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Aromatase inhibitors: synthesis, biological activity, and structure of 1,2-imidazolylmethylcyclopentanol derivatives. 1995

A Kato, and Y Ikeda, and N Sugita, and T Nitta, and H Enari, and A Kashima, and M Konno, and K Niimura
Biomedical Research Laboratories, Kureha Chemical Industry Co. Ltd., Tokyo, Japan.

Two series of 1,2-disubstituted imidazolylmethylcyclopentanol derivatives (5a-d, 10a-d) were prepared by using easily available methyl 2-oxocyclopentanecarboxylate as the starting material. Evaluation of the aromatase inhibitory activities in vitro was performed. Their activities were compared with those of a steroidal aromatase inhibitor, Formestane, and a non-steroidal inhibitor, Fadrozole. Among these compounds, the aromatase inhibitory activities of 5d, 10a, 10b, 10c, 11a, 15a, and 15b were more potent than Formestane. One compound, 1-(4-chlorobenzyl)-cis-2-(1H-imidazol-1-ylmethyl)cyclopentanol+ ++ (10a) was in particular identified as a potent aromatase inhibitor in vitro, exhibiting an IC50 value of 4 x 10(-8)M. The enantiomers of 10a were separated, and their absolute configuration were determined by X-ray crystallography.

UI MeSH Term Description Entries
D008861 Microsomes Artifactual vesicles formed from the endoplasmic reticulum when cells are disrupted. They are isolated by differential centrifugation and are composed of three structural features: rough vesicles, smooth vesicles, and ribosomes. Numerous enzyme activities are associated with the microsomal fraction. (Glick, Glossary of Biochemistry and Molecular Biology, 1990; from Rieger et al., Glossary of Genetics: Classical and Molecular, 5th ed) Microsome
D010920 Placenta A highly vascularized mammalian fetal-maternal organ and major site of transport of oxygen, nutrients, and fetal waste products. It includes a fetal portion (CHORIONIC VILLI) derived from TROPHOBLASTS and a maternal portion (DECIDUA) derived from the uterine ENDOMETRIUM. The placenta produces an array of steroid, protein and peptide hormones (PLACENTAL HORMONES). Placentoma, Normal,Placentome,Placentas,Placentomes
D011247 Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH. Gestation,Pregnancies
D003517 Cyclopentanes A group of alicyclic hydrocarbons with the general formula R-C5H9. Cyclopentadiene,Cyclopentadienes,Cyclopentene,Cyclopentenes,Cyclopentane
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D005260 Female Females
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000735 Androstenedione A delta-4 C19 steroid that is produced not only in the TESTIS, but also in the OVARY and the ADRENAL CORTEX. Depending on the tissue type, androstenedione can serve as a precursor to TESTOSTERONE as well as ESTRONE and ESTRADIOL. 4-Androstene-3,17-dione,delta-4-Androstenedione,4 Androstene 3,17 dione,delta 4 Androstenedione
D047072 Aromatase Inhibitors Compounds that inhibit AROMATASE in order to reduce production of estrogenic steroid hormones. Aromatase Inhibitor,Inhibitor, Aromatase,Inhibitors, Aromatase
D018360 Crystallography, X-Ray The study of crystal structure using X-RAY DIFFRACTION techniques. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) X-Ray Crystallography,Crystallography, X Ray,Crystallography, Xray,X Ray Crystallography,Xray Crystallography,Crystallographies, X Ray,X Ray Crystallographies

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