Anton Dolzhenko
Monash University (Malaysia), School of Pharmacy, Department Member
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Curtin University, Perth, Pharmacy, Adjunct add
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Anton V. Dolzhenko received his degree (with Distinction) in Pharmacy in 2000 and then a PhD degree in Medicinal Chem... moreAnton V. Dolzhenko received his degree (with Distinction) in Pharmacy in 2000 and then a PhD degree in Medicinal Chemistry in 2004, both from the Perm State Pharmaceutical Academy (Russia). After that he joined National University of Singapore and worked there for 6 years before he moved to the School of Pharmacy, Curtin University (Australia) in 2010 and continued his academic career as a Senior Lecturer. In 2013, he joined Monash University Malaysia, where he has been working as an Associate Professor and the Deputy Head (Research) of School of Pharmacy. He also act as the Director of the NMR Campus Infrastructure Platform, which he established in the campus. His current research interests include synthetic and structural aspects of chemistry of nitrogen heterocycles. He has been actively working on the development of new synthetic methods for the preparation of potentially bioactive compounds. He is particularly interested in green chemistry approaches for drug discovery. edit
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Exploring the pharmacologically important pyrazolo[1,5-a][1,3,5]triazin-7(6H)-one scaffold for the construction of new bioactive compounds, we developed a synthesis of 4-phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one (4)... more
Exploring the pharmacologically important pyrazolo[1,5-a][1,3,5]triazin-7(6H)-one scaffold for the construction of new bioactive compounds, we developed a synthesis of 4-phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one (4) via S-alkylation of 2-phenyl-4-thioxopyrazolo[1,5-a][1,3,5]triazine-7(6H)-one (3), prepared by the double ring closure of pyrazole and triazine rings upon the treatment of 1-cyanoacetyl-4-benzoylthiosemicarbazide (2) with alkali. The antiproliferative activity of 4 against human lung cancer (A549) and human breast cancer (MDA-MB231) cell lines was investigated. Compound 4 was found to be more active against lung cancer cells than breast cancer cells.
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ABSTRACT For Abstract see ChemInform Abstract in Full Text.
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The effective and clean procedure for the preparation of 5-amino-3-(het)aryl-1,2,4-triazoles (3a-c) via cyclization of (het)aroylaminoguanidines (2a-c) in water was reported. Two tautomeric forms, namely... more
The effective and clean procedure for the preparation of 5-amino-3-(het)aryl-1,2,4-triazoles (3a-c) via cyclization of (het)aroylaminoguanidines (2a-c) in water was reported. Two tautomeric forms, namely 5-amino-3-(het)aryl-1,2,4-triazoles (A) and 3-amino-5-(het)aryl-1,2,4-triazoles (B) were found to exist in tautomeric equilibrium. Form A was a predominant tautomer in DMSO solution (KT = 9-33).
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... A B Compound R KT ∆G298 2a H 1.35 -0.74 2b MeO 2.56 -2.33 2c Me 1.89 -1.58 2d F 1.08 -0.19 ... 5. (a) Capuano, L.; Schrepfer, HJ Chem. Ber. 1971, 104, 3039-3047; (b) Hirata, T.; Twanmoh, L.- M.; Wood, HB, Jr.; Goldin, A.; Driscoll, J.... more
... A B Compound R KT ∆G298 2a H 1.35 -0.74 2b MeO 2.56 -2.33 2c Me 1.89 -1.58 2d F 1.08 -0.19 ... 5. (a) Capuano, L.; Schrepfer, HJ Chem. Ber. 1971, 104, 3039-3047; (b) Hirata, T.; Twanmoh, L.- M.; Wood, HB, Jr.; Goldin, A.; Driscoll, J. J. Heterocycl. Chem. 1972, 9, 99-106; (c) ...
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The synthesis of 2,5,7-triamino[1,2,4]triazolo[1,5-a][1,3,5]triazines was developed. The 3,5-diamino-1,2,4-triazoles were prepared using partial aminolysis of dimethyl N-cyanodithiocarbonimidate followed by cyclization of the obtained... more
The synthesis of 2,5,7-triamino[1,2,4]triazolo[1,5-a][1,3,5]triazines was developed. The 3,5-diamino-1,2,4-triazoles were prepared using partial aminolysis of dimethyl N-cyanodithiocarbonimidate followed by cyclization of the obtained N-substituted N’-cyano-S-methylisothioureas with hydrazine. The reaction of 3,5-diamino-1,2,4-triazoles with cyanoguanidine was found to afford 2,5,7-triamino[1,2,4]triazolo[1,5-a][1,3,5]triazines. The structure of the compounds obtained was established using NMR spectroscopy.
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ABSTRACT
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In the title compound, C16H13N7O, the 1,2,4-triazolo[1,5-a][1,3,5]triazine heterocyclic system is essentially planar (r.m.s. deviation = 0.0375 Å). The attached benzene ring lies almost in the mean plane of... more
In the title compound, C16H13N7O, the 1,2,4-triazolo[1,5-a][1,3,5]triazine heterocyclic system is essentially planar (r.m.s. deviation = 0.0375 Å). The attached benzene ring lies almost in the mean plane of 1,2,4-triazolo[1,5-a][1,3,5]triazine [dihedral angle = 1.36 (23)°], while the pyridine ring is turned out of this plane by the aminomethyl bridge [dihedral angle = 69.22 (9)°]. The amino group H atom is involved in intramolecular hydrogen bonding with a triazole N atom. In the crystal, molecules are connected via C(=O)NH...N hydrogen bonds into C(11) chains parallel to [100]. The amino group H atom acts as a hydrogen-bond donor, forming an NH...O=C hydrogen bond with the carbonyl O atom, which links the molecules into C(6) chains running along [011] and [01overline{1}].
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A series of 20 substituted amides and hydrazides of succinic acid were synthesized and studied with respect to their action upon the blood glucose level in intact rats. The structure-activity relationship is considered. Substances... more
A series of 20 substituted amides and hydrazides of succinic acid were synthesized and studied with respect to their action upon the blood glucose level in intact rats. The structure-activity relationship is considered. Substances exhibiting maximum hypoglycemic activity were additionally characterized by the acute toxicity and the hypoglycemic effect on the model of alloxan diabetes in rats. It was found that 4-aminobenzoyl hydrazide is more effective and less toxic than the reference compounds metformin and glyclazide.
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Previously, we have reported on a series of substituted amides and acylhydrazides of phthalic acid possessing hypertensive [2] and hypoglycemic [3, 4] activity. We have studied a series of substituted monoamides and acylhydrazides of... more
Previously, we have reported on a series of substituted amides and acylhydrazides of phthalic acid possessing hypertensive [2] and hypoglycemic [3, 4] activity. We have studied a series of substituted monoamides and acylhydrazides of phthalic acid (I – XI) that can be also of interest as potential antibacterial agents [5, 6] and anticonvulsants [7 – 12]. Compounds I – XI were obtained by acylating the corresponding substituted amines and hydrazides of carboxylic acids with phthalic anhydride under mild conditions using the well-known procedure [2 – 4]. The proposed structures of the newly synthesized compounds were confirmed by spectroscopic data (Table 1).
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Previously we studied a series of isoquinoline derivatives exhibiting antiaggregant effect with respect to thrombocytes [1 – 5] and possessing hypotensive properties [6 – 8]. At the same time, derivatives of 1-chloromethylisoquinoline [9... more
Previously we studied a series of isoquinoline derivatives exhibiting antiaggregant effect with respect to thrombocytes [1 – 5] and possessing hypotensive properties [6 – 8]. At the same time, derivatives of 1-chloromethylisoquinoline [9 – 11] are still not characterized with respect to pharmacological activity. To our knowledge, the properties of 1-methylisoquinoline esters were also never reported in the literature. When the ester residue represents an aromatic or benzyl fragment, such molecules differ from papaverine by the presence of an oxygen bridge. In this context, it was of interest to compare the pharmacological properties of these esters and papaverine. The aim of our study was to determine the effect of 1-chloromethyl-3,4-dihydroisoquinolines (II) and benzo[f]isoquinoline esters (IV) on the thrombocyte aggregation and arterial pressure in experimental animals. The latter compounds were selected as objects for the investigation because previously we observed a pronounced hypotensive activity in benzo[f]isoquinoline derivatives [7, 8]. The series of chloromethylisoquinolines IIa – IIe was synthesized by means of the interaction of carbinols Ia – Ie with chloroacetonitrile under the Ritter cyclocondensation conditions [1 – 3, 7, 8]. Esters IVa – IVf were obtained via reactions of compound III, obtained previously by the same method [7], with alcohols and phenols under conditions of phase-transfer catalysis [12]. In particular, the interaction of III with benzyl alcohol to yield compound IVa (R = PhCH2) [12] proceeds in a KOH/benzene system and is catalyzed by 18-crown-6. The interaction between III and phenols, proceeding in a 50 % NaOH/CH2Cl2 system and catalyzed by tetrabutylammonium hydrosulfate, led to phenyl esters IVb – IVf. Data on the yields, structures (R–R), and properties of the synthesized compound are presented in Tables 1 – 3.
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ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select... more
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select... more
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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ABSTRACT 1H-Pyrazolo[3,4-b]pyridin-ylguanidine (IV) is synthesized as a new convenient synthon for heterocyclic chemistry by selective guanylation of amine (II).
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ABSTRACT 1H-Pyrazolo[3,4-b]pyridin-ylguanidine (IV) is synthesized as a new convenient synthon for heterocyclic chemistry by selective guanylation of amine (II).
... A B Compound R KT ∆G298 2a H 1.35 -0.74 2b MeO 2.56 -2.33 2c Me 1.89 -1.58 2d F 1.08 -0.19 ... 5. (a) Capuano, L.; Schrepfer, HJ Chem. Ber. 1971, 104, 3039-3047; (b) Hirata, T.; Twanmoh, L.- M.; Wood, HB, Jr.; Goldin, A.; Driscoll, J.... more
... A B Compound R KT ∆G298 2a H 1.35 -0.74 2b MeO 2.56 -2.33 2c Me 1.89 -1.58 2d F 1.08 -0.19 ... 5. (a) Capuano, L.; Schrepfer, HJ Chem. Ber. 1971, 104, 3039-3047; (b) Hirata, T.; Twanmoh, L.- M.; Wood, HB, Jr.; Goldin, A.; Driscoll, J. J. Heterocycl. Chem. 1972, 9, 99-106; (c) ...
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ABSTRACT 1H-Pyrazolo[3,4-b]pyridin-ylguanidine (IV) is synthesized as a new convenient synthon for heterocyclic chemistry by selective guanylation of amine (II).