New phosphorylated derivatives of anabasine and of lupinine,and their anticholinesterase properties

A series of new phosphorylated esters of anabasine, lupinine, and piperidine differing by the nature of the alkyl radicals attached to the phosphorus atom has been synthesized. The results of investigations of the antiesterase properties of the compounds in relation to the acetylcholinesterase of human blood erythrocytes and of the turnip moth and the carboxylesterase of porcine kidney have shown a selectivity of their action in relation to the insect enzyme and a substantially lower activity towards esterases of warm-blooded animals.A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax 627071. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 66–70, January–February, 1994.     

Synthesis and anticholinesterase activites of a number of derivatives of the alkaloid lupinine

A series of new lupinine derivatives and their methiodides has been synthesized. It has been shown that they are powerful reversible inhibitors of acetylcholinesterase and butyrylcholinesterase.A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 513–515, July–August, 1990.     

Synthesis and anticholinesterase activities of O-phosphorylated derivatives ofd-allylpseudoephedrine

An immunochemical investigation has been made of the culture liquid after the cultivation of ten strains of the microorganisms Yersinia pseudotuberculosis. It has been shown that in the process of vital activity all the strains investigated, to a greater or smaller degree, produce into the culture medium products of catabolic breakdown consisting of fragments of receptor proteins which are possibly, regulators of metabolic processes taking place under the influence of the constantly changing conditions of the growth medium.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 436–439, May–June, 1993.     

New flavonoid-containing derivatives of lupinine

An oxazine ring was annelated to benzopyran-4-one and benzopyran-2-one cores by reacting 7-hydroxyisoflavones and 7-hydroxycoumarins with lupinylamine and formalin. The new derivatives 9,10-dihydro4H,8 H-chromeno[8,7-e][1,3]oxazin-4-one and 9,10-dihydro-2 H,8 H-chromeno[8,7-e][1,3]oxazin-2-one containing a lupinine moiety in the 9-position were prepared.     

Mass-spectrometric investigation of some new derivatives of the alkaloid lupinine

The mass spectra of some new derivatives of lupinine have been studied with the use of the spectra of metastable ions. On the basis of the results of an investigation of DADI spectra it has been shown that in the formation of low-mass quinolizidine ions the ions with m/z 152–150 are of considerable importance.A. S. Sadykov Institute of Biororganic Chemistry, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 508–512, July–August, 1990.     

Synthesis of organophosphorus derivatives of lupinine and epilupinine and their interaction with cholinesterases

Conclusions Some esters of O-alkyl methylphosphonic acid and thioesters of O-alkyl methylthiophosphonic acid derived from the alkaloids lupinine and epilupinine have been prepared. These were found to be reversible competitive inhibitors of acetylcholinesterase and butyrylcholinesterase.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 650–654, March, 1987.     

Synthesis and anticholinesterase activities of O-phosphorylated derivatives ofd-allylpseudoephedrine

The synthesis of O-phosphorylated derivatives of d-allylpseudoephedrine under the conditions of phase-transfer catalysis is described. The results of a study of their anticholinesterase properties are given.Institute of Organic Synthesis and Coal Chemistry, National Academy of Sciences, Republic of Kazakhstan, Karaganda. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 408–411, May–June, 1994.     

Synthesis,antioxidant and anticholinesterase activities of novel quinoline-aminophosphonate derivatives

A series of 20 novel α-aminophosphonate derivatives bearing quinoline or quinolone moiety was designed and synthesized via Kabachnik-Fields reaction in the presence of triethylammonium acetate as a solvent and catalyst under ultrasound irradiation. This procedure affords products in high yields and short reaction times. Molecular structures of the synthesized compounds 4a-g and 5a-m were confirmed using various spectroscopic methods. The antioxidant activity of these compounds was evaluated by eight complementary in vitro tests. The anticholinesterase activity (AChE, BChE) of these compounds were also evaluated. In addition, theoretical calculations of all compounds were investigated as corrosion inhibitors using density functional theory (DFT). The results revealed that 16 of these compounds exhibited high levels of antioxidant activities depending on the assay and that most compounds showed more potent inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE).     

Synthesis and biologic properties of new thiazolylbenzodioxane derivatives

Reaction of 4-(1,4-benzodioxan-2-yl)thiazol-2-amine with acid chlorides afforded N-substituted amides which further were reduced into the corresponding amines. A new method was developed of preparation of 2-acetyl-1,4-benzodioxane, the initial compound in the synthesis of thiazolylbenzodioxane and numerous derivatives of this series. The adreno- and sympatholytic as well as antihypoxic effect of the obtained biheterocyclic 1,4-benzodioxane derivatives were investigated.     

Synthesis and photoluminescent properties of new ceramidine derivatives

A series of new ceramidine derivatives 8a–f has been synthesized in 4–5 steps involving a Wittig reaction of ceramidonine with various triphenylphosphonium bromides. Their UV and photoluminescence (PL) properties are reported. The compounds showed medium to strong PL between 502 and 522 nm at a concentration of 1 × 10⁻⁵ M CH₂Cl₂. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 23:66–73, 2012; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.20753     

Synthesis of organophosphorus derivatives of lupinine and solasodine and investigation of their cholinergic activities

The synthesis of lupinine O-(dialkyl phosphate)s and of solasodine O-(diethyl phosphate) has been achieved under the conditions of phase-transfer catalysis-and their antienzyme activities have been studied.     

Synthesis of organophosphorus derivatives of lupinine and solasodine and investigation of their cholinergic activities

The synthesis of lupinine O-(dialkyl phosphate)s and of solasodine O-(diethyl phosphate) has been achieved under the conditions of phase-transfer catalysis-and their antienzyme activities have been studied.Institute of Organic Synthesis and Coal Chemistry, Kazakhstan Academy of Sciences, Karaganda. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 541–542, September–October, 1992.     

Synthesis,characterization, and antioxidant and anticholinesterase activities of pyrazolo derivatives

Twenty-four pyrazolo derivatives (1–4)(a-f) were synthesized and characterized by FTIR, ¹H, and ¹³C NMR (Nuclear Magnetic Resonance), and elemental analysis. The synthesized compounds were also investigated for their antioxidant and anticholinesterase activities. The compounds (3–4)(a-f) carrying morpholine ring were more active than the piperidinyl containing compounds (1–2)(a-f) in both activities. The compound 4f showed higher activity in both assays as compared with the others. Additionally, the anticholinesterase activity test provided higher values than the galantamine in the BChE assay. Therefore, compound 4f can be used as anticholinesterase agent and/or anticholinesterase assay standard.     

Synthesis and antibacterial properties of new 8-nitrofluoroquinolone derivatives

The objective of this research was the preparation of new 8-nitrofluoroquinolone models and investigation of their antibacterial properties. The work initially involved large scale preparation of the synthon 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (3), followed by introduction of substituted primary amine appendages at the C-7 position to give derivatives 9a-g, in which the amino group is appended to substituted benzenes or aromatic heterocycles, is part of a primary alpha-amino acid or just a simple primary aliphatic amine. This nucleophilic aromatic substitution step was a very simple procedure since the 8-nitro group of the above synthon facilitated the addition of weak nucleophiles at C-7. All compounds prepared were fully identified and characterized using NMR, IR, EA and MS, and were consistent with expected structures. The prepared targets and the intermediates have shown interesting antibacterial activity against gram positive and/or gram negative strains. In particular, the p-toluidine, p-chloroaniline and aniline derivatives showed good activity against S. aureus with MIC range approximately 2-5 microg/mL. In conclusion, more lipophilic groups seem to enhance activity against gram positive strains.     

Synthesis and physicochemical properties of new fluorescent derivatives of cytosine

Sixteen new fluorescent N⁴‐(E)‐stilbenyloxyalkylcarbonyl‐cytosines 9–16 and N⁴‐(E)‐stilbenyloxyalkylcarbonyl‐1‐methylcytosines 17–24 have been synthesized. The differences in ¹H and ¹³C NMR spectra in two solvents (DMSO and TFA) have been pointed out and discussed. Assignment of the signals in the spectra of the compounds 9–24 in NMR in DMSO‐d₆ solutions has been made the basis of the homonuclear (COSY) and heteronuclear (HETCOR) spectra. The effect of the substituent (Cl, Br, NO₂) on the stilbene moiety on the fluorescence spectrum of each compound has been discussed.     

Synthesis and antioxidant properties of some new thiazolyl coumarin derivatives

ABSTRACT

A three-component one-pot synthesis of new thiazolyl coumarin derivatives was carried out by condensing 3-acetyl-4-hydroxycoumarin, arylaldehydes, thiourea and ammonium acetate at reflux in DMC. The optimization details of the developed novel protocol are recorded. In addition, we have also synthesized these compounds via another second route in two steps. High atom-economy, excellent yields, simple procedure, and mild reaction conditions are the important features of this one-pot protocol. The chemical structures of the newly synthesized compounds were elucidated by using analytical (IR, ¹H NMR, ¹³C NMR). Further, all the compounds were screened for their antioxidant activities.     

Synthesis,structure, and properties of new spirooxindolodibenzodiazepine derivatives

An acid-catalyzed reaction of 3-(2-aminophenylamino)-5,5-dimethylcyclohexen-1-one with isatines leads to the formation of the earlier undescribed 3,3-dimethyl-2,3,4,5,10,11-hexahydrospiro[1H-dibenzo[b,e][1,4]diazepine-11,3′-2H-indole]-1,2′-dione derivatives (6). Spiranes 6 upon heating undergo auto-redox rearrangement with disintegration to 3,3-dimethyl-1,2,3,4-tetrahydrophenazine and the corresponding oxindole. Crystals of four derivatives of compound 6 were studied by X-ray diffraction method.     

Synthesis and liquid crystal properties of new banana-shaped cinnamoyl derivatives

Three new achiral five-ring banana-shaped homologous series have been synthesized and their liquid crystalline properties studied by polarizing microscopy, differential scanning calorimetry, and electro-otpical analysis. The compounds consist of two identical mesogenic structures of bis (alkoxycinnamoyloxybenzoates) linked on a different central ring (unsubstituted or methyl-substituted). The length of the terminal alkoxy groups was varied from heptyloxy to dodecyloxy; the hexadecyloxy group was also included in the study. It was found that the polymorphism of compounds can be strongly dependent upon molecular structure in this class of compound. In particular, substituents on the central ring may exert a significant effect on the type of mesophase observed.     

Synthesis and liquid crystal properties of new banana-shaped cinnamoyl derivatives

Three new achiral five-ring banana-shaped homologous series have been synthesized and their liquid crystalline properties studied by polarizing microscopy, differential scanning calorimetry, and electro-otpical analysis. The compounds consist of two identical mesogenic structures of bis (alkoxycinnamoyloxybenzoates) linked on a different central ring (unsubstituted or methyl-substituted). The length of the terminal alkoxy groups was varied from heptyloxy to dodecyloxy; the hexadecyloxy group was also included in the study. It was found that the polymorphism of compounds can be strongly dependent upon molecular structure in this class of compound. In particular, substituents on the central ring may exert a significant effect on the type of mesophase observed.     

Synthesis, structure, and anticholinesterase activity of some organophosphorus derivatives of anabasine

Anabasine derivatives based on methylphosphonothoic acid have been synthesized. It has been shown by PMR spectroscopy that in solution O-alkyl O-[-(anabasin-1-yl)ethyl] methylphosphonothioates exist in two stereomeric forms, which is due to the influence of the optically active anabasine residue. It has been shown that these compounds are competitive reversible inhibitors of acetylcholinesterase and of butyrylcholinesterase.Institute of Bioorganic Chemistry of the Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 561–565, July–August, 1987.