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1.
Инвентарный номер: нет.
   
   K 46

   
    Kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine, (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline using N-tosyl-(S)-prolyl chloride [Text] / V. P. Krasnov, G. L. Levit, I. M. Bukrina, I. N. Andreeva, L. Sh. Sadretdinova, M. A. Koroleva, M. I. Kodess, V. N. Charushin, O. N. Chupakhin // Tetrahedron: Asymmetry . - 2003. - Vol. 14, № 14. - P1985-1988. - Bibliogr. : p. 1988 (6 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Acylation of racemic 2,3-dihydro-3-methyl-4H-1,4-benzoxazine, 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline with N-tosyl-(S)-prolyl chloride resulted in their kinetic resolution with the predominant formation of (R,S)-diastereoisomeric amides, des being 80, 66 and 38%, respectively. Recrystallisation of the amides followed by acid hydrolysis gave individual (R)-enantiomers of heterocyclic amines

\\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2003, v.14, p.1985.pdf
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2.
Инвентарный номер: нет.
   
   K 46

   
    Kinetic resolution of heterocyclic amines by reaction with optically active acid chlorides. The effect of reaction conditions on the diastereoselectivity of acylation of (±)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine [Electronic resource] / V. P. Krasnov, G. L. Levit, M. A. Koroleva, I. M. Bukrina, L. Sh. Sadretdinova, I. N. Andreeva, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1253-1256
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The influence of the reaction conditions (solvent, base) on the diastereoselectivity of acylation of (±)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine with (S)-naproxen and N-tosyl-(S)-proline chlorides was studied. The highest diastereoselectivity was observed for the reaction carried out in benzene in the presence of aliphatic tertiary amines

\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1253.pdf
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3.
Инвентарный номер: нет.
   
   K 46

   
    Kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine in the reaction with (S)-naproxen chloride: A theoretical study [Electronic resource] / V. A. Potemkin, V. P. Krasnov, G. L. Levit, E. V. Bartashevich, I. N. Andreeva, M. B. Kuzminsky , N. A. Anikin, V. N. Charushin, O. N. Chupakhin // Mendeleev Communications. - 2004. - Vol. 14, № 2. - P69-70 : ил. - Библиогр.: с. 70 (14 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
KINETIC RESOLUTION -- CHLORIDE -- COMPUTATION METHODS
Аннотация: The kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4- benzoxazine by the action of (S)-naproxen chloride was theoretically studied based on various computation methods.

\\\\Expert2\\nbo\\Mendeleev Communications\\2004, v.14, p.69.pdf
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4.
Инвентарный номер: нет.
   
   A 19

   
    Acylative kinetic resolution of racemic amines using N-phthaloyl-(S)-amino acyl chlorides [Text] / D. A. Gruzdev, G. L. Levit, V. P. Krasnov, E. N. Chulakov, L. Sh. Sadretdinova, A. N. Grishakov, M. A. Ezhikova, M. I. Kodess, V. N. Charushin // Tetrahedron: Asymmetry . - 2010. - Vol. 21, № 8. - P936-942
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A comparative study of the kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using N-phthaloyl-(S)-amino acyl chlorides as chiral acylating agents is described. Temperature and solvent effects on the stereochemical features have been examined. It has been found that N-phthaloyl-(S)-phenylalanyl and N-phthaloyl-(S)-2-phenylglycyl chlorides bearing aromatic substituents close to the stereogenic centre are more stereoselective acylating agents than N-phthaloyl-(S)-alanyl chloride. For the preparative kinetic resolution of racemic amines N-phthaloyl-(S)-phenylalanyl chloride proved to be the most appropriate chiral acylating agent

\\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2010, v. 21, p.936.pdf
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5.
Инвентарный номер: нет.
   
   S 89

   
    Structures of the racemate and (S)-enantiomer of 7,8-difluoro-3-methyl-2,3-dihydro-4H-[1,4]benzoxazine [Electronic resource] / P. A. Slepukhin, D. A. Gruzdev, E. N. Chulakov, G. L. Levit, V. P. Krasnov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 955-960. - Bibliogr. : p. 960 (17 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
ENANTIOMERS -- RACEMATES -- ORGANOFLUORINE COMPOUNDS
Аннотация: The comparative X ray diffraction study of racemic and (S) enantiomer of 7,8 difluoro 3 methyl 2,3 dihydro 4H [1,4]benzoxazine was carried out. The both forms of benzoxazine are crystallized in the orthorhombic crystal system, the (S) enantiomer is crystallized in the chiral space group P212121, while the racemate is crystallized in the centrosymmetric Pbca space group. The bond lengths and bond and torsional angles in the both molecules are almost equal. The packing of the racemate is characterized by a closer interaction of polar NH...О groups.

\\\\expert2\\NBO\\Russian Chemical Bulletin\\2011, 60 (5), 955-960.pdf
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6.
Инвентарный номер: нет.
   
   S 91

   
    Substituent effect on the stereoselectivity of acylation of racemic heterocyclic amines with N-phthaloyl-3-aryl-(S)-alanyl chlorides [Text] / G. L. Levit, D. A. Gruzdev, V. P. Krasnov, E. N. Chulakov, L. Sh. Sadretdinova, M. A. Ezhikova, M. I. Kodess, V. N. Charushin // Tetrahedron: Asymmetry . - 2011. - Vol. 22, № 2. - P185-189. - Bibliogr. : p. 189 (17ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The acylative kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using acyl chlorides of N-phthaloyl-(S)-phenylalanine, N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine and N-phthaloyl-O-methyl-(S)-tyrosine as chiral resolving agents has been carried out. It is shown that the effectiveness of an acylative kinetic resolution depends on the electronic effects of substituents in the phenyl fragment of the acylating agent and increases as the electron-donating properties of the para-substituent (OMe H NO2) in phenyl fragment of N-phthaloyl-3-aryl-(S)-alanyl chlorides increase; conducting the process at a reduced temperature also contributes to an enhancement of the kinetic resolution

\\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2011, v. 22, p.185.pdf
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7.
Инвентарный номер: нет.
   
   G 90

    Gruzdev, D. A.
    Acylative kinetic resolution of racemic heterocyclic amines using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains / D. A. Gruzdev, G. L. Levit, V. P. Krasnov // Tetrahedron: Asymmetry . - 2012. - Vol.23. - С. 1640-1646. - Bibliogr.: p. 1645-1646 (15 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
HETEROCYCLIC AMINES -- RACEMIC AMINES -- ACYL CHLORIDES
Аннотация: A comparative study of the acylative kinetic resolution of racemic 2-methyl-1,2,3,4 tetrahydroquinoline and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains has been carried out. The influence of steric factors on the stereoselectivity of the acylation was demonstrated. The (S)-enantiomers of the heterocyclic amines (ee >99%) were obtained in good yields via a kinetic resolution protocol using N-phthaloyl-(S)-leucyl chloride

\\\\expert2\\NBO\\Tetrahedron Asymmetry\\2012, v. 23, p.1640.pdf
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8.
Инвентарный номер: нет.
   
   A 10

   
    A comparative study on the acylative kinetic resolution of racemic fluorinated and non-fluorinated 2-methyl-1,2,3,4-tetrahydroquinolines and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines [Electronic resource] / D. A. Gruzdev, E. N. Chulakov, G. L. Levit, M. A. Ezhikova, M. I. Kodess, V. P. Krasnov // Tetrahedron: Asymmetry . - 2013. - Vol.24, №19. - С. 1240-1246. - Bibliogr. : p. 1246 (21 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
RACEMIC FLUORINATED -- 1,2,3,4-TETRAHYDROQUINOLINES -- BENZOXAZINES
Аннотация: The acylative kinetic resolution of racemic 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline, 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine, and their non-fluorinated analogues with (S)-naproxen and N-phthaloyl-(S)-amino acyl chlorides has been carried out. It has been shown that the presence of fluorine atoms in the aromatic fragment of a heterocyclic amine results in the increasing stereoselectivity of acylation with (S)-naproxen acyl chloride and in a decrease in the efficiency of acylative kinetic resolution using N-phthaloyl-(S)-amino acyl chlorides. A method for the preparation of enantiopure (S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (ee >99%) was developed

\\\\expert2\\NBO\\Tetrahedron Asymmetry\\2013, in Press, Corr. Proof, 4 Sept.pdf
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9.
Инвентарный номер: нет.
   
   F 62

   
    Five-membered 2,3-dioxo heterocycles: CI. Reaction of 3-aroylpyrrolo[2,1-c] [1,4]benzoxazine-1,2,4-triones with arylhydrazines. Crystal and molecular structure of substituted 2-hydrazonopyrrolo[2,1-c][1,4]benzoxazine [Electronic resource] / I. V. Mashevskaya, N. V. Suchkova, L. V. Kusina, P. A. Slepukhin, A. N. Maslivets // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2014. - Vol.50, №3. - С. 425-428. - Bibliogr. : p. 428 (6 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
NUCLEOPHILIC ATTACK -- HETEROCYCLES -- 1,2,4-TRIONES
Аннотация: A new direction of nucleophilic attack was revealed in the reactions of 3-aroylpyrrolo[2,1-c][1,4]-benzoxazine-1,2,4-triones with o-tolylhydrazine and 2-hydrazinylbenzoic acid hydrochloride, which afforded the corresponding hydrazones at the C2=O carbonyl group, substituted 2-(2-o-tolylhydrazono)pyrrolo[2,1-c]-[1,4]benzoxazine-1,4(2H)-diones and pyrrolo[2,1-c][1,4]benzoxazin-2(4H)-ylidenehydrazinylbenzoic acids. The structure of (Z)-2-{2-[3-benzoyl-1,4-dioxo-1H-pyrrolo[2,1-c][1,4]benzoxazin- 2(4H)-ylidene]hydrazinyl}-benzoic acid was determined by X-ray analysis

\\\\expert2\\nbo\\Russian Journal of Organic Chemistry\\2014, 50, (3), 425-428.pdf
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10.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis of dispiro heteroanalogs of pyrrolizidine alkaloids: Crystal and molecular structure of substituted 3',4",5-trioxodispiro[(2",5"- cyclohexadiene)-1"(4"H),7'-[7H]pyrrolizine-2'(3'H),2-[2H]pyrrole] -1'-carboxamide [Electronic resource] / V. V. Konovalova, Y. S. Rozhkova, Yu. V. Shklyaev, P. A. Slepukhin, A. N. Maslivets // ARKIVOC. - 2014. - №4. - С. 124-134. - Bibliogr. : p. 134 (14 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
HETEROCYCLIZATION -- PYRROLIZIDINE ALKALOIDS -- BENZOXAZINE
Аннотация: 3-Aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones react with substituted 2-(3,3-dimethyl-8-oxo-2-azaspiro[4.5]deca-6,9-dien-1-ylidene) acetamides to produce substituted 3',4",5-trioxodispiro[(2",5"- cyclohexadiene)-1"(4"H),7'-[7H]pyrrolizine-2'(3'H),2-[2H]pyrrole] systems. The crystal and molecular structure of substituted 3',4",5- trioxodispiro[(2",5"-cyclohexadiene)-1"(4"H),7'-[7H] pyrrolizine-2'(3'H),2-[2H]pyrrole]-1'-carboxamide was confirmed by X-ray analysis

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11.
Инвентарный номер: нет.
   
   N 10

   
    N-Tosyl-(S)-Prolyl Chloride in Kinetic Resolution of Racemic Heterocyclic Amines [Electronic resource] / D. A. Gruzdev, S. A. Vakarov, G. L. Levit, V. P. Krasnov // Chemistry of Heterocyclic Compounds. - 2014. - Article in Press. - С. 1-13
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
H-[1,4]BENZOXAZINE -- ACYLATION -- AMINES
Аннотация: The kinetic resolution of racemic heterocyclic amines via acylation with N-tosyl-(S)-prolyl chloride was systematically investigated. It was established that racemic mixtures of aromatic amines could be resolved with high efficiency, while the acylation of 2- and 3-methylpiperidines occurred with low diastereoselectivity. A method for the preparation of enantiomerically pure (3 R)-7,8-difluoro-3-methyl-3,4-dihydro-2 H-[1,4]benzoxazine was developed

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12.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis of novel purin-6-yl conjugates with heterocyclic amines linked via 6-aminohexanoyl fragment [Electronic resource] / E. V. Verbitskiy, E. M. Cheprakova, P. A. Slepukhin, M. A. Kravchenko, S. N. Skornyakov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Mendeleev Communications. - 2015. - Vol. 25. - С. 412-414. - Bibliogr. : p. 414 (30 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
2-AMINOPURINE -- PURIN-6-YL -- HETEROCYCLIC AMINES
Аннотация: Novel conjugates of purine and 2-aminopurine linked with heterocyclic amines, including chiral derivatives of 3,4-dihydro- 2H-[1,4]benzoxazine, 3,4-dihydro-2H-[1,4]benzothiazine and 1,2,3,4-tetrahydroquinoline, by 6-aminohexanoyl fragment at the 6-position of purine moiety were obtained. For this purpose, replacement of the chlorine atom in 2-amino-6-chloropurine or 6-chloropurine by direct nucleophilic substitution reaction with 6-aminohexanamides or the coupling of 6-(purin-6-ylamino)-6- hexanoic acid with nitrogen heterocycles were used.

\\\\expert2\\nbo\\Mendeleev Communications\\2015, v.25, p. 412.pdf
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13.
Инвентарный номер: нет.
   
   B 60

   
    Biotechnological synthesis of new nucleosides based on 2-aminopurine with a bulky 7,8-difluoro-3,4-dihydro-3-methyl-2 h-[1,4]benzoxazine residue at C6 position [Electronic resource] / B. Z. Eletskaya, D. A. Gruzdev, A. Yu. Vigorov, I. D. Konstantinova, G. L. Levit, V. P. Krasnov, V. N. Charushin, A. I. Miroshnikov // FEBS Journal. - 2015. - Vol. 282, № S1 : 40th Congress of the Federation-of-European-Biochemical-Societies (FEBS) - The Biochemical Basis of Life, Berlin, Germany, Jul 04-09 2015. - С. 162
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
BIOTECHNOLOGICAL SYNTHESIS -- 2-AMINOPURINE -- NUCLEOSIDES

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14.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis and antiherpetic activity of novel purine conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine / O. A. Vozdvizhenskaya, V. L. Andronova, G. A. Galegov [et al.] // Chemistry of Heterocyclic Compounds. - 2021. - Vol. 57, № 4. - P490–497
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
6-CHLOROPURINE -- ANTIVIRAL ACTIVITY -- HERPES SIMPLEX VIRUS TYPE 1
Аннотация: A method for the synthesis of novel purine conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine containing fragments of ω-amino acids with different lengths of the polymethylene chain as a linker has been developed. It was found in experiments in vitro that the obtained compounds are active against the herpes simplex virus type 1, including the acyclovir-resistant strain.

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15.
Инвентарный номер: нет.
   
   N 89

   
    Novel purine conjugates with N-heterocycles: synthesis and anti-influenza activity / V. P. Krasnov, V. V. Zarubaev, D. V. Gruzdev [et al.] // Chemistry of Heterocyclic Compounds. - 2021. - Vol. 57, № 4. - P498-504
УДК
Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
6-CHLOROPURINE -- HETEROCYCLIC AMINES -- ANTIVIRAL ACTIVITY -- INFLUENZA A AND B VIRUSES
Аннотация: A number of novel amides were synthesized by coupling of 6-[(9H-purin-6-yl)amino]hexanoic acid to heterocyclic amines. The antiviral activity of the obtained compounds, as well as of purine conjugates in which 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine is linked to position 6 of purine through a fragment of ɷ-amino acids with varying lengths of polymethylene chains against influenza A and B viruses was studied in vitro. Purine derivatives have been shown to have moderate activity against influenza A (H1N1) virus. The antiinfluenza activity and cytotoxicity of conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine depend on the length of the linker fragment.

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16.
Инвентарный номер: нет.
   

   
    Synthesis of pyrimidine conjugates with 4-(6-amino-hexanoyl)-7,8-difluoro-3,4-dihydro-3-methyl-2h-[1,4] benzoxazine and evaluation of their antiviral activity / V. P. Krasnov, V. V. Musiyak, G. L. Levit [et al.] // Molecules. - 2022. - Vol. 27, № 13. - Ст. 4236
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PYRIMIDINE
Аннотация: A series of pyrimidine conjugates containing a fragment of racemic 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine and its (S)-enantiomer attached via a 6-aminohexanoyl fragment were synthesized by the reaction of nucleophilic substitution of chlorine in various chloropyrimidines. The structures of the synthesized compounds were confirmed by 1H, 19F, and 13C NMR spectral data. Enantiomeric purity of optically active derivatives was confirmed by chiral HPLC. Antiviral evaluation of the synthesized compounds has shown that the replacement of purine with a pyrimidine fragment leads to a decrease in the anti-herpesvirus activity compared to the lead compound, purine conjugate. The studied compounds did not exhibit significant activity against influenza A (H1N1) virus.

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