475232-29-2

Upstream product

• 41183-13-5 1-(3-benzyloxy-4-methoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 189083-79-2 14-(3-hydroxy-4-methoxyphenyl)-3-hydroxy-2,11,12-trimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 215715-43-8 β,β-dibromo-3-isopropoxy-4-methoxystyrene 
• 1225441-64-4 3-hydroxy-2,11,12-trimethoxy-14-[4-methoxy-3-(methoxymethoxy)phenyl]-6H-[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 570402-54-9 dimethyl 1-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-bis(trifluoromethanesulfonyloxy)pyrrole-2,5-dicarboxylate 
• 623550-16-3 4-bromo-1-methoxy-2-(methoxymethoxy)benzene 
• 919082-49-8 14-(3-acetoxy-4-methoxyphenyl)-3-acetoxy-2,11,12-trimethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 475232-32-7 3-isopropoxy-14-(3-isopropoxy-4-methoxyphenyl)-2,11,12-trimethoxy-6H-[1]benzopyrano-[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 121-33-5 vanillin 
• 1192217-74-5 7-isopropoxy-8-methoxy[1]benzopyrano[3,4-b]pyrrol-4(3H)-one 
• 570402-52-7 dimethyl 3,4-dihydroxy-1-[2-(3,4-dimethoxyphenyl)ethyl]pyrrole-2,5-dicarboxylate 
• 570402-50-5 dimethyl N-[2-(3,4-dimethoxyphenyl)ethyl]iminodiacetate 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 

Relevant academic research and scientific papers

Synthesis of lamellarins via regioselective assembly of 1,2-diarylated [1]benzopyrano[3,4-b]pyrrol-4(3H)-one core

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

Synthesis, structure-activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues

Lamellarin α and six different types of lamellarin α 20-sulfate analogues were synthesized and their structure-activity relationships were investigated using a single round HIV-1 vector infection assay. All lamellarin sulfates having pentacyclic lamellarin core exhibited anti-HIV-1 activity at a 10 μM concentration range regardless of the number and position of the sulfate group. On the other hand, non-sulfated lamellarin α and ring-opened lamellarin sulfate analogues did not affect HIV-1 vector infection in similar concentrations. The lamellarin sulfates utilized in this study did not exhibit unfavorable cytotoxic effect under the concentrations tested (IC50 > 100 μM). Confocal laser scanning microscopic analysis indicated that hydrophilic lamellarin sulfates were hardly incorporated in the cell. HIV-1 Env-mediated cell-cell fusion was suppressed by lamellarin sulfates. These results suggested that lamellarin sulfates have a novel anti-HIV-1 activity besides the previously reported integrase activity inhibition, possibly at a viral entry step of HIV-1 replication.

Divergent synthesis of lamellarin α 13-sulfate, 20-sulfate, and 13,20-disulfate

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 of natural and unnatural lamellarins with saturated and unsaturated D-rings

(Chemical Equation Presented) Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and α-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.

Total synthesis and evaluation of lamellarin α 20-Sulfate analogues

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