- CONVERSION OF DOPA TO TETRAHYDROISOQUINOLINES AND STIZOLOBIC ACID IN A CALLUS CULTURE OF STIZOLOBIUM HASSJOO
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Isolation and identification of L-3-carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline and L-1-methyl 3-carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline from seeds and callus of S. hassjoo are described.Administration of -labelled DOPA to a callus culture of this legume resulted in the incorporation of radioactivity into L-3-carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, L-1-methyl-3-carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline and stizolobic acid, which was confirmed by constant specific radioactivity after co-crystallization with authentic samples of each compound. - Key Word Index - Stizolobium hassjoo; Leguminosae; Yokohama velvet bean; tetrahydroisoquinolines; stizolobic acid; DOPA; callus culture.
- Saito, Koshi,Obata-Sasamoto, Hamako,Hatanaka, Shin-Ichi,Noguchi, Hiroshi,Sankawa, Ushio,Komamine, Atsushi
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- Anticancer activity of ruthenium(II) arene complexes bearing 1,2,3,4-tetrahydroisoquinoline amino alcohol ligands
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Ruthenium complexes offer potential reduced toxicity compared to current platinum anticancer drugs. 1,2,3,4-tetrahydrisoquinoline amino alcohol ligands were synthesised, characterised and coordinated to an organometallic Ru(II) centre. These complexes were evaluated for activity against the cancer cell lines MCF-7, A549 and MDA-MB-231 as well as for toxicity in the normal cell line MDBK. They were observed to be moderately active against only the MCF-7 cells with the best IC50 value of 34 μM for the cis-dia-stereomeric complex C4. They also displayed excellent selectivity by being relatively inactive against the normal MDBK cell line with SI values ranging from 2.3 to 7.4.
- Chelopo, Madichaba P.,Pawar, Sachin A.,Sokhela, Mxolisi K.,Govender, Thavendran,Kruger, Hendrik G.,Maguire, Glenn E. M.
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supporting information
p. 407 - 414
(2013/10/01)
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- Preparation of chiral 1,2,3,4-tetrahydro-6,7-dialkoxy-3-isoquinolinecarboxylic acid and derivatives
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The present invention relates to a process for the production of (S)-1,2,3,4-tetrahydro-6,7-dialkoxy-3-isoquinolinecarboxylic acid compounds (1) and their derivatives from Levodopa (L-Dopa). The ultimately prepared compounds are used as intermediates for, but not limited to, the preparation of substituted derivatives of 1,2,3,4-tetrahydro-6,7-dialkoxy-3-isoquinolinecarboxylic acid wherein R1is hydrogen, lower alkyl, C2-C12 acyl, or R1O together are methylenedioxy; R2is hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, substituted aryl, aralkyl or substituted aralkyl group; and R3is hydrogen, C2-C12 acyl group, benzyl, alkoxylcarbonyl group, or aralkoxyl carbonyl group.
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Page/Page column 2-3; 5-6; 8; 12
(2008/06/13)
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- PREPARATION OF CHIRAL 1,2,3,4-TETRAHYDRO-6,7-DIALKOXY-3-ISOQUINOLINECARBOXYLIC ACID AND DERIVATIVES BY REACTING LEVODOPA WITH FORMALDEHYDE OR FORMALDEHYDE PRECURSORS
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A process for preparation of (S)-1,2,3,4-tetrahydro-6,7-dialkoxy-3-isoquinolinecarboxylic acid compounds and their derivatives of the formula (1) the process compring: (i) reacting Levodopa of formula (2) with formaldehyde or formaldehyde precursors to obtain (S)-1,2,3,4-tetrahydro-6,7-dihydroxy-3-isoquinolinecarboxylic acid of formula (3); (ii) protecting the amino group of formula (3); (iii) alkylating the phenol groups of formula (4) to form compound of formula (5); and (iv) esterifying the carcoxylic acid of formula (5) and optionally removing N-protecting group wherein R1 is hydrogen, lower alkyl, C2-C12 acyl, or R1O together are methylenedioxy; R2 is hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, substituted aryl, aralkyl or substituted aralkyl group; R3 is hydrogen, C2-C12 acyl group, benzyl, alkoxylcarbonyl group, or aralkoxyl carbonyl group; wherein P is the protecting group selected from alkoxycarbonyl, acyl, alkyl, aryl, siryl, sulfenyl and sulfonyl.
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- A new efficient synthetic process for the construction of the pentacyclic core of marine alkaloid ecteinascidins
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The pentacyclic core of ecteinascidins was constructed from two fundamental building blocks, the 1,2,3,4-tetrahydroisoquinoline derivative and the substituted phenylalanine derivative, via 8 steps using readily available L-Dopa as starting material. The k
- Tang, Ye-Feng,Liu, Zhan-Zhu,Chen, Shi-Zhi
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p. 7091 - 7094
(2007/10/03)
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- 2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines
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Antibacterial activity is exhibited by 3-acylamino-2-oxoazetidines having in the 1-position an activating group of the formula STR1 wherein R is STR2 and R4 is STR3
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- Biomimetic approach to potential benzodiazepine receptor agonists and antagonists
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Several β-carbolines, isoquinolines, imidazopyridines, and canthin-6-ones prepared in biomimetic fashion were tested for their ability to bind the benzodiazepine receptor. Methyl isoquinoline-3-carboxylate, methyl 6,7-dimethoxyisoquinoline-3-carboxylate,
- Guzman,Cain,Larscheid,Hagen,Cook,Schweri,Skolnick,Paul
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p. 564 - 570
(2007/10/02)
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