76786-97-5

Upstream product

• 262855-01-6 1-(3-methoxyphenyl)-2-nitroethan-1-ol 
• 100-39-0 benzyl bromide 
• 156-38-7 4-hydroxyphenylacetate 
• 591-31-1 3-methoxy-benzaldehyde 
• 39188-62-0 2-(4-(benzyloxy)phenyl)acetyl chloride 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 6547-53-1 2-[4-(benzyloxy)benzyl]acetic acid 
• 76787-10-5 N-<(3-methoxyphenyl)ethyl>-4-(benzyloxy)phenylacetamide 

Downstream Products

• 81625-28-7 4-(6-Methoxy-isoquinolin-1-ylmethyl)-phenol 
• 81625-17-4 1-(4-hydroxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 61273-84-5 6-Methoxy-1-{4-(phenylmethoxy)benzyl]-1,2,3,4-tetrahydroisoquinoline 
• 76786-98-6 1-(4-benzyloxybenzyl)-1,2,3,4-tetrahydro-6-methoxy-2-methyl-isoquinoline 
• 76786-99-7 1,2,3,4,5,8-hexahydro-1-(4-hydroxybenzyl)-6-methoxy-2-methylisoquinoline 

Relevant academic research and scientific papers

Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products

Despite the therapeutic potential of marine-derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug-like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully devised to construct a library of 59 systematically designed lamellarin analogs, which were then subjected to cytotoxicity and log P determinations. Along with the 25 first-generation lamellarins previously synthesized in our laboratory, the structure-activity and structure-lipophilicity relationships were extensively evaluated. Our results clearly indicated the additional structural requirements around the lamellarin skeleton which, when combined with those reported previously, can provide invaluable guidance for further modifications to increase the aqueous solubility of these compounds.

Synthesis of 1,2,3,4-Tetrahydroisoquinolines

Several aspects of 1,2,3,4-tetrahydroisoquinoline synthesis have been examined.An improved synthesis of 2-(m-methoxyphenyl)ethylamine (4) is reported. m-Anisaldehyde (5) was treated with potassium cyanide and ethyl chloroformate to yield O-(ethoxycarbonyl)-3-methoxymandelonitrile (7).Hydrogenation afforded 2-(m-methoxyphenyl)ethylamine (4) in 87percent yield overall.Some observations have been made regarding the reduction of 3,4-dihydroisoquinolines derived from the Bischler-Napieralski reaction.Amides 3a and 3c were cyclized with phosphorus oxychloride, followed by reduction to the corresponding tetrahydroisoquinolines 1a and 1c.It was shown that 1a and 1c were contaminated with 4percent of 2a and 3percent of 2c, respectively.Both 2a and 2c were independently synthesized by routes with general applicability to 8-alkoxy-1,2,3,4-tetrahydroisoquinolines.