3208-26-2Relevant articles and documents
DITERPENOID COMPOUNDS THAT ACT ON PROTEIN KINASE C (PKC)
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, (2021/04/02)
This present disclosure relates to protein kinase C (PKC) modulating compounds, methods of treating a subject with cancer using the compounds, and combination treatments with a second therapeutic agent.
Synthesis and glycosidase inhibition of: N-substituted derivatives of 1,4-dideoxy-1,4-imino-d-mannitol (DIM)
Yang, Lin-Feng,Shimadate, Yuna,Kato, Atsushi,Li, Yi-Xian,Jia, Yue-Mei,Fleet, George W. J.,Yu, Chu-Yi
, p. 999 - 1011 (2020/02/15)
N-Substituted derivatives of 1,4-dideoxy-1,4-imino-d-mannitol (DIM), the pyrrolidine core of swainsonine, have been synthesized efficiently and stereoselectively from d-mannose with 2,3:5,6-di-O-isopropylidene DIM (10) as a key intermediate. These N-substituted derivatives include N-alkylated, N-alkenylated, N-hydroxyalkylated and N-aralkylated DIMs with the carbon number of the alkyl chain ranging from one to nine. The obtained 33 N-substituted DIM derivatives were assayed against various glycosidases, which allowed a systematic evaluation of their glycosidase inhibition profiles. Though N-substitution of DIM decreased their α-mannosidase inhibitory activities, some of the derivatives showed significant inhibition of other glycosidases.
Synthesis and biological evaluation of some undecanone derivatives
Meka, Bharani,Ravada, Suryachandra Rao,Kancharla, Harikrishna,Golakoti, Trimurtulu
, p. 3106 - 3124 (2017/10/06)
The total synthesis of Ardisinone E [15, 1-(2,4,6-trihydroxy phenyl)-11-(2-hydroxyphenyl)-undecan-1-one], a natural diarylundecanone, isolated from Ardisia arborescens, was accomplished along with 16 new diarylundecanone analogs (18a–p), by modified Wittig reaction. The structures of the compounds were confirmed by 1H, 13C and mass spectral data. Compound 15 showed potent cytotoxic activity with an ED50 of 4.19 μg/mL in brine shrimp lethality assay model. Compounds 18c, 18e, 18j, 18k, 18l, and 18m exhibited strong anti-oxidant activity with IC50 values of 18.75, 12.28, 18.35, 11.04, 12.05, and 11.32 μg/mL, respectively, in NBT free radical assay. Compounds 18e, 18k, and 18m also showed significant 5-lipoxyganase enzyme inhibitory potential with IC50 values of 12.8, 15.23, and 15.23 μg/mL, respectively.
Syntheses of (-)-(2R,3R,6S)-irnigaine and (+)-(2R,3R,6S)-N- methylirnigaine
Pahl, Axel,Wartchow, Rudolf,Meyer, Hartmut H.
, p. 2095 - 2096 (2007/10/03)
Syntheses of irnigaine 1 and the N-methyl derivative 10 were performed starting from chiral building block 2. Synthetic and spectroscopic data are given including the absolute structure of I by an X-ray structure of the hydrochloride.
Enantioselective total synthesis of Irniine and Bgugaine, bioactive 2-alkylpyrrolidine alkaloids
Jossang, Akino,Melhaoui, Ahmed,Bodo, Bernard
, p. 755 - 766 (2007/10/03)
An asymmetric total synthesis of the 2-(R)-alkylpyrrolidines, (-)-irniine (1a) and (-)-bgugaine (1b), toxic and antibiotic components of the tubers of Arisarum vulgare, and (+)-(S)-irniine (1c), was carried out by condensation of the corresponding 4-oxoalkanoic acid (9) with chiral phenylglycinol. Acids (9) were prepared from a hetero-organocuprate (I) complex, generated by reaction of methylcopper (I) with alkylmagnesium bromides and methyl chlorocarbonylpropionate. Alkaloids (1a, 1b and 1c) displayed anti Gram(+) bacterial (MIC 12.5 - 50 μg/ml) and antifungal (MIC 6.25 - 50 μg/ml) activities.
Anti-inflammatory furanones
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, (2008/06/13)
New 5-hydroxy-2-furanone compounds having anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis.
Synthesis and Identification of ω-Phenylalkylcatechols in Burmese Lac
Jefferson, Alan,Sargent, Melvyn V.,Wangchareontrakul, Sirichai
, p. 19 - 25 (2007/10/02)
The presence of 3-(10'-phenyldecyl)- (2) (2percent), 3-(12'-phenyldodecyl)- (3) (6percent), 4-(10'-phenyldecyl)- (4) (0.3percent) and 4-(12'-phenyldodecyl)-benzene-1,2-diol (5) (0.3percent) in Burmese lac, the sap of Melanorrhoea usitata Wall has been confirmed by the synthesis of these compounds and a comparison of the gas chromatographic retention times and the mass spectral characteristic of their bis-O-(trimethylsilyl) derivatives with the derivatives of the natural products.Typically, 3,4-bis(benzyloxy)benzaldehyde (7) on Wittig reaction with triphenyl(11-phenylundecyl)phosphonium bromide (20) and subsequent catalytic hydrogenation of the resultant olefin gave compound (5) in 59percent overall yield.