PF-1092C
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| Category | Bioactive by-products |
| Catalog number | BBF-03341 |
| CAS | |
| Molecular Weight | 262.3 |
| Molecular Formula | C15H18O4 |
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Description
PF-1092C 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(3) nM.
Specification
| Synonyms | PF 1092C; PF1092C |
| IUPAC Name | (4aR,5R,6R,7S)-6,7-dihydroxy-3,4a,5-trimethyl-4,5,6,7-tetrahydrobenzo[f][1]benzofuran-2-one |
| Canonical SMILES | CC1C(C(C=C2C1(CC3=C(C(=O)OC3=C2)C)C)O)O |
| InChI | InChI=1S/C15H18O4/c1-7-10-6-15(3)8(2)13(17)11(16)4-9(15)5-12(10)19-14(7)18/h4-5,8,11,13,16-17H,6H2,1-3H3/t8-,11-,13+,15+/m0/s1 |
| InChI Key | AMAJXAHZCGMNST-JPRMETQZSA-N |
Properties
| Appearance | Colorless Needle Crystal |
| Melting Point | 171-172°C (dec.) |
Reference Reading
1. Nonsteroidal progesterone receptor ligands (I): synthesis and SAR of new tetrahydronaphthofuranone derivatives
Rie Shinei, Ken-ichi Kurihara, Kiyoshi Tanabe, Yuji Tabata, Yasushi Kurata, Shigeru Hoshiko, Tsuneo Okonogi Bioorg Med Chem. 2006 Jul 15;14(14):4850-61. doi: 10.1016/j.bmc.2006.03.018. Epub 2006 Mar 31.
We have synthesized a series of nonsteroidal progesterone receptor (PR) ligands, tetrahydronaphthofuranones, structurally based on the fungal metabolite PF1092C. Structure-activity relationship studies revealed that substituents at the 6- and 7-positions were critical for PR binding affinity and for agonist or antagonist activity. Compounds in this series, exemplified by 19i, exhibited high affinity and high specificity for PR over other steroid hormone receptors and acted as selective PR antagonists. Further modification of PF1092C may generate compounds of potential pharmacological interest.
2. In vitro and in vivo characterization of novel nonsteroidal progesterone receptor antagonists derived from the fungal metabolite PF1092C
Yuji Tabata, Yumiko Iizuka, Naomi Takei Masuda, Rie Shinei, Ken ichi Kurihara, Tsuneo Okonogi, Shigeru Hoshiko, Yasushi Kurata J Steroid Biochem Mol Biol. 2002 Oct;82(2-3):217-23. doi: 10.1016/s0960-0760(02)00157-7.
We studied the pharmacological effects of novel nonsteroidal progesterone receptor antagonists CP8661 and CP8754, which were synthesized from the fungal metabolite PF1092C. CP8661 possess a tetrahydrobenzindolone skeleton and CP8754 possess a tetrahydronaphthofuranone skeleton. In binding assays for steroid receptors, CP8661 and CP8754 inhibited [(3)H]-progesterone binding to human progesterone receptors (hPR), though they are less potent than RU486. CP8661 also showed moderate affinity to rat androgen receptors (rAR), although CP8754 did not. Neither compound showed affinity to human glucocorticoid receptors (hGR) or human estrogen receptors (hER). In exogeneous and endogeneous PR-dependent enzyme expression assays using human mammary carcinoma T47D, CP8661 and CP8754 showed pure antagonistic activity. In a rabbit endometrial transformation test, CP8661 and CP8754 showed anti-progestational activity by s.c. administration in a dose-dependent manner; meanwhile, these compounds showed no progestational activity at the same dose. These results suggested that CP8661 and CP8754 are in vivo effective pure progesterone receptor antagonists and presented the possibility of synthesizing pure progesterone receptor antagonists from both tetrahydronaphthofuranone and tetrahydrobenzindolone skeletons.
3. 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.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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