ChemInform Abstract: STEVENS-TYPE REARRANGEMENT OF OPEN-CHAIN ANALOGS OF REISSERT COMPOUNDS. EVIDENCE FOR PARTICIPATION BY RADICAL INTERMEDIATES

1981 ◽  
Vol 12 (38) ◽  
Author(s):  
A. P. STAMEGNA ◽  
W. E. MCEWEN
Keyword(s):  
Open Chain ◽  
Radical Intermediates ◽  
Reissert Compounds

ChemInform Abstract: SYNTHETIC USES OF OPEN-CHAIN ANALOGS OF REISSERT COMPOUNDS

1980 ◽  
Vol 11 (29) ◽  
Author(s):  
W. E. MCEWEN ◽  
A. V. GROSSI ◽  
R. J. MACDONALD ◽  
A. P. STAMEGNA
Keyword(s):  
Open Chain ◽  
Reissert Compounds

scholarly journals Metabolic-Hydroxy and Carboxy Functionalization of Alkyl Moieties in Drug Molecules: Prediction of Structure Influence and Pharmacologic Activity

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1937
Author(s):  
Babiker M. El-Haj ◽  
Samrein B.M. Ahmed
Keyword(s):  
Parent Drug ◽  
Structural Features ◽  
Open Chain ◽  
Radical Intermediates ◽  
Drug Molecules ◽  
Drug Classes ◽  
Pharmacologic Activity ◽  
State Of Affairs ◽  
Ester Prodrugs ◽  
Hydroxy Metabolites

Alkyl moieties—open chain or cyclic, linear, or branched—are common in drug molecules. The hydrophobicity of alkyl moieties in drug molecules is modified by metabolic hydroxy functionalization via free-radical intermediates to give primary, secondary, or tertiary alcohols depending on the class of the substrate carbon. The hydroxymethyl groups resulting from the functionalization of methyl groups are mostly oxidized further to carboxyl groups to give carboxy metabolites. As observed from the surveyed cases in this review, hydroxy functionalization leads to loss, attenuation, or retention of pharmacologic activity with respect to the parent drug. On the other hand, carboxy functionalization leads to a loss of activity with the exception of only a few cases in which activity is retained. The exceptions are those groups in which the carboxy functionalization occurs at a position distant from a well-defined primary pharmacophore. Some hydroxy metabolites, which are equiactive with their parent drugs, have been developed into ester prodrugs while carboxy metabolites, which are equiactive to their parent drugs, have been developed into drugs as per se. In this review, we present and discuss the above state of affairs for a variety of drug classes, using selected drug members to show the effect on pharmacologic activity as well as dependence of the metabolic change on drug molecular structure. The review provides a basis for informed predictions of (i) structural features required for metabolic hydroxy and carboxy functionalization of alkyl moieties in existing or planned small drug molecules, and (ii) pharmacologic activity of the metabolites resulting from hydroxy and/or carboxy functionalization of alkyl moieties.

Reactions of the Hydrofluoroborate Salts of Open-Chain Analogues of Reissert Compounds with Some α,β-Ethylenic Esters

1999 ◽  
Vol 1999 (1) ◽  
pp. 297-303 ◽  
Author(s):  
Sandrine Perrin ◽  
Karin Monnier ◽  
Bernard Laude ◽  
Marek Kubicki ◽  
Olivier Blacque
Keyword(s):  
Open Chain ◽  
Reissert Compounds

ChemInform Abstract: Reactions of the Hydrofluoroborate Salts of Open-Chain Analogues of Reissert Compounds with Some α,β-Ethylenic Esters.

ChemInform ◽  
2010 ◽  
Vol 30 (21) ◽  
pp. no-no
Author(s):  
Sandrine Perrin ◽  
Karin Monnier ◽  
Bernard Laude ◽  
Marek Kubicki ◽  
Olivier Blacque
Keyword(s):  
Open Chain ◽  
Reissert Compounds

Synthetic uses of open-chain analogs of Reissert compounds

1980 ◽  
Vol 45 (7) ◽  
pp. 1301-1308 ◽  
Author(s):  
William E. McEwen ◽  
Anthony V. Grossi ◽  
Russell J. MacDonald ◽  
Andrew P. Stamegna
Keyword(s):  
Open Chain ◽  
Reissert Compounds
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