CN103214542A - B-nor-6-(4'-alkyl) aminothizone cholestane compound, and preparation method and application thereof in anticancer drugs - Google Patents
B-nor-6-(4'-alkyl) aminothizone cholestane compound, and preparation method and application thereof in anticancer drugs Download PDFInfo
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- CN103214542A CN103214542A CN2013101359619A CN201310135961A CN103214542A CN 103214542 A CN103214542 A CN 103214542A CN 2013101359619 A CN2013101359619 A CN 2013101359619A CN 201310135961 A CN201310135961 A CN 201310135961A CN 103214542 A CN103214542 A CN 103214542A
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Abstract
The invention discloses a B-nor-6-(4'-alkyl) aminothizone cholestane compound, which has a chemical formula shown in the specification. The B-nor-6-(4'-alkyl) aminothizone cholestane compound disclosed by the invention is prepared from cholesterol by using the chemical methods such as functional group protection, ozonation, cyclization, condensation, deprotection, oxidation and addition. Experiments prove that the B-nor-6-(4'-alkyl) aminothizone cholestane compound disclosed by the invention has an obvious inhibitory effect on various tumor cells, and can be applied to the preparation of drugs for treating cancers.
Description
One, technical field
The present invention relates to a class B-falls-6-(4 '-alkyl) contract ammonia sulphur hydrazone cholestane compound and synthetic method and the application in the preparation antitumor drug.
Two, background technology
Cancer is a kind of malignant tumour, is one of disease to human health and quality of life harm maximum.Seeking efficient, highly selective and the little antitumor drug of side effect is the main direction of medicament research and development.
In antitumor drug, the medicine Finasteride that is used for the treatment of hyperplasia of prostate that Merck in 1992 lists a company belongs to the steroidal amides.In recent years in the research of antitumor drug, there are some to have the report that steroidal compounds falls in B-, for example compound Orostanal can inducing leukemia HL-60 apoptosis (Tomofumi Miyamoto, Kota Kodama, Yuko Aramaki, Ryuichi Higuchi, Rob W.M.Van Soest, Orostanal, a novel abeo-sterol inducing apoptosis in leukemia cell from a marine sponge, Stelletta hiwasaensis, Tetrahedron Letters2001 (42): 6349-6351; Bo Liu, Wei-Shan Zhou, The first stereoselective synthesis of orostanal isolated from a marine sponge Stelletta hiwasaenis, Tetrahedron, 2003 (59): 3379-3384), some above-mentioned compound growing multiplication to some tumour cell in external or body has remarkable restraining effect.
We once provided application for a patent for invention (Chinese invention patent, the application number: 200810073497.4 of a class " 3,6-di-substituted sterides oxime compounds is as antitumor drug "; Publication number: CN101245090A), the while also has been relevant report (Jianguo Cui, Liliang Huang, Lei Fan, Aimin Zhou, Steroids, 2008,73 (3): 252 – 256; Jian-Guo Cui, Lei Fan, Li-Liang Huang, Hong-Li Liu, Ai-Min Zhou.Steroids, 2009,74 (1), 62-72; Jianguo Cui, Lei Fan, Yanmin Huang, Yi Xin, Aimin Zhou, Steroids.2009,74 (12), 989-995).In addition, we also provide the patent of invention (Chinese invention patent of a class " 6-replacement-4-azepine-A-homo-3-oxo steroidal compounds and the application in the preparation antitumor drug thereof ", the patent No.: ZL201010107528.0) and application for a patent for invention (Chinese patent, the application number: 201110009124.2.) of another kind of " 3-replacements-B-Homo-steroidal-B-cyclic lactam compound and preparation method thereof and the application in preparing antitumor drug ".Simultaneously, we have obtained one " B-falls-3; 6-two replaces cholestane compound and preparation method thereof and the application in the preparation antitumor drug " and have authorized (the patent No.: ZL20111079146.3), and delivered relevant report (Chunfang Gan, Lianghua Fan, Jianguo Cui, Yanmin Huang, Yanxiao Jiao, Wanxin Wei, Synthesis of novel ring B abeo-sterol derivatives and their antiproliferative activities.Steroids, 2012 (77): 1061-1068; Gan Chunfang, Li Weiyu, woods Kai good fortune, the synthetic of androstane and anti-tumor activity research, chemical reagent, 2013 (35): 218-222) fall in Huang Yanmin, Cui Jianguo, B-.
Three, summary of the invention
The purpose of this invention is to provide a class B-falls-6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound that contracts, the synthetic method of this compounds and the application in preparation treatment antitumor drug thereof.
B-of the present invention falls-6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound that contracts, have following structural:
The per-cent % of indication of the present invention unless otherwise indicated is mass percent %.
B-of the present invention falls-6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound that contracts, from cholesterol, through protective group, ozonize, cyclisation, condensation, go to protect, the chemical process of oxidation, addition is transformed.
Preparing B-of the present invention falls-and the reaction formula of following some compound in 6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound that contracts is as follows:
B-falls-the preparation route of 6-(4 '-the alkyl)-ammonia sulphur hydrazone cholestane compound that contracts
13%K
2CO
3Be meant that mass percent is 13% the aqueous solution
Showing by vitro inhibition growth of cancer cells proliferation activity test, B-of the present invention falls-and 6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound that contracts has significant inhibitory effect to cancer cell strains such as various tumor cell strains such as liver cancer, cancer of the stomach, nasopharyngeal carcinoma.Therefore, B-of the present invention fall-6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound that contracts can be used for preparing the medicine for the treatment of cancer.
The present invention also provides a kind of anti-tumor drug that is used for, and it contains above-mentioned B-and falls-6-(4 '-alkyl) ammonia sulphur hydrazone cholestane compound and pharmaceutically acceptable auxiliary contract.This medicine can be made the form of injection, tablet, pill, capsule, suspension agent or emulsion and use, and its route of administration can be oral, or through subcutaneous, vein or intramuscular injection.
Four, embodiment
The invention will be further described by the following examples.
Embodiment 1
The preparation method of intermediate product
Intermediate product (1)
Take by weighing 5.018g, the cholesterol of 13mmol is dissolved in the 40mL pyridine, after the dissolving fully, slowly drips the 4.0mL diacetyl oxide, after diacetyl oxide adds, continues to stir 0.5 hour, then reactant is left standstill 24h under room temperature.Adding distil water 15mL with 10mL * 3 ethyl acetate extractions, uses 1mol.L respectively again
-1Dilute hydrochloric acid is washed, saturated NaHCO
3Solution 10mL washes 1 time, and washing 10mL * 3 are washed to neutrality with saturated common salt at last.Anhydrous sodium sulfate drying filters, and decompression steams solvent, when relatively large solid is separated out, stops distillation, and the solid that heating for dissolving is separated out leaves standstill and allows it separate out crystallization.Obtain white plates crystal 15.308g after suction filtration and the drying, productive rate 96%.Product structure is analyzed definite through IR, NMR and MS.
Intermediate product (2)
Take by weighing 110mg intermediate product 1 and pack in the reaction flask, add 16mL methylene dichloride and 4mL methyl alcohol.Place the ethyl acetate vacuum flask of cooled with liquid nitrogen, when treating that system temperature is cooled to-78 ℃, feed and be rich in O
3Oxygen Flow, after reaction is finished, add the 2mL dimethyl sulphide, be warming up to stirred overnight at room temperature.Decompression extracts most of solvent and obtains oily matter, and this oily matter adds the layering of 10mL distilled water with the dissolving of 50mL methylene dichloride, tells the organic layer anhydrous sodium sulfate drying.Decompression extracts solvent, obtains water white oily matter, drying.Use V
Sherwood oil: V
Ethyl acetateThe eluent rapid column chromatography of=4:1 separates, and obtains oily compound 2108mg, productive rate 91%.Product structure is analyzed definite through IR, NMR and MS.
Intermediate product (3)
Take by weighing 478mg intermediate product 2 in the 100mL round-bottomed flask, add 22mL benzene and 4.78g neutral alumina, stirring reaction 24h under the room temperature does not have stopped reaction behind the raw material, in this mixture impouring silica gel short column, with a large amount of CH
2Cl
2Flushing until no product point, extracts solvent and obtains transparent oily matter 445mg.The silica gel column chromatography separation obtains white solid compound 3377mg, productive rate 85%.Product structure is analyzed definite through IR, NMR and MS.
Embodiment 2
B-falls-preparation of 6-(4 '-the alkyl)-ammonia sulphur hydrazone cholestane compound that contracts
B-falls-3 beta-acetoxyl group-5s-hydroxyl-courage steroid-6-(4 '-methyl) ammonia sulphur hydrazone (1) contracts
Take by weighing 246mg, the intermediate product 3 of 0.534mmol is dissolved in the 60mL dehydrated alcohol, splashes into 2mL Glacial acetic acid control pH value of solution ≈ 4, disposable adding 56mg, and the 4-methyl thiosemicarbazide of 0.533mmol, V is used in reaction in 60 ℃ of oil baths are stirred
Ethyl acetate: V
Sherwood oil=1:2 developping agent carries out TLC and follows the tracks of reaction, and no raw material point is a stopped reaction behind about 2h.Decompression extracts solvent and obtains the white solid mixture.Add distilled water,, merge organic layer, respectively wash 1 time the organic layer anhydrous sodium sulfate drying respectively with saturated aqueous common salt 10mL, saturated sodium bicarbonate solution 10mL with ethyl acetate 20mL * 3 extractions.Filter, decompression extracts solvent, obtains the yellow oily mixture.Mixture adopts 300-400 order silica gel to carry out column chromatography for separation, eluent: V
Ethyl acetate: V
Sherwood oil=1:2 obtains compound 1222mg, productive rate: 75.9%, and m.p.:89-92 ℃.The spectroscopic data of compound 5: IR (KBr) v/cm
-1: 3432,2950,2860,2350,1720,1634,1552,1462,1377,1254,1176,1070;
1H NMR (CDCl
3, 300MHz) δ: 9.873 (1H, s, NH), 7.360 (1H, q, J=4.5Hz, NHCH
3), 7.176 (1H, d, J=7.5Hz, C
6-H), 4.25-4.13 (1H, m, C
3-H), 3.112 (3H, d, J=4.5Hz, CH
3NH), 0.944 (3H, s, 19-CH
3), 0.910 (3H, d, J=5.4Hz, 21-CH
3), 0.861 (3H, d, J=6.6Hz, 26or27CH
3), 0.858 (3H, d, J=6.6Hz, 26or27CH
3), 0.670 (3H, s, 18-CH
3);
13C NMR (CDCl
3, 75MHz) δ: 178.1 (C=S), 178.0 (3-C=O), 148.3 (6-C), 83.1 (5-C), 70.1 (3-C), 56.7 (7-C), 55.9 (14-C), 55.4 (17-C), 53.0 (9-C), 45.1 (13-C), 44.6 (10-C), 42.8 (8-C), 40.5 (12-C), 39.6 (24-C), 39.4 (22-C), 36.2 (30-C), 35.6 (4-C), 31.0 (20-C), 30.5 (1-C), 28.5 (16-C), 28.0 (25-C), 24.9 (2-C), 23.8 (15-C), 22.8 (23-C), 22.5 (27-C), 21.7 (26-C), 21.5 (11-C), 19.5 (3-CH
3), 18.8 (21-C), 18.3 (19-C), 12.4 (18-C); HREIMS m/z:548.3890[M+H]
+, (calcd.for C
31H
54N
3O
3S, 548.3886).
-3 β fall in B-, 5 beta-dihydroxyies-courage steroid-6-(4 '-methyl) ammonia sulphur hydrazone (2) contracts
(174mg 0.318mmol) uses 30mL CH to take by weighing compound 1
3After the OH dissolving, add 13%K
2CO
3Solution 4mL, stirring reaction 1h does not have raw material point stopped reaction under the room temperature, uses V
Ethyl acetate: V
Sherwood oilThe developping agent of=1:2 carries out TLC and follows the tracks of reaction, adds a small amount of distilled water after the removal of solvent under reduced pressure, with ethyl acetate 20mL * 3 extractions, merges organic layer, respectively washes 1 time anhydrous sodium sulfate drying respectively with saturated aqueous common salt 10mL, saturated sodium bicarbonate solution 10mL.Obtain the yellow oily mixture except that after desolvating.Adopt 300-400 order silica gel to carry out column chromatography for separation, eluent: V
Ethyl acetate: V
Sherwood oil=1:2 obtains compound 690.1mg, productive rate: 56.1%, and m.p.:103-106 ℃.The spectroscopic data of compound 2: IR (KBr) v/cm
-1: 3375,2946,2864,1552,1462,1377,1328,1258,1181,1070,1017,939;
1H NMR (CDCl
3, 300MHz) δ: 9.225 (1H, s, NH), 7.394 (1H, q, J=4.5Hz, NHCH
3), 7.102 (1H, d, J=7.8Hz, C
6-H), 5.14-5.02 (1H, m, C
3-H), 3.186 (3H, d, J=4.8Hz, CH
3NH), 0.903 (3H, s, 19-CH
3), 0.894 (3H, d, J=6.3Hz, 21-CH
3), 0.847 (3H, d, J=6.6Hz, 26or27CH
3), 0.844 (3H, d, J=6.6Hz, 26or27CH
3), 0.662 (3H, s, 18-CH
3);
13C NMR (CDCl
3, 75MHz) δ: 177.5 (C=S), 149.4 (6-C), 84.4 (5-C), 67.1 (3-C), 56.4 (7-C), 56.2 (14-C), 55.1 (17-C), 51.7 (9-C), 45.3 (13-C), 44.7 (10-C), 43.6 (8-C), 43.0 (12-C), 39.7 (24-C), 39.5 (22-C), 36.2 (30-C), 35.6 (4-C), 30.9 (20-C), 28.5 (1-C), 28.1 (16-C), 28.0 (25-C), 27.3 (2-C), 24.5 (15-C), 23.8 (23-C), 22.8 (27-C), 22.5 (26-C), 21.6 (11-C), 18.8 (21-C), 18.6 (19-C), 12.5 (18-C); HREIMS m/z:506.3781[M+H]
+, (calcd.for C
29H
52N
3O
2S, 506.3780).
B-falls-3 beta-acetoxyl group-5s-hydroxyl-courage steroid-6-(4 '-ethyl)-ammonia sulphur hydrazone (3) contracts
Take by weighing 282mg, the intermediate product 3 of 0.613mmol is dissolved in the 75mL dehydrated alcohol, splashes into 2mL Glacial acetic acid control pH value of solution ≈ 4, disposable adding 75mg, and the 4-ethylenebis dithiocarbamate Urea,amino-of 0.622mmol, V is used in reaction in 60 ℃ of oil baths are stirred
Ethyl acetate: V
Sherwood oilThe developping agent of=1:2 carries out TLC and follows the tracks of reaction, and no raw material point is a stopped reaction behind about 1.5h.Decompression extracts solvent and obtains the yellow oily mixture, adds a small amount of distilled water, with ethyl acetate 20mL * 3 extractions, merges organic layer, respectively washes 1 time the organic layer anhydrous sodium sulfate drying respectively with saturated aqueous common salt 10mL, saturated sodium bicarbonate solution 10mL.Filter, decompression extracts solvent, obtains the yellow oily mixture.Mixture adopts 300-400 order silica gel to carry out column chromatography for separation, eluent: V
Ethyl acetate: V
Sherwood oil=1:4 obtains compound 3265mg, productive rate: 77.0%; M.p.:79-83 ℃.The spectroscopic data of compound 7: IR (KBr) v/cm
-1: 3456,3367,2950,2860,1732,1638,1458,1376,1360,1311,1176,1091,1066,1008,931,796,632;
1H NMR (CDCl
3, 300MHz) δ: 9.394 (1H, s, NH); 7.318 (1H, t, J=5.4Hz, NHCH
2), 7.122 (1H, d, J=7.5Hz, C
6-H), 4.97-5.16 (1H, m, C
3-H), 3.58-3.70 (2H, m, 4 '-CH
2), 2.038 (3H, s, 3-CH
3), 0.902 (1H, t, J=6.6Hz, 4 '-CH
3), 0.926 (3H, s, 19-CH
3), 0.891 (3H, d, J=6.6Hz, 21-CH
3), 0.841 (3H, d, J=6.6Hz, 26or27CH
3), 0.838 (3H, d, J=6.6Hz, 26or27CH
3), 0.652 (3H, s, 18-CH
3); .
13C NMR (CDCl
3, 75MHz) δ: 176.9 (C=S), 170.2 (3-C=O), 148.4 (C=N), 83.05 (4-C), 69.9 (3-C), 56.1 (7-C), 55.8 (14-C), 55.4 (17-C), 55.8 (9-C), 45.1 (10-C), 44.5 (8-C), 42.7 (13-C), 40.5 (4 '-CH
2), 39.6 (24-C), 39.4 (12-C), 39.2 (4-C), 36.2 (22-C), 35.6 (20-C), 30.4 (1-C), 28.5 (25-C), 28.0 (2-C), 24.9 (16-C), 23.8 (15-C), 22.8 (23-C), 22.5 (11-C), 21.7 (26and27-C), 21.5 (3-CH
3), 18.7 (21-C), 18.4 (18-C), 14.4 (4 '-CH
3), 12.4 (19-C); HREIMS m/z:562.4085[M+H]
+, (calcd.for C
32H
56N
3O
3S, 562.4042).
-3 β fall in B-, 5 beta-dihydroxyies-6-courage steroid-6-(4 '-ethyl) ammonia sulphur hydrazone (4) contracts
Raw material is a compound 3, and synthetic method is similar to compound 4, the productive rate of compound 4: 77.5%, and m.p.:103-106 ℃.The spectroscopic data of compound 8: IR (KBr) v/cm
-1: 3367,2942,2856,1630,1548,1471,1389,1225,1307,1078,1008,943,866,800;
1H NMR (CDCl
3, 300MHz) δ: 9.608 (1H, s, NH), 7.274 (1H, t, J=5.4Hz, NHCH
2), 7.207 (1H, d, J=7.5Hz, C
6-H), 4.13-4.30 (1H, m, C
3-H), 3.53-3.78 (2H, m, 4 '-CH
2), 0.923 (3H, s, 19-CH
3), 0.916 (3H, d, J=5.2,21-CH
3), 0.902 (1H, t, J=6.6Hz, 4 '-CH
3), 0.870 (3H, d, J=6.6Hz, 26or27CH
3), 0.866 (3H, d, J=6.6Hz, 26or27CH
3), 0.686 (3H, s, 18-CH
3);
13CNMR (CDCl
3, 75MHz) δ: 176.6 (C=S), 149.3 (C=N), 84.1 (4-C), 67.2 (3-C), 56.2 (7-C), 55.5 (14-C), 52.0 (17-C), 45.4 (9-C), 44.7 (10-C), 43.5 (8-C), 42.8 (13-C), 39.7 (4 '-CH
2), 39.5 (24-C), 39.2 (12-C), 36.2 (4-C), 35.6 (22-C), 28.5 (20-C), 28.2 (1-C), 28.0 (25-C), 27.5 (2-C), 24.6 (16-C), 23.8 (15-C), 22.8 (23-C), 22.6 (11-C), 21.6 (26and27-C), 18.8 (21-C), 18.5 (18-C), 14.5 (4 '-CH
3), 12.5 (19-C).
Embodiment 3
Present embodiment be adopt B-of the present invention fall-6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound that contracts suppresses the test result of growth of tumour cell proliferation activity test to some tumour cell.
Select part B-of the present invention fall-6-(4 '-alkyl) contract ammonia sulphur hydrazone cholestane compound test its to human hepatoma cell strain Bel7404, human nasopharyngeal epithelioma 1 CNE, the inhibition growing multiplication effect of stomach cancer cell line SGC7901.Adopt the MTT method, carry out vitro cytotoxicity and measure.The B-that adds different concns in 96 orifice plates in the logarithmic phase cell of cultivating falls-6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound that contracts, carry out 3 parallel tests simultaneously, compare with control group.Cultivate after 72 hours, add MTT, measure its absorbancy, calculate the inhibition growth of tumour cell respectively and breed to 50% o'clock compound concentrations, with IC
50Value representation, the result is as shown in table 1:
Table 1 B-falls-6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound anti tumor activity in vitro test result that contracts (MTT method, IC
50, μ mol/L)
Listed compound is to human hepatoma cell, cervical cancer cell, the inhibiting IC of stomach cancer cell from table 1
50Value as can be seen, B-of the present invention falls-6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound that contracts has the good restraining effect to these three kinds of tumour cells, as the inhibition IC of 6 couples of human hepatoma cell strain Bel7404 of compound
50Value is 4.0 μ mol/L, to the inhibition IC of human nasopharyngeal epithelioma 1 CNE
50Value is 9.9 μ mol/L.
Claims (4)
1. a class B-falls-6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound that contracts, and it is characterized in that this compound chemical structure formula is as follows:
2. the described B-of claim 1 falls-preparation method of 6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound that contracts, and it is characterized in that, and B-falls-and the preparation route of 6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound that contracts is as follows:
。
3. B-falls-6-(4 '-alkyl) application of ammonia sulphur hydrazone cholestane compound in the preparation antitumor drug of contracting according to claim 1.
According to claim 1 B-fall-6-(4 '-alkyl) the ammonia sulphur hydrazone cholestane compound that contracts is the application of medicinal compositions in the preparation antitumor drug of activeconstituents.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447937A (en) * | 2014-12-17 | 2015-03-25 | 广西师范学院 | B-norcholestane benzimidazole compound as well as preparation method and application thereof |
| CN105859821A (en) * | 2016-04-18 | 2016-08-17 | 广西师范学院 | 22-nor-stigmasta thiosemicarbazone compound and preparing method and application thereof |
| CN106866774A (en) * | 2016-12-23 | 2017-06-20 | 广西师范学院 | For antineoplastic compound and its production and use |
| CN110330543A (en) * | 2019-07-31 | 2019-10-15 | 广西万德药业有限公司 | 3- acetyl group -5- hydroxyl-B- norcholesterol -6-(N- methyl) contracting ammonia sulphur hydrazone, preparation method and its usage |
| WO2021016954A1 (en) * | 2019-07-31 | 2021-02-04 | 广西万德药业有限公司 | 3-acetyl-5-hydroxy-b-norcholesterol-6-(n-methyl)thiosemicarbazone, and preparation method therefor and use thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102146115A (en) * | 2011-01-17 | 2011-08-10 | 广西师范学院 | 3-substituent-B-Homo-steride-B-cyclolactam compound as well as preparation method and application to preparing antitumor medicaments |
| CN102286055A (en) * | 2011-06-29 | 2011-12-21 | 广西师范学院 | B-drop-3, 6-disubstituted cholestane compound and preparation method and application thereof to preparation of antitumor drug |
-
2013
- 2013-04-18 CN CN2013101359619A patent/CN103214542A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102146115A (en) * | 2011-01-17 | 2011-08-10 | 广西师范学院 | 3-substituent-B-Homo-steride-B-cyclolactam compound as well as preparation method and application to preparing antitumor medicaments |
| CN102286055A (en) * | 2011-06-29 | 2011-12-21 | 广西师范学院 | B-drop-3, 6-disubstituted cholestane compound and preparation method and application thereof to preparation of antitumor drug |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447937A (en) * | 2014-12-17 | 2015-03-25 | 广西师范学院 | B-norcholestane benzimidazole compound as well as preparation method and application thereof |
| CN104447937B (en) * | 2014-12-17 | 2016-06-08 | 广西师范学院 | Cholestane benzimidazoles compound and its production and use drops in a kind of B- |
| CN105859821A (en) * | 2016-04-18 | 2016-08-17 | 广西师范学院 | 22-nor-stigmasta thiosemicarbazone compound and preparing method and application thereof |
| CN106866774A (en) * | 2016-12-23 | 2017-06-20 | 广西师范学院 | For antineoplastic compound and its production and use |
| CN110330543A (en) * | 2019-07-31 | 2019-10-15 | 广西万德药业有限公司 | 3- acetyl group -5- hydroxyl-B- norcholesterol -6-(N- methyl) contracting ammonia sulphur hydrazone, preparation method and its usage |
| WO2021016954A1 (en) * | 2019-07-31 | 2021-02-04 | 广西万德药业有限公司 | 3-acetyl-5-hydroxy-b-norcholesterol-6-(n-methyl)thiosemicarbazone, and preparation method therefor and use thereof |
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Application publication date: 20130724 |