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1.
Article in English | MEDLINE | ID: mdl-24109421

ABSTRACT

In the title compound, C9H8N2O2S, the sulfamoyl -NH2 group is involved in inter-molecular hydrogen bonding with the sulfonamide O and quinoline N atoms. In the crystal, mol-ecules are linked into dimers via pairs of N-H⋯N hydrogen bonds, forming an R 2 (2)(10) motif. The dimers are further assembled into chains parallel to the b axis through N-H⋯O hydrogen bonds, generating a C(4) motif. The crystal packing is additionally stabilized by inter-molecular C-H⋯O inter-actions. The crystal studied was a non-merohedral twin with a domain ratio of 0.938 (2):0.062 (2). Density functional theory (DFT) calculations, at the B3LYP/6-31 G(d,p) level of theory, were used to optimize the mol-ecular structure and to determine inter-action energies for the title compound. The resulting inter-action energy is ∼4.4 kcal mol(-1) per bridge for the C(4) chain and ∼5.9 kcal mol(-1) per bridge for the R 2 (2)(10) motif.

2.
Arch Pharm (Weinheim) ; 346(3): 180-8, 2013 Mar.
Article in English | MEDLINE | ID: mdl-23381952

ABSTRACT

The solid-phase synthesis of a new series of 19 biomimetics of long-chain arylpiperazines, namely flexible quinoline sulfonamides of aryl(heteroaryl)oxy-/heteroarylthio-ethyl 4-aminomethylpiperidines, is reported. Various structural modifications applied followed by biological evaluation for 5-HT1A, 5-HT6, and 5-HT7 receptors gave further support of a possible replacement of arylpiperazine with aryloxy-/arylthio-ethyl derivatives of alicyclic amines and control of receptor selectivity upon diversification in the aryl(heteroaryl)oxy-/heteroarylthio-ethyl fragment.


Subject(s)
Piperidines/chemical synthesis , Quinolines/chemical synthesis , Receptor, Serotonin, 5-HT1A/metabolism , Receptors, Serotonin/metabolism , Sulfonamides/chemical synthesis , Drug Design , Ethers , HEK293 Cells , Humans , Molecular Structure , Piperidines/chemistry , Piperidines/pharmacology , Protein Binding , Quinolines/chemistry , Quinolines/pharmacology , Radioligand Assay , Receptor, Serotonin, 5-HT1A/genetics , Receptors, Serotonin/genetics , Solid-Phase Synthesis Techniques , Structure-Activity Relationship , Sulfonamides/chemistry , Sulfonamides/pharmacology , Transfection
3.
Eur J Med Chem ; 60: 42-50, 2013 Feb.
Article in English | MEDLINE | ID: mdl-23279866

ABSTRACT

A series of new quinoline- and isoquinoline-sulfonamide analogs of aripiprazole was synthesized to explore the influence of two structural features - replacement of ether/amide moiety with sulfonamide one, and localization of a sulfonamide group in the azine moiety. In contrast to aripiprazole, compound 33 (N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propyl)quinoline-7-sulfonamide) and 39 (N-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butyl)isoquinoline-3-sulfonamide) displaying multireceptor 5-HT(1A)/5-HT(2A)/5-HT(7)/D(2)/D(3) profile, and behaving as 5-HT(1A) agonists, D(2) partial agonists, and 5-HT(2A)/5-HT(7) antagonists, produced significant antidepressant activity in FST in mice. On the other hand, their 4-isoquinolinyl analog 40 (N-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butyl)isoquinoline-4-sulfonamide), with similar receptor binding and functional profile, additionally displayed remarkable antipsychotic properties in the MK-801-induced hyperlocomotor activity in mice.


Subject(s)
Antidepressive Agents/pharmacology , Antipsychotic Agents/pharmacology , Dopamine D2 Receptor Antagonists , Piperazines/chemistry , Piperazines/pharmacology , Quinolones/chemistry , Quinolones/pharmacology , Receptors, Dopamine D3/antagonists & inhibitors , Receptors, Serotonin/metabolism , Animals , Antidepressive Agents/chemical synthesis , Antidepressive Agents/chemistry , Antipsychotic Agents/chemical synthesis , Antipsychotic Agents/chemistry , Aripiprazole , Behavior, Animal/drug effects , Dizocilpine Maleate/pharmacology , Dose-Response Relationship, Drug , Isoquinolines/chemical synthesis , Isoquinolines/chemistry , Isoquinolines/pharmacology , Mice , Molecular Structure , Motor Activity/drug effects , Piperazines/chemical synthesis , Quinolines/chemical synthesis , Quinolines/chemistry , Quinolines/pharmacology , Quinolones/chemical synthesis , Receptors, Dopamine D2/metabolism , Receptors, Dopamine D3/metabolism , Structure-Activity Relationship , Sulfonamides/chemical synthesis , Sulfonamides/chemistry , Sulfonamides/pharmacology
4.
Acta Crystallogr Sect E Struct Rep Online ; 68(Pt 10): o2826, 2012 Oct 01.
Article in English | MEDLINE | ID: mdl-23125632

ABSTRACT

In the title compound, C(9)H(8)N(2)O(2)S, the sulfamoyl NH(2) group is involved in intra-molecular N-H⋯N and inter-molecular N-H⋯O hydrogen bonding. In the crystal, molecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers, which are further associated through π-π stacking inter-actions between the quinoline benzene rings [centroid-centroid distance = 3.649 (1) Å] into a one-dimensional polymeric structure extending along the a axis.

5.
Bioorg Med Chem ; 20(4): 1545-56, 2012 Feb 15.
Article in English | MEDLINE | ID: mdl-22277589

ABSTRACT

Two series of arylpiperazinyl-alkyl quinoline-, isoquinoline-, naphthalene-sulfonamides with flexible (13-26) and semi-rigid (33-36) alkylene spacer were synthesized and evaluated for 5-HT(1A), 5-HT(2A), 5-HT(6), 5-HT(7) and selected compounds for D(2), D(3), D(4) receptors. The compounds with a mixed 5-HT and D receptors profile 16 (N-{4-[4-(3-chlorophenyl)-piperazin-1-yl]-butyl}-3-quinolinesulfonamide) and 36 (4-(4-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethyl}-piperidine-1-sulfonyl)-isoquinoline), displaying antagonistic activity at 5-HT(7), 5-HT(2A), D(2) postsynaptic sites, produced antidepressant-like effects in the forced swim test in mice and showed significant anxiolytic activity in the plus-maze test in rats. The lead compound 36, a multi-receptor 5-HT(2A)/5-HT(7)/D(2)/D(3)/D(4) agent, also displayed significant antipsychotic properties in the MK-801-induced hyperlocomotor activity in mice.


Subject(s)
Central Nervous System/drug effects , Sulfonamides/chemical synthesis , Sulfonamides/pharmacology , Animals , Antipsychotic Agents/chemical synthesis , Antipsychotic Agents/chemistry , Antipsychotic Agents/pharmacology , Isoquinolines/chemical synthesis , Isoquinolines/chemistry , Isoquinolines/pharmacology , Mice , Piperazines/chemical synthesis , Piperazines/chemistry , Piperazines/pharmacology , Quinolines/chemical synthesis , Quinolines/chemistry , Quinolines/pharmacology , Rats , Receptor, Serotonin, 5-HT1A , Receptor, Serotonin, 5-HT2A , Receptors, Serotonin/metabolism , Structure-Activity Relationship , Sulfonamides/chemistry
6.
Bioorg Med Chem ; 19(22): 6750-9, 2011 Nov 15.
Article in English | MEDLINE | ID: mdl-22001327

ABSTRACT

Novel arene- and quinolinesulfonamides were synthesized using different solutions and a solid-support methodology, and were evaluated for their affinity for 5-HT(1A), 5-HT(2A), 5-HT(6), and 5-HT(7) receptors. Compound 54 (N-Ethyl-N-[4-(1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinolin-2-yl)butyl]-8-quinolinesulfonamide) was identified as potent 5-HT(7) antagonist (K(i)=13 nM, K(B)=140 nM) with good selectivity over 5-HT(1A), 5-HT(2A), 5-HT(6) receptors. In the FST in mice, it reduced immobility in a manner similar to the selective 5-HT(7) antagonist SB-269970.


Subject(s)
Quinolines/chemistry , Receptors, Serotonin/chemistry , Sulfonamides/chemistry , Animals , Antidepressive Agents/chemical synthesis , Antidepressive Agents/chemistry , Antidepressive Agents/metabolism , Antidepressive Agents/pharmacology , Binding, Competitive , Humans , Kinetics , Ligands , Locomotion/drug effects , Male , Mice , Quinolines/chemical synthesis , Quinolines/metabolism , Quinolines/pharmacology , Rats , Receptors, Serotonin/metabolism , Structure-Activity Relationship , Sulfonamides/chemical synthesis , Sulfonamides/metabolism , Sulfonamides/pharmacology
7.
J Phys Chem A ; 115(6): 1027-39, 2011 Feb 17.
Article in English | MEDLINE | ID: mdl-21247179

ABSTRACT

This paper presents the results of experimental studies of hydrogen-bonded 2-pyridone crystal IR spectra. Spectral studies have demonstrated the existence of two anhydrous solid-state phases of each compound, namely the α and the ß phases. Hydrogen bonds in the high-temperature α phase of these crystals have been estimated to be 40% stronger than the hydrogen bonds in the ß phase, which are stable at room temperature. The mechanism of the phase transition in the solid-state 2-pyridone is proposed on the basis of the IR spectral data. This was possible by taking into account small changes in the geometry of heterocyclic molecular skeletons, which accompany the electron density redistribution in the hydrogen bonds occurring during the transition. The phase transition is connected with a partial change in the hydrogen bond nature from the N(+)-H···O(-) in the α phase, to the N-H···O hydrogen bonds in the ß phase crystals.


Subject(s)
Crystallization/methods , Models, Molecular , Phase Transition , Pyridones/chemistry , Spectrophotometry, Infrared/methods , Crystallography, X-Ray/methods , Electrons , Hydrogen Bonding , Molecular Structure , Temperature , Vibration
8.
Magn Reson Chem ; 46(2): 182-5, 2008 Feb.
Article in English | MEDLINE | ID: mdl-18088082

ABSTRACT

The complete 1H and 13C NMR spectral assignments of seven positional isomers of N,N-dimethylsulfamoylquinolines 2-8 and quinoline have been made using 1D and 2D NMR techniques, including COSY, HMQC and HMBC experiments. Deltadelta(H) and Deltadelta(C) substituent effects induced by the sulfamoyl group were determined. The sulfamoyl substituent affects proton and carbon chemical shifts both in the parent and in the fused (pyridine or benzene) ring.


Subject(s)
Nuclear Magnetic Resonance, Biomolecular , Quinolines/chemistry , Sulfonamides/chemistry , Isomerism , Molecular Structure , Quinolines/chemical synthesis , Sulfonamides/chemical synthesis
9.
Magn Reson Chem ; 42(10): 903-4, 2004 Oct.
Article in English | MEDLINE | ID: mdl-15366066

ABSTRACT

1H NMR assignment, including the values of delta(H) and J(H,H) for the cyclopropane moiety, and 13C NMR and 15N NMR spectral data for ciprofloxacin are presented.


Subject(s)
Ciprofloxacin/chemistry , Magnetic Resonance Spectroscopy/methods , Carbon Isotopes , Ciprofloxacin/isolation & purification , Hydrogen , Molecular Structure , Nitrogen Isotopes , Reference Standards
10.
Acta Crystallogr C ; 58(Pt 1): o32-3, 2002 Jan.
Article in English | MEDLINE | ID: mdl-11781488

ABSTRACT

The title compound, C6H7NS, is planar, with endo-C-N-C bond angles of 118.7 (2) degrees and 118.8 (2) degrees, and C-S bond lengths of 1.697 (2) and 1.692 (2) A for the two symmetrically independent molecules. 1-methylpyridinium-4-thiolate is the major contributor to the molecular structure in the solid state.


Subject(s)
Antineoplastic Agents/chemistry , RNA/chemistry , Crystallography, X-Ray , Hydrogen Bonding , Models, Molecular , Pyridines
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