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8b,8c-Diphenyl-2,6-bis(4-pyridyl-meth-yl)-perhydro-2,3a,4a,6,7a,8a-hexa-aza-cyclo-penta-[def]fluorene-4,8-dithione chloro-form solvate.

ABSTRACT: In the thio-glycoluril system of the title compound, C(32)H(30)N(8)S(2)·CHCl(3), the two pyridine rings are roughly parallel, forming a dihedral angle of 7.2?(1)°, and the distance between the centroids of the two phenyl rings is 3.951?(5)?Å. The chloro-form solvent mol-ecule is linked to the main mol-ecule via a weak C-H?N hydrogen bond.

SUBMITTER: Deng C

PROVIDER: S-EPMC3006766 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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8b,8c-Diphenyl-2,6-bis(4-pyridyl-meth-yl)-perhydro-2,3a,4a,6,7a,8a-hexa-aza-cyclo-penta-[def]fluorene-4,8-dithione chloro-form solvate.

Deng Cong C Shu Wenming W Zhang Dongxue D

Acta crystallographica. Section E, Structure reports online 20100605 Pt 7

In the thio-glycoluril system of the title compound, C(32)H(30)N(8)S(2)·CHCl(3), the two pyridine rings are roughly parallel, forming a dihedral angle of 7.2 (1)°, and the distance between the centroids of the two phenyl rings is 3.951 (5) Å. The chloro-form solvent mol-ecule is linked to the main mol-ecule via a weak C-H⋯N hydrogen bond. ...[more]

PMID: 21587774

Similar Datasets

2,6-Bis(2-hydroxy-ethyl)-8b,8c-diphenyl-perhydro-2,3a,4a,6,7a,8a-hexa-azacyclo-penta-[def]fluorene-4,8-dithione.

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2,6-Bis(2-chloro-ethyl)-8b,8c-diphenyl-perhydro-2,3a,4a,6,7a,8a-hexa-azacyclo-penta-[def]fluorene-4,8-dithione.

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4,4'-[8b,8c-Bis(ethoxycarbonyl)-4,8-dioxo-2,3,5,6-tetra-hydro-1H,4H-2,3a,4a,6,7a,8a-hexa-azacyclo-penta-[def]fluorene-2,6-diyl]dipyridinium bis-(tetra-fluorido-borate).

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Synthesis, structure, and antitumor activity of 2,9-disubstituted perhydro 2,3a,7b,9,10a,14b-hexaazadibenzotetracenes.

Project description:Catalytic methods for the synthesis of previously unknown 2,9-disubstituted 3bR*,7aR*,10bR*,14aR*-cis-14c,14d-perhydro-2,3a,7b,9,10a,14b-hexaazadibenzotetracenes have been developed. The structures were established by 1D (1H, 13C) and 2D (COSY, HSQC, HMBC) NMR spectroscopy, MALDI TOF/TOF mass spectrometry, and X-ray diffraction analysis. Primary screening of the synthesized perhydro hexaazadibenzotetracenes for antitumor activity was carried out.

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cAMP-specific phosphodiesterases 8A and 8B, essential regulators of Leydig cell steroidogenesis.

Project description:Phosphodiesterase (PDE) 8A and PDE8B are high-affinity, cAMP-specific phosphodiesterases that are highly expressed in Leydig cells. PDE8A is largely associated with mitochondria, whereas PDE8B is broadly distributed in the cytosol. We used a new, PDE8-selective inhibitor, PF-04957325, and genetically ablated PDE8A(-/-), PDE8B(-/-) and PDE8A(-/-)/B(-/-) mice to determine roles for these PDEs in the regulation of testosterone production. PF-04957325 treatment of WT Leydig cells or MA10 cells increased steroid production but had no effect in PDE8A (-/-)/B(-/-) double-knockout cells, confirming the selectivity of the drug. Moreover, under basal conditions, cotreatment with PF-04957325 plus rolipram, a PDE4-selective inhibitor, synergistically potentiated steroid production. These results suggest that the pool(s) of cAMP regulating androgen production are controlled by PDE8s working in conjunction with PDE4. Likewise, PDE8A (-/-)/B(-/-) cells had higher testosterone production than cells from either PDE8A(-/-) or PDE8B(-/-) mice, suggesting that both PDE8s work in concert to regulate steroid production. We further demonstrate that combined inhibition of PDE8s and PDE4 greatly increased PKA activity including phosphorylation of cholesterol-ester hydrolase (CEH)/hormone-sensitive lipase (HSL). CEH/HSL phosphorylation also was increased in PDE8A(-/-)/B(-/-) cells compared with WT cells. Finally, combined inhibition of PDE8s and PDE4 increased the expression of steroidogenic acute regulatory (StAR) protein. Together these findings suggest that both PDE8A and PDE8B play essential roles to maintain low cAMP levels, thereby suppressing resting steroidogenesis by keeping CEH/HSL inactive and StAR protein expression low. They also suggest that in order for PDE inhibitor therapy to be an effective stimulator of steroidogenesis, both PDE8 isozymes and PDE4 need to be simultaneously targeted.

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N-substituted cis-4a-(3-hydroxyphenyl)-8a-methyloctahydroisoquinolines are opioid receptor pure antagonists.

Project description:N-Substituted cis-4a-(3-hydroxyphenyl)-8a-methyloctahydroisoquinolines (6a-g) were designed and synthesized as conformationally constrained analogues of the trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine (4) class of opioid receptor pure antagonists. The methyloctahydroisoquinolines 6a-g can exist in conformations where the 3-hydroxyphenyl substituent is either axial or equatorial, similar to the (3-hydroxyphenyl)piperidines 4. The 3-hydroxyphenyl equatorial conformation is responsible for the antagonist activity observed in the (3-hydroxyphenyl)piperidine antagonists. Single-crystal X-ray analysis of 6a shows that the 3-hydroxyphenyl equatorial conformation is favored in the solid state. Molecular modeling studies also suggest that the equatorial conformation has lower potential energy relative to that of the axial conformation. Evaluation of 6a-g in the [(35)S]GTP-gamma-S in vitro functional assay showed that they were opioid receptor pure antagonists. N-[4a-(3-Hydroxyphenyl)-8a-methyl-2-(3-phenylpropyl)octahydroisoquinoline-6-yl]-3-(piperidin-1-yl)propionamide (6d) with a K(e) of 0.27 nM at the kappa opioid receptor with 154- and 46-fold selectivity relative to those of the micro and delta receptors, respectively, possessed the best combination of kappa potency and selectivity.

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cAMP-specific phosphodiesterase 8A and 8B isoforms are differentially expressed in human testis and Leydig cell tumor.

Project description:Cyclic adenosine monophosphate/Protein kinase A (cAMP/PKA) signaling pathway is the master regulator of endocrine tissue function. The level, compartmentalization and amplitude of cAMP response are finely regulated by phosphodiesterases (PDEs). PDE8 is responsible of cAMP hydrolysis and its expression has been characterized in all steroidogenic cell types in rodents including adrenal and Leydig cells in rodents however scarce data are currently available in humans. Here we demonstrate that human Leydig cells express both PDE8A and PDE8B isoforms. Interestingly, we found that the expression of PDE8B but not of PDE8A is increased in transformed Leydig cells (Leydig cell tumors-LCTs) compared to non-tumoral cells. Immunofluorescence analyses further reveals that PDE8A is also highly expressed in specific spermatogenic stages. While the protein is not detected in spermatogonia it accumulates nearby the forming acrosome, in the trans-Golgi apparatus of spermatocytes and spermatids and it follows the fate of this organelle in the later stages translocating to the caudal part of the cell. Taken together our findings suggest that 1) a specific pool(s) of cAMP is/are regulated by PDE8A during spermiogenesis pointing out a possible new role of this PDE8 isoform in key events governing the differentiation and maturation of human sperm and 2) PDE8B can be involved in Leydig cell transformation.

| S-EPMC9585345 | biostudies-literature

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