475232-29-2Relevant articles and documents
Synthesis of lamellarins via regioselective assembly of 1,2-diarylated [1]benzopyrano[3,4-b]pyrrol-4(3H)-one core
Fukuda, Tsutomu,Katae, Takatoshi,Harada, Issei,Iwao, Masatomo
, p. 950 - 971 (2017/07/28)
A modular synthesis of lamellarins has been developed. The key reactions in this synthesis are the assembly of 1,2-diarylated [1]benzopyrano- [3,4-b]pyrrol-4(3H)-ones from a preexisting [1]benzopyrano[3,4-b]pyrrol- 4(3H)-one core and the appropriate arylb
Divergent synthesis of lamellarin α 13-sulfate, 20-sulfate, and 13,20-disulfate
Fukuda, Tsutomu,Ohta, Takeshi,Saeki, Sho,Iwao, Masatomo
scheme or table, p. 841 - 846 (2010/10/05)
A divergent synthesis of three sulfate derivatives of lamellarin α, namely, lamellarin α 13-sulfate (2), 20-sulfate (1), and 13,20-disulfate (4) has been achieved via a common intermediate (6) in which 13-OH and 20-OH of the lamellarin core are differentially protected by MOM and benzyl groups, respectively. Compound (6) in turn was prepared using sequential Suzuki-Miyaura coupling of 3,4-dihydroxypyrrole bistriflate (7) as a key reaction.
Total synthesis and evaluation of lamellarin α 20-Sulfate analogues
Ridley, Christian P,Reddy, M. Venkata Rami,Rocha, Genalyn,Bushman, Frederic D,Faulkner
, p. 3285 - 3290 (2007/10/03)
In order to explore the influence of sulfate groups on the bioactivity profiles of marine alkaloids of the lamellarin class, three such alkaloids, lamellarin α lamellarin α 13,20-disulfate and H, were synthesized and their activities against HIV-1 integrase and cancer cell ines were compared with those of lamellarin α 20-sulfate, which is a selective inhibitor of HIV-1 integrase. Lamellarin α does not inhibit HIV-1 integrase but shows moderate cytotoxicity with good cell line selectivity. Lamellarin α13,20-disulfate is a moderate inhibitor of both HIV-1 integrase and cancer cell lines. Lamellarin H is a more potent inhibitor of HIV-1 integrase but lacked the specificity required to be medicinally useful. Copyright