Pyrrolo[2,1-α]isoquinoline as a skeleton for the synthesis of bioactive lamellarin H

Abstract

Lamellarin H has been shown to be active against the topoisomerase of the Molluscum contagiosum virus (MCV) and to have anti-HIV properties. 1-(3,4-dimethoxy-phenyl)-8,9-dimethoxy-2-(2,4,5-trimethoxy-phenyl)-pyrrolo[2,1-alpha] isoquinoline (intermediate 2) is the skeleton for the synthesis of lamellarin H and its derivatives. The synthesis of intermediate 2 is reported here in detail. The intermediate formed is identified by means of IR spectrum, UV spectrum, MS, (1)H NMR, (13)C NMR and melting point measurements.

Lamellarins and Related Pyrrole-Derived Alkaloids from Marine Organisms

“…35 The next year the same group reported the synthesis of the second intermediate of lamellarin H 37, 1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-2-(2,4,5trimethoxyphenyl)-pyrrolo-[2,1-R]-isoquinoline. 114…”

“…The fabricated intermediate, 2,4,5-trimethoxy-α-chloroacetophenone, was the key starting material for this synthesis . The next year the same group reported the synthesis of the second intermediate of lamellarin H 37 , 1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-2-(2,4,5-trimethoxyphenyl)-pyrrolo-[2,1-α]-isoquinoline …”

Anticancer Properties of Lamellarins

“… A diazaindeno[2,1- b ]phenanthrenone derivative, designed on the basis of molecular modeling of the Lam-D-topoI complex, 100-fold less cytotoxic than Lam-D but maintaining a reduced capacity to inhibit topoisomerase I [ 63 ]. Pyrrolo[2,1- a ]isoquinolines, represented by the open chain derivative 1 ( Figure 3 ), an intermediate in the synthesis of the bioactive lamellarin H [ 64 ]. The same authors also described the synthesis of the corresponding 5,6-dihydro pyrrolo[2,1- a ]isoquinolines [ 65 ].…”

“…Pyrrolo[2,1- a ]isoquinolines, represented by the open chain derivative 1 ( Figure 3 ), an intermediate in the synthesis of the bioactive lamellarin H [ 64 ]. The same authors also described the synthesis of the corresponding 5,6-dihydro pyrrolo[2,1- a ]isoquinolines [ 65 ].…”

SOLVENT FREE SYNTHESIS OF PYRROLO[2,1-a]ISOQUINOLINES UNDER MICROWAVE-IRRADIATION: AN ANTIOXIDANT POTENT.

“…Moreover, this type of compounds can be used as Positron Emission Tomography(PET) radiotracers for imaging serotonin uptake sites [12].The varied biological activities of pyrrolo [2,1-a]isoquinoline derivatives have attracted the attention of organic chemists and a number of synthetic methodologies have been developed for this system [13][14][15][16][17][18][19][20].…”