Side chain azasteroids and thiasteroids as sterol biosynthesis inhibitors with antifungal, antitrypanosomal and antileishmanial activities:
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| Main Author: | |
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| Format: | Book |
| Language: | English |
| Published: |
München
Hut
2006
|
| Edition: | 1. Aufl. |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Item Description: | Zugl.: München, Univ., Diss., 2006 |
| Physical Description: | 310 S. graph. Darst. |
| ISBN: | 3899633733 |
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| 008 | 060801s2006 xx d||| m||| 00||| eng d | ||
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| 040 | |a DE-604 |b ger |e rakwb | ||
| 041 | 0 | |a eng | |
| 049 | |a DE-355 |a DE-19 |a DE-29T |a DE-12 | ||
| 100 | 1 | |a Renard, Delphine |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Side chain azasteroids and thiasteroids as sterol biosynthesis inhibitors with antifungal, antitrypanosomal and antileishmanial activities |c von Delphine Renard |
| 250 | |a 1. Aufl. | ||
| 264 | 1 | |a München |b Hut |c 2006 | |
| 300 | |a 310 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Zugl.: München, Univ., Diss., 2006 | ||
| 650 | 0 | 7 | |a Antibiotikum |0 (DE-588)4002257-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Steroidderivate |0 (DE-588)4686773-9 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Stickstoffverbindungen |0 (DE-588)4183288-7 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Schwefelverbindungen |0 (DE-588)4180438-7 |2 gnd |9 rswk-swf |
| 655 | 7 | |0 (DE-588)4113937-9 |a Hochschulschrift |2 gnd-content | |
| 689 | 0 | 0 | |a Steroidderivate |0 (DE-588)4686773-9 |D s |
| 689 | 0 | 1 | |a Stickstoffverbindungen |0 (DE-588)4183288-7 |D s |
| 689 | 0 | 2 | |a Antibiotikum |0 (DE-588)4002257-2 |D s |
| 689 | 0 | |5 DE-604 | |
| 689 | 1 | 0 | |a Steroidderivate |0 (DE-588)4686773-9 |D s |
| 689 | 1 | 1 | |a Schwefelverbindungen |0 (DE-588)4180438-7 |D s |
| 689 | 1 | 2 | |a Antibiotikum |0 (DE-588)4002257-2 |D s |
| 689 | 1 | |5 DE-604 | |
| 856 | 4 | 2 | |m Digitalisierung UB Regensburg |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014894627&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
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TABLE
General Introduction
Chapter I 3
Bibliographical overview of
I. Sterol
1.1. Biosynthesis of isopentenyl diphosphate via the mevalonate pathway
1.2.
1.3.
trypanosomatids
1.4.
1.5.
1.6.
1.7.
II. Ergosterol biosynthesis inhibitors as antifungal agents
II
11.1.1.
II.
II.1.3. Morpholines 16
II.2. Search for new ergosterol biosynthesis inhibitors M>
11.2.1
II.2.
112.12.
11.2.2. A24(28)-Sterol
11.2.3. Inhibitors of both A24<25)-sterol methyitransferase and A2<K28)-sterol 27
reductase
III.
HI.
Ш.2.
Ш.З
IV. Planned Work
Chapter II 42
Synthesis of side chain aza- and thiasteroids
I. Derivatives containing a nitrogen atom at position
1.1. Derivatives containing a nitrogen atom at position
animation reaction
1.1.1.
1.
1.
(3Ä>ergosta-7,22-(£)-dien-3-yl
1.
amino)-ethanol
1.2.
1.2.1.
1.2.2.
1.2.3.
П.
П.1
П.
П.1.2.
side chain
И. 1.З.
П.
II.
II.l
II.1.6.1. Monoalkylhydrazine: Ethylhydrazine oxalate
II.
11.1.7.
II.
fi
II.
ПЛ
II.
II.2. Isoxazolidines, five membered ring heterocycles in the side chain
II.2.
11.2.2.
11.2.3. The nitrone on the steroid nucleus
II.3
11.3.1. Synthesis and use of4-picolyllithium
11.3.2. The
11.3.3. Deprotection of the acetate group at position
11.3.4. N-Alkylation reaction
11.3.4.1. N-Methylation of the 2-picolyl derivatives
11.3.4.2. N-Methylation of the 3-picolyl derivatives and 4-picolyl
derivatives
H.3.4.3. N-Butylation of
Chapter III 108
Biological Results
I.
II.
ILI.
11.2. Compounds submitted to the screening and the results
11.3. Explication of the determination of the inhibited enzyme
11.4. Structure-activity relationships
III. Tests against Trypanosoma cruzi and Leishmania brazUiensis
IV. Azasteroids tested against Trypanosoma brucei brucei and the
Une J774.1
V. Cytotoxicity assay on human leukemia cell line HL60
Conclusion
Experimental part
I. General comments
II. Synthesis procedures
Ergosta-7,22-(£)-dien-3-one
(3S,20S)-20-Formylpregn-7-en-3-yl acetate
5a,6-Dihydroergosterol
(3i?)-(Ergosta-7,22-(£)-dien-3-yl)-methylamme (72a) 160
(3S)-(ETgosta-7,22-(£)-dien-3-yl)-methylamine (72b)
4
N'-[(35)-(Ergosta-7,22-(£)-dien-3-yl)]-N,N-dimethylethane-l,2-diamine(73b)
[(3Ä)-(Ergosta-7,22-(£)-dien-3-yl)]-(2-methoxy-ethyl)-amme (74a)
[(35)4Ergosta-7,22-(£>dien-3-yl)]-(2-meťhoxy-ethyl)-amine
167
[(3/?)-(Ergosta-7^2-(£)-dieti-3-yl)-ammo]-acetic
l-acetic
[(3Ä)-(Ergosta-7,22-(£)-dien-3-yl)]-pyridin-2-ylmethylamine
[(35)4Ergosta-7,22-(£)-dien-3-yl)]-pyridm-2-ylmethylamine (76b) 170
(3Ä>Ergosta-7,22-(£)-dien-3-yl-hydroxylamine (77)
(3Ä>Ergosta-7,22-(£)-dien-3-yl-amine (78)
4,5,6,7-Tetrachloro-2-[(3Ä)-ergosta-7,22-(S)-dien-3-yl]-isomdole-1,3-
dione
174
(3Ä)-(Ergosta-7,22-(£)-dien-3-yl-amino)-ethanoI (80)
176
a-3-one
177
Mixture of 3-a2a-J4-homo-ergostan-7)22-(£)-dien-4-one (82a) and 4-aza-v4-homo-
ergostan-7,22-(£)-dien-3-one
179
Mixture of ^-homo-N-benzyl-3-azaergostan-7,22-(£)-dien-4-one (83a) and A-
homo-N-benzyl-4-azaergostan-7,22-(£)-dien-3-one(83ß)
4-Aza-^-homo-ergostan-7,22-(£)-diene (84a)
3-Aza-.¿f-homo-ergostan-7,22-(£)-diene
Ergosteryl acetate
5a,6-Dihydroergosteryl acetate
(35',205>20-[(2-Dimethylamino-e%lammo)-methyl]-pregn-7-en-3-yl acetate
(35,20S)-20-[(2-Diethylamino-ethylamino)-methyl]-pregn-7-en-3-yl acetate
(35,20S)-20-[(3-Dimethylamino-propylamino)-methyl]-pregn-7-en-3-yl acetate 187
(94)
(3S,205)-20-(Butylamino-methyl)-pregn-7-en-3-yl acetate
189
(3S,205)-20-[(2-Piperidin-l-yl-ethylamino)-methyl]-pregn-7-en-3-yl acetate
(3S,20S)-20-[(2-Dimethylammo-ethylamino)-methyl]-pregn-7-en-3-ol(98) 192
(3S,20S)-20-[(2-Diethylamino-ethylamino)-methyl]-pregn-7-en-3-ol
(35',205)-20-[(3-Dimethylamino-propylammo)-methyl]-pregn-7-en-3-ol(100)
(3S,205)-20-(Burylamino-methyl)-pregn-7-en-3-ol
(3S,205)-20-[(2-Pyrrolidin-l-yl-ethylamino)-methyl]-pregn-7-en-3-ol(102) í96
(3£20S)-204(2-Piperidin4-yl-emylainmo)meuyl]-pregn-7-en-3-ol(103)
(35,20S)-20-(Methylammo-methyl)-pregn-7-en-3-yl
(3S,205)-20-(Ethylamino-methyl)-pregn-7-en-3-yl
(3£20S>20-(Propylammo-methyl)-pregn-7-en-3-yl
(3S,20S)-20-(Pentylamino-methyl)-pregn-7-en-3-yl
(3S,205)-20-(Dodecylamno-me%l)-pregn-7-en-3-yl
(SA^OA^O-ÍIsobutylamino-methy^-pregn^-en-S-yl
Mixture of
acetate
yl acetate
(3S;20S)-20-(Meuylammometliyl)-pregn-7-en-3-ol (111)
(3S,20S)-20-(EUylammo-methyl)-pregn-7-en-3-ol
(3S,20S>20-(Propylamno-methyl)-pregn-7-en-3-ol
QSČOSylO-iPentylBxnino-methyiyprega-l-ea-i-ol
(3S,20S)-20-(Dodecylamino-methyl)-pregn-7-en-3-ol
(35,205>20-(Isobutylamino-methyl)-pregn-7-en-3-ol
Mixture of (35,20S)-20-[(15)-(l,2-dimethyl-propylamino)-methyl]-pregn-7-en-3-ol 213
and(35,205)-20-[(l^)41,2-dimethyl-propylamino)-methyl]-pregn-7-en-3-ol(117)
(3S,205)-20-[(N-Butyl-N-methyl-amino)-methyl]-pregn-7-en-3-yl acetate
(35,205)-20-[(N-Butyl-N-methyl-amino)-methyl]-pregn-7-en-3-ol
N-Butyl-N,N-dimethyl-[(3S,205)-(3-hydroxypregn-7-en-20-yl>methyl]-
ammonium iodide
Mixture of
methylamine-N-oxide
AíSAcetoxypregn^en^OyOmethylJNbutylNmethylamme
N-oxide
(Л^)-К-Ви1у1-[(35Д05)ЧЗ-Ьуагохурге^-7-еп-20-у1)-Ы-теи1у1]-Н-теШу1атте-
N-oxide
(205)-20-(Butylamino-methyl)-pregn-7-en-3-one
[(3A,20S)-20-(Butylanňno-methyl)-pregn-7-en-3-yl]-methyl-amine (125a) 224
t(35,205)-20-(Bulylamiiio-methyl)-pregn-7-en-3-yl]-methyl-amme (125b) 22^
Butyl-[(3Ä,205>20-(butylammo-raethyl)-pregn-7-en-3-yl]-amine
ButyH(3S;20S)-204butylarmno-me1byl)^regn-7-en-3-yl]-amme
(35^0í)-20-(Propylammo-ethyl)-pTegn-7-ea-343l
Mixture of
yl
(129)
Mixture of
ol and
(3S,20Ä)-20-(Formylme%l)-pregn-7-en-3-yl
(35l,20Ä)-243-Hydroxypregn-7-en-20-yl)-ethanal (131)
(SS^O^^O-ÍPropylamino-eťhy^-pregn^-en-S-yl
(3^,205)-20-[(2-ЕЉу1а2:о)-теЉу1]-ргеЕп-7-еп-3-о1
(35,205)-20-[(Piperidin-l-ylimino)-methyl]-pregn-7-en-3-yl
(3S,205)-20-[(Piperidm-l-ylimmo>methyl]-pregn-7-en-3-ol
п-З-оі
acetate
(35,205)-20-[(2-rerř-butoxycarbonylaniino-ethylammo)-methyl]-pregn-7-en-3-ol
(142)
Mixture of
and(35,205)-20-[(2-aminoethyIammo)-methyl]-pregn-14-en-3-ol(143ß)
Mixture of
(35;20j>-20-[(2-ammoethylamino)-methyl]-pregn-8()4)-en-3-oJ(144ß)
n-S-ol
l-methanoic acid
(35,205)-20-Chlorocarbonylpregn-7-en-3-yl
(35,205>20-Butylcarbamoylpregn-7-en-3-yl
(35,205>20-(2-Dimethylaminoethylcarbamoyl>pregn-7-en-3-yl
(SS^O^^O-ÍS-DimethylaminopropylcarbamoyO-pregn^-en-S-yl
(35,205)-N-Butyl-(3-hydroxypregn-7-en-20-yl)-methanamide
(35,205)-N-(Dimethylammoethyl)-(3-hydroxypregn-7-en-20-yl)-meťhaiiamide 2^2
(158)
(159)
(3S,20S)-20-(Butylsulfanyl-metàyl)-pregn-7-en-3-ol
(3A,205)-20-Hydroxymethylpregti-7-en-3-yl
yl
(3,S,20S)-20-Iodomethylpregii-7-eii-3-yl acetate
(3S,20Ą-20-(Butyłsulfanyl-methyl)-pregn-7-en-3-yl
(Ä^-S-Butyi-Ka^^O^-S^S-hydroxypregn^-en^O-yO-methylJ-S-methyl-
sulfonium
(3S¿0S)-204(i?^)-Burylsulfmyl-me%l]-pregn-7-eri-3-yl
en-S-ol
З-уі
п-З-оі
O^ÍSAcetoxypregn^en^OyO-methylidenej-N-methylamine-N-
oxide
(35,20Ä)-20-(2-Methyl-5-phenyl-isoxazolidin-3-yl)-pregn-7-en-3-yl
Mixture of diastereoisomers of
methyl-isoxazolidine-S-carboxylic acid ethyl ester
Mixture of diastereoisomers of
isoxazolidin-3-yl)-pregn-7-en-3-ol(175)
2-Picolyltriphenylphosphonium chloride 2^
(3A,20A)-20-P-(Pyridin-2-yl)-(£)-ethenyl]-pregn-7-eii-3-yl
S-Picolyltriphenylphosphonium chloride 27^
(35,20i?)-20-[2-(Pyridin-3-yl)-(Z)-ethenyl]-pregn-7-en-3-yl acetate (178a) 272
(35,20Ä)-20-[2-(Pyridin-3-yl)-(£)-ethenyl]-pregn-7-en-3-yl
4-Picolyltriphenylphosphonium chloride 274
(З^гО^-гО-РЧРугіат^-уіНА-еиіеиуЦ-рге^^-еп-З-уі
(35,20Ä)-20-[24Pyridm-4-ylH£)-ethenyl]-pregn-7-en-3-yl
(35,20Ä)-20-[2-(Pyridin-3-yl)-(£)-ethenyl]-pregn-7-en-3-ol (180)
(3S,20R)-20-[2-(Pyrìdm-2-yl)-(E)-eih(myl]-pTegn-7-en-3-ol
(35f,20i?)-20-[2-(Pyridin-3-yl)-(Z)-ethenyl]-pregn-7-en-3-ol
(3S,20K)-20-[2-CPyrìdia-4-yìy(E)-etheayì]-preffi-7-en-3-ol
2-[(35,20Ä)-(3-AcetoxypTegn-7-en-20-yl)-(£)-ethen-l-yl)]-l-methylpyridinium
iodide
2-[(3Ä,20Ä)-(3-Hydroxypregn-7-en-20-yl)-(£>ethen-l-yi)]-l-methylpyridinium
iodide
3-[(3S,20Ä)-(3-Acetoxypregn-7-en-20-yl)-(Z)-ethenyl)]-l-methylpyridinium
(186)
S-KSS^OfíHS-Hydroxypregn^-en^O-ylHZí-ethenyOl-l-meťhylpyridinium 284
iodide
iodide
3-[(35,20Ä)-(3-Hydroxypregn-7-en-20-ylH£>ethenyl)]-l-methylpyridinium 286
iodide
4-[(35,20Ä>(3-Acetoxypregn-7-en-20-yl)4^)-ethen-l -ylJ}-\
iodide
4-[(35i,20Ä)-(3-Hydroxypregn-7-en-20-yl)-(£)-ethen-l-yl)]-l-methylpyridinium 288
iodide
Mixture of
pyridinium
yl)-(£)-ethen-l-yl)]-pyridmium
III. Procedure for biological assays 29^
ПІЛ.
III.2. Procedure for the ergosterol biosynthesis screening test 292
Ш.2.1.
111.2.2. Determination of the EC50 293
111.2.3. Treatment of the biomass obtained by filtration 293
ПГ.2.4.
Ш.2.5.
Ш.З.
Ш.4.
Ш.5.
Ш.6.
Ш.7.
III.
III.7.2. MTT assay 301
References 302 |
| adam_txt |
TABLE
General Introduction
Chapter I 3
Bibliographical overview of
I. Sterol
1.1. Biosynthesis of isopentenyl diphosphate via the mevalonate pathway
1.2.
1.3.
trypanosomatids
1.4.
1.5.
1.6.
1.7.
II. Ergosterol biosynthesis inhibitors as antifungal agents
II
11.1.1.
II.
II.1.3. Morpholines 16
II.2. Search for new ergosterol biosynthesis inhibitors M>
11.2.1
II.2.
112.12.
11.2.2. A24(28)-Sterol
11.2.3. Inhibitors of both A24<25)-sterol methyitransferase and A2<K28)-sterol 27
reductase
III.
HI.
Ш.2.
Ш.З
IV. Planned Work
Chapter II 42
Synthesis of side chain aza- and thiasteroids
I. Derivatives containing a nitrogen atom at position
1.1. Derivatives containing a nitrogen atom at position
animation reaction
1.1.1.
1.
1.
(3Ä>ergosta-7,22-(£)-dien-3-yl
1.
amino)-ethanol
1.2.
1.2.1.
1.2.2.
1.2.3.
П.
П.1
П.
П.1.2.
side chain
И. 1.З.
П.
II.
II.l
II.1.6.1. Monoalkylhydrazine: Ethylhydrazine oxalate
II.
11.1.7.
II.
fi
II.
ПЛ
II.
II.2. Isoxazolidines, five membered ring heterocycles in the side chain
II.2.
11.2.2.
11.2.3. The nitrone on the steroid nucleus
II.3
11.3.1. Synthesis and use of4-picolyllithium
11.3.2. The
11.3.3. Deprotection of the acetate group at position
11.3.4. N-Alkylation reaction
11.3.4.1. N-Methylation of the 2-picolyl derivatives
11.3.4.2. N-Methylation of the 3-picolyl derivatives and 4-picolyl
derivatives
H.3.4.3. N-Butylation of
Chapter III 108
Biological Results
I.
II.
ILI.
11.2. Compounds submitted to the screening and the results
11.3. Explication of the determination of the inhibited enzyme
11.4. Structure-activity relationships
III. Tests against Trypanosoma cruzi and Leishmania brazUiensis
IV. Azasteroids tested against Trypanosoma brucei brucei and the
Une J774.1
V. Cytotoxicity assay on human leukemia cell line HL60
Conclusion
Experimental part
I. General comments
II. Synthesis procedures
Ergosta-7,22-(£)-dien-3-one
(3S,20S)-20-Formylpregn-7-en-3-yl acetate
5a,6-Dihydroergosterol
(3i?)-(Ergosta-7,22-(£)-dien-3-yl)-methylamme (72a) 160
(3S)-(ETgosta-7,22-(£)-dien-3-yl)-methylamine (72b)
4
N'-[(35)-(Ergosta-7,22-(£)-dien-3-yl)]-N,N-dimethylethane-l,2-diamine(73b)
[(3Ä)-(Ergosta-7,22-(£)-dien-3-yl)]-(2-methoxy-ethyl)-amme (74a)
[(35)4Ergosta-7,22-(£>dien-3-yl)]-(2-meťhoxy-ethyl)-amine
167
[(3/?)-(Ergosta-7^2-(£)-dieti-3-yl)-ammo]-acetic
l-acetic
[(3Ä)-(Ergosta-7,22-(£)-dien-3-yl)]-pyridin-2-ylmethylamine
[(35)4Ergosta-7,22-(£)-dien-3-yl)]-pyridm-2-ylmethylamine (76b) 170
(3Ä>Ergosta-7,22-(£)-dien-3-yl-hydroxylamine (77)
(3Ä>Ergosta-7,22-(£)-dien-3-yl-amine (78)
4,5,6,7-Tetrachloro-2-[(3Ä)-ergosta-7,22-(S)-dien-3-yl]-isomdole-1,3-
dione
174
(3Ä)-(Ergosta-7,22-(£)-dien-3-yl-amino)-ethanoI (80)
176
a-3-one
177
Mixture of 3-a2a-J4-homo-ergostan-7)22-(£)-dien-4-one (82a) and 4-aza-v4-homo-
ergostan-7,22-(£)-dien-3-one
179
Mixture of ^-homo-N-benzyl-3-azaergostan-7,22-(£)-dien-4-one (83a) and A-
homo-N-benzyl-4-azaergostan-7,22-(£)-dien-3-one(83ß)
4-Aza-^-homo-ergostan-7,22-(£)-diene (84a)
3-Aza-.¿f-homo-ergostan-7,22-(£)-diene
Ergosteryl acetate
5a,6-Dihydroergosteryl acetate
(35',205>20-[(2-Dimethylamino-e%lammo)-methyl]-pregn-7-en-3-yl acetate
(35,20S)-20-[(2-Diethylamino-ethylamino)-methyl]-pregn-7-en-3-yl acetate
(35,20S)-20-[(3-Dimethylamino-propylamino)-methyl]-pregn-7-en-3-yl acetate 187
(94)
(3S,205)-20-(Butylamino-methyl)-pregn-7-en-3-yl acetate
189
(3S,205)-20-[(2-Piperidin-l-yl-ethylamino)-methyl]-pregn-7-en-3-yl acetate
(3S,20S)-20-[(2-Dimethylammo-ethylamino)-methyl]-pregn-7-en-3-ol(98) 192
(3S,20S)-20-[(2-Diethylamino-ethylamino)-methyl]-pregn-7-en-3-ol
(35',205)-20-[(3-Dimethylamino-propylammo)-methyl]-pregn-7-en-3-ol(100)
(3S,205)-20-(Burylamino-methyl)-pregn-7-en-3-ol
(3S,205)-20-[(2-Pyrrolidin-l-yl-ethylamino)-methyl]-pregn-7-en-3-ol(102) í96
(3£20S)-204(2-Piperidin4-yl-emylainmo)meuyl]-pregn-7-en-3-ol(103)
(35,20S)-20-(Methylammo-methyl)-pregn-7-en-3-yl
(3S,205)-20-(Ethylamino-methyl)-pregn-7-en-3-yl
(3£20S>20-(Propylammo-methyl)-pregn-7-en-3-yl
(3S,20S)-20-(Pentylamino-methyl)-pregn-7-en-3-yl
(3S,205)-20-(Dodecylamno-me%l)-pregn-7-en-3-yl
(SA^OA^O-ÍIsobutylamino-methy^-pregn^-en-S-yl
Mixture of
acetate
yl acetate
(3S;20S)-20-(Meuylammometliyl)-pregn-7-en-3-ol (111)
(3S,20S)-20-(EUylammo-methyl)-pregn-7-en-3-ol
(3S,20S>20-(Propylamno-methyl)-pregn-7-en-3-ol
QSČOSylO-iPentylBxnino-methyiyprega-l-ea-i-ol
(3S,20S)-20-(Dodecylamino-methyl)-pregn-7-en-3-ol
(35,205>20-(Isobutylamino-methyl)-pregn-7-en-3-ol
Mixture of (35,20S)-20-[(15)-(l,2-dimethyl-propylamino)-methyl]-pregn-7-en-3-ol 213
and(35,205)-20-[(l^)41,2-dimethyl-propylamino)-methyl]-pregn-7-en-3-ol(117)
(3S,205)-20-[(N-Butyl-N-methyl-amino)-methyl]-pregn-7-en-3-yl acetate
(35,205)-20-[(N-Butyl-N-methyl-amino)-methyl]-pregn-7-en-3-ol
N-Butyl-N,N-dimethyl-[(3S,205)-(3-hydroxypregn-7-en-20-yl>methyl]-
ammonium iodide
Mixture of
methylamine-N-oxide
AíSAcetoxypregn^en^OyOmethylJNbutylNmethylamme
N-oxide
(Л^)-К-Ви1у1-[(35Д05)ЧЗ-Ьуагохурге^-7-еп-20-у1)-Ы-теи1у1]-Н-теШу1атте-
N-oxide
(205)-20-(Butylamino-methyl)-pregn-7-en-3-one
[(3A,20S)-20-(Butylanňno-methyl)-pregn-7-en-3-yl]-methyl-amine (125a) 224
t(35,205)-20-(Bulylamiiio-methyl)-pregn-7-en-3-yl]-methyl-amme (125b) 22^
Butyl-[(3Ä,205>20-(butylammo-raethyl)-pregn-7-en-3-yl]-amine
ButyH(3S;20S)-204butylarmno-me1byl)^regn-7-en-3-yl]-amme
(35^0í)-20-(Propylammo-ethyl)-pTegn-7-ea-343l
Mixture of
yl
(129)
Mixture of
ol and
(3S,20Ä)-20-(Formylme%l)-pregn-7-en-3-yl
(35l,20Ä)-243-Hydroxypregn-7-en-20-yl)-ethanal (131)
(SS^O^^O-ÍPropylamino-eťhy^-pregn^-en-S-yl
(3^,205)-20-[(2-ЕЉу1а2:о)-теЉу1]-ргеЕп-7-еп-3-о1
(35,205)-20-[(Piperidin-l-ylimino)-methyl]-pregn-7-en-3-yl
(3S,205)-20-[(Piperidm-l-ylimmo>methyl]-pregn-7-en-3-ol
п-З-оі
acetate
(35,205)-20-[(2-rerř-butoxycarbonylaniino-ethylammo)-methyl]-pregn-7-en-3-ol
(142)
Mixture of
and(35,205)-20-[(2-aminoethyIammo)-methyl]-pregn-14-en-3-ol(143ß)
Mixture of
(35;20j>-20-[(2-ammoethylamino)-methyl]-pregn-8()4)-en-3-oJ(144ß)
n-S-ol
l-methanoic acid
(35,205)-20-Chlorocarbonylpregn-7-en-3-yl
(35,205>20-Butylcarbamoylpregn-7-en-3-yl
(35,205>20-(2-Dimethylaminoethylcarbamoyl>pregn-7-en-3-yl
(SS^O^^O-ÍS-DimethylaminopropylcarbamoyO-pregn^-en-S-yl
(35,205)-N-Butyl-(3-hydroxypregn-7-en-20-yl)-methanamide
(35,205)-N-(Dimethylammoethyl)-(3-hydroxypregn-7-en-20-yl)-meťhaiiamide 2^2
(158)
(159)
(3S,20S)-20-(Butylsulfanyl-metàyl)-pregn-7-en-3-ol
(3A,205)-20-Hydroxymethylpregti-7-en-3-yl
yl
(3,S,20S)-20-Iodomethylpregii-7-eii-3-yl acetate
(3S,20Ą-20-(Butyłsulfanyl-methyl)-pregn-7-en-3-yl
(Ä^-S-Butyi-Ka^^O^-S^S-hydroxypregn^-en^O-yO-methylJ-S-methyl-
sulfonium
(3S¿0S)-204(i?^)-Burylsulfmyl-me%l]-pregn-7-eri-3-yl
en-S-ol
З-уі
п-З-оі
O^ÍSAcetoxypregn^en^OyO-methylidenej-N-methylamine-N-
oxide
(35,20Ä)-20-(2-Methyl-5-phenyl-isoxazolidin-3-yl)-pregn-7-en-3-yl
Mixture of diastereoisomers of
methyl-isoxazolidine-S-carboxylic acid ethyl ester
Mixture of diastereoisomers of
isoxazolidin-3-yl)-pregn-7-en-3-ol(175)
2-Picolyltriphenylphosphonium chloride 2^
(3A,20A)-20-P-(Pyridin-2-yl)-(£)-ethenyl]-pregn-7-eii-3-yl
S-Picolyltriphenylphosphonium chloride 27^
(35,20i?)-20-[2-(Pyridin-3-yl)-(Z)-ethenyl]-pregn-7-en-3-yl acetate (178a) 272
(35,20Ä)-20-[2-(Pyridin-3-yl)-(£)-ethenyl]-pregn-7-en-3-yl
4-Picolyltriphenylphosphonium chloride 274
(З^гО^-гО-РЧРугіат^-уіНА-еиіеиуЦ-рге^^-еп-З-уі
(35,20Ä)-20-[24Pyridm-4-ylH£)-ethenyl]-pregn-7-en-3-yl
(35,20Ä)-20-[2-(Pyridin-3-yl)-(£)-ethenyl]-pregn-7-en-3-ol (180)
(3S,20R)-20-[2-(Pyrìdm-2-yl)-(E)-eih(myl]-pTegn-7-en-3-ol
(35f,20i?)-20-[2-(Pyridin-3-yl)-(Z)-ethenyl]-pregn-7-en-3-ol
(3S,20K)-20-[2-CPyrìdia-4-yìy(E)-etheayì]-preffi-7-en-3-ol
2-[(35,20Ä)-(3-AcetoxypTegn-7-en-20-yl)-(£)-ethen-l-yl)]-l-methylpyridinium
iodide
2-[(3Ä,20Ä)-(3-Hydroxypregn-7-en-20-yl)-(£>ethen-l-yi)]-l-methylpyridinium
iodide
3-[(3S,20Ä)-(3-Acetoxypregn-7-en-20-yl)-(Z)-ethenyl)]-l-methylpyridinium
(186)
S-KSS^OfíHS-Hydroxypregn^-en^O-ylHZí-ethenyOl-l-meťhylpyridinium 284
iodide
iodide
3-[(35,20Ä)-(3-Hydroxypregn-7-en-20-ylH£>ethenyl)]-l-methylpyridinium 286
iodide
4-[(35,20Ä>(3-Acetoxypregn-7-en-20-yl)4^)-ethen-l -ylJ}-\
iodide
4-[(35i,20Ä)-(3-Hydroxypregn-7-en-20-yl)-(£)-ethen-l-yl)]-l-methylpyridinium 288
iodide
Mixture of
pyridinium
yl)-(£)-ethen-l-yl)]-pyridmium
III. Procedure for biological assays 29^
ПІЛ.
III.2. Procedure for the ergosterol biosynthesis screening test 292
Ш.2.1.
111.2.2. Determination of the EC50 293
111.2.3. Treatment of the biomass obtained by filtration 293
ПГ.2.4.
Ш.2.5.
Ш.З.
Ш.4.
Ш.5.
Ш.6.
Ш.7.
III.
III.7.2. MTT assay 301
References 302 |
| any_adam_object | 1 |
| any_adam_object_boolean | 1 |
| author | Renard, Delphine |
| author_facet | Renard, Delphine |
| author_role | aut |
| author_sort | Renard, Delphine |
| author_variant | d r dr |
| building | Verbundindex |
| bvnumber | BV021680398 |
| ctrlnum | (OCoLC)162456703 (DE-599)BVBBV021680398 |
| edition | 1. Aufl. |
| format | Book |
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| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV021680398 |
| illustrated | Illustrated |
| index_date | 2024-07-02T15:11:12Z |
| indexdate | 2024-12-20T11:02:14Z |
| institution | BVB |
| isbn | 3899633733 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-014894627 |
| oclc_num | 162456703 |
| open_access_boolean | |
| owner | DE-355 DE-BY-UBR DE-19 DE-BY-UBM DE-29T DE-12 |
| owner_facet | DE-355 DE-BY-UBR DE-19 DE-BY-UBM DE-29T DE-12 |
| physical | 310 S. graph. Darst. |
| publishDate | 2006 |
| publishDateSearch | 2006 |
| publishDateSort | 2006 |
| publisher | Hut |
| record_format | marc |
| spelling | Renard, Delphine Verfasser aut Side chain azasteroids and thiasteroids as sterol biosynthesis inhibitors with antifungal, antitrypanosomal and antileishmanial activities von Delphine Renard 1. Aufl. München Hut 2006 310 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Zugl.: München, Univ., Diss., 2006 Antibiotikum (DE-588)4002257-2 gnd rswk-swf Steroidderivate (DE-588)4686773-9 gnd rswk-swf Stickstoffverbindungen (DE-588)4183288-7 gnd rswk-swf Schwefelverbindungen (DE-588)4180438-7 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Steroidderivate (DE-588)4686773-9 s Stickstoffverbindungen (DE-588)4183288-7 s Antibiotikum (DE-588)4002257-2 s DE-604 Schwefelverbindungen (DE-588)4180438-7 s Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014894627&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Renard, Delphine Side chain azasteroids and thiasteroids as sterol biosynthesis inhibitors with antifungal, antitrypanosomal and antileishmanial activities Antibiotikum (DE-588)4002257-2 gnd Steroidderivate (DE-588)4686773-9 gnd Stickstoffverbindungen (DE-588)4183288-7 gnd Schwefelverbindungen (DE-588)4180438-7 gnd |
| subject_GND | (DE-588)4002257-2 (DE-588)4686773-9 (DE-588)4183288-7 (DE-588)4180438-7 (DE-588)4113937-9 |
| title | Side chain azasteroids and thiasteroids as sterol biosynthesis inhibitors with antifungal, antitrypanosomal and antileishmanial activities |
| title_auth | Side chain azasteroids and thiasteroids as sterol biosynthesis inhibitors with antifungal, antitrypanosomal and antileishmanial activities |
| title_exact_search | Side chain azasteroids and thiasteroids as sterol biosynthesis inhibitors with antifungal, antitrypanosomal and antileishmanial activities |
| title_exact_search_txtP | Side chain azasteroids and thiasteroids as sterol biosynthesis inhibitors with antifungal, antitrypanosomal and antileishmanial activities |
| title_full | Side chain azasteroids and thiasteroids as sterol biosynthesis inhibitors with antifungal, antitrypanosomal and antileishmanial activities von Delphine Renard |
| title_fullStr | Side chain azasteroids and thiasteroids as sterol biosynthesis inhibitors with antifungal, antitrypanosomal and antileishmanial activities von Delphine Renard |
| title_full_unstemmed | Side chain azasteroids and thiasteroids as sterol biosynthesis inhibitors with antifungal, antitrypanosomal and antileishmanial activities von Delphine Renard |
| title_short | Side chain azasteroids and thiasteroids as sterol biosynthesis inhibitors with antifungal, antitrypanosomal and antileishmanial activities |
| title_sort | side chain azasteroids and thiasteroids as sterol biosynthesis inhibitors with antifungal antitrypanosomal and antileishmanial activities |
| topic | Antibiotikum (DE-588)4002257-2 gnd Steroidderivate (DE-588)4686773-9 gnd Stickstoffverbindungen (DE-588)4183288-7 gnd Schwefelverbindungen (DE-588)4180438-7 gnd |
| topic_facet | Antibiotikum Steroidderivate Stickstoffverbindungen Schwefelverbindungen Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014894627&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT renarddelphine sidechainazasteroidsandthiasteroidsassterolbiosynthesisinhibitorswithantifungalantitrypanosomalandantileishmanialactivities |