Synthesis of 14C or 3H-labelled indometacin farnesil (E-0710)

Autor:	Mannen Mishima, Chihiro Yamato, Shinya Abe, Isao Yamatsu, Seiichi Kobayashi
Rok vydání:	1991
Předmět:	Stereochemistry Organic Chemistry Farnesol Prodrug Biochemistry Analytical Chemistry chemistry.chemical_compound chemistry Pharmacokinetics Drug Discovery medicine Moiety Radiology Nuclear Medicine and imaging Indometacin farnesil Spectroscopy medicine.drug
Zdroj:	Journal of Labelled Compounds and Radiopharmaceuticals. 29:619-624
ISSN:	0362-4803
DOI:	10.1002/jlcr.2580290602
Popis:	A 14C or 3H-labelled, 7:3 (2E:2Z) isomeric mixture of 6E-3, 7, 11-trimethyl-2, 6, 10-dodecatrienyl-1-(p-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate (indometacin farnesil; IMF), a prodrug of indomethacin, was synthesized in order to study the pharmacokinetic profiles of this drug. Esterification of a 7:3 (2E:2Z) isomeric mixture of 6E-3, 7, 11-trimethyl-2, 6, 10-dodecatrienol [farnesol (3)] with [2-14C] indomethacin [14C-IND (1)] or [G-3H] indomethacin [3H-IND (2)] gave the corresponding 14C or 3H-labelled indometacin farnesil [14C-IMF (4) or 3H-IMF (5)]. On the otherhand, [3-14C] 6E-3, 7, 11-trimethyl-2, 6, 10-dodecatrienol [14C-F (8)] which was obtained from [2-14C] 5E-6, 10-dimethylundeca-5, 9-dien-2-one [14C-geranyl acetone (7)] in two steps, was esterified with indomethacin to give farnesyl moiety 14C-labelled indometacin farnesil 14C-F-IMF (6) 1.
Databáze:	OpenAIRE
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