Synthesis of new derivatives of 3β-hydroxy18βH-olean-9,12-dien-30-oic acid

Михайлова, Л. Р.; Khudobko, M. V.; Балтина, Л. А.; Спирихин, Л. В.; Кондратенко, Р. М.

doi:10.1007/s10600-009-9336-8

Cited by 15 publications

(5 citation statements)

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“…The study of steroidal compounds was further extended by Natalija et al [109] and described the synthesis and configurational analysis of novel steroidal D-ring-substituted heterocycles and evaluated their cytotoxic and antimicrobial resistance properties. Scheme 35 displays the reaction of 21-hydroxyprogesterone (110) with LR in toluene or CH 2 Cl 2 , affording a complex mixture of products, out of which four D-ring-substituted products were, with two tautomeric pairs, isolated and characterized, namely The two tautomeric pairs are (111,112) and (113,114). The synthesized compounds exist as diastereomers in an 8:2 ratio, varying in configuration at the phosphorus atom.…”

Section: Synthesis Of Biologically Active Steroids and Terpenoidsmentioning

confidence: 99%

“…The two tautomeric pairs are (111,112) and (113,114). The synthesized compounds exist as diastereomers in an 8:2 ratio, varying in configuration at the phosphorus atom.…”

Section: Synthesis Of Biologically Active Steroids and Terpenoidsmentioning

confidence: 99%

“…New derivatives of 3β-hydroxy-18β-H-olean-9,12-dien-30-oic acid (118), a GLA analog modified in ring C, were synthesized by Mikhailova et al [113]. Oxidation of (118) by pyridinium dichromate (PDC) in CH2Cl2, trailed by refluxing in NH 2 OH•HCl in anhydrous pyridine for 1 h, formed 3-hydroxyimine (119).…”

Section: Synthesis Of Biologically Active Steroids and Terpenoidsmentioning

confidence: 99%

“…The reaction of (119) with SOCl 2 in anhydrous dioxane at 10 • C produced (120). The thio analogs (121) were yielded on reaction with LR in toluene for 5 h [113] (Scheme 37). The synthesis of plant terpenoids should be explored for other compounds with potent biological activities.…”

Section: Synthesis Of Biologically Active Steroids and Terpenoidsmentioning

confidence: 99%

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A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

Khatoon

Abdulmalek

2021

Molecules

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Lawesson’s reagent (LR) is a well-known classic example of a compound with unique construction and unusual chemical behavior, with a wide range of applications in synthetic organic chemistry. Its main functions were rounded for the thionation of various carbonyl groups in the early days, with exemplary results. However, the role of Lawesson’s reagent in synthesis has changed drastically, and now its use can help the chemistry community to understand innovative ideas. These include constructing biologically valuable heterocycles, coupling reactions, and the thionation of natural compounds. The ease of availability and the convenient usage of LR as a thionating agent made us compile a review on the new diverse applications on some common functional groups, such as ketones, esters, amides, alcohols, and carboxylic acids, with biological applications. Since the applications of LR are now diverse, we have also included some new classes of heterocycles such as thiazepines, phosphine sulfides, thiophenes, and organothiophosphorus compounds. Thionation of some biologically essential steroids and terpenoids has also been compiled. This review discusses the recent insights into and synthetic applications of this famous reagent from 2009 to January 2021.

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Section: Synthesis Of Biologically Active Steroids and Terpenoidsmentioning

confidence: 99%

“…The two tautomeric pairs are (111,112) and (113,114). The synthesized compounds exist as diastereomers in an 8:2 ratio, varying in configuration at the phosphorus atom.…”

Section: Synthesis Of Biologically Active Steroids and Terpenoidsmentioning

confidence: 99%

Section: Synthesis Of Biologically Active Steroids and Terpenoidsmentioning

confidence: 99%

Section: Synthesis Of Biologically Active Steroids and Terpenoidsmentioning

confidence: 99%

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A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

Khatoon

Abdulmalek

2021

Molecules

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“…We demonstrated this previously using 3-hydroxyolean-9(11),12-dien-30-oic acid as an example [9]. The A-homo-4-aza derivative (5) was isolated in 76% yield after recrystallization from EtOH.…”

mentioning

confidence: 92%

Beckmann rearrangement of 11-deoxo-glycyrrhetic acid 3-ketoxime

2009

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Synthetic transformations of bioactive plant metabolites represent an active direction of modern organic and bioorganic chemistry that seeks to synthesize new biologically active compounds with new structures that are promising in medicine [1,2]. Beckmann rearrangement of triterpenoid ketoximes has been studied using as examples allobetulone [3], lupenone [4], β-amyrin [5], friedelin [6], 18α-and 18β-glycyrrhetic acids [7], and oleanolic acid [8]. As a rule, Beckmann rearrangement of triterpenoid 3-ketoximes forms lactams (aza derivatives) and 3,4-seco-nitriles. It was shown previously that aza derivatives of oleanolic acid are interesting as promoters of percutaneous transport of bioactive compounds [8]. This is very important for the development of external drug forms and cosmetics.In order to prepare new biologically active derivatives of 11-deoxo-glycyrrhetic acid (GLA) (1), one of the minor triterpenoids from roots of Glycyrrhiza glabra L. and G. uralensis Fisher, we performed synthetic transformations of the methyl ester of 11-deoxo-GLA (2) on ring A (Scheme 1). Oxidation of 2 by pyridinium dichromate (PDC) in CH 2 Cl 2 at room temperature produced the 3-ketone (3) in 70% yield, reaction of which with NH 2 OH⋅HCl in anhydrous Py by refluxing for 1 h formed the pure (TLC) 3-hydroxyimine (3-ketoxime) (4) in 84% yield. Its stereochemistry was not determined. The 13 C NMR spectrum of 4 contained a resonance at δ 166.5 ppm, which was shifted to strong field by 51 ppm compared with the spectrum of starting 3 as a result of forming the C=N-bond.Reaction of 4 with SOCl 2 in anhydrous dioxane at 10°C formed lactam 5, the methyl ester of A-homo-4-aza-3-oxo-11-deoxoolean-12-en-30-oic acid, as a result of a first-order Beckmann rearrangement. We demonstrated this previously using 3-hydroxyolean-9(11),12-dien-30-oic acid as an example [9]. The A-homo-4-aza derivative (5) was isolated in 76% yield after recrystallization from EtOH.

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Does One Keto Group Matter? Structure‐Activity Relationships of Glycyrrhetinic Acid Derivatives Modified at Position C‐11

Csuk¹,

Schwarz²,

Kluge³

et al. 2011

Archiv der Pharmazie

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Several triterpenoic acids display a remarkable cytotoxicity on tumor cells. Glycyrrhetinic acid - the main content of the licorice root - possesses an apoptotic effect on tumor cells. Previous studies pointed out the presence of a keto group at position C-11 in glycyrrhetinic acid derivatives as the main reason for its apoptotic activity. Several pairs of derivatives were synthesized differing only at position C-11. These compounds were tested in a sulforhodamine B colorimetric assay for cytotoxicity screening on 12 tumor cell lines and mouse embryonic fibroblasts (NIH3T3). Our results show that there is no direct relation between the existence of the C-11 keto group and the apoptotic activity of the compounds.

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Synthesis of new derivatives of 3β-hydroxy18βH-olean-9,12-dien-30-oic acid

Cited by 15 publications

References 15 publications

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

Beckmann rearrangement of 11-deoxo-glycyrrhetic acid 3-ketoxime

Does One Keto Group Matter? Structure‐Activity Relationships of Glycyrrhetinic Acid Derivatives Modified at Position C‐11

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