FIELD: chemistry.
SUBSTANCE: present invention relates to a method for synthesis of a compound of formula (I):
where R1a is independently allyl, crotyl, prenyl or benzyl; R1b is independently CF3, OR2 or NHR3; R1c is H; R1d is independently an OH, O-protecting group, NO2 or NHR3; R1b and R1d are not identical; R1e is independently C1-C6 alkyl, OH, OR2, NO2, NHR3, NMeR3 or SR2; R1f is independently H, OH, O-protective group, NO2, NHR3, NHC=NH(NH2), N(OH)(CO)Me or COOH; R1g is independently H, C1-C6 alkyl or OH; and not more than one of R1f or R1g can be H; R3 is independently H, CH3, (CO)H, (CO)Me, SO2Me, CH2COOR2, CO(CH2)nNH2 or CO(CH2)nCOOH, where n is 0, 1 or 2; or R1e and R1f form a five-membered heterocyclic ring containing a carbonyl group, when R1e is independently OH, NH2 or NHMe, and R1f is NH2, so that nitrogen in R1f is bridged through a carbonyl group with oxygen or nitrogen in R1e, and R1g is H; R2 is independently methyl, ethyl, propyl, isopropyl, butyl, isobutyl, trifluoromethyl or O-protective group, when R2 is attached to O. This method involves a step of combining a compound of formula (II) (module A) with a compound of formula (III) (module B) to obtain a compound of formula (IV) (module C):
In the compound of formula (II), X is a halogen or a hydroxyl group, where the halogen is selected from the group consisting of F, Cl, Br, I and At, in the compound of formula (IV) R4 is C1-C6 alkyl. Invention also relates to a compound of formula (I) and to methods of treating cancer, atopic dermatitis and psoriasis using said compound or a pharmaceutical composition containing said compound.
EFFECT: creation of a new process which provides effective and industrially applicable production of number of 2-substituted hydroxystilbene compounds, are promising for use in treating cancer and diseases or disorders of the skin.
33 cl, 18 dwg, 8 tbl
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Authors
Dates
2024-10-16—Published
2020-12-23—Filed