1617-72-7Relevant articles and documents
Synthesis and characterization of some new 1,2,3-thiadiazole and 1,2,3-selenadiazole triterpene derivatives from allobetulone and 2-oxoallobetulin
Dinh Ngoc, Thuc
, p. 1665 - 1671 (2020/04/30)
The synthesis of new 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives from triterpenoid ketones has been investigated via the corresponding semicarbazones. The intermediates 5, 8 have also been isolated, separated and their structures identified. The Hurd–Mori reaction and Lalezari method have been applied to synthesize a series of new substances 6 and 7. The regioselectivity of the functionalization mostly was centered at the C-3 position for the products 9 and 10. The structures of these compounds were confirmed by 2D-NMR spectroscopy.
Synthesis of 1,2-azole derivatives on the basis of α,β-unsaturated triterpene aldehydes
Nazarov, Mikhail A.,Tolmacheva, Irina A.,Eroshenko, Daria V.,Maiorova, Olga A.,Dmitriev, Maksim V.,Grishko, Victoria V.
, p. 1321 - 1328 (2020/11/18)
[Figure not available: see fulltext.] α,β-Unsaturated lupane and 19β,28-epoxy-18α-oleanane aldehydes were used in the synthesis of triterpenoids bearing substituted 1,2-azole moieties (1-acetyl-3-methyl-4,5-dihydro-1H-pyrazole and 3-methyl-4,5-dihydroisoxazole) at the rings А and Е. The route of synthesis for these 1,2-azole derivatives of triterpenes included an aldol condensation of α,β-unsaturated aldehydes with acetone, the products of which (α,β-unsaturated methyl ketone and β-hydroxy ketone) underwent a further cycloaddition reaction with acetylhydrazide and hydroxylamine. Cytotoxic activity studies of the synthesized compounds against seven cancer cell lines (Hep-2, HCT116, MS, RD TE32, A549, MCF-7, and PC-3) showed that the highest cytotoxicity (IC50 0.66–11.97 μM) against all tested cell lines was exihbited by 19β,28-epoxy-18α-oleanane aldehyde and the products of its condensation reactions with acetone and acetylhydrazide.
Betulinol derivative and hydrophilic modification product thereof, nano solution and preparation method of nano solution
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Paragraph 0076; 0090-0095, (2020/11/09)
The invention relates to a betulin derivative and a hydrophilic modification product thereof, and a nano solution and a preparation method thereof, wherein the betulin derivative is a product obtainedby an esterification reaction of the 3-hydroxyl of betulin or the derivative thereof and the carboxyl in a benzoic acid derivative, the hydrophilic modification product is dispersed in water, a metalhydroxide salt is added, stirring is performed for 30-300 minutes at 25-90 DEG C, naturally cooling is performed to room temperature so as to make the compound form a carboxyl metal salt, a surfactant accounting for 0.1-10% of the volume of the reaction system is added, and ultrasonic treatment is performed for 0-60 min to obtain the nano colloid aqueous solution of the hydrophilic modification product of betulin and derivatives thereof, wherein the nano colloid aqueous solution is good in dispersity, ideal in particle size range and easy to absorb by organisms.
Antiviral compound, preparation and synthesis method thereof
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Paragraph 0060-0063, (2020/11/09)
The invention discloses a compound for inhibiting a virus silencing suppressor, and a synthesis method thereof, and a preparation, and belongs to the pharmaceutical technology, wherein the structure of the compound is represented by a formula (I).
The synthesis of α,β-unsaturated 18αH,19βH-ursane methyl ketones
Nazarov, Mikhail A.,Tolmacheva, Irina A.,Grishko, Victoria V.
, p. 267 - 276 (2020/02/13)
An efficient and facile synthetic technique of a new α,β-unsaturated ketones of 18αH,19βH-ursane type from betulin and a possibility of their further heterocyclization to C20 pyrazoline derivative are reported. The synthetic scheme involves aldol condensa
Allobetulin Ring A Contraction Effected by Sulfur Diethylaminotrifluoride
Fedorov,Samoilenko,Shafeeva,Abzianidze,Trishin, Yu. G.
, p. 1948 - 1950 (2018/11/24)
The action of sulfur diethylaminotrifluoride on 19β,28-epoxyoleanan-3-ol (allobetulin) causes dehydration of the terpenoid and isomerization of the ring A via its contraction to isopropylcyclopentene ring resulting in 19β,28-epoxy-A-neo-18α-olean-3(5)-ene (α-allobetulin) in a high yield.
Pd-catalyzed synthesis of 2-alkynyl derivatives of 19β,28-epoxy-18α-olean-1-en-3-one
Shakhmaev,Sunagatullina, A. Sh.,Abdullina,Zorin
, p. 1705 - 1709 (2017/12/29)
Basing on Sonogashira reaction of 2-iodo-19β,28-epoxy-18α-olean-1-en-3-one with alkynes an effective approach was developed to the synthesis of 2-alkynyl derivatives of 19β,28-epoxy-18α-olean-1-en-3-one. Initial 2-iodo-19β,28-epoxy-18α-olean-1-en-3-one was obtained by isomerization of the accessible betulin into allobetulin in the presence of Amberlyst 15, oxidation of allobetulin to 19β,28-epoxy-18α-olean-1-en-3-one under the action of 2-iodoxybenzoic acid, and iodination of the obtained enone in the presence of DMAP.
Synthesis of Allobetulin Using Phenylthiourea
Mamaeva,Kalieva,Tashenov,Bakibaev,Nurpeiis,Zamanova
, p. 904 - 906 (2017/10/07)
A new method for preparing allobetulin via thermal rearrangement of betulin in the presence of phenylthiourea without using acidic reagents was found.
Sugar migration induced by the Wagner-Meerwein rearrangement of 28-O-glycosyl-betulin derivatives
Korda, Anna,Pakulski, Zbigniew,Cmoch, Piotr,Gwardiak, Katarzyna,Karczewski, Romuald
, p. 1740 - 1744 (2017/03/08)
Treatment of betulin-type saponins, in which the sugar moiety is connected at the 28-position, with TMSOTf affords 3-O-substituted allobetulin saponins. This unprecedented migration of the sugar part is driven by the Wagner-Meerwein rearrangement of the betulin core. According to our mechanistic studies an oxocarbenium ion released during the rearrangement reacts with the free 3-OH group of the triterpene affording the final allobetulin saponin. Migration rate depends on the size and configuration of the sugar moiety.
Lupane and 18α-oleanane derivatives substituted in the position 2, their cytotoxicity and influence on cancer cells
Borkova, Lucie,Gurska, Sona,Dzubak, Petr,Burianova, Renata,Hajduch, Marian,Sarek, Jan,Popa, Igor,Urban, Milan
, p. 120 - 131 (2016/06/06)
Lupane derivatives containing an electronegative substituent in the position 2 of the skeleton are often cytotoxic, however, the most active compounds are not selective enough. To further study the influence of a substituent in the position 2 in lupane and 18α-oleanane derivatives on their biological properties, we prepared a set of 38 triterpenoid compounds, 19 of them new, most of them substituted in the position 2. From betulin, we obtained 2-bromo dihydrobetulonic acid and 2-bromo allobetulon and their substitutions yielded derivatives with various substituents in the position 2 such as amines, amides, thiols, and thioethers. Nitration of allobetulon and dihydrobetulonic acid gave 2-nitro and 2,2-dinitro derivatives. Fifteen derivatives had IC50 50 4.6 μM and caused significant block of the tumor cells in S and slightly in G2/M transition and caused strong inhibition of DNA and RNA synthesis at 5 × IC50. 2-Amino allobetulin is the most active derivative of 18α-oleanane skeletal type prepared in our research group to date.
