Preparation of 6-Methyl Steroids by the “Oxo Reaction”

Beal, P. F.; Rebenstorf, Melvin A.; Pike, J. E.

doi:10.1021/ja01514a054

Cited by 23 publications

(6 citation statements)

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“…Treatment of hydrocortisone (3) with lithium in liquid NH 3 led to a complex mixture. [4] This could be attributed to undesirable reactions on the hydroxyacetyl-carbinol residue at C17, which was thus protected with a robust bismethylenedioxy function to give compound 4. [5] Reduction of 4 with lithium in liquid NH 3 provided the desired 5a-H-3-one derivative 5 in good yield.…”

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confidence: 99%

Expeditious Synthesis of Hippuristanol and Congeners with Potent Antiproliferative Activities

Dang

Liu

et al. 2009

Chemistry A European J

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confidence: 99%

Expeditious Synthesis of Hippuristanol and Congeners with Potent Antiproliferative Activities

Dang

Liu

et al. 2009

Chemistry A European J

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“…Steroid 4a was obtained as a white solid: mp 180-182 °C (lit. 33 , s), 1.12 (3H, d, J ) 7.5 Hz), 1.07 (3H, s), 0.64 (3H, s); 13 C NMR (CDCl3) δ 213. 10, 209.38, 63.55, 56.38, 49.65, 44.43, 44.01, 41.75, 38.77, 37.32, 36.16, 35.05, 33.48, 32.60, 31.28, 30.76, 24.96, 24.25, 22.58, 22.14, 20.85, 13.19.…”

Section: Methodsmentioning

confidence: 99%

“…Steroid 6a was obtained as a white solid: mp 147-149 °C (lit. 33 mp 152-153 °C; lit. 34 mp 153-154 °C); IR (KBr) 2942, 1711, 1382, 1351 cm -1 ; 1 H NMR (CDCl3) δ 2.54 (1H, t, J ) 9.0 Hz), 2.12 (3H, s), 1.02 (3H, s), 0.81 (3H, d, J ) 6.6 Hz), 0.63 (3H, s); 13 Steroid 6b was obtained as a white solid: mp 102-104 °C (lit.…”

Section: Methodsmentioning

confidence: 99%

Neurosteroid Analogues. 10. The Effect of Methyl Group Substitution at the C-6 and C-7 Positions on the GABA Modulatory and Anesthetic Actions of (3α,5α)- and (3α,5β)-3-Hydroxypregnan-20-one

et al. 2005

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The planar 5alpha-reduced steroid (3alpha,5alpha)-3-hydroxypregnan-20-one and the nonplanar 5beta-reduced steroid (3alpha,5beta)-3-hydroxypregnan-20-one act at GABA(A) receptors to induce general anesthesia. The structural features of the binding sites for these anesthetic steroids on GABA(A) receptors have not been determined. To determine how structural modifications at the steroid C-6 and C-7 positions effect the actions of these anesthetic steroids, an axial or equatorial methyl group was introduced at these positions. The analogues were evaluated (1) in [(35)S]-tert-butylbicyclophosphorothionate binding experiments, (2) in electrophysiological experiments using rat alpha(1)beta(2)gamma(2L) GABA(A) receptors expressed in Xenopus laevis oocytes, and (3) as tadpole anesthetics. The effects of methyl group substitution in the 5alpha- and 5beta-reduced series of compounds were strikingly similar. In both series, a 6beta-Me group gave compounds with actions similar to or greater than those of the parent steroids. A 6alpha-, 7beta- or 7alpha-Me substituent resulted in reduced potency for inhibition of radioligand binding, GABA(A) receptor modulation and tadpole anesthesia. Because of the similar effects of methyl group substitution in the two series of compounds and previous results from other studies showing that structural modifications in the steroid D ring/side chain region produce similar effects regardless of the stereochemistry of the A,B-ring fusion, we propose that either the 3alpha-hydroxyl groups of planar and nonplanar anesthetic steroids hydrogen bond to different amino acids on GABA(A) receptors or that this critical hydrogen bonding group interacts with membrane lipids instead of the receptor.

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“…A utilização de complexos organometálicos na funcionalização de esteróides foi recentemente descrito por Kollar [35] num artigo de revisão, onde fi ca patente que a hidroformilação também permite introduzir um grupo formilo, num único passo e de forma diasterosselectiva, em duplas ligações internas de núcleos de esteróides. A primeira hidroformilação deste tipo de substratos foi descrita por Pike e Wender [36], nos anos 50, utilizando como catalisador o complexo [CoH(CO) 4 ] em quantidades estequiométricas e recorrendo a condições de reacção muito severas.…”

Section: Hidrofomilações Catalíticas Homogéneasunclassified

Complexos de Metais de Transição em Química Fina e Medicinal Aplicações na Indústria Farmacêutica

Pereira¹,

Moreno²

2010

BSPQuimica

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Preparation of 6-Methyl Steroids by the “Oxo Reaction”

Cited by 23 publications

References 0 publications

Expeditious Synthesis of Hippuristanol and Congeners with Potent Antiproliferative Activities

Expeditious Synthesis of Hippuristanol and Congeners with Potent Antiproliferative Activities

Neurosteroid Analogues. 10. The Effect of Methyl Group Substitution at the C-6 and C-7 Positions on the GABA Modulatory and Anesthetic Actions of (3α,5α)- and (3α,5β)-3-Hydroxypregnan-20-one

Complexos de Metais de Transição em Química Fina e Medicinal Aplicações na Indústria Farmacêutica

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