Bioactive Marine Mollusc Film Lo Su Intermediate Synthesis And Structure

Lamellarins are a group of polycyclic pyrrole alkaloids that were isolated from the marine mollusc. Some lamellarins exhibit a wide array of interesting and significant biological activities, which include cell division inhibition, cytotoxicity, HIV-1 integrasa inhibition and immunomodulation. 1- (3. 4-Dimethoxy-phenyl) - 8,9- dimethoxy- 2-(2,4,5- trimethoxy-phenyl)-pyrrole[2,l-α]isoquinoline ( I ) is the key intermediate. The formed intermediate was identified by means of IR spectrum, HPLC, UV spectrum, HNMR and melting point measurement.1. Synthesis of 2,4,5-trimethoxy-α-chlor-acetophenone for lamellarin H and its derivatives.1,2,4-trimethoxy-benzene with chloroacetonitrile forms 2,4,5-trimethoxy α-chlor-acetophenone under the anhydrous condition, white solid with shape of needle was obtained. The yield is 82.3%. We had checked that melting point of the solid is 163-164℃. By the same way, we had got 2,4,5-trimethoxy-a-bromo-acetophenone. The yield is 92.68% and its shape is white needle solid. The melting point of the solid is 151-152℃. We have got the best conditions throught the orthogonal tests.2. Synthesis of skeleton, l-(3,4-Dimethoxy-phenyl)-8,9-dimethoxy-2-(2,4,5 -trimethoxy-phenyl)-pyrrole[2,l-ajisoquinoline (I ), for lamellarin H and its derivatives.Synthesis of the Lamellarin skeleton( I )was achieved by Knorr condensing 2,4,5-trimethoxy-a-chlor-acetophenone with subsituted benzylisoquinoline.lt was separated by silica gel chromatofraphic method. Under optimized reaction conditions,the key intermediate ( I ) (up to 65-70% )was obtained..3. ( I ) is a new compounds. The formed intermediate (I) was identified by means of IR spectrum, UV spectrum, MS, 1 HNMR, H-HCOSY, H-HNOESY,HSQC,HMBC and melting point measurement.