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(2S,3S,3aS,6S,7aR)-3-Hy-droxy-2-[(2R,3S*)-3-isopropyl-oxiran-2-yl]-3,6-dimethyl-3,3a,5,6,7,7a-hexa-hydro-1-benzofuran-4(2H)-one.

ABSTRACT: In the title compound, C(15)H(24)O(4), the six-membered ring shows a distorted chair conformation and the five-membered ring adopts an envelope conformation with the C atom bearing the methyl and OH groups as the flap. In the crystal, O-H?O hydrogen bonds link the mol-ecules into chains running along the a-axis direction.

SUBMITTER: Ding M

PROVIDER: S-EPMC3470321 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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(2S,3S,3aS,6S,7aR)-3-Hy-droxy-2-[(2R,3S*)-3-isopropyl-oxiran-2-yl]-3,6-dimethyl-3,3a,5,6,7,7a-hexa-hydro-1-benzofuran-4(2H)-one.

Ding Mingruo M Zhang Qiaoyin Q Chen Lei L Huang Nianyu N Wang Junzhi J

Acta crystallographica. Section E, Structure reports online 20120919 Pt 10

In the title compound, C(15)H(24)O(4), the six-membered ring shows a distorted chair conformation and the five-membered ring adopts an envelope conformation with the C atom bearing the methyl and OH groups as the flap. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into chains running along the a-axis direction. ...[more]

PMID: 23125734

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Project description:Enhancing stress resilience in at-risk populations could significantly reduce the incidence of stress-related psychiatric disorders. We have previously reported that the administration of (R,S)-ketamine prevents stress-induced depressive-like behavior in male mice, perhaps by altering α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPAR)-mediated transmission in hippocampal CA3. However, it is still unknown whether metabolites of (R,S)-ketamine can be prophylactic in both sexes. We administered (R,S)-ketamine or its metabolites (2R,6R)-hydroxynorketamine ((2R,6R)-HNK) and (2S,6S)-hydroxynorketamine ((2S,6S)-HNK) at various doses 1 week before one of a number of stressors in male and female 129S6/SvEv mice. Patch clamp electrophysiology was used to determine the effect of prophylactic drug administration on glutamatergic activity in CA3. To examine the interaction between ovarian hormones and stress resilience, female mice also underwent ovariectomy (OVX) surgery and a hormone replacement protocol prior to drug administration. (2S,6S)-HNK and (2R,6R)-HNK protected against distinct stress-induced behaviors in both sexes, with (2S,6S)-HNK attenuating learned fear in male mice, and (2R,6R)-HNK preventing stress-induced depressive-like behavior in both sexes. (R,S)-ketamine and (2R,6R)-HNK, but not (2S,6S)-HNK, attenuated large-amplitude AMPAR-mediated bursts in hippocampal CA3. All three compounds reduced N-methyl-D-aspartate receptor (NMDAR)-mediated currents 1 week after administration. Furthermore, ovarian-derived hormones were necessary for and sufficient to restore (R,S)-ketamine- and (2R,6R)-HNK-mediated prophylaxis in female mice. Our data provide further evidence that resilience-enhancing prophylactics may alter AMPAR-mediated glutamatergic transmission in CA3. Moreover, we show that prophylactics against stress-induced depressive-like behavior can be developed in a sex-specific manner and demonstrate that ovarian hormones are necessary for the prophylactic efficacy of (R,S)-ketamine and (2R,6R)-HNK in female mice.

Dataset Information

(2S,3S,3aS,6S,7aR)-3-Hy-droxy-2-[(2R,3S*)-3-isopropyl-oxiran-2-yl]-3,6-dimethyl-3,3a,5,6,7,7a-hexa-hydro-1-benzofuran-4(2H)-one.

Publications

(2S,3S,3aS,6S,7aR)-3-Hy-droxy-2-[(2R,3S*)-3-isopropyl-oxiran-2-yl]-3,6-dimethyl-3,3a,5,6,7,7a-hexa-hydro-1-benzofuran-4(2H)-one.

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Dataset Information

(2S*,3S*,3aS*,6S*,7aR*)-3-Hy-droxy-2-[(2R*,3S*)-3-isopropyl-oxiran-2-yl]-3,6-dimethyl-3,3a,5,6,7,7a-hexa-hydro-1-benzofuran-4(2H)-one.

Publications

(2S*,3S*,3aS*,6S*,7aR*)-3-Hy-droxy-2-[(2R*,3S*)-3-isopropyl-oxiran-2-yl]-3,6-dimethyl-3,3a,5,6,7,7a-hexa-hydro-1-benzofuran-4(2H)-one.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets

(2S,3S,3aS,6S,7aR)-3-Hy-droxy-2-[(2R,3S*)-3-isopropyl-oxiran-2-yl]-3,6-dimethyl-3,3a,5,6,7,7a-hexa-hydro-1-benzofuran-4(2H)-one.

(2S,3S,3aS,6S,7aR)-3-Hy-droxy-2-[(2R,3S*)-3-isopropyl-oxiran-2-yl]-3,6-dimethyl-3,3a,5,6,7,7a-hexa-hydro-1-benzofuran-4(2H)-one.