Structure and conformation of an antidepressant drug, nitroxazepine hydrochloride monohydrate

Usha, R.; Bhadbhade, Mohan M.; Venkatesan, Κ.; Nagarajan, Kowliki; David, J.

doi:10.1107/s0567740882007432

Cited by 6 publications

(2 citation statements)

References 3 publications

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“…As an index of the folding of the two aromatic rings, the angle formed by each of them with the plane p 1 defined by C (7), N(1), O(4)[S(1)] was considered (t 4 ). 20…”

Section: Molecular Geometry: General Considerationsmentioning

confidence: 99%

Investigation on the flexibility of chiral tricyclic derivatives

et al. 2008

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In the perspective of generating libraries for broad screening purposes, the inversion barrier of enantiomeric conformers of various tricyclic compounds, characterized by a seven-membered ring featuring a lactam group with two aromatics condensed at its opposite sides, has been investigated by ab initio calculations and NMR spectroscopy. Solid-state structure characterizations by single-crystal X-ray diffraction have been also carried out. The aim was to assess if moving from ethers to sulfides and sulfones derivatives, causes the racemization barrier to vary. Investigation was also extended to thiolactam congeners. Structural and electronic effects were investigated on the energetics of the inversion process and structure-property relationships evidenced. Results suggest that the ring inversion of the oxo derivatives is easier with respect to the corresponding S/SO 2 ones. Also amide molecules have, on the whole, smaller barriers with respect to the corresponding thioamide ones.

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“…As an index of the folding of the two aromatic rings, the angle formed by each of them with the plane p 1 defined by C (7), N(1), O(4)[S(1)] was considered (t 4 ). 20…”

Section: Molecular Geometry: General Considerationsmentioning

confidence: 99%

Investigation on the flexibility of chiral tricyclic derivatives

et al. 2008

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“…17,21 Interestingly, years later some are found to have even anti HIV activity, particularly the tetracyclic analogues of 4 22 ! Among various studies carried out on 5 can be mentioned the determination of structure and conformation in the solid state 23 and in solution 24 in collaboration with Profs K Venkatesan and G Govil respectively.…”

Section: Antidepressant Activity -Sintamilmentioning

confidence: 99%

Creative research in the chemical industry – Four decades in retrospect

Nagarajan¹

2006

J Chem Sci

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My professional research career spanning more than four decades has been largely devoted to synthetic medicinal chemistry (Ciba, Bombay-now Mumbai-21 years) followed by an equal number of years in process development of drugs, crop protection chemicals (Searle, Bombay) and drugs and speciality chemicals (Recon and Hikal, Bangalore). These efforts have involved several collaborators including many from other institutions and offered multitudinous challenges calling for continuous creativity in industrial setups. I was fortunate to have had a conducive environment to be able to respond to these challenges. I attempt to offer the readers in the ensuing pages a flavour of the excitement that has marked these years.

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Conformation and intermolecular interation of the antidepressant drugs nitroxazepine and imipramine in aqueous solutions and model membranes

Srivastava¹,

Phadke²,

Govil³

et al. 1987

Magnetic Reson in Chemistry

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Complete assignments of the proton magnetic resonance spectra of nitroxazepine and imipramine have been made using 1D and 2D techniques. The drugs are found to aggregate through stacking intereactions between the tricyclic moieties at higher concentrations in aqueous solutions. The changes in the chemical shifts with increasing concentration of the two antidepressant drugs show qualitative agreement with the stacking patterns and conformations observed in crystal structures. The conformations of the propyl moiety of the two drugs in aqueous solution and in lipid bilayers are very different. In D20, the drugs exist in an extended chain conformation which is similar to the crystal structure. In lipid bilayers they acquire a folded structure. The folded structures probably facilitate the binding of the hydrophobic regions of the drugs to the interior of lipid bilayers.

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Structure and conformation of an antidepressant drug, nitroxazepine hydrochloride monohydrate

Cited by 6 publications

References 3 publications

Investigation on the flexibility of chiral tricyclic derivatives

Investigation on the flexibility of chiral tricyclic derivatives

Creative research in the chemical industry – Four decades in retrospect

Conformation and intermolecular interation of the antidepressant drugs nitroxazepine and imipramine in aqueous solutions and model membranes

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