Synthesis of betulonic acid amides

Antimonova, A. N.; Uzenkova, N. V.; Petrenko, N. I.; Шакиров, М. М.; Шульц, Э. Э.; Толстиков, Г. А.

doi:10.1007/s10600-008-9054-7

Cited by 6 publications

(9 citation statements)

References 7 publications

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“…Compounds 1 [17], 2 -6 [18], 7 [19], 8 -11, 13 -18, 21, 23 -25 [18], 12, 19, 20 [21], 22 [22], 26, 27 [23], 28 [16], 29 -33 [17], 34 [24], 35 [25], 36, 38 [24], 39, 40 [26], 40 -45 [20], 46, 47 [27], 48 [28] obtained according to the previously described methods. (20 mL), and the mixture was stirred for 2 h at room temperature, then the solvent was removed in vacuo.…”

Section: Methodsmentioning

confidence: 99%

“…To continue our efforts towards developing new promising antiviral agents among triterpenoids [10][11][12][16][17][18][19][20][21], here we present new data on in vitro antiviral screening of a broad series of nitrogen lupane triterpenoids modified at C3, C20 and C28 positions ( Figure 1) in relation to their activity against Flu A (H1N1, H3N2 and H5N1). Forty-seven derivatives (1-36, 38-48) have been synthesized as described previously [16][17][18][19][20][21][22][23][24][25][26][27][28], while four compounds (37, 49-51) are new.…”

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confidence: 99%

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Structure – Anti-influenza Type a Activity Relationship among a Series of Nitrogen Lupane Triterpenoids

Смирнова

Казакова

2018

Natural Product Communications

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Fifty-one derivatives of lupeol, betulin, betulonic and acanthochlamic acids modified at C3, C20 and C28 of the lupane core including four new ones (37, 49-51) and forty-seven previously synthesized derivatives (1-36, 36-48) were screened for their in vitro anti-influenza type A (H1N1, H3N2 and H5N1) activity at the NIAID. The selectivity index (SI) against Flu A for tested triterpenoids ranged from > 20 to 0. Betulonic acid 2-aminopyridinylamide was a leader being active against H1N1, H3N2 and H5N1 with SI > 20, 1.8 and 5.3, respectively. The betulonic acid methoxy-and nitro-substituted benzalhydrazides showed selectivity only against H5N1, while lupeol and 3-oximino-betulonic acid benzalhydrazides were active against three types of Flu A. A-seco-aminoderivatives were more effective than the initial acanthochlamic acid against H1N1, but practically inactive against H3N2, with bis-N-methylpiperazinylamide as a leader in this series. Triterpenoids with a long-chain substituent at C17 containing amide or hydrazide bonds with aromatic or heterocyclic fragments exert positive influence on the activity.

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Structure – Anti-influenza Type a Activity Relationship among a Series of Nitrogen Lupane Triterpenoids

Смирнова

Казакова

2018

Natural Product Communications

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“…Betulonic acid diethylentriamine conjugate showed partial activity against methicillin-resistant S. aureus and the fungi C. neoformans [265]. [265,275], 268 [281], 269 [265], 270, 271 [300], 272, 273, 290 [298], 275, 299 [299], 276 [294,303], 277 [258], 278 [259], 279 [260], 280 [295,299], 281, 292 [302], 282 [289], 283 [274], 284 [304], 285 [287], 286 [291], 287 [284], 288 [277], 289 [285], 291 [283], 293 [296], 294 [280], 295 [297], 296 [279], 297 [274].…”

Section: Terpene-and Triterpene-based Polyamine Derivativesmentioning

confidence: 99%

From Marine Metabolites to the Drugs of the Future: Squalamine, Trodusquemine, Their Steroid and Triterpene Analogues

Казакова

Giniyatullina

Babkov

et al. 2022

IJMS

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This review comprehensively describes the recent advances in the synthesis and pharmacological evaluation of steroid polyamines squalamine, trodusquemine, ceragenins, claramine, and their diverse analogs and derivatives, with a special focus on their complete synthesis from cholic acids, as well as an antibacterial and antiviral, neuroprotective, antiangiogenic, antitumor, antiobesity and weight-loss activity, antiatherogenic, regenerative, and anxiolytic properties. Trodusquemine is the most-studied small-molecule allosteric PTP1B inhibitor. The discovery of squalamine as the first representative of a previously unknown class of natural antibiotics of animal origin stimulated extensive research of terpenoids (especially triterpenoids) comprising polyamine fragments. During the last decade, this new class of biologically active semisynthetic natural product derivatives demonstrated the possibility to form supramolecular networks, which opens up many possibilities for the use of such structures for drug delivery systems in serum or other body fluids.

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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].…”

mentioning

confidence: 99%

“…The yields of the target compounds were 74.9-89.8%. The structures of the amides were established using IR and NMR spectra and a comparison with those for analogous compounds [5,6,12]. The 13 C NMR spectra of the synthesized compounds 2-7 contained resonances for the betulonic moiety and the corresponding number of C resonances for the amine component (Table 1).…”

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confidence: 99%

Synthesis and antibacterial activity of betulonic acid amides with piperazine derivatives

Chue

Chang²,

Ten

2011

Chem Nat Compd

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Synthesis of betulonic acid amides

Cited by 6 publications

References 7 publications

Structure – Anti-influenza Type a Activity Relationship among a Series of Nitrogen Lupane Triterpenoids

Structure – Anti-influenza Type a Activity Relationship among a Series of Nitrogen Lupane Triterpenoids

From Marine Metabolites to the Drugs of the Future: Squalamine, Trodusquemine, Their Steroid and Triterpene Analogues

Synthesis and antibacterial activity of betulonic acid amides with piperazine derivatives

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