Efficient synthesis of the first betulonic acid–acetylene hybrids and their hepatoprotective and anti-inflammatory activity

Vasilevsky, S. F.; Govdi, Anastasia I.; Шульц, Э. Э.; Шакиров, М. М.; Сорокина, И. В.; Толстикова, Т. Г.; Baev, Dmitry S.; Толстиков, Г. А.; Alabugin, Igor V.

doi:10.1016/j.bmc.2009.05.059

Cited by 47 publications

(22 citation statements)

References 28 publications

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“…However, triterpenoid derivatives with triple bonds, except for a few reports [2][3][4], are relatively unknown. Therefore, their synthesis is a critical problem.…”

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confidence: 98%

Synthesis and structure of an acetylene derivative of lupeol

2011

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The synthesis and x-ray crystal structure of 3-acetoxy-29-norlup-20(30)-yne were carried out.Acetylene compounds are known to be a rather representative group of natural metabolites with pronounced anticancer activity [1]. However, triterpenoid derivatives with triple bonds, except for a few reports [2][3][4], are relatively unknown. Therefore, their synthesis is a critical problem. Furthermore, the alkyne group is one of the most convenient moieties in the design of new compounds because of its high reactivity and ease of functionalization [5].We synthesized lupeol (1) derivative using the previously reported method for preparing triterpenoids with an alkyne moiety [4]. Refluxing 3-acetoxy-29-nor-20-oxolupeol (2) and POCl 3 in Py produced 3-acetoxy-29-norlup-20(30)-yne (3) in 77% yield after purification by column chromatography (Scheme 1). Scheme 1The resonance of the acetylenic proton appeared in the PMR spectrum of 3 as a characteristic doublet at G 2.03 ppm with SSCC 2.2 Hz. The resonance of the C20(30) triple bond was observed in the 13 C NMR spectrum at G 67.8 and 90.8 ppm. The molecular and crystal structures of 3 were established unambiguously by an x-ray structure analysis. The symmetric unit of the unit cell contained two molecules of 3 (A and Ac) with the same absolute configuration and nearly identical structures (Fig. 1, which shows molecule A) that were similar to those of related compounds characterized by us earlier [4,6,7]. All six-membered rings had the chair conformation and were situated trans relative to each other. The five-membered ring had a slightly distorted envelope conformation with C17 deviating by 0.690(8) A° [by 0.685(8) A° for C17c in Ac] from the plane of the other ring atoms. The crystal structure of 3 was stabilized by ordinary van-der-Waals interactions. Deprotection of the acetate under alkaline conditions produced lupeol acetylene derivative 4 from 3.

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“…However, triterpenoid derivatives with triple bonds, except for a few reports [2][3][4], are relatively unknown. Therefore, their synthesis is a critical problem.…”

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confidence: 98%

Synthesis and structure of an acetylene derivative of lupeol

2011

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“…Chen et al reported that the nitric oxide releasing derivatives of oleanolic acid inhibit HCC tumor growth in vivo [15]. On the other hand, betulonic acidacetylene hybrids showed hepatoprotective and anti-inflammatory activities [16]. The conjugation of two bioactive compounds is an effective strategy that is now well accepted [17].…”

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confidence: 98%

Hybrids of 3α-methoxyserrat-14-en-21β-ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2) and various anti-oxidants as cancer chemopreventive agents

Tsujii

Yamada

Kajimoto

et al. 2010

European Journal of Medicinal Chemistry

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“…It is an available and convenient starting material for synthesizing new biologically active compounds [3][4][5][6]. Compounds with antioxidant, anti-inflammatory, antibacterial, hepatoprotective, antiviral, antitumor, and immunostimulant properties have been found among the synthesized derivatives of betulonic acid [4,[7][8][9][10][11][12]. Compounds with various substituents on C-28, in particular peptides [8] and amides [4,8,12], are well-known among them.…”

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confidence: 99%