Recent advances in azasteroids chemistry

Ibrahim‐Ouali, Malika; Rocheblave, Luc

doi:10.1016/j.steroids.2007.12.013

Cited by 49 publications

(14 citation statements)

References 109 publications

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“…e experiments were carried out with above ketones (1, 2, and 3) and 2-azidoethanol in dichloromethane. us, when 2azidoethanol was added to a solution of steroidal ketone (1) in BF 3 -OEt 2 , TiCl 4 , SnCl 4 , or H 2 SO 4 , respectively, vigorous gas evolution was observed immediately. en a saturated aqueous NaHCO 3 solution was added in the reaction mixture followed by standard workup resulted in the formation of desired N-substituted azasteroid (4) (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…Steroidal chemistry has been an area of intense research not from an organic chemist perspective but also for an endocrinologist because of its fundamental importance in an array of biological functions [1]. e replacement of one or more carbon atoms of a steroidal moiety by a heteroatom alters its chemical properties which in certain cases lead to development of useful molecules or drugs [2].…”

Section: Introductionmentioning

confidence: 99%

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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%

Section: Introductionmentioning

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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“…In the D-ring, this corresponds to migration of the highly substituted C-13 carbon vs. migration of the C-16 carbon methylene group. The standard outcome of a classic Beckmann or Schmidt rearrangement—which have been previously carried out on steroids 20 – 22 —is the exclusive migration of C-13, whereas the migration of C-16 is unknown except through multistep sequences 22 .…”

Section: Introductionmentioning

confidence: 99%

Reagent-controlled regiodivergent ring expansions of steroids

Charaschanya

Aubé

2018

Nat Commun

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Ring expansion provides a powerful way of introducing a heteroatom substituent into a carbocyclic framework. However, such reactions are often limited by the tendency of a given substrate to afford only one of the two rearrangement products or fail to achieve high selectivity at all. These limitations are particularly acute when seeking to carry out late-stage functionalization of natural products as starting points in drug discovery. In this work, we present a stereoelectronically controlled ring expansion sequence towards selective and flexible access to complementary ring systems derived from common steroidal substrates. Chemical diversification of the reaction intermediate affords over 100 isomerically pure analogs with spatial and functional diversity. This regiodivergent rearrangement, and the concept of using chiral reagents to affect regiocontrol in chiral natural products, should be broadly applicable to late-stage natural product diversification programs.

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“…The synthesis of some aza-homosteroid compounds with unusual and interesting structures had been reported recently [9,10,11,12,13,14]. These compounds exhibited cytotoxic, antibacterial, antileukemic, and antiandrogenic activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Some New Aza-B-homocholestane Derivatives as Anticancer Agents

et al. 2014

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Using analogues of some marine steroidal oximes as precursors, a series of aza-B-homocholestane derivatives possessing different substituted groups at the 3-position of the steroidal nucleus were synthesized. Their biological activity against cancer cell proliferation was determined with multiple cancer cell lines. Aza-B-homocholestane derivatives possessing 3-hydroxyl, 3-hydroximino and 3-thiosemicarbazone groups displayed remarkable cytotoxicity to cancer cells via apoptosis inducing mechanism. Compounds 5, 10, 12, 15 and 18 exhibited better potency to inhibit cancer cell proliferation. In addition, compound 15 was further evaluated with three dimensional (3D) multicellular spheroids assay to determine its potency against spheroid growth. The structure-activity relationship (SAR) generated in the studies is valuable for the design of novel chemotherapeutic agents.

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Recent advances in azasteroids chemistry

Cited by 49 publications

References 109 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

Reagent-controlled regiodivergent ring expansions of steroids

Synthesis and Evaluation of Some New Aza-B-homocholestane Derivatives as Anticancer Agents

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