Selective Oxidation of Triterpene Alcohols by Sodium Hypochlorite

Флехтер, О. Б.; Ashavina, O. Yu.; Смирнова, И. Е.; Балтина, Л. А.; Галин, Ф. З.; Kabal'nova, N. N.; Толстиков, Г. А.

doi:10.1023/b:conc.0000033930.76751.b7

Cited by 17 publications

(5 citation statements)

References 8 publications

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“…Allobetulin ( 2 ) can be simply oxidized to the synthetically valuable allobetulone ( 4 ) by chromium(VI) reagents [ 2 , 33 , 34 ], Swern reaction [ 35 ] or sodium hypochlorite [ 36 ]. As mentioned previously, 4 can also be prepared in a one-pot procedure from betulin ( 1 ) [ 15 ].…”

Section: Simple Functionalisation Reactions Of Allobetulin Analogsmentioning

confidence: 99%

Allobetulin and Its Derivatives: Synthesis and Biological Activity

2011

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This review covers the chemistry of allobetulin analogs, including their formation by rearrangement from betulin derivatives, their further derivatisation, their fusion with heterocyclic rings, and any further rearrangements of allobetulin compounds including ring opening, ring contraction and ring expansion reactions. In the last part, the most important biological activities of allobetulin derivatives are listed. One hundred and fifteen references are cited and the relevant literature is covered, starting in 1922 up to the end of 2010.

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Section: Simple Functionalisation Reactions Of Allobetulin Analogsmentioning

confidence: 99%

Allobetulin and Its Derivatives: Synthesis and Biological Activity

2011

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“…These results include mostly oxime and amide functions at C3 or C28 positions. For example, 3-oxime of betulonic acid and L-leucine-28-amide demonstrated 90% suppression of influenza virus A H7N1 (EC 50 2.17, MTT/EC 50 392.16) [26,27] 3β-and 3α-amino-derivatives of oleanolic acid possessed inhibitory activity on HCV protease [28].…”

Section: Resultsmentioning

confidence: 99%

Azepanodipterocarpol is potential candidate for inhibits influenza H1N1 type among other lupane, oleanane, and dammarane A-ring amino-triterpenoids

et al. 2022

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“…These results primarily include amide functions at C28 positions. Thus, betulonic acid L -leucine-amide demonstrated 90% suppression of the influenza virus A H7N1 (EC 50 2.17, MTT/EC 50 392.16) [ 41 , 42 ]. Lupane 3,4-seco-3,28-bis-methylpiperazine-amide showed IC 50 27 µM and SI 7.1 against the Flu A H1N1 strain [ 43 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

et al. 2022

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A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) oleanonic acid derivatives, holding some cyclic amines, linear polyamines and benzylaminocarboxamides at C28, has been synthesized and screened for antiviral activity against influenza A/PuertoRico/8/34 (H1N1) and Dengue virus serotypes of DENV-1, -2, -3, -4. It was found that 28-homopiperazine 2 and 3-N-phthalyl 22 amides of oleanonic acid demonstrated high potency with selectivity index SI 27 (IC50 21 μM) and 42 (IC50 12 μM). Oleanonic acid aminoethylpiperazine amide 6 and C-azepano-erythrodiol 23 appeared to be the most effective compounds against DENV-1 (IC50′s 67 and 107 μM) and -2 (IC50′s 86 and 68 μM correspondingly) serotypes.

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Selective Oxidation of Triterpene Alcohols by Sodium Hypochlorite

Cited by 17 publications

References 8 publications

Allobetulin and Its Derivatives: Synthesis and Biological Activity

Allobetulin and Its Derivatives: Synthesis and Biological Activity

Azepanodipterocarpol is potential candidate for inhibits influenza H1N1 type among other lupane, oleanane, and dammarane A-ring amino-triterpenoids

Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

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