28342-26-9

Upstream product

• 30597-04-7 ethoxybocconine 
• 139332-34-6 6-hydroxydihydrochelirubine 
• 66209-37-8 2-(2-methoxy-4,5-methylenedioxyphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene 
• 55950-30-6 5-methoxy-13-methyl-6,13-dihydro-7H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-14-one 
• 139332-32-4 10-nitromethoxysanguinarine 
• 139332-33-5 10-aminodihydrosanguinarine 
• 131984-76-4 10-hydroxydihydrosanguinarine 
• 55950-31-7 oxychelirubine 
• 55950-29-3 5,6-dimethoxy-benzo[1,3]dioxole-4-carboxylic acid (7,8-dihydro-naphtho[2,3-d][1,3]dioxol-5-yl)-methyl-amide 
• 28342-31-6 6-Ethoxy-5,6-dihydrosanguinarine 

Downstream Products

• 30044-85-0 chelirubine chloride 

Relevant academic research and scientific papers

ENZYMIC 10-O-HYDROXYLATION AND 10-O-METHYLATION OF DIHYDROSANGUINARINE IN DIHYDROCHELIRUBINE FORMATION BY ESCHSCHLOLTZIA

Two new enzymes involved in benzophenanthridine alkaloid biosynthesis, dihydrosanguinarine-10-hydroxylase and 10-hydroxydihydrosanguinarine-10-O-methyltransferase, have been found in cell-free extracts derived from Eschscholtzia californica cell suspension culturees.The hydroxylase is a microsome-associated, cytochrome P-450-dependent monooxygenase which acts specifically at C-10 of dihydrosanguinarine.The methyltransferase, enriched 60-fold and partially characterized, methylates only the hydroxyl moiety at C-10 to form dihydrochelirubine.Both enzymes were found to be highly substrate specific.Key Word Index: Eschscholtzia californica; Papaveraceae; benzophenanthridine alkaloids; dihydroanguinarine-10-hydroxylase; 10-hydroxydihydrosanguinarine-10-O-methyltransferase.

Anomalous substituent effects in the Bischler-Napieralski reaction of 2-aryl aromatic formamides

Treatment of some 1-naphthylformamides (or formanilides) possessing a 2,4,5-trioxygenated phenyl substituent at the 2-position with POCl3 caused an unprecedented carbon insertion reaction into a benzene ring, producing 7-5 ring (azaazulene) systems as valence isomers of isoquinoline skeletons. Precise examination of this abnormal Bischler-Napieralski reaction (BNR) using various substrates led to the following scope and limitations: (i) the 7-5 ring systems were constructed when either 2-alkoxy-4,5-methylenedioxyphenyl- or 4,5-dialkoxy-2-hydroxyphenyl-substituted formamides were used as a starting substrate; (ii) in the former case the formyl carbon was inserted into the C1-C6 bond of the 2-phenyl group, and normal isoquinoline cyclization competed with an abnormal carbon insertion reaction; (iii) the presence of a hydroxy group at the 2′-position as in the latter cases caused exclusive carbon insertion, in which alternative C1-C2 insertion products were quantitatively formed; (iv) 3,6-dimethoxy-2-hydroxyphenyl-substituted formanilide electronically equivalent to 4,5-dialkoxy-2-hydroxy derivatives produced an indole-pyrone as an abnormal BNR product. Theoretical approaches using the PM-3 method indicated that these abnormal BNRs could be triggered by ipso attack at the 1′-position yielding spiro intermediates. Ring cleavege of the six-membered ring in the spiro intermediates to a ketene function followed by recyclization was proposed for the 2′-hydroxy-directed abnormal BNRs leading to the C1-C2 insertion product or the indole-pyrone derivative.