Synthesis of dihalocarbene derivatives of estafiatin guaianolide

Jalmakhanbetova, R. I.; Ралдугин, В. А.; Bagryanskaya, I. Yu.; Gatilov, Yu. V.; Шакиров, М. М.; Атажанова, Г. А.; Адекенов, С. М.

doi:10.1007/s10600-007-0189-8

Cited by 7 publications

(5 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The reactions of estafiatin and arglabin with dihalocarbenes have been studied. 372,373 The microbiological transformations of dehydrocostus lactone by the fungi Mucor polymorphosporus and Aspergillus candidus have been studied, 284 whilst the plant growth regulating activity of several derivatives of this lactone has also been evaluated. 374 The pharmacological activity of inuviscolide has been investigated.…”

Section: Eremophilane and Bakkanementioning

confidence: 99%

Natural sesquiterpenoids

Fraga

2008

Nat. Prod. Rep.

View full text Add to dashboard Cite

show abstract

Section: Eremophilane and Bakkanementioning

confidence: 99%

Natural sesquiterpenoids

Fraga

2008

Nat. Prod. Rep.

View full text Add to dashboard Cite

show abstract

“…For example, for the synthesis of cyclopropane derivative we studied the interaction of arglabin 64 with dichlorocarbon generated from chloroform in the conditions of interphase catalysis with the presence of dicyclohexane-18-crown-6-ether. Thereat, compounds 65-67 were synthesized [49]. To study the cyclopropanation reaction we carried out the interaction of estafiatin 68 with dichlorocarbon [:ССl 2 ] generated from chloroform with the presence of dicyclohexane-18-crown-6-ether and alkali solution.…”

Section: Synthesis Of Chlorine-containing Sesquiterpene Lactonesmentioning

confidence: 99%

“…To study the cyclopropanation reaction we carried out the interaction of estafiatin 68 with dichlorocarbon [:ССl 2 ] generated from chloroform with the presence of dicyclohexane-18-crown-6-ether and alkali solution. Colourless crystalline substance 69 was obtained [50]. For further transformation of arglabin tetrachlorocarbene derivative, the molecule 66 was subjected to the interaction with pyridine.…”

Section: Synthesis Of Chlorine-containing Sesquiterpene Lactonesmentioning

confidence: 99%

Heteroatom-Containing Natural Sesquiterpene Lactones and Methods for their Obtaining

Адекенов¹,

Атажанова²

2013

Eur Chem Tech J

View full text Add to dashboard Cite

This review shows the data about isolated heteroatom-containing sesquiterpene lactones from various genera of Asteraceae family, natural occurence, isolation methods and their biological activity. Chlorinecontaining sesquiterpene lactones were isolated from genera of Artemisia L., Achillea L., Acroptilon Cass, Centaurea L., Chartolepis Cass, Eupatorium L., Jurinea Cass, Rhaponticum Adams, Saussurea DC. The greatest quantity of chlorine-containing sesquiterpene lactones were isolated from Centaurea genus. 25 new sesquiterpene lactones with chlorine atom in molecule were isolated and characterized. The sesquiterpene lactones, which in their structure contained a sulphur atom as a component of various alkoxyl-, thiohydroxygroups and acid residues, were isolated from genera of Eupatorium L., Petasites Mill, Helenium L., Acritopappus R.M. King and H. Rob., Arctium L., Saussurea DC. Nitrogen atom in the structure of natural sesquiterpene lactones is present in the form of amino groups as a part of ester groups as well as amino acids as Michael adducts. Nitrogen-containing sesquiterpene lactones were isolated from Acanthospermum Schrank, Saussurea DC. Isolated heteroatom-containing sesquiterpene lactones possess bactericidal, antifungal, cytotoxic, antiviral, virucidal, antiulcer and others activities. Another method for obtaining heteroatom-containing sesquiterpene lactones is a directed synthesis of chlorine-, fluorine-, bromine-, sulphur- and nitrogen-containing sesquiterpene lactones. On the basis of sesquiterpene lactone artemisinin known as an effective antimalarial preparation, we synthesized over 200 derivatives, among which fluorine-, chlorine-, bromine-, nitrogen-, sulphur- and azide-containing derivatives of artemisinin were obtained.

show abstract

“…Opisano modyfikację pierścienia laktonowego prowadzącą do dibromometylenowych pochodnych arglabiny, a w kolejnym etapie do bis-dibromometylenowych pochodnych (Ryc. 4) [13,14]. Enancjoselektywna synteza arglabiny przeprowadzona została po raz pierwszy w roku 2007 przez badaczy niemieckich [12].…”

Section: Podobnie W Grupie Eudesmanolidów Występują Związki Hamujące ...unclassified

Arglabina – Lakton Seskwiterpenowy O Właściwościach Przeciwnowotworowych

Grech‐Baran¹,

Pietrosiuk²

2010

pps

View full text Add to dashboard Cite

W pracy przedstawiono aktualny stan wiedzy na temat biogenezy laktonów seskwiterpenowych oraz właściwości biologicznych i mechanizmu działania arglabiny, jednego z ważnych metabolitów z tej grupy. Arglabina - [1(R),10(S)-epoksy-5(S),5(S),7(S)-gwaja-3(4),11(13)-dien-6,12-nolid], należy do grupy laktonów seskwiterpenowych o szkielecie typu gwajanolidu. Występuje w kilku gatunkach z rodzaju Artemisia (Asteraceae). Po raz pierwszy związek ten wyizolowano i oznaczono w kwiatach i liściach gatunku Artemisia glabella Kar. et Kir. Badania biologiczne wykazały silne właściwości przeciwzapalne, a przede wszystkim przeciwnowotworowe arglabiny.

show abstract

Synthesis of dihalocarbene derivatives of estafiatin guaianolide

Cited by 7 publications

References 7 publications

Natural sesquiterpenoids

Natural sesquiterpenoids

Heteroatom-Containing Natural Sesquiterpene Lactones and Methods for their Obtaining

Arglabina – Lakton Seskwiterpenowy O Właściwościach Przeciwnowotworowych

Contact Info

Product

Resources

About