Zur Kenntnis der Ring‐systeme im Cholesterin. (26. Mitteilung über Cholesterin)

Windaus, A.; Dalmer, O.

doi:10.1002/cber.19190520121

Cited by 38 publications

(10 citation statements)

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“…e present work reports convenient synthesis of N-substituted azacholestanes from a modi�ed version of Schmidt 2 and 3) were synthesized by the literature method [43][44][45][46]. e experiments were carried out with above ketones (1, 2, and 3) and 2-azidoethanol in dichloromethane.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Spectral Characterization, andIn VitroCytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction

Nami

Khan

Alam

et al. 2013

Journal of Spectroscopy

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The present paper reports the synthesis and spectroscopic characterization of few N-2′-hydroxyethyl-substituted azacholestanes using BF3-OEt2, TiCl4, SnCl4, and H2SO4as catalysts in moderate yields by a modified version of Schmidt reaction. A notable feature is the passivity of SnCl4in case of 3β-acetoxy-N-2′-hydroxyethyl-6-aza-B-homo-5α-cholestan-7-one and 3β-chloro-N-2′-hydroxyethyl-6-aza-B-homo-5α-cholestan-7-one. However, the reaction was unsuccessful in case of N-2′-Hydroxyethyl-6-aza-B-homo-5α-cholestan-7-one. Another striking aspect is the attainment of high yield in case of H2SO4as catalyst. The semisolid compounds are characterized using various spectroscopic techniques such as FT-IR,1H-NMR and mass spectra, and microanalytical data. A reaction mechanism has been proposed on the basis of previous studies. Moreover, the compounds have also been screened for theirin vitrocytotoxicity against human colon carcinoma cell line, HCT116, and human liver hepatocellular carcinoma cell line, HepG2, using doxorubicin as standard. On the basis of IC50values, 3β-chloro-N-2′-hydroxyethyl-6-aza-B-homo-5α-cholestan-7-one (5) was found to inhibit the cancer cells most effectively.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Spectral Characterization, andIn VitroCytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction

Nami

Khan

Alam

et al. 2013

Journal of Spectroscopy

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“…For ring conformations, see: Cremer & Pople (1975). For the synthesis, see: Windaus & Dalmer (1919 Symmetry codes: (i) x þ 1; y; z; (ii) Àx þ 1; y À 1 2 ; Àz þ 1; (iii) Àx þ 1; y þ 1 2 ; Àz þ 2.…”

Section: Related Literaturementioning

confidence: 99%

Bis(guanidinium) tris(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)zirconate(II) tetrahydrate

Tabatabaee¹,

Adineh²,

Derikvand³

et al. 2012

Acta Cryst E

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“…For ring conformations, see: Cremer & Pople (1975). For the synthesis, see: Windaus & Dalmer (1919). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 Symmetry codes: (i) x þ 1; y; z; (ii) Àx þ 1; y À 1 2 ; Àz þ 1; (iii) Àx þ 1; y þ 1 2 ; Àz þ 2.…”

Section: Related Literaturementioning

confidence: 99%

3β-Chloro-5α-cholestan-6-one

et al. 2012

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The asymmetric unit of the title compound, C27H45ClO, consists of two crystallographically independent molecules. In both molecules, the three cyclohexane rings in the steroid fused-ring systems adopt chair conformations, while the cyclopentane ring adopts a half-chair conformation in one molecule and an envelope conformation in the other. In the crystal, the molecules are linked into a two-dimensional network by weak C—H⋯O hydrogen bonds. The crystal studied is a nonmerohedral twin with a refined ratio of twin components of 0.264 (3):0.736 (3).

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Zur Kenntnis der Ring‐systeme im Cholesterin. (26. Mitteilung über Cholesterin)

Cited by 38 publications

References 3 publications

Synthesis, Spectral Characterization, andIn VitroCytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction

Synthesis, Spectral Characterization, andIn VitroCytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction

Bis(guanidinium) tris(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)zirconate(II) tetrahydrate

3β-Chloro-5α-cholestan-6-one

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Zur Kenntnis der Ring‐systeme im Cholesterin. (26. Mitteilung über Cholesterin)

Cited by 38 publications

References 3 publications

Synthesis, Spectral Characterization, andIn VitroCytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction

Synthesis, Spectral Characterization, andIn VitroCytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction

Bis(guanidinium) tris(pyridine-2,6-dicarboxylato-κ3O2,N,O6)zirconate(II) tetrahydrate

3β-Chloro-5α-cholestan-6-one

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Bis(guanidinium) tris(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)zirconate(II) tetrahydrate