The Quantitative Analysis of Steric Effects in Heteroaromatics

Gallo, R.; Roussel, Christian; Berg, Ulf

doi:10.1016/s0065-2725(08)60255-x

Cited by 72 publications

(33 citation statements)

References 426 publications

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“…Thus, the 2-bromomyristoyl ester of thymidine (5b), which has a half-life of 15.3 min upon incubation Antiviral Chemistry & Chemotheropy S{S) with porcme liver esterase, was inactive against HlVinfected T4 lymphocytes. The longer half-life for compound 5bmay be attributable to steric shielding by the a-bromo atom of the ester moiety since bulky substituents such as bromo (Br) may shield the ester group from attack by the enzyme (Gallo et al, 1988). The observed differences in ester hydrolysis rates (stability) are attributed to both steric and electronic variations in the fatty acid moiety of these ester compounds (5a-h).…”

Section: Antiviral Activitymentioning

confidence: 99%

Syntheses and Biological Evaluation of 5′-O-Myristoyl Derivatives of Thymidine against Human Immunodeficiency Virus

Parang

Wiebe

Knaus

1997

Antivir Chem Chemother

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; Fax: + 1 403 492 1217.--S ummary A series of 5'-O-acyl derivatives of thymidine (dThd) were prepared by direct acylation of thymidine using the Mitsunobu reaction. Further reaction of the bromo analogues with sodium azide gave azido ester analogues. Anti-human immunodeficiency virus type 1 (HIV-1) activities were determined against HIV-infeeted T4 lymphocytes. 5'-0-( 12-Azidododecanoyl)thymidine exhibited moderate activity (EC so 4.6 11M) against HIVinfected T4 lymphocytes. 5'-0-(2-Bromotetradecanoyl)-thymidine was found to be the most stable ester (t 1/2 15.3 min) to hydrolysis by porcine liver esterase in vitro. Partition coefficients (P) in n-octanol-phosphate buffer were determined (log1 Prange 4.15-6.72) and compared with the theoreticaPvalues calculated (log10 P 3.96-6.53) using the PALLAS program. Anti-HIV structure-activity data suggest that the experimental partition coefficient should be in the 10glo P 4.6-4.8 range for optimum anti-HIV activity. The structures of these thymidine analogues were optimized using molecular mechanics (MM+ force field) and semi-empirical quantum mechanics PM3 calculations. The moderately active compounds adopted a similar C-2' endo sugar conformation and exhibited similar energies for the lowest energy conformer. A quantitative structure-activity relationship (QSAR) regression equation was developed, based on the optimized structures and anti-HIV data using the SciQSAR program, which showed that log P was a determinant of anti-HIV activity.

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Section: Antiviral Activitymentioning

confidence: 99%

Syntheses and Biological Evaluation of 5′-O-Myristoyl Derivatives of Thymidine against Human Immunodeficiency Virus

Parang

Wiebe

Knaus

1997

Antivir Chem Chemother

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“…On the basis of data in the literature, the apparent size of a methyl group is larger than the apparent size of a methoxy group in rotational processes in biphenyl. 7,8 It can thus be inferred that the regioisomer with the low barrier is 1, and the one with the high barrier is 2.…”

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confidence: 99%

Atropisomerism in some N,N'-diaryl-2-iminothiazoline derivatives: chiral separation and configurational stability

Bouchekara¹,

Djafri²,

Vanthuyne³

et al. 2003

Arkivoc

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Semi-preparative resolution of the atropisomers by chiral liquid chromatography and determination of the barriers to rotation has allowed an unequivocal identification of the regioisomers produced by the reaction between N-(2-methoxyphenyl)-N'-(2-methylphenyl)thiourea and α-chloroacetone. Attention is drawn on the potential use of these optically pure atropisomers as new non-biaryl ligands for enantioselective metal catalysis.

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“…Thanks to our longstanding interest in N-arylthiazolin-2-thione atropisomers, [5][6][7][8][9][10][11][12] it was clear that restricted rotation about the two N-aryl axes might lead to stable atropisomers and thus 1 would be a new example of ''atropisomeric molecular triad'' B-A-B, in which A is a 1,2-disubstituted benzene and B is a thiazoline-2-thione derivative. 13 In a study of atropisomeric molecular triad of the B-A-B type, several issues have to be addressed :…”

Section: -4mentioning

confidence: 99%

Synthesis, chiral separation, and absolute configuration of bis‐(N‐aryl) atropisomeric triads: 1,2‐Bis‐[4‐methyl‐2‐(thi)oxo‐2,3‐dihydrothiazol‐3‐yl]‐benzene

Roussel¹,

Kaid-Slimane²,

Andreoli³

et al. 2008

Chirality

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In this work, a series of 1,2-bis-[4-methyl-2-(thi)oxo-2,3-dihydrothiazol-3-yl]-benzene has been prepared. These atropisomeric molecular triads were exclusively found to exist in the anti-form. They were separated into enantiomers by liquid chromatography on a chiral support. The absolute configurations of the enantiomers were determined using a chemical correlation method together with chiral chromatography. The barriers to interconversion of the enantiomers were determined.

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The Quantitative Analysis of Steric Effects in Heteroaromatics

Cited by 72 publications

References 426 publications

Syntheses and Biological Evaluation of 5′-O-Myristoyl Derivatives of Thymidine against Human Immunodeficiency Virus

Syntheses and Biological Evaluation of 5′-O-Myristoyl Derivatives of Thymidine against Human Immunodeficiency Virus

Atropisomerism in some N,N'-diaryl-2-iminothiazoline derivatives: chiral separation and configurational stability

Synthesis, chiral separation, and absolute configuration of bis‐(N‐aryl) atropisomeric triads: 1,2‐Bis‐[4‐methyl‐2‐(thi)oxo‐2,3‐dihydrothiazol‐3‐yl]‐benzene

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