169566-46-5Relevant academic research and scientific papers
First synthesis of saponarin, 6-C- and 7-O-di-β-D-glucosylapigenin
Misawa, Kazufumi,Takahashi, Yasuko,Sato, Shingo
, p. 776 - 780 (2013)
Saponarin, apigenin 6-C- and 7-O-bis-β-D-glucoside, was synthesized in an overall yield of 37% via 11 steps, which included the C-glycosylation of 2,4-O-dibenzylphloroacetophenone, the introduction of a cinnamoyl residue by aldol condensation, the formati
Targeting type 2 diabetes with c-glucosyl dihydrochalcones as selective sodium glucose co-transporter 2 (sglt2) inhibitors: Synthesis and biological evaluation
Jesus, Ana R.,Vila-Vi?osa, Diogo,Machuqueiro, Miguel,Marques, Ana P.,Dore, Timothy M.,Rauter, Amélia P.
, p. 568 - 579 (2017/02/05)
Inhibiting glucose reabsorption by sodium glucose co-transporter proteins (SGLTs) in the kidneys is a relatively new strategy for treating type 2 diabetes. Selective inhibition of SGLT2 over SGLT1 is critical for minimizing adverse side effects associated with SGLT1 inhibition. A library of C-glucosyl dihydrochalcones and their dihydrochalcone and chalcone precursors was synthesized and tested as SGLT1/SGLT2 inhibitors using a cell-based fluorescence assay of glucose uptake. The most potent inhibitors of SGLT2 (IC50 = 9.23 nM) were considerably weaker inhibitors of SGLT1 (IC50 = 10.19 μM). They showed no effect on the sodium independent GLUT family of glucose transporters, and the most potent ones were not acutely toxic to cultured cells. The interaction of a C-glucosyl dihydrochalcone with a POPC membrane was modeled computationally, providing evidence that it is not a pan-assay interference compound. These results point toward the discovery of structures that are potent and highly selective inhibitors of SGLT2.
Exploiting the therapeutic potential of 8-β- d -glucopyranosylgenistein: Synthesis, antidiabetic activity, and molecular interaction with islet amyloid polypeptide and amyloid β-peptide (1-42)
Jesus, Ana R.,Dias, Catarina,Matos, Ana M.,De Almeida, Rodrigo F.M.,Viana, Ana S.,Marcelo, Filipa,Ribeiro, Rogério T.,Macedo, Maria P.,Airoldi, Cristina,Nicotra, Francesco,Martins, Alice,Cabrita, Eurico J.,Jiménez-Barbero, Jesús,Rauter, Amélia P.
, p. 9463 - 9472 (2015/02/02)
8-β-d-Glucopyranosylgenistein (1), the major component of Genista tenera, was synthesized and showed an extensive therapeutical impact in the treatment of STZ-induced diabetic rats, producing normalization of fasting hyperglycemia and amelioration of exce
Glucose uptake enhancing activity of puerarin and the role of C-glucoside suggested from activity of related compounds
Kato, Eisuke,Kawabata, Jun
supporting information; experimental part, p. 4333 - 4336 (2010/09/18)
Chemical treatment of diabetes mellitus is widely studied and controlling of blood glucose level is the main course of therapy. In type 2 diabetes mellitus, insulin resistance is the major problem. An isoflavone C-glucoside, puerarin (1), is known to enhance glucose uptake into the insulin sensitive cell and is thought to be a candidate for treatment of diabetes mellitus. We synthesized 1 and several derivatives to apply for the structure-activity relationship study. The result against 3T3-L1 adipocyte indicated that the C-glucoside part of 1 is unconcerned in its activity when tested in vitro and the main structure responsible for its activity was the isoflavone moiety.
Concise synthesis of chafurosides A and B
Furuta, Takumi,Nakayama, Miho,Suzuki, Hirotaka,Tajimi, Hiroko,Inai, Makoto,Nukaya, Haruo,Wakimoto, Toshiyuki,Kan, Toshiyuki
supporting information; experimental part, p. 2233 - 2236 (2009/10/02)
The regioselective synthesis of chafurosides A (1) and B (2) from the same methyl ketone 5 was accomplished using a novel protecting group strategy. Both flavone rings were constructed from β-diketone intermediate 4, which was readily obtained by condensation of an acyl donor and ketone 5. Construction of the dihydrofuran ring was achieved via an intramolecular Mitsunobu reaction.
Synthesis of 8-C-glucosylflavones
Kumazawa,Kimura,Matsuba,Sato,Onodera
, p. 183 - 193 (2007/10/03)
The syntheses of orientin, parkinsonin A, isoswertiajaponin, and parkinsonin B, which are 8-C-β-D-glucopyranosyl-3′,4′,5,7-tetrahydroxyflavone, 5-methyl orientin, 7-methyl orientin, and 5,7-dimethyl orientin, respectively, are reported herein. The C-glucosyl phloroacetophenone derivatives were obtained via a regio- and stereoselective O → C glycosyl rearrangement. Aldol condensation of the C-glucosyl phloroacetophenone derivatives with 3,4-bisbenzyloxybenzaldehyde afforded the corresponding C-glucosylchalcones. Construction of the flavone system by reaction with I2-Me2SO, followed by the elimination of the 5-benzyl protecting group in the flavone structure, yielded an orientin derivative and a isoswertiajaponin derivative. Methylation of the orientin derivatives with dimethyl sulfate afforded the parkinsonin A derivative, the isoswertiajaponin derivative, and the parkinsonin B derivative. Finally, hydrogenolysis of these C-glucosylflavone derivatives led to the four 8-C-glucosylflavones. The NMR spectra of these C-glucosylflavones showed a duplication of signals corresponding to a major rotamer, along with a minor one. Based on NOESY experiments in Me2SO at ambient temperature, they adopted conformations in which the H-2″ and H-4″ protons in the glucose moiety were oriented toward the B-ring in the flavone structure.
Regioselective acetyl transfer from the aglycon to the sugar in C-glycosylic compounds facilitated by silica gel
Kumazawa, Toshihiro,Akutsu, Yasuyuki,Matsuba, Shigeru,Sato, Shingo,Onodera, Jun-Ichi
, p. 129 - 137 (2007/10/03)
2'-O-Acetyl C-glycosylic compounds (C-glycosides) were prepared via regioselective acetyl transfer from aglycons to sugar moieties with silica gel in the presence of unprotected primary and secondary hydroxyl groups. Copyright (C) 1999 Elsevier Science Lt
Practical synthesis of a C-glycosyl flavonoid via O→C glycoside rearrangement
Kumazawa,Ohki,Ishida,Sato,Onodera,Matsuba
, p. 1379 - 1384 (2007/10/02)
The C-glycosylation of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride and 2-acetylphloroglucinol 3,5-bis(alkyl ether) in the presence of boron trifluoride etherate as an activator stereoselectively gave the β-C-glucoside in a good yield via O→C glycos
