Studies on Dihydroisocoumarin (I). A Practical Synthesis of 3-Hydroxyhomophthalic Acid

Wagatsuma, S.; Higuchi, Shigesada; Ito, Hideo; Nakano, Takashi; Naoi, Y.; Saito, Kiyoshi; Matsui, T.; Takahashi, Yukio; Nishi, A.; Sano, Seiyo

doi:10.1080/00304947309356468

Cited by 20 publications

(7 citation statements)

References 2 publications

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“…(from chloroform-light petroleum) (Found: C, 67.75; H, 4.55. C23H1807 requires C, 67.98; H, 4.46%); m/z 406 ( M + , <O.l%), 364 (18), and 322 (100). -The reaction between 2-hydroxy-4-methoxy-6methylacetophenone (6c) and dimethyl 3-methoxyhomophthalate (7d) was performed in the usual manner, though with a reflux time of 8 h. After purification by flash chromatography with hexane-benzene-et hyl aceta te-formic acid (8 : 8 : 2 : 1) as eluant, the 11-hydroxybenzoxanthone (8e) was obtained as orange needles (42%), m.p.…”

Section: Ll -Dihydroxy-3-methoxy-l -Methyl-l2h-benzo[b]xanthen-12-one...mentioning

confidence: 99%

A synthesis of bikaverin (7,12-dihydro-6,11-dihydroxy-3,8-dimethoxy-1-methyl-10H-benzo[b]xanthene-7,10,12-trione) and some related benzoxanthones and quinones

KJAER¹,

Kjær²,

Risbjerg³

1983

J. Chem. Soc., Perkin Trans. 1

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Section: Ll -Dihydroxy-3-methoxy-l -Methyl-l2h-benzo[b]xanthen-12-one...mentioning

confidence: 99%

A synthesis of bikaverin (7,12-dihydro-6,11-dihydroxy-3,8-dimethoxy-1-methyl-10H-benzo[b]xanthene-7,10,12-trione) and some related benzoxanthones and quinones

KJAER¹,

Kjær²,

Risbjerg³

1983

J. Chem. Soc., Perkin Trans. 1

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“…1). Conversion of compound (1) into the masked o-quinone (2) followed by a stereospecific addition of benzylvinyl ether yields the-substituted nordenudatine intermediate (3) (4) is subjected to a Wagner rearrangement which yields the "pyro-oxo" der"ivative (5). A further simple adjustrnent of functionality finally gives the aconite alkaloid (6).…”

Section: The Synthesis Of the Polysubstituted Delphinine Systemmentioning

confidence: 98%

Total synthesis of delphinine-type alkaloids by simple, fourth generation methods

Wiesner¹

1979

Pure and Applied Chemistry

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“…A solution of 9.0 g (0.06 mol) 7-hydroxy-l-indanone (1) [35] in dried acetone (400 mL) is treated with 15.0 g (0.11 mol) K2CO3, 1.5 g (0.009 mol) KI and 18 mL (0.2 mol) 1-bromopropane. The reaction mixture is heated under reflux at a temperature of 65 °C (intensive condenser).…”

Section: -Propoxy-1-indanone (3)mentioning

confidence: 99%

Structure Activity Relationship of Homochiral 7-Substituted 1-Aminoindans as 5-HT1A Receptor Ligands

Landsiedel-Maier

Frahm²

1998

Arch. Pharm. Pharm. Med. Chem.

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A series of homochiral 7‐substituted 1‐aminoindans was prepared by means of asymmetric reductive amination from racemic 7‐substituted 1‐indanones via E‐imines and E‐imine/ enamine mixtures, respectively, and subjected to 5‐hydroxytryptamine (5‐HT) receptor subtype binding studies. The ee’s of the title compounds were determined by HPLC of the corresponding Mosher’s amides and range from 96 to 99.9%. The absolute configuration was elucidated by means of correlation CD spectroscopy. On the basis of the pKI values obtained from various test systems, structure activity relationships have been established with respect to the absolute configuration, degree of N‐alkylation, and the type of 7‐substituents. The tested 1‐aminoindans show the highest affinity to the 5‐HT1A receptor, with decreasing magnitude for the 5‐HT2A, 5‐HT1D, and 5‐HT2C receptors. The highest affinities for the 5‐HT1A receptor were observed for the R‐(–)‐7‐propoxy‐1‐(di‐n‐propylamino)indan hydrochloride (R‐(–)‐30), S,S′‐(+)‐7‐benzylamido‐1‐(1‐phenylethylamino)indan hydrochloride [S,S′‐(+)‐19] and R‐(–)‐7‐methoxy‐1‐(di‐n‐propylamino)indan hydrogenembonate (R‐(–)‐29) with pKI = 7.07 ± 0.19, 6.40 ± 0.09, and 6.22 ± 0.10, respectively, in comparison to 8‐OH‐DPAT with pKI = 8.70 ± 0.30. Nearly all other compounds showed low affinity at all 5‐HT receptors tested. The three above mentioned ligands were tested on HeLa cells (cell line HA6) expressing recombinant human 5‐HT1A receptors for their effects on forskolin‐stimulated cAMP accumulation in intact cells. Both the di‐n‐propylamino substituent bearing R‐(–)‐30 and R‐(–)‐29 acted as efficacious agonists with a pEC50 value of 5.89 ± 0.20 for R‐(–)‐30 compared to 5‐HT with a pEC50 value of 8.06 ± 0.14. S,S′‐(+)‐19 with the 1‐phenylethylamino substituent was devoid of intrinsic activity up to the highest tested concentration (10 μM).

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Studies on Dihydroisocoumarin (I). A Practical Synthesis of 3-Hydroxyhomophthalic Acid

Cited by 20 publications

References 2 publications

A synthesis of bikaverin (7,12-dihydro-6,11-dihydroxy-3,8-dimethoxy-1-methyl-10H-benzo[b]xanthene-7,10,12-trione) and some related benzoxanthones and quinones

A synthesis of bikaverin (7,12-dihydro-6,11-dihydroxy-3,8-dimethoxy-1-methyl-10H-benzo[b]xanthene-7,10,12-trione) and some related benzoxanthones and quinones

Total synthesis of delphinine-type alkaloids by simple, fourth generation methods

Structure Activity Relationship of Homochiral 7-Substituted 1-Aminoindans as 5-HT1A Receptor Ligands

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