(+)-3-Oxoandrosta-1,4-diene-17β-carboxylic acid: catemeric hydrogen bonding in a steroidal keto acid

The title ketocarboxylic acid, synthesized from the anti‐inflammatory clocortolone pivalate, crystallizes as C21H23ClO4·C6H12O, with one molecule of steroid and one of 3,3‐dimethylbutanone per asymmetric unit. The carboxyl group is highly ordered and the steroid molecules form translational carboxyl‐to‐ketone hydrogen‐bonding catemers [O...O = 2.682 (3) Å and O—H...O = 158°] that utilize the 3‐ketone group, with one chain proceeding in the [110] direction and the other in the [10] direction. One close intermolecular C—H...O=C contact is present, which involves the solvent O atom, but neither it nor the Cl atom nor the 11‐ketone group play any role in the classical hydrogen bonding.

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“…For the A-ring geometry of a related steroid dienone, see: Thompson et al (1999). Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

“…The A-ring is highly planar (Thompson et al, 1999), with C10 only 0.095 (2) Å out of the average plane for all six ring atoms. The C6-C7 double bond plane (C5-C6-C7-C8) lies at a 13.27 (2)° dihedral angle to this average A-ring plane.…”

Section: S1 Commentmentioning

confidence: 99%

9α-Chloro-16α-methyl-3,11-dioxoandrosta-1,4,6-triene-17β-carboxylic acid pinacolone solvate: catemeric hydrogen bonding and pinacolone solvation in a steroidal diketo acid derived from a commercial glucocorticoid

et al. 2007

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“…This suggests a reason why it may be an inhibitor of human type 1 17β-dehydrogenase. The structures of the 8,14-isoestratriene 5, 18 quinestrol 6, 19 3α-hydroxy-5α-androstane-4,17-dione, 20 androst-4-ene-3,6,17trione, 21 3,17-dioxo-4-oxa-androstane-5α-carbaldehyde, 22 17oxo-17a-oxa-17a-homo-5α-androstane-3α,4β-diacetate 23 and 3-oxoandrosta-1,4-diene-17β-carboxylic acid 24 have been reported. The crystal structures of different polymorphic forms of the testosterone 5α-reductase inhibitor finasteride 7 have been described.…”

mentioning

confidence: 99%

Steroids: reactions and partial synthesis (1999)

Hanson

2001

Nat. Prod. Rep.

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Pregna-1,4,20-trien-3-one, a cytotoxic marine steroid from the marine soft coralNephtheasp.

2010

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The title compound, C21H28O, was isolated from the cytotoxic lipid extract of the Fidjian soft coral Nephthea sp. The steroid showed inhibitory activity to human colon adenocarcinoma SW480 cells (IC50 = 2.5 µg ml−1). The molecular structure indicates that the A ring is almost planar (r.m.s. deviation = 0.032 Å), the B and C rings adopt chair conformations and the five-membered D ring is a half-chair. The B/C and C/D ring junctions are trans-fused.

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(+)-3-Oxoandrosta-1,4-diene-17β-carboxylic acid: catemeric hydrogen bonding in a steroidal keto acid

Cited by 3 publications

References 6 publications

9α-Chloro-16α-methyl-3,11-dioxoandrosta-1,4,6-triene-17β-carboxylic acid pinacolone solvate: catemeric hydrogen bonding and pinacolone solvation in a steroidal diketo acid derived from a commercial glucocorticoid

9α-Chloro-16α-methyl-3,11-dioxoandrosta-1,4,6-triene-17β-carboxylic acid pinacolone solvate: catemeric hydrogen bonding and pinacolone solvation in a steroidal diketo acid derived from a commercial glucocorticoid

Steroids: reactions and partial synthesis (1999)

Pregna-1,4,20-trien-3-one, a cytotoxic marine steroid from the marine soft coralNephtheasp.

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