Burkhon Elmuradov

• Doctor of Sciences (chemistry)
• Deputy-director at Yunusov Institute of the Chemistry of Plant Substances

4-(6-phenyl-7H-[1,2,4]-triazolo-[3,4-b] -[1,3,4] -thiadiazine-3-yl) -aniline compound belongs to the group of triazole derivatives, belongs to class IV low-toxic compounds in acute toxicity, and sodium belongs to the compounds of this group, taking into account the presence of Due to its abilityto block ion channels, it can be concluded that the 1....

In this article, it has been experimentally confirmed that 5-(p-aminophenyl)-4-amino-1,2,4-triazole-3(2H)-thione belongs to the class of low-toxic psychopharmacological activity in doses of 0.1; 0.5; 1.0; 5.0 and 10.0 mg/kg and is not inferior to comparable anticonvulsant drugs carbamazepine and convulex. KEYWORDS

A number of new deoxyvasicinone (2,3‐dihydropyrrolo[2,1‐b]quinazolin‐9(1H)‐one) and mackinazolinone (6,7,8,9‐tetrahydro‐11H‐pyrido[2,1‐b]quinazolin‐11‐one) derivatives with aryl substituents at C7/C8 and at C5 are reported. These compounds are rare representatives of their kind and were prepared in high yields by Suzuki‐Miyaura cross‐coupling react...

methylation of quinazoline-4-thione with methyl iodide, dimethylsulfate and methyltosylate in various solvents was studied. It is shown that the reaction proceeds to N3, O4 and N1 atoms depending on the nature of the alkylating agent, solvent and temperature.

Epilepsy is a chronic non-communicable disease of the brain, which is estimated that five million people are diagnosed with epilepsy every year worldwide. In this regard the study studied the anticonvulsant properties of annulated 4-(6-phenyl-7H-[1,2,4] triazolo [3,4-b] [1,3,4] thiadiazin-3-yl)-aniline. Anticonvulsant activity was evaluated in vari...

6-Sulfonamid-2-N(metil)-3-metilxinazolin-4-onlarni α-naftil izotsionati va potash ishtirokida, aseton erituvchisida reaksiyalari olib borildi. Natijada yaxshi unumlar bilan bisiklik xinazolin hosilalari qatorida sulfonilmochevinalar olindi. Olingan moddalarni tuzilishi zamonaviy IQ- va YaMR- spektrlari yordamida tahlil qilindi.

The mixture of isomeric 1-butyl-5/6-chloro-2-methyl-1H-benzo[d]imidazoles have been obtained from the butylation reacton of 5-chloro-2-methyl-1H-benzo[d]imidazole. Crystallization of hydrochlorides of product compounds resulted in monohydrated cocrystal of the isomers, structure of which have been determined by single crystal X-ray diffraction anal...

The mixture of isomeric 1-butyl-5/6-chloro-2-methyl-1H-benzo[d]imidazoles have been obtained from the butylation reacton of 5-chloro-2-methyl-1H-benzo[d]imidazole. Crystallization of hydrochlorides of product compounds resulted in monohydrated cocrystal of the isomers, structure of which have been determined by single crystal X-ray diffraction anal...

In this article, as a continuation of scientific research on the study of the neurological activity of newly synthesized compounds, the results of studies of the neutropic activity of the 1,2,4 triazole derivative are presented. At the same time, the motor and search activity of compound D-378 was studied in the study conditions, the effect...

At the Yunusov Institute of Plant Chemistry of the Academy of Sciences of the Republic of Uzbekistan, a number of scientists conducted extensive pharmaco-toxicological studies to study the biological activity of vincane hydrochloride and its derivatives. Based on these studies, a number of studies were conducted not only on the special pharmacologi...

The article presents data on the study of the anxiolytic activity of compounds representing new triazole derivatives – combinations of two privileged structures. At the "Raised Cruciform labyrinth" installation, such indicators of the studied compounds, the time of exit into the open sleeve, the number of exits and the total time spent in it wer...

Resume. In this presented article, it was presented that 5-(p-Aminophenyl)-1,3,4-oxadiazole-2-tion (conditionally D-111) at doses of 10, 30 and 60 mg / kg when administered orally to white mice with various analyzers, including strychnine (1.2 mg / kg subcutaneously), and also orally in doses of 10 and 30 mg/kg. the anticonvulsant activity of the s...

These papers present a study of the synthetic compound potassium salt 5-(o-aminophenyl)-1,3,4-oxadiazol-2-thione (D-361) at doses of 10; 30 and 60 mg/kg by oral administration on motor activity, locomotor action of phenamine, haloperidol catalepsy and M-cholinergic receptors in experimental animals. Based on the results of the experiment, it was...

The title compound, C12H13N3OS, was synthesized via the Willgerodt–Kindler method. The benzimidozole moiety is essentially planar (r.m.s. deviation = 0.0084 Å). The thio­amide group is inclined by 54.80 (14)° to the benzimidazole ring system. The morpholine ring is disordered over two sets of sites [ratio 0.841 (11):0.159 (11)], with chair conforma...

The mol­ecular structure of the title compound, C11H9BrN2O, is almost planar. The benzene and pyrimidine rings are essentially coplanar, with r.m.s. deviations of 0.0130 Å, and the largest displacement is for the flap atom of the di­hydro­pyrrole moiety [0.154 (7) Å]. Hirshfeld surface analyses revealed that the crystal packing is dominated by H⋯H,...

The asymmetric unit of the title compound, C16H13N3OS, comprises two mol­ecules (A and B) with similar conformations that differ mainly in the orientation of the phenyl group relative to the rest of the mol­ecule, as expressed by the Cthio­amide—Nthio­amide—Cphen­yl—Cphen­yl torsion angle of 49.3 (3)° for mol­ecule A and of 5.4 (3)° for mol­ecule B...

The title compounds, 6-nitro­quinazolin-4(3H)-one (C8H5N3O3; I), 6-amino­quinazolin-4(3H)-one (C8H7N3O; II) and 4-amino­quinazolin-1-ium chloride–4-amino­quinazoline–water (1/1/2), (C8H8N3⁺·Cl⁻·C8H7N3·2H2O; III) were synthesized and their structures were determined by single-crystal X-ray analysis. In the crystals of I and II, the quinazoline mol­e...

The crystal structures of three mackinazolinone derivatives (2-amino-6,7,8,9-tetra­hydro-11H-pyrido[2,1-b]quinazolin-11-one at room temperature, and 2-nitro-6,7,8,9-tetra­hydro-11H-pyrido[2,1-b]quinazolin-11-one and N-(11-oxo-6,8,9,11-tetra­hydro-7H-pyrido[2,1-b]quinazolin-2-yl)benzamide at 100 K) are explored using X-ray crystallography. To deline...

В книге рассмотрены методы синтеза, модификации и биологическая активность полициклических дигидро- и тетрагидрохиназолин-4-онов, содержащие атомы азота, кислорода, серы и имеющие заместители в ароматическом кольце, α-положении и т.д. Обсуждены химические превращения их: реакции электрофильного и нуклеофильного замещения, реакции по атому азота N-1...

Novel ferrocene conjugates of tricyclic quinazoline derivatives are prepared by condensation of active C‐6 methylene groups of mackinazolinones with ferrocenecarbaldehyde. Following this route the conjugated parent alkaloid as well as derivatives with nitro, amino, and alkanoylamino groups at C‐2 were attached at the ferrocene moiety, thereby signi...

A quinazolinthione, C17H14N2OS, was synthesized by the condensation reaction of 6,7,8,9-tetra­hydro-11H-pyrido[2,1-b]quinazolin-11-thione with furfural. The mol­ecule crystallizes in the monoclinic system (Cc space group) and has an E configuration with respect to the exocyclic C=C bond. In the crystal, mol­ecules are linked through C—H⋯π(furan) in...

A series of novel substituted hydrazone-bearing (unsymmetrical azines, RR1C=N–N=CR2R3) tricyclic quinazoline derivatives are reported. All novel compounds were characterized by ¹H, ¹³C nuclear magnetic resonance (NMR), and Fourier-transform infrared (FT-IR) analyses. An important intermediate (E/Z)-hydrazono-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazol...

The method for chemoselective synthesis of aminobenzylic derivative of the alkaloid mackinazolinone was developed and studied its structurein the crystal. It was found that reduction of Schiff base (intermediate, 4) by sodium borohydride at room temperature goes selectively through reduction only of azomethine (N=CH) bond; wherein does not affect t...

New 2-alkylthio-5-(4-N-acetyl(N-chloroacetyl)aminophenyl)-1,3,4-oxadiazoles were synthesized. Optimal conditions for the synthesis were found. The physicochemical characteristics and structures of the synthesized compounds were established. On the example of compound 10 we carried out X-ray diffraction analysis (XRD). The antibacterial and antifung...

Poster about synthesis and redox properties of alkaloid-ferrocene conjugates

Series of arylidene- and arylhydroxymethyl derivatives of 1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-one and 2,3,4,10-tetrahydro-1H-pyrido[2,1-b]quinazolin-10-one were synthesized. Schiff bases were synthesized from amine derivatives. Hydroxymethylidene derivatives and arylaminomethylidene-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-ones and -2,...

Abstract: in the result of conducted investigations have been received the one of the optically active isomer – Sitofilure – aggregation pheromone of rice and grainary weevils which are an economically important pest of stored grains in the Uzbekistan. Direct asymmetric catalytic aldol reaction has been successfully performed using propionaldehy...

Selective C-formyl­ation of 8,9,10,11-tetra­hydro­pyrido[2′,3′:4,5]pyrimido[1,2-a]-azepin-5(7H)-one has been studied for the first time. It was revealed that formyl­ation proceeds by the formation of an inter­mediate salt, which due to the re-amination process on treatment with aqueous ammonia transformed into the corresponding (E)-11-(amino­methyl...

Unusual formation of (E)-11-(aminomethylidene)-8,9,10,11-tetrahydropyrido[2’,3’:4,5]pyrimido[1,2-a]azepin-5(7H)-one and its crystal structure. Acta Cryst. 2017. -E73. –P. 1497–1500.

Deoxyvasicine thione (III) and mackinazoline thione (6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazoline-11-thione, IV) were synthesized and condensed with aromatic and heterocyclic aldehydes at the α-methylene [CH2-3 (III) or CH2-6 (IV)]. Either 3- and 6-arylidene derivatives (V – XIII) or 6-hydroxymethylaryl derivatives (XIV) were formed depending on...

Selective S-alkoxycarbonylation of isomeric - 5-(2-pyridyl)- (1), 5-(3-pyridyl)- (2), and 5-(4-pyridyl)- 1,3,4-oxadiazol-2-thiones (3) have been studied and novel series of S-substituted derivatives (7-15) have been synthesized and characterized by physical methods of research. No formation of the amides - N-substituted derivatives (A) was observed...

While growing 2-ethylbenzimidazole crystals from methanol, polymorph 1с is obtained. In polymorphs 1а-с, 2-ethylbenzimidazole molecules have a different arrangement in the packing and the position of the ethyl group relative to the benzimidazole plane. At the same time, the character (sequence) of intermolecular N–H…N bonds is maintained. In polymo...

(E)-11-(Aminomethylidene)-10,11-dihydropyrido[2,3-d]azepano[1,2-a]pyrimidin-5(7H)-one was synthesized at formylation of 2,3-pentamethylenepyrido[2,3-d]pyrimidin-4-one. The reamination takes place in reaction condition.

Annotation. In this manuscript, we are first time reporting the Raman-spectrum of quinazolin-2,4-dione and deoxypeganine hydrochloride and the observed bands assigned by means of DFT/6-31G(d,p) method. It was observed that the main bands caused by the vibrations of benzene ring and skeleton vibrations of the whole molecule. Besides, carbonyl group’...

The scientific and applied achievements of Institute of the Chemistry of Plant Substances (ICPS) on the development of products for agriculture for the last years are summarized. Also included different research areas, working to find new promising drugs based on natural, heterocyclic compounds and their synthetic analogues. In this mini review man...

The first organometallic derivatives of tricyclic quinazoline derivatives are prepared by condensation of the active C-3 methylene group of 7H-deoxyvasicinones with ferrocenecarbaldehyde. By following this route the conjugated parent alkaloid and derivatives with nitro, amino, as well as some alkanoylamino groups at C-7 were attached at the ferroce...

The quantum chemical calculations of the energies, electronic structures, and geometries for the products and intermediates of the ipso-nitration of 5,6-dimethyl-substituted 2-oxo- and 2-thioxothieno[2,3-d]pyrimidin-4-ones, as well as 6-methyl-5-nitrothieno[2,3-d]pyrimidin-4-one and 3,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-5-carboxylic...

Quantum chemical calculations of energies, electronic structures, and molecular geometries of 3,5,6-trimethylthieno[2,3-d]pyrimidin-4-one (1), tricyclic 2,3-tri-, 2,3-tetra-, and 2,3-pentamethylene-substituted 5,6-dimethylthieno[2,3-d]pyrimidin-4-ones (2—4), carboxylic acids 5—8 resulting from oxidation of compounds 1—4 at the methyl group in posit...

Review: results of the last 15-20 years201 refs.

The deuterium exchange rate of the α-methylene of deoxyvasicinone (1) and mackinazolinone (2) and their seven- (3) and eight-membered (4) homologs was studied in neutral, acidic, and basic media. It was found that the exchange rate depended on the number of methylenes in the polymethylene ring and the medium. The deuterium exchange rate decreased i...

Series of diethyl 2,5-diaminothiophene-3,4-dicarboxylate (DDTD) derivatives: azomethines of DDTD (2a-l) have been synthesized and screened for their anticancer, antimicrobial and anti-diabetic activities. The novel synthesized compounds were characterized by 1H, 13C NMR, MS and FT-IR analyses. All compounds were evaluated for their antiproliferativ...

Recently a novel derivatives of the alkaloid deoxyvasicinone attached to ferrocene have been synthesized [6]. Continuing these investigations, herein we studied interaction of the alkaloid mackinazolinone (2,3-tetramethylene-3,4-dihydroquinazoline-4-one, 1) and its 6-nitro-(2)- ,-amino-(3) and-acetylamino derivatives (4), which containing an active...

Peganum harmala Alkaloid deoxyvasicinone (1), which was isolated from Peganum harmala possesses antimicrobial, anti-inflammatory and antidepressant activities. 1 Therefore chemical transformations of natural compounds and their synthetic analogues are a perspective direction for the creation of new derivatives with various activities. 2,3 There is...

Interactions of 5,6-dimethyl- (1), 3,5,6-trimethylthieno[2,3-d]pyrimidin-4(3H)-ones (2) and 2,3-dimethyl- (5-7), 2-methyl-3-methoxycarbonylthieno[2,3-d]dihydropyrrolo-, - tetrahydropyrido-, tetrahydroazepino[1,2-a]pyrimidin-4-ones (14-16) with nitrating mixture were investigated. For the first time it is shown, that in dependence on the presence of...

The title mol­ecule, C12H12N2OS, is planar, with an r.m.s. deviation of 0.04 Å. In the crystal, the N atom adjacent to the carbonyl group is sp²-hybridized. The crystal structure is stabilized by π–π stacking inter­actions observed between thio­phene and pyrimidinone rings of c-glide-related mol­ecules [centroid–centroid distance = 3.9554 (13) Å] a...

Methods for preparing of 8-nitro- and 8-aminomackinazolinones were improved. 8-Acetyl(benzoyl)aminomackinazolinones reacted smoothly with aromatic aldehydes and furfurol in glacial acetic acid to give the corresponding 4-arylidene-substituted derivatives. Reaction of 8-aminomackinazolinone with aromatic aldehydes in glacial acetic acid was accompan...

The reactions of 2,3-tri-,-tetramethylene-7,8–dihydro-6Н–thieno[2,3-d]pyrrolo[1,2-a] pyrimidine-4-ones (1a,b) and 2,3-dimethyl-,-tri-,-tetra-,-pentamethylene-6,7,8,9-tetrahydropyrido[1,2-a]thieno[2,3-d]pyrimidine–4-ones (4a-d), containing active methylene groups in positions 8 or 9, with aromatic aldehydes under acidic and alkaline conditions go de...

From 2-amino-3-ethoxycarbonyl-4,5-dimethyl-, -polymethylenethiophenes (1-4) were synthesized 2,3-disubstituted thieno[2,3-d]dihydropyrrolo-, tetrahydropyrido-, and tetrahydroazepino[1,2-a]pyrimidin-4-ones (5-16) for pharmacological investigations. The 12 compounds (5-16) were individually evaluated for their antiproliferative activities on mammalia...

The thioanalog of mackinazolinone (2,3,4,10-tetrahydro-1 H-pyrido[2,1-b]quinazolin-10-one) was synthesized for the first time by reacting it with P2S5. The thioanalog was reacted with aromatic aldehydes and Vilsmeier- Haack reagent (DMF + POCl3) to produce 4-arylidene- and -hydroxymethylidenemackinazolinthiones, respectively. The reactions of 4-hyd...

In the crystal, mol­ecules of the title compound, C11H10N2S, are connected by C—H⋯N inter­actions around threefold axes. Furthermore, they form stacks along the c axis showing π–π inter­actions between pyrimidine rings [centroid–centroid distance = 3.721 (1) Å]. The central ring is essentially planar with an r.m.s. deviation of 0.007 Å. The five-me...

A new method for formylation of deoxyvasicinone (DOV) was developed. Nucleophilic substitution of α-hydroxy- and -dimethylaminomethylidene-DOV by isomeric aminophenols and benzoic acids to give α-arylaminomethylidene-DOV was studied.

2,3-Dimethyl- and 2,3-tri-, 2,3-tetra-, and 2,3-pentamethylene-substituted 8-arylidene-6,7-dihydro-pyrrolo[1,2-a]thieno[2,3-d]pyrimidin-4-ones were synthesized by the reaction of 2,3-dimethyl- and 2,3-tri-, 2,3-tetra-, and 2,3-pentamethylene-7,8-dihydropyrrolo[1,2-a]thieno[2,3-d]pyrimidin-4(6H)-ones with benzaldehyde, its 4-dimethylamino-, 3,4-dime...

In the crystal structure of the title compound, C18H17N3O3·H2O, the mol­ecules are linked by O—H⋯O and O—H⋯N hydrogen bonds, resulting in a chain along the a axis. The crystal structure is stabilized by weak inter­molecular C—H⋯π (ring) hydrogen bonds and aromatic π⋯π stacking inter­actions [centroid–centroid distance = 3.902 (1) Å] between the pyr...

There are two independent mol­ecules in the asymmetric unit of the title compound, C12H12N2O3S. With the exception of the methyl­ene groups, a mean plane fitted through all non-H atoms of each mol­ecule has an r.m.s. deviation of 0.035 Å for one mol­ecule and 0.120 Å for the second. In one of the independent mol­ecules, the methyl­ene groups was re...

The Pd-catalyzed arylation of isoalantolactone by deoxyvasicinone and lappaconitine halides occurred with formation mainly of cross-coupling products with the (E)-configuration of the double bond. Another three compounds were isolated from the reaction of isoalantolactone with 6-bromodeoxyvasicinone. These were the lactone diarylation product, a co...

The title compound, C20H19N3O, was obtained by condensation of 2,3-dihydro-1H,9H-pyrrolo­[2,1-b]quinazolin-9-one (alkaloid de­oxy­vasicinone, isolated from Peganum Harmala) with 4-(dimethyl­amino)­benzaldehyde in the presence of sodium methoxide. The 2,3-dihydro-1H,9H-pyrrolo­[2,1-b]quinazolin-9-one part of the mol­ecule is roughly planar (r.m.s. d...

6-Acetylamino- and -benzoylamino-9-arylidenedeoxyvasicinones were synthesized by reaction of 6-amino(3), -acetylamino- (4), and -benzoylamino- (5) -deoxyvasicinones (DOV) with aromatic aldehydes and furfurol in glacial acetic acid. It was shown that the amino group of 6-aminodeoxyvasicinone underwent acylation upon reaction with aldehydes to form 6...