PF-1092B
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| Category | Bioactive by-products |
| Catalog number | BBF-03340 |
| CAS | |
| Molecular Weight | 304.34 |
| Molecular Formula | C17H20O5 |
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Description
PF-1092B is a nonsteroidal progesterone receptor ligand produced by Penicillium oblatum. It was shown to competitively inhibit [3H]-progesterone binding to porcine uteri cytosol preparations with IC50 of 2.2 x 10(2) nM.
Specification
| Synonyms | PF 1092B; PF1092B |
| IUPAC Name | [(4aR,5R,6R,7S)-6-hydroxy-3,4a,5-trimethyl-2-oxo-4,5,6,7-tetrahydrobenzo[f][1]benzofuran-7-yl] acetate |
| Canonical SMILES | CC1C(C(C=C2C1(CC3=C(C(=O)OC3=C2)C)C)OC(=O)C)O |
| InChI | InChI=1S/C17H20O5/c1-8-12-7-17(4)9(2)15(19)14(21-10(3)18)6-11(17)5-13(12)22-16(8)20/h5-6,9,14-15,19H,7H2,1-4H3/t9-,14-,15+,17+/m0/s1 |
| InChI Key | KNICLZOLCPFMLS-RAGLCQRRSA-N |
Properties
| Appearance | Colorless Needle Crystal |
Reference Reading
1. Fungal metabolites, PF1092 compounds and their derivatives, are nonsteroidal and selective progesterone receptor modulators
Y Tabata, Y Iizuka, J Kashiwa, N T Masuda, R Shinei, K Kurihara, T Okonogi, S Hoshiko, Y Kurata Eur J Pharmacol. 2001 Nov 2;430(2-3):159-65. doi: 10.1016/s0014-2999(01)01382-6.
The potential of new nonsteroidal progesterone receptor ligands, the derivatives of PF1092C ((4aR,5R,6R,7S)-6,7-dihydroxy-4a,5,6,7-tetrahydro-3,4a,5-trimethylnaphtho[2,3-b]furan-2(4H)-one) discovered from fungal metabolites, was evaluated. PF1092A ((4aR,5R,6R,7S)-6-acetoxy-7-hydroxy-4a,5,6,7-tetrahydro-3,4a,5-trimethylnaphtho[2,3-b]furan-2(4H)-one) showed good and moderate affinity for porcine and human progesterone receptors in in vitro receptor binding assays, respectively, and partial agonist activity for the progesterone receptor, as determined in assays of two types of progesterone-dependent enzymes in human mammary carcinoma T47D cells. The derivative of PF1092C, CP8481, ((4aR,5R,6R,7S)-6-(2-furancarbonyloxy)-7-hydroxy-4a,5,6,7-tetrahydro-3,4a,5-trimethylnaphtho[2,3-b]furan-2(4H)-one) possessed better affinity for both progesterone receptors and showed less cross-reactivity for other steroid receptors, such as rat androgen receptor, human glucocorticoid receptor, and human estrogen receptor, and was a more potent modulator of the progesterone receptor than PF1092A. CP8400 ((4aR,5R,6R,7S)-6,7-diacetoxy-4a,5,6,7-tetrahydro-3,4a,5-trimethylnaphtho[2,3-b]furan-2(4H)-one) and CP8401 ((4aR,5R,6R,7S)-6,7-dipropionyloxy-4a,5,6,7-tetrahydro-3,4a,5-trimethylnaphtho[2,3-b]furan-2(4H)-one), other derivatives, were indicated to be progesterone receptor antagonists. These results suggest that PF1092 compounds can serve as a new pharmacophore for potent and specific nonsteroidal progesterone receptor modulators.
2. Nonsteroidal progesterone receptor ligands (II); synthesis and SAR of new tetrahydrobenzindolone derivatives
Ken-ichi Kurihara, Rie Shinei, Kiyoshi Tanabe, Yuji Tabata, Yasushi Kurata, Shigeru Hoshiko, Tsuneo Okonogi Bioorg Med Chem. 2006 Jul 15;14(14):4862-78. doi: 10.1016/j.bmc.2006.03.022. Epub 2006 Mar 31.
The human progesterone receptor (PR) binding affinity and the PR agonistic or antagonistic potency of tetrahydronaphthofuranone derivatives were shown previously to be markedly influenced by substituents at the 6- and 7-positions. Here, we synthesized tetrahydrobenzindolones possessing a lactam ring, which enabled us to modify the 6- and 7-positions more freely, since tetrahydrobenzindolones are chemically more stable than tetrahydronaphthofuranones. The tetrahydrobenzindolone derivatives generally showed higher PR binding affinity than the corresponding tetrahydronaphthofuranones. We also succeeded in separating the agonistic and antagonistic activities by choosing suitable substituent groups at the 6- and/or 7-position(s) of the tetrahydrobenzindolone. The effects of representative agonists, 12c (CP8668), and 14a (CP8816), and a representative antagonist, 15f (CP8661), were confirmed in in vivo tests. In this report, we mainly describe the synthesis and structure-activity relationships (SAR) of tetrahydrobenzindolone derivatives, as new nonsteroidal PR ligands.
3. PF1092A, B and C, new nonsteroidal progesterone receptor ligands produced by Penicillium oblatum. II. Physico-chemical properties and structure elucidation
Y Tabata, M Hatsu, Y Kurata, K Miyajima, M Tani, T Sasaki, Y Kodama, T Tsuruoka, S Omoto J Antibiot (Tokyo). 1997 Apr;50(4):309-13. doi: 10.7164/antibiotics.50.309.
The structures of PF1092A (1), B (2) and C (3), new nonsteroidal progesterone receptor ligands produced by Penicillium oblatum, were elucidated by spectroscopic analyses. These compounds possess an eremophilane-type sesquiterpene carbon skeleton and differ only in that 1 and 2 are different monoacetates of 3. The absolute configurations of 1-3 were determined by single crystal X-ray diffraction analysis of the 4-bromobenzoyl ester of PF1092A and by measuring the optical rotations of the acetylation products of these compounds.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
