Synthesis of 20-hydroxyecdysone oxime, its diacetonide, and their 14,15-anhydro derivatives
Abstract
20-Hydroxyecdysone oxime, its diacetonide, and the corresponding 14,15-anhydro derivatives were synthesized. Conditions were found for the preparation of the Z-and E -oximes, and their characteristics 1 H and 13 C NMR parameters were determined.
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Ecdysteroid 6-oximation can result in 3 different types of product mixtures depending on the neutralization procedure.
“Our results confirm previous observations that ecdysteroid 6-oximation can result in 3 different types of product mixtures depending on the neutralization procedure [22]”
From Nitrogen-containing ecdysteroid derivatives vs. multi-drug resistance in cancer: Preparation and antitumor activity of oximes, oxime ethers and a lactam (2018) · cites this paper as [22]
Cites
Phytoecdysteroids from the Juice of Serratula coronata L. (Asteraceae)
Odinokov, V. N., Galyautdinov, I. V., Nedopekin, D. V., Khalilov, L. M., Shashkov, A. S., Kachala, V. V., Dinan, L., & Lafont, R. (2002) · Insect Biochemistry and Molecular Biology · doi:10.1016/s0965-1748(01)00106-0 · Cited by 80 · see citing works
Self-citationRodrı́guez, J., Núñez, L., Peixinho, S., et al. (1997) · Tetrahedron Letters · doi:10.1016/s0040-4039(97)00163-9 · Cited by 66 · see citing works
Synthesis of 6-hydroximino-3-oxo steroids, a new class of aromatase inhibitor
Holland, H. L., Kumaresan, S., Tan, L., & Njar, V. C. O. (1992) · Journal of the Chemical Society Perkin Transactions 1 · doi:10.1039/p19920000585 · Cited by 39 · see citing works
Transformation of 20-Hydroxyecdysone Acetonides into Podecdysone B
Одиноков, В. Н., Galyautdinov, I. V., Nedopekin, D. V., et al. (2003) · Russian Journal of Organic Chemistry · doi:10.1023/b:rujo.0000003183.84168.79 · Cited by 10 · see citing works
Self-citationОдиноков, В. Н., Савченко, Р. Г., Афонькина, С. Р., et al. (2005) · Russian Journal of Organic Chemistry · doi:10.1007/s11178-005-0173-3 · Cited by 9 · see citing works
Orifluoroacetylation and dehydration of 20-hydroxyecdysone acetonides. Synthesis of stachisterone B
Одиноков, В. Н., Galyautdinov, I. V., Nedopekin, D. V., et al. (2003) · Russian Chemical Bulletin · doi:10.1023/a:1022433423370 · Cited by 9 · see citing works
Self-citationОдиноков, В. Н., Савченко, Р. Г., Nazmeeva, S. R., et al. (2002) · Russian Chemical Bulletin · doi:10.1023/a:1021377207689 · Cited by 5 · see citing works
Method for mild trimethylsilylation of the 14α-hydroxy group in ecdysteroids
Одиноков, В. Н., Савченко, Р. Г., Nazmeeva, S. R., et al. (2002) · Russian Chemical Bulletin · doi:10.1023/a:1021393611323 · Cited by 4 · see citing works
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Vágvölgyi, M., Martins, A., Kulmány, Á., Zupkó, I., Gáti, T., Simon, A., Tóth, G., & Hunyadi, A. (2018) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2017.12.032 · Cited by 37 · see citing works
- Authors
- Galyautdinov, I. V., Ves’kina, N. A., Afon’kina, S. R., Khalilov, L. M., & Odinokov, V. N.
- Affiliations
- Russian Academy of Sciences (RU)
- Corresponding author
- Galyautdinov, I. V.
- Venue
- Russian Journal of Organic Chemistry
- Publisher
- Pleiades Publishing Ltd
- Published
- 2006-09
- Volume
- 42
- Issue
- 9
- Pages
- 1333-1339
- ISSN
- 0022-3271 (ISSN-L)
- 1070-4280
- 1608-3393
- OpenAlex
- W2952001235
- Cited by
- 13
- References
- 8
- Citations by year
- 2024: 1 · 2022: 1 · 2021: 2 · 2017: 1 · 2016: 2 · 2015: 1 · 2012: 1
- FWCI
- 0.54
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Russian Journal of Organic Chemistry (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Genetics › Estrogen and related hormone effects
- Keywords
- 20-hydroxyecdysone, oximes, ecdysteroids, NMR spectroscopy, stereochemistry
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