19825-40-2Relevant academic research and scientific papers
SILICON-MEDIATED C-ISOPRENYLATION OF PHENOLS
Sarma, D N,Baruah, P,Pandey, U C,Sharma, R P
, p. 5581 - 5584 (1984)
C-isoprenylation of phenols has been effected using a combination of isoprene and in situ generated iodotrimethylsilane or hydrogen iodide.
Magnesium dicarboxylates promote the prenylation of phenolics that is extended to the total synthesis of icaritin
Fu, Xuewen,Lu, Xiaoxia,Wang, Chun,Wen, Yongju,Xiong, Wei,Zhang, Guolin,Zhang, Jichao
, p. 1117 - 1124 (2022/02/16)
The prenylation of phenolic substrates promoted by magnesium dicarboxylates was developed. An investigation of the scope demonstrated that substrates with electron-donating group(s) gave better yields than those with electron-withdrawing group(s). Althoug
Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones
Escobar, Gustavo,González, Luis A.,Qui?ones, Wiston,Robledo, Sara,Upegui, Yulieth
, (2021/12/02)
American trypanosomiasis (Chagas disease) caused by the Trypanosoma cruzi parasite, is a severe health problem in different regions of Latin America and is currently reported to be spreading to Europe, North America, Japan, and Australia, due to the migration of populations from South and Central America. At present, there is no vaccine available and chemotherapeutic options are reduced to nifurtimox and benznidazole. Therefore, the discovery of new molecules is urgently needed to initiate the drug development process. Some acetophenones and chalcones, as well as chromane-type substances, such as chromones and flavones, are natural products that have been studied as trypanocides, but the relationships between structure and activity are not yet fully understood. In this work, 26 compounds were synthesized to determine the effect of hydroxyl and isoprenyl substituents on trypanocide activity. One of the compounds showed interesting activity against a resistant strain of T. cruzi, with a half effective concentration of 18.3 μM ± 1.1 and an index of selectivity > 10.9.
Preparation method and application of natural product Xanthoangelol D and derivative thereof
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Paragraph 0005; 0008, (2019/11/28)
The invention discloses a preparation method and application of an isopentenyl chalcone natural product and a derivative thereof. The structural general formula (I) and (II) of the isopentenyl chalcone natural product and the derivative thereof are as follows. Compared with a novel isopentenyl chalcone derivative, the obtained natural product Xanthoangelol D has inhibitory activity improved to a certain degree on bacillus subtilis. The preparation rout of the preparation method has fewer process steps, raw materials are easily available, and the preparation method is suitable for industrial production.
Synthetic methods for prenylated chalcones and pyranochalcones
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Paragraph 0017, (2017/04/27)
The inventors of the present invention invented a simple and effective way to synthesize compounds 1-9 of natural prenylated chalcones and pyrano chalcones by using Claisen-Schmidt condensation as a main step. In addition, an anti-inflammatory effect of synthetic compounds was evaluated in RAW 264.7 macrophages which were stimulated with a lipopolysaccharide. As a result, chalcone compounds having prenyl groups in a ring A (an acetophenone part) show weak inhibition or no inhibition on the generation of nitrogen oxide while chalcones (5, 6, 8, and 9) having no prenyl groups in the ring A show normal or good activity, and have no cytotoxicity.COPYRIGHT KIPO 2017
Synthesis and pharmacological properties of naturally occurring prenylated and pyranochalcones as potent anti-inflammatory agents
Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
supporting information, p. 698 - 702 (2016/05/19)
An efficient approach has been developed for the synthesis of naturally occurring prenylated chalcones viz. kanzonol C (1), stipulin (2), crotaorixin (3), medicagenin (4), licoagrochalcone A (5) and abyssinone D (6) along with the pyranochalcones paratocarpin C (7), anthyllisone (8) and 3-O-methylabyssinone A (9). The key step of the synthesis is a Claisen-Schmidt condensation. Subsequently, their anti-inflammatory effects were investigated in lipopolysaccharides (LPSs)-induced RAW-264.7 macrophages. Of the synthesized chalcones, compounds 5 (IC50 = 10.41 μmol/L), 6 (IC50 = 9.65 μmol/L) and 8 (IC50 = 15.34 μmol/L) show remarkable activity with no cytotoxicity. Compound 9 (IC50 = 4.5 μmol/L) exhibits maximum (83.6%) nitric oxide (NO) inhibition, but shows slight cytotoxicity. The results reveal that the chalcones bearing the prenyl group at 3- and/or 5-position on ring A (acetophenone moiety), i.e., 1-4 and 7 show weak, or no inhibition activity, whereas chalcones having the prenyl group only on ring B (aldehyde part), i.e., 5, 6 and 8 show significant activity on the production of inflammatory mediated NO with no cytotoxicity.
Synthesis of isobavachalcone and some organometallic derivatives
Grealis, John P.,Mueller-Bunz, Helge,Ortin, Yannick,Casey, Michael,McGlinchey, Michael J.
, p. 332 - 347 (2013/03/13)
Isobavachalcone [2′,4,4′-trihydroxy-3′-(3″-methyl- 2″-butenyl)chalcone, 1] is a prenylated chalcone that has broad biological activity, in particular against neuroblastomas, the most common cancer in infancy. It is currently commercially available at a cost of 190/mg by extraction from Psoralea corylifolia and a number of other African and Asian plants. Several synthetic routes have been explored, and the most efficient procedure involves the palladium-catalysed Stille coupling of 3-iodo-2,4-bis(methoxymethoxy)acetophenone (25) with prenyltributyltin, Claisen-Schmidt condensation with 4-(methoxymethoxy)benzaldehyde to form the triply MOM-protected prenylchalcone 27 and finally deprotection with 2 M HCl in methanol to form isobavachalcone in an overall yield of 15 % over five steps. The X-ray crystal structures of 2,4-dihydroxy-3-iodoacetophenone (21) and of several prenylated chalcones are reported, including the elucidation of their hydrogen-bonding networks in the solid state. The synthetic route has been extended to include organometallic derivatives in which the 4-(methoxymethoxy) benzaldehyde used in the Claisen-Schmidt condensation has been replaced by formylferrocene, formylruthenocene or (η5-formylcyclopentadienyl) (η4-tetraphenylcyclobutadiene)cobalt to form the corresponding analogues of isobavachalcone containing organometallic sandwich moieties.
Synthesis and insight into the structure-activity relationships of chalcones as antimalarial agents
Tadigoppula, Narender,Korthikunta, Venkateswarlu,Gupta, Shweta,Kancharla, Papireddy,Khaliq, Tanvir,Soni, Awakash,Srivastava, Rajeev Kumar,Srivastava, Kumkum,Puri, Sunil Kumar,Raju, Kanumuri Siva Rama,Wahajuddin,Sijwali, Puran Singh,Kumar, Vikash,Mohammad, Imran Siddiqi
, p. 31 - 45 (2013/02/25)
Licochalcone A (I), isolated from the roots of Chinese licorice, is the most promising antimalarial compound reported so far. In continuation of our drug discovery program, we isolated two similar chalcones, medicagenin (II) and munchiwarin (III), from Crotalaria medicagenia, which exhibited antimalarial activity against Plasmodium falciparum. A library of 88 chalcones were synthesized and evaluated for their in vitro antimalarial activity. Among these, 67, 68, 74, 77, and 78 exhibited good in vitro antimalarial activity against P. falciparum strains 3D7 and K1 with low cytotoxicity. These chalcones also showed reduction in parasitemia and increased survival time of Swiss mice infected with Plasmodium yoelii (strain N-67). Pharmacokinetic studies indicated that low oral bioavailability due to poor ADME properties. Molecular docking studies revealed the binding orientation of these inhibitors in active sites of falcipain-2 (FP-2) enzyme. Compounds 67, 68, and 78 showed modest inhibitory activity against the major hemoglobin degrading cysteine protease FP-2.
Synthesis of four natural prenylflavonoids and their estrogen-like activities
Dong, Xiaowu,Fan, Yongjian,Yu, Lingjun,Hu, Yongzhou
, p. 372 - 376 (2008/02/11)
Four prenylflavonoids, bavachin 1, isobavachin 2, 7,4′-dihydroxy-8- prenylflavone 3, and 8-prenylapigenin 4 were synthesized and recognized for possessing estrogen-like activity in MCF-7/BOS cells, as evaluated by an estrogen-screening assay. All compound
Total synthesis of munchiwarin, a triprenylated chalcone from Crotalaria medicagenia
Narender,Reddy, K. Papi,Shweta,Srivastava, Kumkum,Mishra,Puri
, p. 5369 - 5372 (2008/09/17)
An efficient method is developed for the synthesis of the modified triprenylated chalcone, munchiwarin (1), isolated from the roots of Crotalaria medicagenia. The synthesis of 1 utilizes a Claisen-Schmidt condensation between 2,4-dihydroxy-3,5-C-diprenyl
