Important fluorinated drugs in experimental and clinical use

Ismail, Fyaz M.D.

doi:10.1016/s0022-1139(02)00201-4

Cited by 377 publications

(138 citation statements)

References 47 publications

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“…The values of the endocyclic torsion angles, P, and ν max were confirmed using the online pseudorotation tool supplied in the Cactus software (http://cactus.nci.nih.gov/Pseurot). The five endocyclic torsion angles are related to the H-H vicinal torsion angles by the linear relation (eq 1) (1) A plot of the HH torsion against the endocyclic torsions yields a straight line with slope equal to A and y intercept equal to B. All plots from the three nucleosides 2-4 (for puckering amplitude values of both 30° and 38°) gave straight lines with correlation coefficients > 0.998 (see Supporting Information).…”

Section: Determination Of Coefficients a And Bmentioning

confidence: 99%

“…1 The highly electronegative nature of the fluorine atom imparts very different electrostatic properties to a molecule, and this effect may in turn influence the conformation of the system to which it has been incorporated in unique ways. These distinct changes are installed without major disturbances to the steric properties of the molecule due to the small size and high "compactness" of the fluorine.…”

Section: Introductionmentioning

confidence: 99%

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Comprehensive Structural Studies of 2′,3′-Difluorinated Nucleosides: Comparison of Theory, Solution, and Solid State

et al. 2008

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The conformations of three 2′,3′-difluoro uridine nucleosides were studied by X-ray crystallography, NMR spectroscopy, and ab initio calculations in an attempt to define the roles that the two vicinal fluorine atoms play in the puckering preferences of the furanose ring. Two of the compounds examined contained fluorine atoms in either the arabino or xylo dispositions at C2′ and C3′ of a 2′, 3′-dideoxyuridine system. The third compound also incorporated fluorine atoms in the xylo configuration on the furanose ring but was substituted with a 6-azauracil base in place of uracil. A battery of NMR experiments in D 2 O solution was used to identify conformational preferences primarily from coupling constant and NOE data. Both 1 H and 19 F NMR data were used to ascertain the preferred sugar pucker of the furanose ring through the use of the program PSEUROT. Compound-dependent parameters used in the PSEUROT calculations were newly derived from complete sets of conformations calculated from high-level ab initio methods. The solution and theoretical data were compared to the conformations of each molecule in the solid state. It was shown that both gauche and antiperiplanar effects may be operative to maintain a pseudodiaxial arrangement of the C2′and C3′ vicinal fluorine atoms. These data, along with previously reported data by us and others concerning monofluorinated nucleoside conformations, were used to propose a model of how fluorine influences different aspects of nucleoside conformations.

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Section: Determination Of Coefficients a And Bmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Comprehensive Structural Studies of 2′,3′-Difluorinated Nucleosides: Comparison of Theory, Solution, and Solid State

et al. 2008

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“…Особливо важливими в цьому від-ношенні є сполуки, що містять також один або де-кілька атомів Флуору оскільки добре відомо, що заміна атома Гідрогену на Флуор або введення трифлуорометильної групи замість метильної мо-же покращити фармакодинамічні та фармакокіне-тичні характеристики з одночасною зміною елек-тронних, ліпофільних та стеричних параметрів, а також стійкості до метаболізму [1,2]. Через це син-тез селективно флуорованих аналогів біологіч-но активних сполук є одним із перспективних су-часних підходів до пошуку ефективних біомедич-них препаратів.…”

Section: -R-2-r F -4-оxo-thiazolidines Thiazinanes and Bezothiazinaunclassified

“…1) показав, що прооксидантний ефект є найвищим для сполук, які містять фраг-мент бензотіазинанону (7а,b, 8) або тіазинано-ну (фосфонат 5b). В той же час для тіазолідино-1a, 3a, 5a, 7а: R = P(O)(OEt) 2 , R F = CF 3 1b, 3b, 5b, 7b: R= P(O)(OEt) 2 , R F = CHF 2 2, 4, 6, 8: R = COOMe, R F = CF 3…”

Section: -R-2-r F -4-оxo-thiazolidines Thiazinanes and Bezothiazinaunclassified

Synthesis, the antioxidant and antibacterial activity of fluoroalkyl substituted thiazolidinones and thiazinanones incorporating an aminophosphonate or aminocarboxylate fragment

Yelenich¹,

Rassukana²,

Khomutnyk³

et al. 2014

J. org. pharm. chem.

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“…Fluorine has played a pivotal role in novel drug discovery for modulating physical and biological properties of the molecules [15][16]. Numerous drugs containing fluorine includes antipsychotic such as fluphenazine, HIV protease inhibitors such as tipranavir, antibiotics such as Ofloxacin and trovafloxacin and anesthetics such as haloethane [17][18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of Some New Fluoro Formazans

Shinde¹,

Deshmukh²,

Kottapalle³

et al. 2016

J. Pure App. Chem. Res.

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A series of fluoro-substituted formazan derivatives has been synthesized from the salts of diazonium chloride and fluoro schiff base in pyridine. The structures of newly synthesized formazans were established based on IR, 1 H NMR, and mass spectral data. All the synthesized compounds were screened for their antimicrobial activity. Some of the compounds showed very good activity compared to the standard drugs against all pathogenic bacteria and fungi.

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Important fluorinated drugs in experimental and clinical use

Cited by 377 publications

References 47 publications

Comprehensive Structural Studies of 2′,3′-Difluorinated Nucleosides: Comparison of Theory, Solution, and Solid State

Comprehensive Structural Studies of 2′,3′-Difluorinated Nucleosides: Comparison of Theory, Solution, and Solid State

Synthesis, the antioxidant and antibacterial activity of fluoroalkyl substituted thiazolidinones and thiazinanones incorporating an aminophosphonate or aminocarboxylate fragment

Synthesis and Antimicrobial Evaluation of Some New Fluoro Formazans

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