Synthesis of isotopically labeled CIS-(3aR)-(-)-2,3,3a,4,5,9b-hexahydro-3-(N-propyl)-1H-benz[e]indole-9-carboxamide, a 5-HT1A receptor agonist
The title compound is a potent and selective 5‐HT1A receptor agonist with clinical potentials for treating anxiety and depression. It has been labeled with stable and radioactive isotopes to support ADME studies in animals and human subjects. Its carboxamide group was labeled with C‐14, C‐13, or C‐1...
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| Published in | Journal of labelled compounds & radiopharmaceuticals Vol. 39; no. 11; pp. 891 - 900 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Chichester
John Wiley & Sons, Ltd
01.11.1997
Wiley |
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| Abstract | The title compound is a potent and selective 5‐HT1A receptor agonist with clinical potentials for treating anxiety and depression. It has been labeled with stable and radioactive isotopes to support ADME studies in animals and human subjects. Its carboxamide group was labeled with C‐14, C‐13, or C‐13, N‐15, and O‐18. To provide a radioligand for investigating the receptor binding characteristics of the compound, we also labeled it with tritium in the N‐propyl group to obtain the high specific activity of 86.7 Ci/mmol. © 1997 John Wiley & Sons, Ltd. |
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| AbstractList | The title compound is a potent and selective 5‐HT1A receptor agonist with clinical potentials for treating anxiety and depression. It has been labeled with stable and radioactive isotopes to support ADME studies in animals and human subjects. Its carboxamide group was labeled with C‐14, C‐13, or C‐13, N‐15, and O‐18. To provide a radioligand for investigating the receptor binding characteristics of the compound, we also labeled it with tritium in the N‐propyl group to obtain the high specific activity of 86.7 Ci/mmol. © 1997 John Wiley & Sons, Ltd. The title compound is a potent and selective 5-HT1A receptor agonist with clinical potentials for treating anxiety and depression. It has been labeled with stable and radioactive isotopes to support ADME studies in animals and human subjects. Its carboxamide group was labeled with C-14, C-13, or C-13, N-15, and O-18. To provide a radioligand for investigating the receptor binding characteristics of the compound, we also labeled it with tritium in the N-propyl group to obtain the high specific activity of 86.7 Ci/mmol. |
| Author | Hsi, Richard S. P. Lin, Chiu-Hong Stolle, Wayne T. Easter, John A. Haadsma-Svensson, Susanne R. Ackland, Mark J. |
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| Cites_doi | 10.1021/jm00060a014 10.1021/jm00004a018 10.1021/jm00067a018 10.1021/jm00140a002 10.1021/jo01351a092 10.1246/bcsj.49.3177 10.1246/bcsj.48.3298 10.1016/0014-2999(83)90230-3 10.1016/0165-6147(87)90231-8 10.1002/jlcr.2580230608 10.1007/BF01276574 |
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| Keywords | synthesis aryl cyanation O-18 tritium catalytic reduction C-14 isotopic labeling C-13 CIS-(3AR)-(-)-2,3,3A,4,5,9B-HEXAHYDRO-3-PROPYL-1H-BENZINDOLE-9-CARBOXAMIDE N-15 DERIVATIVES Agonist Nitrogen 15 Isotope labelling Radiolabelling Nitrogen heterocycle Oxygen 18 Psychotropic Tritium Hydrogen Isotopes Tricyclic compound Cis stereoisomer Tranquillizer Carboxamide Aromatic compound Carbon 14 Carbon 13 5-HT1A receptor Enantiomer(-) |
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Chem. 24: 921 (1981). – reference: Middlemiss D. N. and Fozard, J. R. - Eur. J. Pharm. 90: 151 (1983). – reference: Traber J. and Glaser, T. - Trends Pharmacol. Sci. 8: 432 (1987). – reference: Kuo G., Dewey R., Perchonok C., McCarthy M. and Newton, J. - J. Labelled Compds. and Radiopharm. 23: 625 (1986). – reference: Takagi K., Okamoto T., Sakakibara Y., Ohno A. and Hayama, N. - Bull. Chem. Soc. Japan 48 3298 (1975). – reference: Friedman L. and Schecter, H. - J. Org. Chem. 26: 2522 (1961). – reference: Takagi K., Okamoto T., Sakakibara Y., Ohno A. and Hayama, N. - Bull. Chem. Soc. Japan 49: 3177 (1976). – reference: Hall J. H. and Gisler, M. - J. Or. Chem. 41: 23 (1976). – volume: 55 start-page: 169 year: 1988 publication-title: J. Neural Transm. – volume: 8 start-page: 432 year: 1987 publication-title: Trends Pharmacol. Sci. – volume: I start-page: 571 year: 1958 – volume: 24 start-page: 921 year: 1981 publication-title: J. Med. 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| Snippet | The title compound is a potent and selective 5‐HT1A receptor agonist with clinical potentials for treating anxiety and depression. It has been labeled with... The title compound is a potent and selective 5-HT1A receptor agonist with clinical potentials for treating anxiety and depression. It has been labeled with... |
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| SubjectTerms | aryl cyanation Biochemical Research Methods Biochemistry & Molecular Biology Biological and medical sciences C-13 C-14 catalytic reduction Chemistry Chemistry, Analytical Chemistry, Medicinal Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives isotopic labeling Life Sciences & Biomedicine Medical sciences N-15 Neuropharmacology O-18 Organic chemistry Pharmacology & Pharmacy Pharmacology. Drug treatments Physical Sciences Preparations and properties Psycholeptics: tranquillizer, neuroleptic Psychology. Psychoanalysis. Psychiatry Psychopharmacology Science & Technology synthesis tritium |
| Title | Synthesis of isotopically labeled CIS-(3aR)-(-)-2,3,3a,4,5,9b-hexahydro-3-(N-propyl)-1H-benz[e]indole-9-carboxamide, a 5-HT1A receptor agonist |
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