Synthesis and conformational study of <i>P</i>‐heterocyclic androst‐5‐ene derivatives

Frank, Éva; Schäfer, Balázs; Mucsi, Zoltán; Keglevich, György

doi:10.1002/hc.20372

Cited by 18 publications

(2 citation statements)

References 31 publications

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“…In contrast, the synthesis of cyclic alkyl arylphosphonates III by the reaction of a nucleophilic arylmetal species with a corresponding cyclic chlorophosphate is rather challenging (Scheme , D) . However, cyclic alkyl arylphosphonates III , -amidates IV , and -amides V are readily accessible by the reaction of arylphosphonyl dichlorides with diols, amino alcohols, and diamines (Scheme , E).…”

Section: Resultsmentioning

confidence: 99%

Phosphine Oxides from a Medicinal Chemist’s Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery

2020

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Phosphine oxides and related phosphorus-containing functional groups such as phosphonates and phosphinates are established structural motifs that are still underrepresented in today’s drug discovery projects, and only few examples can be found among approved drugs. In this account, the physicochemical and in vitro properties of phosphine oxides and related phosphorus-containing functional groups are reported and compared to more commonly used structural motifs in drug discovery. Furthermore, the impact on the physicochemical properties of a real drug scaffold is exemplified by a series of phosphorus-containing analogs of imatinib. We demonstrate that phosphine oxides are highly polar functional groups leading to high solubility and metabolic stability but occasionally at the cost of reduced permeability. We conclude that phosphine oxides and related phosphorus-containing functional groups are valuable polar structural elements and that they deserve to be considered as a routine part of every medicinal chemist’s toolbox.

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Section: Resultsmentioning

confidence: 99%

Phosphine Oxides from a Medicinal Chemist’s Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery

2020

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“…In contrast to the conformationally diverse 1,3,2-oxazaphosphorinane analogues, the corresponding 1,3,2-N,N,P heterocycles are characterized by chair or twist-chair conformations [25,26]. Assignment of the P configuration and detection of the predominant conformation of the 1,3,2-diheterophosphorinanes in solution necessitate different NMR techniques [4][5][6][7], but X-ray crystallography [27,28] and ab initio calculations [29][30][31][32][33] are also important tools for stereostructural analysis.…”

Section: Introductionmentioning

confidence: 99%

6-Membered P-Heterocycles: Ring-Condensed 1,3,2-Diheterophosphorinane 2-Chalcogenides

Frank¹,

Wölfling²

2007

COC

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Literature publications (up to the end of 2006) relating to the synthesis, biological significance and conformational behaviour of carbocycle-and heterocycle-condensed six-membered tetracoordinate P(V) 1,3,2-diheterophosphorinanes are reviewed. The replacement of carbon atoms of cyclohexane by P and O and/or N to form 1,3,2-dioxa-, 1,3,2-oxaza-or 1,3,2-diazaphosphorinanes introduces lone pair electrons instead of hydrogens and changes the bond angles and bond lengths, and can thereby lead to significantly different stereostructural preferences of the hetero ring as compared with those of cyclohexane. Although monocyclic 1,3,2-diheterophosphorinanes often exist in a chair conformation in both the solid and solution states, the existence of conformations other than a chair can predominate in some cases for steric and stereoelectronic reasons associated with the presence of bulky groups on the P-containing ring or in polycyclic rigid systems.After a brief account on the most important pharmacological and stereochemical features, involving the configuration assignment and conformation determination of P-diheterophosphorinanes, the present review mainly focuses on the synthesis and stereostructural studies of carbo-and heterocycle-condensed derivatives, where the fused ring may exert considerable effects on the conformational behaviour of the P-hetero ring.

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ChemInform Abstract: Synthesis and Conformational Study of P‐Heterocyclic Androst‐5‐ene Derivatives.

et al. 2008

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Synthesis and conformational study of P‐heterocyclic androst‐5‐ene derivatives

Abstract: The reactions of (20R)-3β-acetoxy- 21-hydroxymethylpregn-5-en-20-ol (2) and (20R)-3β- acetoxypregn-5-ene-20,21-diol (11)

Cited by 18 publications

References 31 publications

Phosphine Oxides from a Medicinal Chemist’s Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery

Phosphine Oxides from a Medicinal Chemist’s Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery

6-Membered P-Heterocycles: Ring-Condensed 1,3,2-Diheterophosphorinane 2-Chalcogenides

ChemInform Abstract: Synthesis and Conformational Study of P‐Heterocyclic Androst‐5‐ene Derivatives.

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