Browse > Article

Efficient Synthesis of 2-Aminoindan and cis-(${\pm}$)-4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one  

Kim, Min-Woo (College of Pharmacy, Catholic University of Daegu)
Ma, Eun-Sook (College of Pharmacy, Catholic University of Daegu)
Publication Information
YAKHAK HOEJI / v.50, no.6, 2006 , pp. 403-408 More about this Journal
Abstract
1-Amino-5,6-dimethoxyindan hydrochloride was synthesized from 3- (3,4-dirnethoxyphenyl)propionic acid by intramolecular Friedel-Crafts acylation, oximation with hydroxylamine, and reduction with an overall yield of 74%. 2-Amino-5,6-dimethoxyindan hydrochloride was synthesized from 3-(3,4-dirnethoxyphenyl)propionic acid by intramolecular Friedel-Crafts acylation, oximation with isoamylnitrite, reduction in NaOH and reaction with HCI to form 5,6-dimethoxy-2-indanone, which was reacted with hydroxylamine and reduced with an overall yield of 42%. 5,6-Dimethoxyindan-1,2-dione-2-oxime, which was catalytically hydrogenated to afford cis-, and trans-1-amino-5,6-dimethoxyindan-1-ol as 3 : 1 ratio. This mixture was treated with Li and reacted with chloroacetyl chloride. Cis isomer was acylated and cyclized to synthesize rir -( ${\pm}$ )-7,8-dimethoxy-4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one, but trans isomer was just acylated to form amide.
Keywords
5,6-Dimethoxy-1-indanone; 1-Aminoindan; 2-Aminoindan; cis-(${\pm}$) 4,4a,5,9b -tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Sokoloff, P., Giros, B., Martres, M., Bouthene, M. and Schwarz, J. : Molecular cloning and characterization of novel dopamine receptor $D_{3}$ as a target for neuroleptics. Nature 347, 146 (1990)
2 Cannon, J. G., Dushin, R. G., Long, J. P., Ilhan, M., Jones, N. D. and Schwarzendruber, J. K. : Synthesis and dopaminergic activity of (R)- and (S)-4-hydroxy-2-(di-n-propylamino)indan. J. Med. Chem. 28(4), 515 (1985)   DOI
3 Haadsma-Svensson, S. R., Cleek, K. A., Dinh, D. M., Duncan, J. N., Haber, C. L., Huff, R. M., Lajiness, M. E., Nichols, N. F., Smith, M. W., Svebsson, K. A., Zaya, M. J., Carlsson, A. and Lin, C .H. : Dopamine $D_{3}$ receptor antagonists. 1. Synthesis and structure-Activity relationships of 5,6-dimethoxy-N-alkyland N-alkylaryl-substituted 2-aminoindans. J. Med. Chem. 44, 4716 (2001)   DOI   ScienceOn
4 Gendreau, P. L., Petitto, J. M., Schnauss, R., Frantz, K. J., Van Hartesveldt, C., Gariepy, J. L. and Lewis, M. H. : Effects of the putative $D_{3}$ dopamine receptor antagonist PNU-99194A on motor behavior and emotional reactivity in C57BL/6J mice. Eur. J. Pharmacol. 337, 147 (1997)   DOI
5 Sterling, J., Veinberg, A., Lerner, D., Goldenberg, W.,; Levy, R., Youdim, M. and Finberg, J. : (R)-(${\pm}$)-N-Propargyl-1- aminoindan (rasagiline) and derivatives : highly selective and potent inhibitors of monoamine oxidase B. J. Neural Transm. Suppl. 52, 301 (1998)
6 Carr, K. D., Yamamoto, N., Omura, M., Cabeza de Vaca, S. and Krahne, L. : Effects of the $D_{3}$ dopamine receptor antagonist, U99194A, on brain stimulation and d-amphetamine reward, motor activity, and c-fos expression in ad libitum fed and foodrestricted rats. Psychopharmacology 163, 76 (2002)   DOI
7 Baker, L. E., Svensson, K. A,, Garner, K. J. and Goodwin, A. K. : The dopamine $D_{3}$ receptor antagonist PNU-99194A fails to block (+)-7-OH-DPAT substitution for d-amphetamine or cocaine. Eur. J. Pharmacol. 358, 101(1998)   DOI   ScienceOn
8 Dijksra, D., Hazelhoff, B., Mulder, T. B. A., de Vries, J. B., Wynberg, H. and Horn, A. S. : Synthesis and pharmacological activity of the hexahydro-4H-naphth[1,2-b][1,4]oxazines: a new series of potent dopamine receptor agonists. Eur. J. Med. Chem. 20, 247 (1985)
9 Ma, S. X., Long, J. P., Flynn, J. R., Leonard, P. A. and Cannon, J. G. : Dopaminergic structure-activity relationships of 2- aminoindan and cardiovascular action and dopaminergic activity of 4-hydroxy-5-methyl-2-di-n-propylaminoindan (RD- 211). J. Pharmacol. Exp. Ther. 256(2), 751 (1991)
10 Sunhara, R. K., Guan, H. C., O'Dowd, B. F., Seeman, P., Laurier, L. G., George, S. R., Torchia, J., Van Tol, H. H. M. and Niznik, H. B. : Cloning of the gene for a human dopamine $D_{5}$ receptor with higher affinity for dopamine than $D_{1}$. Nature 350, 614 (1991)   DOI   ScienceOn
11 Panetta, C. A., Sha, D., Torres, E., He, Z., Hussey, C. L., Fang, Z. and Heimer, N. E. Tetracyano-4,7-indanquinodimethanes: The first TCNQs with an indan nucleus. Synthesis 9, 1085 (1997)
12 Civelli, O., Bunzow, J. R. and Grandy, D. K. : Molecular diversity of the dopamine receptor. Annu. Rev. Pharmacol. Toxicol. 32, 281 (1993)
13 Goksu, S. and Secen, H. : Concise syntheses of 2-aminoindans via indan-2-ol. Tetrahedron 61, 6801 (2005)   DOI   ScienceOn
14 Klodzinska, A., Tatarczynska, K. and Stachowicz, E. : 1- Aminoindan-1,5-dicarboxylic acid (AIDA), a rigid (carboxyphenyl) glycine derivative acting on metabotropic glutamate receptors (mGluRs) antagonist. Pharmacology 281(2), 721 (1997)
15 Van Tol, H. H. M., Bunzow, J. R., Guan, H. C., Sunhara, R. K., Man, P., Niznik, H. B. and Civelli, O. : Cloning of the gene for human dopamine $D_{4}$ receptor with high affinity for the antipsychotic clozapine. Nature 350, 610 (1991)   DOI   ScienceOn
16 Jackson, D. M. and Westland-Danielsson, A. : Dopamine receptors: Molecular biology, biochemistry and behavioral aspects. Pharmacol. Ther. 64, 291 (1994)   DOI   ScienceOn
17 Kebabian, J. W. and Calne, D. B. : Multiple receptors for dopamine. Nature 277, 93 (1979)   DOI   ScienceOn
18 Cannon, J. G., Perez, J. Z., Bhatnage,r R. K., Long, J. P. and Sharabi, F. M. : Conformationally restricted congeners of dopamine derived from 2-aminoindan. J. Med. Chem. 25(12), 1442 (1982)   DOI
19 Akunne, H. C., Towners, P., Ellis, G. J., Dijkstra, D., Wikstrom, H., Heffner, T. G., Wise, L. D. and Pugsley, T. A. : Characterization of binding of $[^{3}H]PD$ 128907, a selective dopamine $D_{3}$ receptor agonist ligand, to CHO-K1 cells. Life Sci. 57, 1401 (1995)   DOI   ScienceOn
20 Gray, A. P., Kreifels, S. E. and Li, J. A. : Conformational requirements for direct adrenergic stimulantion. J. Med. Chem. 16, 1023 (1973)   DOI