Derivatives of benzo(c)fluorene: II. Synthesis and biological effect of basic ethers of 7-oxo-7H-benzo(c)fluorene

1982 ◽  
Vol 47 (7) ◽  
pp. 1856-1866 ◽  
Author(s):  
Jiří Křepelka ◽  
Iva Vančurová ◽  
Jiří Holubek ◽  
Milan Mělka ◽  
Karel Řežábek

Alkylation of phenols IIa-IIc with ω-(N,N-dialkylamino)alkyl chlorides IIIa-IIId in an aqueous and/or a two-phase (toluene and aqueous potassium hydroxide) medium, and reactions of phenols IId-IIf with isopropylamine, gave rise to ethers IV-XIX. Compounds IV and V were used to prepare derivatives XX-XXVI. Reduction of the 7-oxo group in the compound V by the action of sodium borohydride produced the 7-hydroxy derivatives XXIV-XXVI, whereas reduction under conditions of the Wolf-Kishner reaction led to derivatives XXVII and XXVIII, respectively, which were also obtained by alkylation of XXIX with IIIa in an anhydrous medium. The compound XXIX was prepared by reduction of compound IIa. Most the of compounds prepared had marked antineoplastic effects, particularly compounds IV and V. Compounds V, VII, IX and XVIII exhibited antibacterial effects, and compounds XVI, XVIII and XXIII were as efficacious in subcutaneous application against encephalomyocarditis virus as Tiloron, used as standard.

1982 ◽  
Vol 47 (7) ◽  
pp. 1867-1872 ◽  
Author(s):  
Iva Vančurová ◽  
Jiří Křepelka ◽  
František Šmejkal

Alkylation of phenols IIa-IIc by the action of ω-(N,N-dialkylamino)alkyl chlorides IIIa-IIId in an anhydrous or a two-phase medium (toluene-aqueous potassium hydroxide) gave rise to the dibasic derivatives IV-XI. In the two-phase medium, alkylation of IIa with IIIc produced the basic ether XII as the main product, a decarboxylation product, and compound VII. In biological test compound IV showed the strongest antibacterial effects on four kinds of bacteria, was efficacious in vivo against the viruses of encephalomyocarditis and vaccinia, and induced the formation of interferon to the same extent as Tiloron. The antineoplastic effects of the compounds were weaker than those observed with compound I (Benfluron) administered to animals with experimental, transplantable tumours.


1984 ◽  
Vol 49 (1) ◽  
pp. 110-121 ◽  
Author(s):  
Jiří Křepelka ◽  
Drahuše Vlčková ◽  
Milan Mělka

Alkylation of derivatives of 4-aryl-1-naphthols (I-V) by 2,3-epoxypropyl chloride in methanolic sodium hydroxide gave epoxy derivatives VI, VIII, IX, XI and XII, apart from products of cleavage of the oxirane ring, VII and X. Analogous alkylation of compounds I, IV and V by 2-(N,N-diethylamino)ethyl chloride hydrochloride in a two-phase medium afforded basic ethers XIII to XV. The cleavage of the oxirane ring in compound VI by the action of primary and secondary amines, piperidine and substituted piperazines led to compounds XVI-XXIV. Reaction of thionyl chloride with compounds XXI, XXII and XXIV gave chloro derivatives XXV-XXVII.Exposure of compound XXII to 4-methylbenzenesulfonyl chloride produced compound XXVIII, retaining the secondary alcoholic group. In an antineoplastic screening in vivo none of the compounds prepared had an appreciable activity. Compound XVII, being an analogue of propranolol, was used in the test of isoproterenolic tachycardia, and showed a beta-lytic effect comparable with that of propranol.


1992 ◽  
Vol 57 (3) ◽  
pp. 439-445
Author(s):  
Magdy A. Wassel ◽  
Nalla K. Allahaverdova ◽  
Tofki G. Alkhazov

To determine the acidic and basic properties of the title catalysts, the adsorption of NH3 and SO2 was compared using pulse method. It was found that this characteristics undergoes changes when the Sn-Mo catalyst is treated with aqueous potassium hydroxide solutions of different concentrations. The catalyst treated with the more concentrated KOH solution possesses mainly properties of a base. When studying the oxidation of ethanol it has been found that the αCO2/αaldehyde conversion ratio increases with the time of contact of the mixture with the catalyst while the αCO2/α acid ratio is not affected. The study of two alcohols deuterated either in OH group (C2H5OD) or in the alkyl group ((C2D5OH) has shown that the substitution of C-H for C-D bond enhances the stability of the primary oxidation product, deuterated ethanal, so that it is not transformed further to acetic acid.


RSC Advances ◽  
2016 ◽  
Vol 6 (22) ◽  
pp. 18490-18501 ◽  
Author(s):  
J. Helmlinger ◽  
C. Sengstock ◽  
C. Groß-Heitfeld ◽  
C. Mayer ◽  
T. A. Schildhauer ◽  
...  

The influence of silver nanoparticle morphology on their dissolution kinetics in ultrapure water as well as their biological effect on eukaryotic and prokaryotic cells was examined.


1980 ◽  
Vol 58 (5) ◽  
pp. 485-493 ◽  
Author(s):  
Wilkins Reeve ◽  
James R. McKee ◽  
Robert Brown ◽  
Sitarama Lakshmanan ◽  
Gertrude A. McKee

Phenyl(trichloromethyl)carbinol undergoes an unimolecular, predominantly intramolecular conversion into potassium α-chlorophenylacetate on stirring with 10 % aqueous potassium hydroxide at 0 °C for several days. Besides providing an interesting example of a 1–2 chlorine shift, the reaction is of potential importance for the synthesis of α-chloro acids. The study of a variety of (trichloromethyl)carbinols shows the reaction is general for secondary (trichloromethyl)carbinols as well as trichloroethanol. The mechanism of the reaction involves the preliminary formation of an epoxide. Several mechanisms are considered for the conversion of the epoxide to the α-chloroacetate anion, but none accounts for all of the experimental facts. Tertiary carbinols break down at the epoxide stage into a ketone and carbon monoxide.


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