New diacetamides based on C -arylphosphorylated derivatives of 2,6-diaminopyridine and 1,3-diaminobenzene
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New diacetamides based on C-arylphosphorylated derivatives of 2,6-diaminopyridine and 1,3-diaminobenzene E. M. Gibadullina,a T. T. Nguyen,b A. G. Strel´nik,a A. S. Sapunova,a A. D. Voloshina,a A. R. Burilov,a and M. A. Pudovika aArbuzov
Institute of Organic and Physical Chemistry, Federal Research Center "Kazan Scientific Center of the Russian Academy of Sciences," 8 ul. Akad. Arbuzova, 420088 Kazan, Russian Federation. E-mail: [email protected] bKazan National Research Technological University, 68 ul. K. Marksa, 420015 Kazan, Russian Federation The reactions of C-arylphosphorylated derivatives of 2,6-diaminopyridine and 1,3-diaminobenzene with acetic anhydride afforded new acylated products. The structures of synthesized diacetamides were determined using the modern physicochemical methods, including a complex of 2D NMR correlation experiments (1H—1H COSY, 1H—13C HSQC, and 1H—13C HMBC). Key words: diacetamide, sterically hindered phenol, benzyl phosphonate, pyridine.
The approach used in organic chemistry for the targeted design of compounds with biological activity is a combination of various pharmacophoric groups in one molecule. Amide bonds represent an important functional moiety of many pharmaceuticals.1 The substances containing diacetamide fragments often act as model compounds that are biochemically significant and involved in hydrogen bonding with diverse substrates.2,3 N,N-(Pyridine-2,6-diyl)diacetamide, which combines the properties of hydrogen bond donor and acceptor,4—6 is used as a flavin receptor7,8 and a fragment bearing triple hydrogen bonding.6,9,10 The binuclear complexes of diphenyltin(IV) dithiocarbamate with the ligands based on 4,4´-bis[2(alkylamino)acetamido]phenylene with anticancer activity in vitro against the cancer cell line of the HepG2 hepatocellular human carcinoma are known.11 The introduction of the sterically hindered phenol fragment into biologically active substances can increase their activity and decrease toxicity.12 The compounds containing sterically hindered phenol fragments are characterized by anti-inflammatory,13 antiviral,14 antimicrobial,15,16 and anticancer17—19 activities. We have previously synthesized20,21 the first representatives of compounds of the new class: C-benzylphosphonate derivatives of 2,6-diaminopyridine and 1,3-diaminobenzene. Among them there are compounds exhibiting the anticancer activity comparable with that of commercial drug Doxorubicin along with a considerably lower cytotoxicity against the normal human cell line Chang liver. The synthesis of these compounds is based on the earlier unknown reactions of 2,6-diaminopyridines and 1,3-diaminobenzenes with
dialkyl/diphenyl (3,5-di-tert-butyl-4-oxocyclohexa-2,5dienylidene)methyl phosphonates 1, which make it possible to synthesize the target products in high yields. The synthesized compounds considered as a new synthetic platform contain two terminal amino groups, which provides wide prospects of purposeful modification. Therefore, the synthesis of new acetamides from 2,6-diaminopyridines and 1,3-dia
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