, 7,8,3′,4′- tetramethoxyisoflavone 41, purpuranin-A 4m and 7,8,3′,4′,5′- pentamethoxyisoflavone 4n and thus the first synthesis of 4n is reported.
- Singh, Om V.,Muthukrishnan,Sunderavadivelu
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p. 2575 - 2581
(2007/10/03)
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- The heck coupling reaction using aryl vinyl ketones: Synthesis of flavonoids
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In our previous communication, an α,β-unsaturated aryl ketone was employed as the substrate olefin, which underwent arylation in the Heck coupling reaction. The use of this reagent has allowed us to design a new strategy for the synthesis of flavonoids. In this paper, we illustrate the versatility of the procedure, which was used for the preparation of several chalcones. According to our synthetic scheme, several aryl iodides, selected in order to obtain chalcones differently substituted in ring B, were treated with α,β-unsaturated ketones. All reported syntheses gave high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Bianco, Armandodoriano,Cavarischia, Claudia,Guiso, Marcella
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p. 2894 - 2898
(2007/10/03)
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- Synthesis and aromatase inhibitory activity of flavanones
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Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors; therefore, in an effort to develop novel anti breast cancer agents, B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern. Methods. A series of flavanones was prepared by cyclisation of 2′hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity of these compounds was investigated using human placental microsomes and radiolabeled [1,2,6,7-3H]-androstenedione as substrate. Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring substitution pattern. Hydroxylation at position 3′ and/or 4′ enhanced the anti-aromatase activity; thus, 3′,4′-dihydroxy-7-methoxyflavanone was found to be twice more potent than aminoglutethimide, the first aromatase inhibitor clinically used. Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.
- Pouget,Fagnere,Basly,Besson,Champavier,Habrioux,Chulia
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p. 286 - 291
(2007/10/03)
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