Influence of a substituent at C3 on the direction of bromination of estra-1,3,5(10)trien-17-ones

Fedorova, O. I.; Morozova, L. S.; Алексеева, Л. М.; Grinenko, G. S.

doi:10.1007/bf00575753

Cited by 3 publications

(2 citation statements)

References 6 publications

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“…519 Bromination of estrone and estrone methyl ether by bromine in dichloromethane containing HCl favored formation of Aring substitution products such as 2-or 4-bromoestrone, whereas bromination of estrone acetate favored the 16-bromo and 16,16-dibromo derivatives. 520 Abul-Hajj 521 investigated the polymeric bromination of the 5β-estrane-3,17-dione by bromine in acetic acid and disclosed that it produced 2αbromo-5β-estrane-3,17-dione (Scheme 155).…”

Section: Saldabols Et Al Carried Out Bromination Of Imidazothiazolesmentioning

confidence: 99%

“…Krebs and Keese treated norcamphor with bromine in the presence of phosphorus trichloride to produce 2,2-dibromonorbornane, which was subsequently isomerized with AlBr 3 in CS 2 at 0 °C to afford 1,2-exodibromonorbornane . Bromination of estrone and estrone methyl ether by bromine in dichloromethane containing HCl favored formation of A-ring substitution products such as 2- or 4-bromoestrone, whereas bromination of estrone acetate favored the 16-bromo and 16,16-dibromo derivatives . Abul-Hajj investigated the polymeric bromination of the 5β-estrane-3,17-dione by bromine in acetic acid and disclosed that it produced 2α-bromo-5β-estrane-3,17-dione (Scheme ).…”

Section: Bromination Reactionsmentioning

confidence: 99%

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Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Saldabols Et Al Carried Out Bromination Of Imidazothiazolesmentioning

confidence: 99%

Section: Bromination Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Synthesis, functionalization and biological activity of arylated derivatives of (+)-estrone

Ivanov

Ejaz

Shah

et al. 2017

Bioorganic & Medicinal Chemistry

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Heterocyclic ring extension of estrone: Synthesis and cytotoxicity of fused pyran, pyrimidine and thiazole derivatives

Mohareb¹,

Al‐Omran²,

Azzam³

2014

Steroids

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The one pot reaction of estrone with the aromatic aldehydes 2a-c and either of malononitrile or ethyl cyanoacetate afforded the fused pyran derivatives 4a-f. On the other hand, carrying the same reaction using thiourea instead of the cyanomethylene reagent gave the fused pyrimidine derivatives 6a-c. The latter compounds reacted with phenacyl bromide to give the thiazolo[3,2-a]pyrimidine derivatives 8a-c. The reaction of the title compound with bromine gave the monobromo derivative 13 which in turn reacted with either thiourea or cyanothioacetamide to give the thiazole derivatives 14 and 16, respectively. The cytotoxicity of the newly synthesized products was evaluated against six human cancer and normal cell lines where the results showed that compounds 4c, 4f, 6b, 8b, 8c, 10, 13, 16, 18c and 19c exhibited optimal cytotoxic effect against the cancer cell lines, with IC50's in the nM range.

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Influence of a substituent at C3 on the direction of bromination of estra-1,3,5(10)trien-17-ones

Cited by 3 publications

References 6 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Synthesis, functionalization and biological activity of arylated derivatives of (+)-estrone

Heterocyclic ring extension of estrone: Synthesis and cytotoxicity of fused pyran, pyrimidine and thiazole derivatives

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