Total Synthesis of the Pyranoisoflavone Kraussianone 1 and Related Isoflavones

Selepe, Mamoalosi A.; Drewes, Siegfried E.; Heerden, Fanie R. van

doi:10.1021/np100407n

Cited by 36 publications

(35 citation statements)

References 34 publications

(99 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The genistein analogues (3–10) were synthesized by Suzuki-Miyaura coupling reactions of 3-iodochromone ( 11 ) with the appropriate boronic acid ( 12–14 ) (Scheme 1) or aryl boronic ester ( 15a–e ) (Scheme 2) [29, 30]. The boronic acids ( 12–14 ) employed to make genistein analogues 3–5 by Suzuki-Miyaura coupling reaction as described in Scheme 1 are commercially available.…”

Section: Results Discussion and Conclusionmentioning

confidence: 99%

Design, Synthesis, and Evaluation of Genistein Analogues as Anti-Cancer Agents

Xiong¹,

Wang²,

Zhang³

et al. 2015

ACAMC

View full text Add to dashboard Cite

Genistein is a bioactive isoflavone derived from soybeans. The tie-in between the intake of genistein and the decreased incidence of some solid tumors (including prostate cancer) has been demonstrated by epidemiological studies. The potential of genistein in treating prostate cancer has also been displayed by in vitro cell-based and in vivo animal experiments. Genistein has entered clinical trials for both chemoprevention and potential treatment of prostate cancer. Even though the low oral bioavailability has presented the major challenges to genistein’s further clinical development, chemical modulation of genistein holds the promise to generate potential anti-prostate cancer agents with enhanced potency and/or better pharmacokinetic profiles than genistein. As part of our ongoing project to develop natural products-based anti-prostate cancer agents, the current study was undertaken to synthesize eight genistein analogues for cytotoxic evaluation in three prostate cancer cell lines (PC-3, DU-145, LNCaP; both androgen-sensitive and androgen-refractory cell lines), as well as one aggressive cervical cancer cell line (HeLa). Eight genistein analogues have been successfully synthesized with Suzuki-Miyaura coupling reaction as a key step. Their in vitro anti-cancer potential was evaluated by trypan blue exclusion assay and WST-1 cell proliferation assay against a panel of four human cancer cell lines. The acquired data suggest i) that the C-5 and C-7 hydroxyl groups in genistein are very important for the cytotoxicity and anti-proliferative activity; and ii) that 1-alkyl-1H-pyrazol-4-yl and pyridine-3-yl might act as good bioisosteres for the 4'-hydroxyphenyl moiety in genistein.

show abstract

Section: Results Discussion and Conclusionmentioning

confidence: 99%

Design, Synthesis, and Evaluation of Genistein Analogues as Anti-Cancer Agents

Xiong¹,

Wang²,

Zhang³

et al. 2015

ACAMC

View full text Add to dashboard Cite

show abstract

“…Target compound 1j was synthesized by coupling 10 to 4-(trifluoromethyl) phenylboronic acid smoothly with 82% yield by using Pd/C as catalyst (as shown in Scheme 3) [29].…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and biological evaluation of pyranoisoflavone derivatives as anti-inflammatory agents

et al. 2014

View full text Add to dashboard Cite

“…The research on muthi plants continued unabated after Drewes retired in 1995, as he stayed on in the Department (1995 -present) as Honorary Research Associate ( Figure 53). The work started in Marion Horn's time (1998), was extended by Mamoalosi Selepe (2008Selepe ( -2011, and with the help of traditional healer Jabu Dhlamini, culminated in the isolation (Drewes et al, 2002) and the total synthesis (Selepe, Drewes & Van Heerden, 2010) of the compound Kraussianone I, often referred to as 'African Viagra'.…”

Section: The Siegfried Ernst Drewes Era 1992-1995mentioning

confidence: 99%

“…A very recent publication (Selepe, Drewes & Van Heerden, 2010) records the total synthesis of so-called ' African Viagra' which was isolated in 2002 (Drewes et al).…”

Section: The Era Of Murray Low 2005-2009mentioning

confidence: 99%