Hideo Sugi

The absolute configuration of cryptostyline—III : Studies on the syntheses of heterocyclic compounds—CCCXCVII

Abstract Optical resolution of (±)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-(3,4,5-trimethoxyphenyl)isoquinoline (XII) with di-p-toluoyl-(+)-tartaric acid gave (−)-isoquinoline (XIII) and (+)-isomer (XIV). The former was transformed to (+)-cryptostyline III (III). A method for the stereochemical study of cryptostyline III by correlation of ORD and CD spectra with those of 1-(R)-phenylisoquinoline analogue (IV) is described.

A Novel Synthetic Anti-Acute Pancreatitis Agent, IS-741

A novel synthetic drug, IS-741, inhibited cell adhesion in vitro and neutrophil in vivo. Thus, IS-741 inhibited the magnification of pancreatic lesion as well as progression to multiple organ failure in acute pancreatitis models. Furthermore, IS-741 at identical plasma concentrations equally improved the survival rates in animals of various species with severe acute pancreatitis. Based on these observations, it was considered that IS-741 inhibited tissue destruction by neutrophil after inhibiting neutrophil infiltration into the pancreas or other important organs in acute pancreatitis. It was also considered that IS-741 demonstrated various anti-acute pancreatitis effects by interrupting a vicious cycle of inflammation. Therefore, IS-741 is expected to become a useful drug for treating acute pancreatitis and multiple organ failure in clinical settings.

Total syntheses of (±)-pronuciferine, (±)-O-methylorientalinone, and (±)-O-methylkreysiginone

Abstract Photolysis of 8-bromo-1,2,3,4-tetrahydro-1-(4-hydroxybenzyl)-6,7-dimethoxy-2-methyl-isoquinoline (21) gave (±)-pronuciferine (2). The same reaction of the phenolic bromoisoquinoline (20 and 23) afforded (±)- O -methylorientalinone (3a or 3b) and (±)- O -methylisoorientalinone (3b or 3a). and (±)- O -methylkreysiginone (5a or 5b).

Studies on total photolytic syntheses of alkaloids-IV : Modified total syntheses of flavinantine, bracteoline, isoboldine and mecambrine by photolysis

Abstract Photolysis of the diazonium salt from 6′-aminoorientaline ( 10 ) gave flavinantine ( 1 ) and bracteoline ( 5 ). The same reaction of 6′-bromoreticuline ( 17 ) and its analog ( 21 ) afforded isoboldine ( 6 ) and mecambrine (fugapavine) ( 7 ), respectively.