CN103254264A - Pregnenolone aromatic aldehydes azine steroid compound and synthetic method thereof as well as application of compound in preparation of antitumor medicines - Google Patents
Pregnenolone aromatic aldehydes azine steroid compound and synthetic method thereof as well as application of compound in preparation of antitumor medicines Download PDFInfo
- Publication number
- CN103254264A CN103254264A CN201310184358XA CN201310184358A CN103254264A CN 103254264 A CN103254264 A CN 103254264A CN 201310184358X A CN201310184358X A CN 201310184358XA CN 201310184358 A CN201310184358 A CN 201310184358A CN 103254264 A CN103254264 A CN 103254264A
- Authority
- CN
- China
- Prior art keywords
- vitarrine
- azine
- compound
- aromatic aldehyde
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 29
- -1 Pregnenolone aromatic aldehydes azine steroid compound Chemical class 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims description 21
- 239000003814 drug Substances 0.000 title abstract description 8
- 229940079593 drug Drugs 0.000 title abstract description 3
- ORNBQBCIOKFOEO-YQUGOWONSA-N Pregnenolone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC2)CC1 ORNBQBCIOKFOEO-YQUGOWONSA-N 0.000 title abstract 3
- 229960000249 pregnenolone Drugs 0.000 title abstract 3
- 238000010189 synthetic method Methods 0.000 title description 5
- 230000000259 anti-tumor effect Effects 0.000 title description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000000126 substance Substances 0.000 claims abstract 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims description 27
- 230000003637 steroidlike Effects 0.000 claims description 24
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- PFLUPZGCTVGDLV-UHFFFAOYSA-N acetone azine Chemical compound CC(C)=NN=C(C)C PFLUPZGCTVGDLV-UHFFFAOYSA-N 0.000 claims description 8
- 239000002246 antineoplastic agent Substances 0.000 claims description 8
- 229940041181 antineoplastic drug Drugs 0.000 claims description 8
- NBHLEUNJGNIKRR-UHFFFAOYSA-N n-(methylideneamino)methanimine Chemical compound C=NN=C NBHLEUNJGNIKRR-UHFFFAOYSA-N 0.000 claims description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- 210000004881 tumor cell Anatomy 0.000 abstract description 8
- 206010028980 Neoplasm Diseases 0.000 abstract description 4
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000003756 stirring Methods 0.000 description 13
- 229960000935 dehydrated alcohol Drugs 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 238000005303 weighing Methods 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229960004756 ethanol Drugs 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- XIIAYQZJNBULGD-UHFFFAOYSA-N (5alpha)-cholestane Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 XIIAYQZJNBULGD-UHFFFAOYSA-N 0.000 description 1
- SLYRGJDSFOCAAI-UHFFFAOYSA-N 1,3-thiazolidin-2-one Chemical compound O=C1NCCS1 SLYRGJDSFOCAAI-UHFFFAOYSA-N 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 241000031091 Synodontis clarias Species 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 238000012925 biological evaluation Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000007541 cellular toxicity Effects 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 208000019065 cervical carcinoma Diseases 0.000 description 1
- XIIAYQZJNBULGD-LDHZKLTISA-N cholestane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XIIAYQZJNBULGD-LDHZKLTISA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 201000000498 stomach carcinoma Diseases 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003571 thiolactams Chemical class 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a pregnenolone aromatic aldehydes azine steroid compound with an azine structure. The chemical structure is represented by a formula which is shown in the specification. Experiments prove that the pregnenolone aromatic aldehydes azine steroid compound provided by the invention has significant inhibiting function to a plurality of tumor cell strains, so that the compound can be used for preparing medicines for treating cancers.
Description
One, technical field
The present invention relates to class Vitarrine aromatic aldehyde azine steroidal compounds and a synthetic method thereof, with and in the application of preparation in the antitumor drug.
Two, background technology
Azine and derivative thereof are the important compounds of a class.Bibliographical information, azines be in biological medicine and pesticide field extensive application, and they have researching value widely in the exploitation of antibiotic, desinsection and medicine such as antitumor.In the study on the synthesis of azines, reported once that a class was as azine-Carbox amide (Chinese invention patent application number: CN200580028484.X) of cancer therapy drug.Simultaneously, in steroidal azines synthetic, once reported a class 6-carbonyl cholestane thiazolidone azines (Salman Ahmad Khan, Abdullah M.Asiria, Mohammed Yusuf.Synthesis and biological evaluation of some thiazolidinone derivatives of steroid as antibacterial agents, European Journal of Medicinal Chemistry, 2009,44:2597 – 2600), this compounds has the excellent antibiotic activity.In the research of antitumor steroidal compounds, once reported courage steroid-4-alkene-B-cyclic lactam compound (Natalija
Mira S.Bielakovi á,
Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities, Steroids, 2007,72:406 – 414), androstane-B cyclic lactam compounds (Anna I.Koutsourea, Mandis A.Fthanasios Papageorgiou, George N Pairas Papagerous, George N.Pairas, Sotiris S.Nikolaropoulos.Bioorganic﹠amp; Medical Chemistry, 2008,16,5207-5212).In the above-claimed cpd some has cytotoxicity external to some tumour cell.Chinese patent ZL2010 1 0107528.0 once provided a class " 6-replacement-4-azepine-A-homo-3-oxo steroidal compounds and the application in the preparation antitumor drug thereof ", and Chinese patent application 201110009124.2 provides another kind of " 3-replacement-B-Homo-steroidal-B-cyclic lactam compound and preparation method thereof and the application in the preparation antitumor drug ".But, relevant Vitarrine aromatic aldehyde azine steroidal compounds and synthetic method thereof, with and application in the preparation antitumor drug do not appear in the newspapers.
Three, summary of the invention
The purpose of this invention is to provide a class Vitarrine aromatic aldehyde azine steroidal compounds.
Another object of the present invention provides the synthetic method of above-claimed cpd.
Further purpose of the present invention provides the application of above-claimed cpd in the preparation antitumor drug.
The present invention is achieved through the following technical solutions above-mentioned purpose:
Vitarrine aromatic aldehyde azine steroidal compounds structural formula of the present invention is as follows:
Vitarrine acetone azine (1) Vitarrine phenyl aldehyde azine (2)
Vitarrine-3-pyridylaldehyde azine (3) Vitarrine-3-thiophenecarboxaldehyde azine (4)
Vitarrine-3-hydroxy benzaldehyde azine (5) Vitarrine-2-naphthaldehyde azine (6)
Vitarrine-4-quinoline aldehyde azine (7) Vitarrine-6-methoxynaphthalene formaldehyde azine (8)
Vitarrine aromatic aldehyde azine steroidal compounds of the present invention by natural steroid compound Vitarrine and hydrazine hydrate reaction, generates the Vitarrine hydrazone.The Vitarrine hydrazone further with different aromatic aldehyde or heteroaromatic aldehyde reaction, obtain Vitarrine aromatic aldehyde azine steroidal compounds.
The reaction of preparation Vitarrine aromatic aldehyde azine steroidal compounds is as follows:
Vitarrine Vitarrine hydrazone
Suppress activity test by cancer cell in vitro and show, Vitarrine aromatic aldehyde azine steroidal compounds of the present invention has significant inhibitory effect to tumor cell lines such as various tumor cell strains such as liver cancer, cancer of the stomach, cervical cancer, colorectal carcinomas.Therefore Vitarrine aromatic aldehyde azine steroidal compounds of the present invention can be used for preparing the medicine for the treatment of cancer.
The present invention also provides a kind of medicine that is used for the treatment of cancer, and it contains above-mentioned Vitarrine aromatic aldehyde azine steroidal compounds and pharmaceutically acceptable auxiliary.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.
The preparation of embodiment 1 Vitarrine acetone azine (1)
Step 1: the preparation of Vitarrine hydrazone
Take by weighing Vitarrine 3.0g, place the 100mL round-bottomed flask, add the 30mL dehydrated alcohol, after 75 ℃ of stirrings are dissolved it fully, add the 4mL85% hydrazine hydrate, stirred 1 hour, there are a large amount of white crystals to separate out, TLC follows the tracks of reaction process, stops heating after the completely dissolve of raw material point, the ice bath cooling, suction filtration, thick product gets target product 2.3g, productive rate: 73% with dichloromethane methanol mixed solvent recrystallization after suction filtration, the oven dry.M.p:207-209 ℃. product structure is analyzed definite through IR, NMR and MS.
Step 2: the preparation of Vitarrine acetone azine (1)
Take by weighing Vitarrine hydrazone 120mg and place the 100mL round-bottomed flask, add the 30mL dehydrated alcohol, stir, the dissolving back adds 1mL acetone fully, in 50 ℃ of following stirring reactions 5 hours, TLC follows the tracks of, no raw material point back termination reaction, underpressure distillation, with ether to its recrystallization, get colourless particulate state crystal 110mg, productive rate: 83%, m.p:187-189 ℃.Product structure is analyzed definite through IR, NMR and MS.
The preparation of embodiment 2 Vitarrine phenyl aldehyde azines (2)
Take by weighing Vitarrine hydrazone 100mg, place the 100mL round-bottomed flask, add the 15mL dehydrated alcohol, stir dissolving back adding 45mg phenyl aldehyde fully, 50C ° is stirred 2h down, and TLC follows the tracks of reaction process, no raw material point back termination reaction, plate layer chromatography separates (chromatographic solution: ethyl acetate: sherwood oil=1:1.6), get the 107mg white powder, productive rate: 89%.m.p:187-189℃。Product structure is analyzed definite through IR, NMR and MS.
The preparation of embodiment 3 Vitarrines-3-pyridylaldehyde azine (3)
Take by weighing Vitarrine hydrazone 100mg and place the 100mL round-bottomed flask, add the 15mL dehydrated alcohol, be warming up to 75 ℃, stirring makes it dissolve back adding 41mg3-pyridylaldehyde fully, reacted 1 hour, TLC follows the tracks of reaction, no raw material point back stopped reaction, underpressure distillation, get yellow oil, add the sherwood oil mixed system to its recrystallization with ethanol, get light yellow crystal, repeat crystallization and get target product 56mg. productive rate three times: 42%; M.p:207-210 ℃.Product structure is analyzed definite through IR, NMR and MS.
The preparation of embodiment 4 Vitarrines-3-thiophenecarboxaldehyde azine (4)
Take by weighing Vitarrine hydrazone 100mg, add the 15mL dehydrated alcohol and dissolve fully, add the 35mg3-thiazole carboxaldehyde.40 degree are stir about 12h down, and TLC follows the tracks of, and stopped reaction after the completely dissolve of raw material point gets faint yellow solid after the underpressure distillation, and thick product adds sherwood oil system recrystallization with ethanol, gets light yellow crystal 109mg, productive rate 80%.M.p:181-183 ℃; Product structure is analyzed definite through IR, NMR and MS.
The preparation of embodiment 5 Vitarrines-3-hydroxy benzaldehyde azine (5)
Take by weighing Vitarrine hydrazone 100mg, place the 100mL round-bottomed flask, add the 15mL dehydrated alcohol, stir under the room temperature and make it dissolve the back fully to add the 37mg3-hydroxy benzaldehyde, 40C ° of stirring reaction 3 hours, TLC are followed the tracks of termination reaction behind the no raw material point, add sherwood oil system recrystallization with dehydrated alcohol after the underpressure distillation, get light yellow crystal 76mg,, productive rate 60%.Product structure is analyzed definite through IR, NMR and MS.
The preparation of embodiment 6 Vitarrines-2-naphthaldehyde azine (6)
Take by weighing Vitarrine hydrazone 100mg and place the 100mL round-bottomed flask, add the 25mL dehydrated alcohol, stir under the room temperature, the dissolving back adds the 65mg1-naphthaldehyde fully, is warming up to the 75C ° of about 1h of reaction, and TLC follows the tracks of, termination reaction after the completely dissolve of raw material point, underpressure distillation.Thick product adds sherwood oil system recrystallization twice with ethanol, gets light yellow crystal 90mg, productive rate 64%.m.p:?200-202℃。Product structure is analyzed definite through IR, NMR and MS.
The preparation of embodiment 7 Vitarrines-4-quinoline aldehyde azine (7)
Take by weighing Vitarrine hydrazone 100mg, place the 100mL round-bottomed flask, add the 15mL dehydrated alcohol, stirring makes it dissolve back adding 47mg4-quinoline aldehyde fully under the room temperature, spends stirring reaction 12h down in 40, it is green that solution gradually becomes, TLC follows the tracks of reaction process, no raw material point back termination reaction, and thick product adds sherwood oil system recrystallization with ethanol after the underpressure distillation, get light green crystal 115mg, productive rate 81%.M.p:202-204 ℃. product structure is analyzed definite through IR, NMR and MS.
The preparation of embodiment 8 Vitarrines-6-methoxynaphthalene formaldehyde azine (8)
Take by weighing Vitarrine hydrazone 100mg, move in the 100mL round-bottomed flask, stir dissolving back adding 57mg6-methoxyl group-2-naphthaldehyde fully, 75C ° of stirring spent the night, and the adularescent precipitation generates, and TLC follows the tracks of, termination reaction after the completely dissolve of raw material point.Thick product re-crystallizing in ethyl acetate gets tip-like clear crystal 100mg, productive rate 66.6%, m.p:183-184 ℃ after the underpressure distillation.Product structure is analyzed definite through IR, NMR and MS.
Embodiment 9
Present embodiment is to adopt Vitarrine aromatic aldehyde azine steroidal compounds of the present invention some tumour cell to be carried out the test result of cell toxicity test.
Adopt the MTT method, Vitarrine aromatic aldehyde azine steroidal compounds of the present invention is carried out growth and proliferation of cell to human cervical carcinoma cell strain (HeLa), colon cancer cell line (HT-29), hepatoma cell strain (Bel-7404) and stomach cancer cell line (SGC-7901) suppress activity test.The Vitarrine aromatic aldehyde azine steroidal compounds of the present invention that adds different concns in the logarithmic phase cell of in 96 orifice plates, cultivating, carry out 3 parallel tests simultaneously, compare with control group, cultivate after 72 hours, add MTT, measure its absorbancy, calculate respectively and suppress growth of tumour cell to 50% o'clock compound concentrations, with IC
50Value representation, the result is as shown in table 1:
Table 1 synthetic compound extracorporeal suppression tumor cell growing multiplication activity (MTT method) (IC
50, μ mol/L)
From the table data as seen, this type of Vitarrine aromatic aldehyde azine steroidal compounds has the obvious growth inhibited proliferation to above-mentioned tumour cell.
Claims (4)
1. a class Vitarrine aromatic aldehyde azine steroidal compounds, chemical structural formula is as follows:
Vitarrine acetone azine (1) Vitarrine phenyl aldehyde azine (2)
Vitarrine-3-pyridylaldehyde azine (3) Vitarrine-3-thiophenecarboxaldehyde azine (4)
Vitarrine-3-hydroxy benzaldehyde azine (5) Vitarrine-2-naphthaldehyde azine (6)
Vitarrine-4-quinoline aldehyde azine (7) Vitarrine-6-methoxynaphthalene formaldehyde azine (8).
2. method for preparing the described Vitarrine aromatic aldehyde of claim 1 azine steroidal compounds, it is characterized in that, comprise the steps: from Vitarrine, at first react with hydrazine hydrate, generate the Vitarrine hydrazone, the Vitarrine hydrazone further with different aromatic aldehyde or heteroaromatic aldehyde reaction, obtain Vitarrine aromatic aldehyde azine steroidal compounds 1-8.
3. the application of Vitarrine aromatic aldehyde azine steroidal compounds as claimed in claim 1 in the preparation antitumor drug.
4. be the application of medicinal compositions in the preparation antitumor drug of activeconstituents with the described Vitarrine aromatic aldehyde of claim 1 azine steroidal compounds.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310184358.XA CN103254264B (en) | 2013-05-19 | 2013-05-19 | Vitarrine aromatic aldehyde azine steroidal compounds and synthetic method thereof and preparing the application in antitumor drug |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310184358.XA CN103254264B (en) | 2013-05-19 | 2013-05-19 | Vitarrine aromatic aldehyde azine steroidal compounds and synthetic method thereof and preparing the application in antitumor drug |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103254264A true CN103254264A (en) | 2013-08-21 |
| CN103254264B CN103254264B (en) | 2016-04-06 |
Family
ID=48958519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310184358.XA Expired - Fee Related CN103254264B (en) | 2013-05-19 | 2013-05-19 | Vitarrine aromatic aldehyde azine steroidal compounds and synthetic method thereof and preparing the application in antitumor drug |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103254264B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105254699A (en) * | 2015-10-29 | 2016-01-20 | 广西师范学院 | 4-(4 minute-trifluoromethyl) phenyl-2-dehydroepiandrosterone-17 minute-hydrazone thiazole as well as preparation method and application thereof |
| WO2023137529A1 (en) * | 2022-01-24 | 2023-07-27 | Australian National University | Anti-parasite compounds |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3232960A (en) * | 1959-10-08 | 1966-02-01 | Upjohn Co | 3-keto-4-fluoro- and 3-keto-4,4-difluorosteroids and process |
| US3268520A (en) * | 1963-01-23 | 1966-08-23 | Bayer Ag | Steroid guanylhydrazones and production thereof |
| CN102816198A (en) * | 2012-09-08 | 2012-12-12 | 广西师范学院 | Preparation method of 3-hydroxy-5-alkenesteroid compounds with ammonia derivative branched chain structure and application thereof in antineoplastic drugs |
-
2013
- 2013-05-19 CN CN201310184358.XA patent/CN103254264B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3232960A (en) * | 1959-10-08 | 1966-02-01 | Upjohn Co | 3-keto-4-fluoro- and 3-keto-4,4-difluorosteroids and process |
| US3268520A (en) * | 1963-01-23 | 1966-08-23 | Bayer Ag | Steroid guanylhydrazones and production thereof |
| CN102816198A (en) * | 2012-09-08 | 2012-12-12 | 广西师范学院 | Preparation method of 3-hydroxy-5-alkenesteroid compounds with ammonia derivative branched chain structure and application thereof in antineoplastic drugs |
Non-Patent Citations (4)
| Title |
|---|
| JI-SONG LI等: "Synthesis and Evaluation of Pregnane Derivatives as Inhibitors of Human Testicular 17r-Hydroxylase/C17，20-Lyase", 《J. MED. CHEM.》, vol. 39, 11 October 1996 (1996-10-11), pages 4335 - 4339 * |
| RAFAT M. MOHAREB，FATIMA AL-OMRAN: "Reaction of pregnenolone with cyanoacetylhydrazine: Novel synthesis of hydrazide–hydrazone, pyrazole, pyridine, thiazole, thiophene derivatives and their cytotoxicity evaluations", 《STEROIDS》, vol. 77, no. 14, 31 December 2012 (2012-12-31), pages 1551 - 1559 * |
| 范良华等: "具有生物活性氮杂甾体化合物的研究进展", 《化学研究与应用》, vol. 24, no. 1, 31 January 2012 (2012-01-31), pages 8 - 15 * |
| 陈思静等: "具有生理活性甾体腙类化合物的研究进展", 《有机化学》, vol. 31, no. 2, 15 February 2011 (2011-02-15), pages 187 - 192 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105254699A (en) * | 2015-10-29 | 2016-01-20 | 广西师范学院 | 4-(4 minute-trifluoromethyl) phenyl-2-dehydroepiandrosterone-17 minute-hydrazone thiazole as well as preparation method and application thereof |
| WO2023137529A1 (en) * | 2022-01-24 | 2023-07-27 | Australian National University | Anti-parasite compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103254264B (en) | 2016-04-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103242406A (en) | Dehydroepiandrosterone aromatic aldehyde azine steroidal compound and synthetic method thereof as well as application thereof in preparation of anti-tumor drugs | |
| TWI272272B (en) | Camptothecin derivatives having antitumor activity | |
| AU2018219967C1 (en) | Stable crystal form of tipiracil hydrochloride and crystallization method for the same | |
| CN102146081B (en) | Indoleacetic acid derivatives and preparation method and application thereof | |
| CN107674083B (en) | A kind of preparation method and applications of the L-Leu ring substituent norcantharidin derivative of the structure containing pyridazinone | |
| AU2016204054A1 (en) | Effect potentiator for antitumor agents | |
| CN106432190B (en) | The naphthalimide compound of one kind aminopyrimidine containing 2-, preparation method and application | |
| CN101245090A (en) | 3,6-di-substituted sterides oximes compound as antineoplastic medicament | |
| CN102286055B (en) | B-drop-3, 6-disubstituted cholestane compound and preparation method and application thereof to preparation of antitumor drug | |
| CN106083704B (en) | Application of-two aryl methylene-N- cyclopropyl piperidine -4- ketone compounds of 3,5- (E) as Hsp90 inhibitor | |
| CN103254264B (en) | Vitarrine aromatic aldehyde azine steroidal compounds and synthetic method thereof and preparing the application in antitumor drug | |
| CN105130897B (en) | The naphthalimide compound of a kind of nitrogenous sulphur substituent group, preparation method and application | |
| CN107286180A (en) | Miscellaneous generation Pyridopyrimidinone derivatives are used as CDK inhibitor and its application | |
| CN102399256A (en) | Glycyrrhetinic acid derivatives and preparation method, medicinal composition and application thereof to preparation of antitumor drug | |
| CN104546843A (en) | Application of pyrazole hydrazone derivative in preparation of anti-breast cancer drug | |
| CN106565681A (en) | Anilinoquinazoline compound containing nitroimidazole group and preparation method and application thereof | |
| CN103172577A (en) | 4-aminoquinoline and 4-aminoquinoline compound and applications of compound | |
| CN104725372A (en) | Tetracyclic indole alkaloid derivative as well as preparation method and application thereof | |
| CN103275161B (en) | 3-hydroxyl cholest-6-keto aromatic aldehyde azine steroidal compound, synthetic method of steroidal compound and application of steroidal compound in preparation of anti-tumour drug | |
| Puszko et al. | Systematic coordination chemistry and cytotoxicity of copper (II) complexes with methyl substituted 4-nitropyridine N-oxides | |
| CN103003270B (en) | Benzofuranone compound and pharmaceutical composition containing same | |
| CN104311539B (en) | A kind of acridine acylhydrazone and its production and use | |
| CN104327063B (en) | Acridine oxadiazole derivative, preparation method and uses thereof | |
| CN107674082B (en) | A kind of preparation method and applications of the D-phenylalanine ring substituent norcantharidin derivative of the structure containing pyridazinone | |
| CN103709135B (en) | Ton ketone derivatives and its preparation method and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20171207 Address after: 518000 Guangdong Province, Shenzhen New District of Longhua City, Dalang street, Longsheng Gold Dragon Road community e-commerce incubator exhibition Tao Commercial Plaza E block 706 Patentee after: Shenzhen step Technology Transfer Center Co., Ltd. Address before: Mingxiu Road East of Nanning city the Guangxi Zhuang Autonomous Region 530001 No. 175 Patentee before: Guangxi Teachers College |
|
| TR01 | Transfer of patent right |
Effective date of registration: 20171227 Address after: 401220 No. 16 group 30 of Yantan village, Changshou District, Chongqing Patentee after: Li Yizhong Address before: 518000 Guangdong Province, Shenzhen New District of Longhua City, Dalang street, Longsheng Gold Dragon Road community e-commerce incubator exhibition Tao Commercial Plaza E block 706 Patentee before: Shenzhen step Technology Transfer Center Co., Ltd. |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20180820 Address after: 518000 Guangdong Shenzhen Longhua New District big wave street Longsheng community Tenglong road gold rush e-commerce incubation base exhibition hall E commercial block 706 Patentee after: Shenzhen step Technology Transfer Center Co., Ltd. Address before: 401220 No. 16 group 30 of Yantan village, Changshou District, Chongqing Patentee before: Li Yizhong |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20181019 Address after: 401120 Chongqing Yubei District Shuangfeng Bridge Street Airport Development Zone Xiangyu Road 15, 1 1 stories. Patentee after: CHONGQING TIANYI HENGHUA TECHNOLOGY CO., LTD. Address before: 518000 Guangdong Shenzhen Longhua New District big wave street Longsheng community Tenglong road gold rush e-commerce incubation base exhibition hall E commercial block 706 Patentee before: Shenzhen step Technology Transfer Center Co., Ltd. |
|
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160406 Termination date: 20190519 |