- Synthesis and cytotoxic activity of some novel steroidal C-17 pyrazolinyl derivatives
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Fourteen novel steroidal C-17 pyrazolinyl derivatives 9a-g and 10a-g were synthesized from commercially available progesterone and tested for their cytotoxic activity against brine shrimp (Artemia salina) and three human cancer cell lines (NCI-H460, HeLa, and HepG2). Some of these synthetic compounds exhibited significant cytotoxic activity, and treatment of HeLa cells with compound 10b resulted in the cell population arrest in the S phase. A structure-activity relationship was discussed.
- Fan, Ning-Juan,Tang, Jiang-Jiang,Li, He,Li, Xiao-Jun,Luo, Bo,Gao, Jin-Ming
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- Synthesis of novel 4′-acylamino modified 21E-benzylidene steroidal derivatives and their cytotoxic activities
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A series of 4′-acylamino modified Δ1,4-pregnadien-21E-benzylidene-3,20-dione derivatives (6a–v) was synthesized from the commercially available progesterone (1). These title compounds were evaluated for their toxicity against brine shrimp (Arte
- Fan, Ning-Juan,Han, Yang-Yang,Li, Yuan-Feng,Gao, Jin-Ming,Tang, Jiang-Jiang
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- ENABLING CHOLESTEROL CATABOLISM IN HUMAN CELLS
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Compositions, methods, and systems for modifying sterol metabolism in a subject is disclosed. In some embodiments, the subjects may be administered one or more mammalian cells modified to express at least one sterol degrading enzyme derived from a bacterium. In many embodiments, the cell is a macrophage or monocyte stably expressing three or more enzymes that aid in opening the β ring of cholesterol. The disclosed compositions and methods may be useful in lowering cholesterol levels in a subject in need thereof. In some embodiments, the subject may have a genetic predisposition to atherosclerosis.
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Paragraph 0029; 0039; 0041; 0054; 0060
(2020/07/05)
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- Synthesis of steroidal [1,2,4]triazolo[1,5-a]pyrimidines and their antiproliferative activities
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— A facile strategy for the synthesis of steroidal [1,2,4]triazolo[1,5-a]pyrimidines 5a-g and 6a-g has been accomplished via a one-pot reaction of steroidal ketones, aromatic aldehydes and 3-amino-1,2,4-triazole in the presence of potassium tert-butoxide in refluxing tert-butanol. All the synthesized heterosteroids were evaluated for in vitro antiproliferative activity against human cancer cells by sulforhodamine B (SRB) assays. The preliminary results showed that compounds 6a and 6e possessed potent antiproliferative activities.
- Fan, Ning-Juan,Tang, Jiang-Jiang,Li, Yuan-Feng,Bai, Yu-Bin,Zhao, Xiao-Min
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p. 822 - 831
(2019/08/01)
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- PROCESS FOR PREPARATION OF DYDROGESTERONE
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The present invention relates to process for the preparation of dydrogesterone.
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Paragraph 0079; 0088
(2018/09/08)
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- Potential insecticidal activity of steroidal U-17 pyrazolinyl derivatives
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Agrochemical research, over the last two decades, has resulted in the discovery of chemically novel insecticides, of which steroids-based compounds that mimic the action of hormones have been considered as safe insecticides. In this study, eight steroidal C-17 pyrazolinyl derivatives were resynthesized through molecular hybridization and their insecticidal activities against 4th instar larvae of Mythimna separate were evaluated. These results showed that some compounds exhibited significant insecticidal activities and the susceptibility assays were expressed as the median lethal dose (LD50), of which one of the compounds exerted the most potent insecticidal activity (LD50 = 296 μg g-1), comparable to that of the natural product insecticide, celangulatin V (LD50 = 260 μg g-1). This strategy led to a promising candidate for the development of new steroidal insecticidal agents.
- Fan, Ning-Juan,Wei, Shao-Peng,Gao, Jin-Ming,Tang, Jiang-Jiang
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p. 389 - 392
(2015/02/19)
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- Synthesis and cytotoxicity of some novel 21E-benzylidene steroidal derivatives
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A series of novel derivatives of 21E-benzylidene-pregn-1,4-diene-3,20-dione 7a-g and 21E-benzylidene-4-chloro-pregn-1,4-diene-3,20-dione 8a-g was synthesized from the commercially available progesterone. These title compounds were evaluated for their cyto
- Fan, Ning-Juan,Bai, Yu-Bin,Zhang, Fei-Yu,Luo, Bo,Tang, Jiang-Jiang,Zhang, Qiang-Zhe,Gao, Jin-Ming
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p. 874 - 879
(2013/10/21)
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- A practical Δ1-dehydrogenation of Δ4-3-keto-steroids with DDQ in the presence of TBDMSCl at room temperature
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A mild and efficient Δ1-dehydrogenation of Δ4-3-keto-steroids with DDQ in the presence of tertbutyldimethylchlorosilane at room temperature was developed.
- Chen, Kaixiong,Liu, Chang,Deng, Le,Xu, Guangyu
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experimental part
p. 513 - 516
(2010/06/21)
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- Synthesis of [3H2]-21-diazoprogesterone as a potent photoaffinity labelling reagent for the mineralocorticoid receptor
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[3H2]-21-Diazoprogesterone ([3H2]21DP), a potent photoaffinity labelling reagent, has been synthesized in four steps from progesterone. Tritium has been introduced by homogeneous tritiation with Wilkinson's catalyst.
- Fagart, Jerome,Sobrio, Franck,Marquet, Andree
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p. 791 - 795
(2007/10/03)
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- Novel catalytic activity of immobilized spores under reduced water activity
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Onset of a new catalytic function during transformation of progesterone by immobilized spores of Aspergillus ochraceus TS under reduced water activity is reported. The pathway of transformation, which furnished 1,4-androstadien-17β-ol-3-one and 1,4-androstadien-3,17-dione due to cleavage of C17-C20 bond, is different from normal reaction sequence.
- Dutta, Tapan K.,Samanta, Timir B.
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p. 629 - 632
(2007/10/03)
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- Selective 1-Dehydrogenation of Progesterone by Aspergillus fumigatus
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Fermentation of progesterone with acetone-dried cells of Aspergillus fumigatus in the presence of β-cyclodextrin yields pregna-1,4-diene-3,20-dione as the single isolable product.
- Garai, Subhadra,Banerjee, Sukdeb,Mahato, Shashi B.
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p. 408 - 409
(2007/10/03)
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- Sodium-retaining activity of some natural and synthetic 21-deoxysteroids
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The effect of progesterone and six other C21 -deoxysteroids on renal sodium retention by male adrenaleotomized rats was compared with the effect exerted by the natural corticoids aldosterone, 11-deoxycorticosterone, and corticosterone. Steroids were active in the following order: aldosterone > 11,19-oxidoprogesterone > 5αH-3,20-pregnanedione ≥ 5βH-3,20-pregnanedione > progesterone = 11-ketoprogesterone > 6,19-oxidoprogesterone = 11-keto- 6,19-oxidoprogesterone ≥ corticosterone. All C21-deoxysteroids, except 11,19-oxidoprogesterone, exhibited parabolic log dose-response functions, indicating an effect that opposes renal sodium retention at high doses. 11,19-Oxidoprogesterone and the natural corticoids exhibited normal, exponential, log dose-response curves. Diverse geometric parameters related to molecular planarity were calculated and their correlation with biopharmacological properties was attempted. The best linear regression was obtained for correlation of the concavity of log dose-response parabolas (second-order coefficients) of C21-deoxysteroids with the C3=O/ring D angle of these molecules. A good linear regression could also be obtained for correlation of the affinity of C21-deoxysteroids, except 11,19- oxidoprogesterone, for purified type I mineralocorticoid receptors with those angles. The latter correlation deteriorated upon incorporation of the affinity data for the three natural corticoids, due to similar affinities of these hormones for type I mineralocorticoid receptors, but could be restored when the binding data for the unpurified, corticosterone-binding globulin- containing stage of the receptors were considered. In vivo binding data followed the same trend as that for unpurified receptors.
- Burton,Galigniana,De Lavallaz,Brachet-Cota,Sproviero,Ghini,Lantos,Damasco
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p. 535 - 543
(2007/10/03)
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- Synthesis of 20-Carbaldehydes and 20-Carbonitriles of the Pregnane Series Starting with (20S)-20-Hydroxymethylpregna-1,4-dien-3-one
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An efficient six-step approach to 3-protected (20S)-3β-hydroxypregna-1,5-diene-20-carbaldehydes 8 with potential importance in the synthesis of vitamin D analogues was developed starting with (20S)-20-hydroxymethylpregna-1,4-dien-3-one (1).Oxidation of the 22-hydroxy group of 1 by means of periodinane 2 (Dess-Martin reagent) furnished the aldehyde 3 without epimerization. 3 was protected selectively at C-22 as dimethyl acetal 5.Isomerization to 6 and subsequent reduction of the 3-carbonyl group with calcium borohydride furnished the 3β-alcohol 7a with high stereoselectivity.Cleavage of the acetal to 8a occurred in a homogeneous solution of acetic acid in the presence of small amounts of water and trifluoroacetic acid.After protection of the 3-OH group 8b-d were obtained in 54percent overall yield.The in situ generated aldehyde N,N-dimethylhydrazones of 3, 8a, and 8b were converted in high yields with excellent chemoselectivity into the nitriles 12, 15a, and 15b with magnesium monoperoxyphthalate hexahydrate.The uniform (20S) stereochemistry of 3 and 8a-d was elucidated by 1H-NMR investigations. - Key Words: Pregnanes / Steroids
- Krieg, Reimar,Schoenecker, Bruno
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p. 1025 - 1032
(2007/10/02)
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- Process for the preparation of steroids bearing 17α-hydroxy-20-oxopregnane side chain
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The invention relates to a novel process for the preparation of 17 α-hydroxy-20-oxopregnane derivatives of the general formula (I), STR1 wherein R1 means a hydroxy or an oxo group; and the dotted lines optionally represent one or more additional valence bond(s), with the proviso that the dotted line in the 4-position and the dotted line in the 5-position cannot each simultaneously be an additional valence bond from steroids having 23,24-dinor-17(20)-dehydrocholan-22-oic -22-oic acid structure. According to the process of the invention a steroid derivative having 23,24-dinorcholan-22-oic acid structure, containing a double bond in 17(20)-position, is transformed to 17α, 20-epoxy-23,24-dinorcholanoic acid, the latter is converted to a reactive acid derivative, which is then reacted with a salt-containing azide ion to yield a 17α, 20-epoxy-23,24-dinorcholanoic acyl azide derivative and the azide obtained is reacted with a mineral or organic acid in an aqueous medium.
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- Functionalisation of Saturated Hydrocarbons. Part 7. On the Mechanism of the Degradation of the Cholesterol Side-chain to 20-Ketone by Oxidation with the Gif System
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The oxidation by the Gif system of the two dienones (3) and (15) which lack a 25-H still affords minor amounts of the 20-ketone (12).This indicates that there are two mechanisms for the degradation of the cholesterol side-chain, the major route as previou
- Barton, Derek H. R.,Boivin, Jean,Crich, David,Hill, Christopher H.
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p. 1805 - 1808
(2007/10/02)
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- Functionalisation of Saturated Hydrocarbons. Part 6. Selective Oxidation of Steroids and Related Compounds
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The oxidation of a series of steroids by the Gif system gives, almost without exception, the 20-ketone as major isolated product.The side-chain cleavage is made more selective by modification of rings A or B.The oxidation of oleana-1,12-diene-3,11-dione has also been studied and the two principal products have been identified.
- Barton, Derek H. R.,Boivin, Jean,Hill, Christopher H.
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p. 1797 - 1804
(2007/10/02)
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- Samarium Di-iodide: A Useful Electron Donor in Organic Synthesis
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Samarium di-iodide selectively cleaves the 2-chloroethyl carbamate (1), and fragments the 11α-steroidal xanthate (3), where other reducing reagents fail.
- Ananthanarayan, T. P.,Gallagher, Timothy,Magnus, Philip
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p. 709 - 710
(2007/10/02)
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- Direct Formation of the Steroid Nucleus by a Biomimetic Cyclization
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The aim of this study was to synthesize the trienynol 3 and to study its cyclization.The substrate was synthesized by a convergent route, the key step being the stereoselective Wittig-Schlosser condensation of the known aldehyde 19 with the phosphorane 18
- Johnson, William S.,McCarry, Brian E.,Markezich, R. L.,Boots, Sharon G.
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p. 352 - 359
(2007/10/02)
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