Acetals of lactams and amides of acids. 72. Investigation of reaction of cyclic β-nitroenamines with p-benzoquinone

The process of condensation of p-benzoquinone with the secondary cyclic enamines 2-(2-nitromethylene)pyrrolidine, -piperidine, and -hexahydroazepine is very much dependent on the size of the saturated ring in these compounds. With increasing ring size, the content of derivatives of 5-hydroxybenzofuran decreases, and the quantity of derivatives of 5-hydroxyindole increases; with the seven-membered enamine, a substituted 6-hydroxyindole is also formed. For enamines of the pyrrolidine and piperidine series, 1,4-bis-2-(2-nitromethylene)pyrrolidono- or piperidinohydroquinones are also recovered.For Communication 71, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 357–362, March, 1992.     

Synthesis and photophysical properties of some 6,6″-functionalized terpyridine derivatives

The synthesis and photophysical properties of several 6,6″ symmetrically substituted 4′-aryl-2,2′:6′,2″-terpyridine derivatives are reported herein. The UV-Vis spectra in acetonitrile as well as in dichloromethane show two intense bands in the UV areas 252–262 nm and 275–290 nm while the fluorescence emission spectra are only slightly influenced by chemical derivatization.     

Synthesis and electroluminescent properties of naphthalimide derivatives

Naphthalimide derivatives, N-ethyl-4-acetylamino-l ,8-naphthalimide (EAAN) and polymer with N-propyl-4-acetylamino-l,8-naphthalimide (PAAN) side-chain (P-PAAN) were successfully synthesized. Electroluminescent devices of ITO/PVK(120nm)/EAAN(50nm)/Al(150nm) (Ⅰ) and ITO/PVK P-PAAN( 10:1) (50nm)/Al(150nm) (Ⅱ) constructed with EAAN and P-PAAN as the emitting layer were investigated, whereas the single-layer devices of ITO/EAAN or P-PAAN(50nm)/Al(l50nm) (Ⅲ) were not observed to have any e-mission light. The emission results revealed that the exciton recombination formed by positive and negative charge carriers injected from electrodes of devices Ⅰ and Ⅱ was much more balanced than that of devices Ⅲ, which implied that naphthalimide derivatives are a new type of electron-transporting materials with high performance. The electron-transporting properties of naphthalimide derivatives were also elucidated by investigation of the electroluminescent behaviors from both devices of ITO/PPV (80nm)/Al and ITO/P     

Synthesis and herbicidal activity evaluation of novel β-carboline derivatives

Based on the original structure of harmine, several novel 1,2,3,4-tetrahydro-β-carboline, β-carboline and 1-substituted-β-carboline derivatives bearing a substituted carbohydrazide group at C-3 were designed and synthesized to investigate the structure-activity relationship of their analogues. All of the compounds were characterized by infrared (IR), proton and carbon nuclear magnetic resonance (1H-NMR, 13C-NMR), and mass spectroscopy (MS). The bioassay tests showed that N'-benzylidene-1-phenyl-β-carboline-3-carbohydrazide (C(25)H(18)N(4)O, m.w. 390.4) (c2) and N'-(4-trifluoromethyl-benzylidene)-1-phenyl-β-carboline-3-carbohydrazide (C(26)H(17)N(4)OF(3), m.w. 458) (d2) exhibited good inhibitory activity against dicotyledonous and monocotyledonous weeds, with EC(50) values of 4.83 μM and 14.25 μM, respectively.     

Spectroscopic study of intermolecular complexes between FAD and some β-carboline derivatives

The formation of molecular complexes between flavine adenine dinucleotide (FAD) and some β-carboline derivatives [antidepressant drugs that have a pronounced inhibition of monoamine oxidase (MAO)] has been studied by using electronic absorption and fluorescence spectroscopic methods. Thermodynamic parameters have been determined from the values of association constants for the molecular complexes at various temperatures. The influence of substituents in the β-carboline molecule on the stability of the complexes formed was also investigated.     

Synthesis and antitumor activity of derivatives of 23-hydroxybetulinic acid

A series of natural product 23-hydroxybetulinic acid derivatives were prepared.In the preparation of mono-O-benzoyl ester derivative,it was observed that benzoyl group migrated from 3-O-to 23-O-position during the detritylation.     

Synthesis and characterization of novel β-amino acid derivatives

In the work discussed in this paper, novel β-amino acid derivatives were prepared by Michael addition between 3-substituted-2-propenic acid and hydrazine hydrate. The optimum reaction conditions were determined by analyzing the effects of the ratio of the starting materials, temperature, and reaction time. The conclusions were: reaction temperature 80 °C, reaction time 8 h, n (3-substituted-2-propenic acid)/n (hydrazine hydrate) = 1:15. Products were characterized by measurement of melting point, elemental analysis, and IR and ¹H NMR spectroscopy.     

Synthesis and spectral properties of arylmercury derivatives of α-thiopicolinanilide

A series of thirteen arylmercury derivatives of α-thiopicolinanilide have been synthesizedand characterized by elemental analysis,IR,~1H NMR and MS.The intramolecular coordination andthe substituent effects on the MS and ~(199)Hg NMR behaviours have been studie6.It has been shownthat a linear correlation exists between the ~(199)Hg chemical shifts and the Hammett-Brown constantsσ~+,and the electron-donating groups cause the chemical shift to move upfield.     

Synthesis and complexing power of some acetyl β-cyclodextrin derivatives

New water-soluble acetyl derivatives of β-cyclodextrin were synthesized, and their complexing ability toward phenolphthalein was studied.     

Synthesis and properties of furan derivatives. 1. Synthesis of 3,5-disubstituted Δ2-isoxazolines containing furfuryl fragments

3,5-Disubstituted ²-isoxazolines containing furan fragments have been synthesized by 1,3-dipolar cycloaddition reactions.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 449–452, April, 1991.     

Synthesis and properties of furan derivatives. 3. Synthesis of 1,2-disubstituted δ2-imidazolines containing furfuryl and tetrahydrofurfuryl groups

The condensation of N-furfuryl- and N-tetrahydrofurfurylethylenediamines with hydrochloride salts of iminoesters of carboxylic acids gives 1,2-disubstituted ²-imidazolines containing furfuryl or tetrahydrofurfuryl groups at N¹.For communication 2, see [1]Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1312–1315, October, 1992.     

Synthesis of some 5′-O-amino acid derivatives of uridine as potential inhibitors ofUDP-glucuronosyltransferase

Summary In an attempt to develop potential inhibitors ofUDP-glucuronosyltransferase, some 5-O-amino acid derivatives of uridine were synthesized. N-protectedL-amino acids were coupled at the 5-O-position of 2,3-O-isopropylideneuridine by esterification employing the method of symmetrical anhydrides in presence of 4-dimethylaminopyridine, 5-O-(N-benzyloxycarbonyl-O-tert.butyl-L-threonl)-23-O-isopropylideneuridine (1), 5-O-(N-tert.butyloxycarbonyl-O-benzyl-L-seryl)-2,3-O-isopropylideneuridine and (2), 5-O-(N-tert.butyloxycarbonyl-L-valyl)-2,3-O-isopropylideneuridine (3), and 5-O-(N-tert.butyloxycarbonyl-L-valyl)-2,3-O-isopropylideneuridine (4) were obtained in good yield after column chromatography on silica gel. The treatment of2 withTFA/CH₂Cl₂ (6:1) at room temperature for 30 min led to a selective removal of theBoc group without deblocking of the 2,3-O-isopropylidene group of uridine. Treatment of2 withTFA/H₂O (5:1) at room temperature for 1 h, however, released bothBoc and 2,3-isopropylidene groups. TheZ group of1 was deprotected by catalytic hydrogenolysis over 10% Pd/C/ammonium formate.

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Synthese von 5-O-Aminosäurederivaten des Uridins als potentielle Inhibitoren derUDP-Glukuronosyl-Transferase

Zusammenfassung In einem Versuch, potentielle Inhibitoren derUDP-Glukuronosyl-Transferase zu entwickeln, wurden einige 5-O-Aminosäurederivate des Uridins synthetisiert. N-GeschützteL-Aminosäuren wurden durch Veresterung mit der 5-O-Position des 2,3-isopropylidenuridins gekuppelt (Methode der symmetrischen Anhydride in der Gegenwart von 5-Dimethylaminopyridin). Solcherweise wurden 5-O-(N-Benzyloxycarbonyl-O-tert.butyl-L-threonly)-2,3-O-isopropylidenuridin (1), 5-O-(N-tert.Butyloxycarbonyl-O-benzyl-L-seryl)-2,3-O-isopropylidenuridin (2), 5-O-(N-tert.Butyloxycarbonyl-L-leucyl)-2,3-O-isopropylidenuridin (3) und 5-O-(N-tert.Butyloxycarbonyl-L-valyl)-2,3-O-isopropylidenuridine (4) nach Säulenchromatographie (Kieselgel) in guter Ausbeute hergestellt. Die Behandlung von2 mitTFA/CH₂Cl₂ (6:1) bei Zimmertemperatur (30 min) führte zu einer selektiven Abspaltung derBoc-Gruppe ohne Deblockierung der 2,3-O-Isopropylidengruppe des Uridins. Eine Behandlung von2 mitTFA/H₂O (5:1) bei Zimmertemperatur für 1 Stunde führte hingegen zur Abspaltung sowohl derBoc als auch der 2,3-O-Isopropylidengruppe. DieZ-Gruppe von1 wurde durch katalytische Hydrogenolyse auf 10% Pd/C/Ammoniumformiat abgespalten.

     

Molecular design of multitarget neuroprotectors 2. Synthesis and bioactivity of carbazole—γ-carboline conjugates

Russian Chemical Bulletin - Earlier unknown conjugates of carbazoles and γ-carbolines were obtained by the reaction of 3,6-substituted 9-oxiranylmethylcarbazoles and 2,8-substituted...     

Studies in the field of derivatives of unsaturated phosphonic acids 21. Esters and amides of β-ethylhexoxyvinylphosphonic acid

Summary -(-Ethylhexoxy)-vinylphosphonic dichloride, diethyl, dipropyl, dibutyl, di-isobutyl, di-isoamyl, dihexyl, di-2-ethylhexyl, di-(methoxyethyl) and di(ethoxyethyl) esters of -(-ethylhexoxy)-vinylphosphonic acid, tetramethyldiamide, tetraethyldiamide and dipiperidide -(-ethylhexoxy)-vinylphosphonic acid were prepared and characterized.     

Synthesis of azo derivatives of 4-aminosalicylic acid

For searching a better 4-aminosalicylic acid derivative with higher activity and less side effects against the inflammatory bowel disease, 4-aminosalicylic acid (4-ASA) was protected by benzyloxycarbonyl and acetyl, respectively. The resultant was hydrogenized to remove protective group of amino group, then the product was reacted with NaNO2 to give diazonium salt, which was conjugated with salicylic acid, hydroxybenzene, TV-salicyloyl glycine acid to get azo derivatives of 4-ASA. The azo derivatives were hydrolyzed under the alkaline condition to get the target products. All compounds were characterized by FT-IR, 1H NMR, 13C NMR spectra in details. New derivatives of 4-ASA were characterized. The synthetic route was reasonable and feasible.     

Synthesis and antitumor activity of heterocyclic acid ester derivatives of 20S-camptothecins

A series of heterocyclic acid esters of camptothecins as new compounds had been synthesized by acylation method,their in vitro and in vivo antitumor activities were evaluated.The cytotoxic results showed that 6 possessed the best efficacy on six human cancer cell lines in the six classes of CPTs' derivatives.In vivo testing results indicated that 9 had better antitumor activity against mouse liver carcinoma H_(22) than topotecan.