The geometry at nitrogen in N-phenylsulphonyl-pyrroles and -indoles. The geometry of sulphonamides

Beddoes, Roy L.; Dalton, Lesley; Joule, John A.; Mills, O. S.; Street, J. D.; Watt, C. Ian F.

doi:10.1039/p29860000787

Cited by 147 publications

(153 citation statements)

References 2 publications

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“…of the pyrrole are in general agreement with other pyrrole units in 4,5,6,7-tetrahydroindoles (Beddoes, Dalton, Joule, Mills, Street & Watt, 1986;Law, Lai, Sammes, Katritzky & Mak, 1984). The nitro group is coplanar with the pyrrole ring, the relevant torsion angle being 179.8(2) °.…”

supporting

confidence: 68%

Structure of a tricyclo[3.2.1.02,7]octene derivative: a double bridged central ring in an octahydrobenz[g]-3-nitroindole

Meetsma¹,

Have²,

Leusink³

et al. 1993

Acta Crystallogr C

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supporting

confidence: 68%

Structure of a tricyclo[3.2.1.02,7]octene derivative: a double bridged central ring in an octahydrobenz[g]-3-nitroindole

Meetsma¹,

Have²,

Leusink³

et al. 1993

Acta Crystallogr C

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“…The synthesis of 4,5,6,7-tetrahydroindole derivative 15 (Scheme 2), also proceeding smoothly, followed the same route employed by Huffman and co-workers for the preparation of 1-pentyl-3-(1-naphtoyl)pyrrole (7a). 13 Thus, 12 23 was regioselectively acylated, 24 deprotected by alkaline treatment, and eventually alkylated in standard conditions to give 15. Compound 17 was obtained from 2,5-dimethyl-1-pentylpyrrole 25 (16), prepared by the already mentioned N-alkylation procedure, and g-butyrolactone in polyphosphoric acid, according to the method of Moussavi et al 26 (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and structure–activity relationships of a series of pyrrole cannabinoid receptor agonists

Tarzia

Duranti

Tontini

et al. 2003

Bioorganic & Medicinal Chemistry

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Abstract-We designed and synthesized a series of pyrrole derivatives with the aim of investigating the structure-activity relationship (SAR) for the binding of non-classical agonists to CB 1 and CB 2 cannabinoid receptors. Superposition of two pyrrole-containing cannabinoid agonists, JWH-007 and JWH-161, allowed us to identify positions 1, 3 and 4 of the pyrrole nucleus as amenable to additional investigation. We prepared the 1-alkyl-2,5-dimethyl-3,4-substituted pyrroles 10a-e, 11a-d, 17, 21, 25 and the tetrahydroindole 15, and evaluated their ability to bind to and activate cannabinoid receptors. Noteworthy in this set of compounds are the 4-bromopyrrole 11a, which has an affinity for CB 1 and CB 2 receptors comparable to that of well-characterized heterocyclic cannabimimetics such as Win-55,212-2; the amide 25, which, although possessing a moderate affinity for cannabinoid receptors, demonstrates that the 3-naphthoyl group, commonly present in indole and pyrrole cannabimimetics, can be substituted by alternative moieties; and compounds 10d, 11d, showing CB 1 partial agonist properties. #

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“…The first CSD study of arylsulfonamides was published in 1986 by Beddoes et al 59 At the time, X-ray structures of 49 acyclic sulfonamides were available. The conclusions drawn on the lowest energy conformation have not changed (Figure 9).…”

Section: Sulfonamides and Sulfonesmentioning

confidence: 99%

Small Molecule Conformational Preferences Derived from Crystal Structure Data. A Medicinal Chemistry Focused Analysis

Brameld

Kuhn

Reuter

et al. 2008

J. Chem. Inf. Model.

339

332

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Based on torsion angle distributions of frequently occurring substructures, conformation preferences of druglike molecules are presented, accompanied by a review of the relevant literature. First, the relevance of the Cambridge Structural Database (CSD) for drug design is demonstrated by comparing substructures present in compounds entering clinical trials with those found in the CSD and protein-bound ligands in the Protein Data Bank (PDB). Next, we briefly highlight preferred conformations of elementary acyclic systems, followed by a discussion of sulfonamide conformations. Due to their central role in medicinal chemistry, we discuss properties of aryl ring substituents in depth, including biaryl systems and systems of two aryl rings connected by two acyclic bonds. For a subset of torsion motifs, we also compare torsion angle histograms derived from CSD structures with those derived from ligands in the PDB. Furthermore, selected properties of some six-and seven-membered ring systems are discussed. The article closes with a section on attractive sulfuroxygen contacts.

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The geometry at nitrogen in N-phenylsulphonyl-pyrroles and -indoles. The geometry of sulphonamides

Cited by 147 publications

References 2 publications

Structure of a tricyclo[3.2.1.02,7]octene derivative: a double bridged central ring in an octahydrobenz[g]-3-nitroindole

Structure of a tricyclo[3.2.1.02,7]octene derivative: a double bridged central ring in an octahydrobenz[g]-3-nitroindole

Synthesis and structure–activity relationships of a series of pyrrole cannabinoid receptor agonists

Small Molecule Conformational Preferences Derived from Crystal Structure Data. A Medicinal Chemistry Focused Analysis

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