Fluorobenzoyl derivatives

Eighty-nine per cent of the variation in the biological data can be explained with the receptor model. On the other hand, a systematic deviation can be noticed. Some compounds (denoted by bold type in Table 24.1) are described by the model as being too weak by a constant factor of 1.0 or 1.5 orders of magnitude when compared with the experimental affinities. The inspection of the molecular formulae identifies those showing the larger deviation as fluorobenzoyl derivatives and those with the smaller deviation as benzoyl derivatives. In all cases, substances which are not optimally described by the model, possess an electron-deficient aromatic system. This leads to the hypothesis that for binding at the real receptor a type of interaction may be important which is... 

The iV -p-fluorobenzoyl derivative of ATP (II) in the presence of 2.64 mAf ATP inactivated the rabbit and carp adenylate kinases by pseudo-first-order kinetics the half-life of the rabbit kinase was 210 min in the presence of 50 /lAf (II), and the half-life of the carp kinase... 

The rehability of these analytical methods may be questionable when chemical shift differences of derivatives are of the same magnitude as variations encountered from solvent, concentration, and temperature influences. Reported fluorine chemical shift ranges for tnfluoroacetylated alcohols (1 ppm), p-fluorobenzoylated sterols (1 ppm), and p-fluorobenzoylated ammo acids (0.5 ppm) are quite narrow, and correct interpretation of the fluonne NMR spectra of these denvatized mixmres requires strict adherence to standardized sampling procedure and NMR parameters. 

Garcia et al. has extended the Batcho-Leimgruber procedure to the synthesis of 2-substituted indoles. Treatment of 36 with o-fluorobenzoyl chloride 37, followed by in situ hydrolysis and deformylation gave ketone 38. Reduction of nitroarylketone 38 with sodium hydrosulfite then furnished indole 39. Similarly, bromoacetylation of 36 gave an acylenamine which was converted into the phthalimido derivative 40. Hydrolysis and deformylation gave phthalimidoketone 41 which underwent reductive cyclization to furnish indole 42. 

New poly(ether ketone)s derived from bis[4-(4-fluorobenzoyl)phenyl]phenyl-phosphine oxide was reported by Fitch et al.106 These polymers are thermally stable and have high i, values (about 200°C). 

Alkylation of flra-chloroaniline (13-1) with 2,2,2-triiluoroethyl trichloromethyl-sulfonate affords the corresponding trifluroethylated derivative (13-2). Reaction of the anion from that with aziridine proper leads to the formation of the diamine (13-3). Acylation of that compound with ortfio-fluorobenzoyl chloride (13-4) proceeds to... 

Acylation of 2-aminobenzothiazoles (274) with 2-fluorobenzoyl chloride followed by thermal cyclization of the intermediate acyl derivatives gave the benzothiazolo[3,2-a]quinazolines (275) (81JHC801). Tetrahydroben-... 

Compared to the previous models, the 3-acyl derivatives tested (benzoyl, 2-fluorobenzoyl, 1-naphthoyl, 2-naphthoyl, and pivaloyl) provided increased total... 

The chloro moiety of thieno[3,4-d]pyrimidine 383 was displaced by 4-(2-methoxyphenyl)piperazine or 4-(4-fluorobenzoyl)piperidine in refluxing propan-2-ol containing sodium bicarbonate and a catalytic amount of sodium iodide. The N-3 protecting group of the resulting derivatives 384 was... 

A series of fluorine-18 labelled 1,2-diazabenzenes 6 have been synthesized28 in the reaction of high specific activity, NCA [18F]fluoride ion with various chloro-substituted pyridazines 7 (equation 8) in radiochemical yields ranging from 11 to 64% [24% yield for R = Me, 64% for R = 4-benzoyl, 11% for R = 4-fluorobenzoyl, 46% for R = (2-thienyl) carbonyl]. The rat biodistribution of pyridazine analogues, more polar than the corresponding phenyl derivatives, has been studied and their applications to radiopharmaceuticals are underway28. 

Anderson GD, Hauser SD, McGarity KL et al. (1996) Selective inhibition of cyclooxygenase (COX)-2 reverses inflammation and expression of COX-2 and interleukin 6 in rat adjuvant arthritis. J Clin Invest 97 2672-2679 Banoglu E, Okcelik Bkupeli E, Unlii S et al. (2003) Amide derivatives of [5-chloro-6-(2-chloro/fluorobenzoyl)-2-benzoxazohnone-3-yl]acetic adds as potential analgesic and anti-inflammatory compounds. Arch Pharm Pharm Med Chem 336 251-257... 

Bromobenzamides couple with arylboronic acids thermal deprotection of the amino group is followed by the formation of a fused pyridin-2-one in good yield. The 4-one ring may be constructed in low yield by stirring at a low temperature (—S °C) a 2-fluorobenzoyl chloride with the lithium derivative of ethyl pyridine-2-acetate. 

A number of protic acids have been used to catalyze acylation reactions. It is assumed that the reactions involve the generation of acylium ions. Polymeric reagents such as Nafion-H have been used for example 2-fluorobenzoyl chloride and toluene give the benzophenone derivatives with an ortho.para ratio of 4 81. ° A zeolite-catalyzed acylation (equation 6) has been reported to afford 4-dodecenoyltol-uene in 96% yield but the yields are low with short chain carboxylic acids. Early examples of the use of trifluoroacetic and perchloric acids reported good yields of products. Some more recent examples are shown in equations (7) to (9). Phosphoric and polyphosphoric acids have been used together with carboxylic acids (equation 10),anhydrides and acylureas (equation 11). °... 

Tetrahydro-l//-xanthene-l,9-diones, synthesised from cyclohexa-l,3-diones and 2-fluorobenzoyl chlorides, are efficient Michael acceptors, offering a route to 4a-substituted xanthone derivatives similar to the secalonic acid half unit (Scheme 12) <97JCS(P1)1819>. 

The 4-fluorobenzoyl groiq)s are introduced by Friedel-Crafts acylation of the 3-phenylindan derivative with 4-fluorobenzoic acid (Scheme 2). 

Kricheldorf HR, Vakhtangishvili L, Schwarz G, Kruger RP (2003) Cyclic hyperbranched poly(ether ketone)s derived from 3,5-bis(4-fluorobenzoyl)phenol. Macromolecules 36 5551-5558... 

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