149379-26-0

Upstream product

• 54313-33-6 2-(3-(benzyloxy)-4-methoxyphenyl)acetyl chloride 
• 1519002-26-6 3,11-diisopropoxy-14-(3-isopropoxy-4-methoxyphenyl)-2,12-dimethoxy-9-(phenylsulfanyl)-8,9-dihydro-6H-[1]-benzopyrano[4′,3′:4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 1519002-27-7 3-(2,2-dimethoxyethyl)-7-isopropoxy-1-(3-isopropoxy-4-methoxyphenyl)-2-(4-isopropoxy-3-methoxyphenyl)-8-methoxy[1]benzopyrano[3,4-b]pyrrol-4(3H)-one 
• 1519002-13-1 methyl 5-(4-isopropoxy-3-methoxyphenyl)-1H-pyrrole-2-carboxylate 
• 1519002-14-2 methyl 4-bromo-5-(4-isopropoxy-3-methoxyphenyl)-1H-pyrrole-2-carboxylate 
• 1519002-15-3 methyl 4-(3-isopropoxy-4-methoxyphenyl)-5-(4-isopropoxy-3-methoxyphenyl)-1H-pyrrole-2-carboxylate 
• 875654-35-6 dimethyl N-[2-(3-isopropoxy-4-methoxyphenyl)ethyl]iminodiacetate 
• 875654-34-5 4-isopropoxy-5-methoxy-2-methoxymethoxyphenylboronic acid 
• 875654-38-9 1-bromo-4-isopropoxy-5-methoxy-2-methoxymethoxybenzene 
• 875654-37-8 2-isopropoxy-1-methoxy-4-methoxymethoxybenzene 
• 871571-19-6 5-bromo-2-methoxyphenyl methanesulfonate 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 21411-27-8 6-(benzyloxy)-1-[3-(benzyloxy)-4-methoxybenzyl]-7-methoxy-3,4-dihydroisoquinoline 
• 36455-21-7 3-benzyloxy-4-methoxyphenylethylamine 

Downstream Products

• 1454845-03-4 3,11-bis(tert-butyldimethylsilyloxy)-14-[3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl]-2,12-dimethoxy-6H-[1]-benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 1454845-04-5 3,11-bis(tert-butoxycarbonyloxy)-14-[3-(tert-butoxycarbonyloxy)-4-methoxyphenyl]-2,12-dimethoxy-6H-[1]-benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 149355-77-1 3,11-bis(acetoxy)-14-(3-acetoxy-4-methoxyphenyl)-2,12-dimethoxy-6H-[1]benzopyrano[4′,3′:4,5]pyrrolo[2,1-a]-isoquinolin-6-one 

Relevant academic research and scientific papers

Design, synthesis, and evaluation of A-ring-modified lamellarin N analogues as noncovalent inhibitors of the EGFR T790M/L858R mutant

A series of A-ring-modified lamellarin N analogues were designed, synthesized, and evaluated as potential noncovalent inhibitors of the EGFR T790M/L858R mutant, a causal factor in the drug-resistant non-small cell lung cancer. Several water-soluble ammonium- or guanidinium-tethered analogues exhibited good kinase inhibitory activities. The most promising analogue, 14f, displayed an excellent inhibitory profile against the T790M/L858R mutant [IC50 (WT) = 31.8 nM; IC50 (T790M/L858R) = 8.9 nM]. The effects of A-ring-substituents on activity were rationalized by docking studies.

Facile and Divergent Synthesis of Lamellarins and Lactam-Containing Derivatives with Improved Drug Likeness and Biological Activities

With the goal to improve the aqueous solubility of lamellarins, the lactone ring in their skeleton was replaced with a lactam moiety in azalamellarins. However, the reported synthetic route produced such derivatives in very low yields. Hence, this study focused on developing an efficient simplified total synthetic scheme that could furnish both azalamellarins and the parent lamellarins from the same pyrrole ester intermediates. Subsequent comparative profiling revealed that the introduced lactone-to-lactam replacement rendered these molecules less lipophilic, whereas their cancer cytotoxicity remained equipotent to that of the parent compounds. Interestingly, their inhibitory activity was significantly enhanced towards the multifaceted GSK-3β enzyme. Our results clearly demonstrate the therapeutic potential of this promising class of marine-derived natural products and justify their further development, especially into anticancer agents.

Modular synthesis of lamellarins via regioselective assembly of 3,4,5-differentially arylated pyrrole-2-carboxylates

A modular synthesis of lamellarins via 3,4,5-differentially arylated pyrrole-2-carboxylate intermediates has been developed. The key reactions employed are Br-Li exchange-methoxycarbonylation of 2,5-dibromo-1-(tert- butoxycarbonyl)-1Hpyrrole (1) followed

Synthesis, resolution, and biological evaluation of atropisomeric (aR)- and (aS)-16-methyllamellarins N: Unique effects of the axial chirality on the selectivity of protein kinases inhibition

The total synthesis of the optically active (aR)- and (aS)-16- methyllamellarins N (3a and 3b) was achieved via resolution on HPLC chiral stationary phase. The kinase inhibitory activities of both enantiomers were evaluated on eight protein kinases releva

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 of lamellarins D, L, and N

Total synthesis of cytotoxic marine alkaloids, lamellarins D, L, and N, has been achieved by using Hinsberg-type pyrrole synthesis and palladium-catalyzed Suzuki-Miyaura coupling of the 3,4-dihydroxypyrrole bistriflate 6 as the key reactions. The total yields of lamellarins D, L, and N from the common intermediate 6 are 54, 58, and 50%, respectively.