Synthesis, stereochemistry and antimicrobial studies of novel oxime ethers of aza/diazabicycles

Parthiban, P.; Aridoss, Gopalakrishnan; Rathika, Paramasivam; Ramkumar, V.; Kabilan, S.

doi:10.1016/j.bmcl.2009.10.042

Cited by 51 publications

(32 citation statements)

References 17 publications

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“…Molecules containing the 3-azabicyclo[3.3.1]nonane nucleus are of great interest due to their presence in a wide range of naturally occurring diterpenoid/norditerpenoid alkaloids and their broad-spectrum biological activities, such as antimicrobial, analgesic, antagonistic, anti-inflammatory and local anesthetic hypotensive activity (Parthiban et al, 2009;Hardick et al, 1996;Jeyaraman & Avila, 1981). Hence, the synthesis of new molecules with the 3-azabicyclo[3.3.1]nonane nucleus and their stereochemical investigation are of interest in the field of medicinal chemistry.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of (E)-2-(4-methoxystyryl)-2,3-dihydro-1H-perimidine acetonitrile monosolvate

2014

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The title compound, C20H18N2O·CH3CN, a perimidine derivative, crystallized as an acetonitrile monosolvate. The planes of the naphthalene ring system and the methoxyphenyl ring are oriented almost perpendicular to one another, with a dihedral angle of 87.61 (6)°. The conformation about the C=C bond is E. The hexahydropyrimidine ring has an envelope conformation, with the methine C atom as the flap. In the crystal, the molecules are linked by N—H⋯N hydrogen bonds involving the acetonitrile solvent molecule as acceptor, forming zigzag chains propagating along [100].

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of (E)-2-(4-methoxystyryl)-2,3-dihydro-1H-perimidine acetonitrile monosolvate

2014

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“…Piperidine is a saturated heterocyclic secondary amine which is associated with a diverse set of biological activities such as antimicrobial, anti-inflammatory, antiviral, antimalarial, general anesthetic, antidepressant, antioxidant, antiepileptic, antitumor, anticonvulsant, and antihyperlipidemic activities [1][2][3][4][5][6][7][8]. Several clinically available drug candidates also possess this moiety in their structure ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant Potential of Piperidine Containing Compounds-a Short Review

Manjusha

Begum

et al. 2018

Asian J Pharm Clin Res

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Piperidine is a saturated heterocyclic ring, considered as a privileged scaffold in view of its role in wide range of biological activities. Piperidine is good candidate molecule for obtaining potent antioxidant agents. The planar nature of this heterocyclic nucleus allows the introduction of substituent groups at different positions on the ring. In the present review, the antioxidant profile of piperidine containing compounds has been focused. The compounds were classified into naturally occurring piperidines, unsaturated piperidines, N-substituted piperidines, piperamides, piperanols, piperidine oximes, and hydrazides.

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“…2r, 6c-diarylpiperidin-4-ones [7][8][9][10][11][12][13][14][15][16][17] and their oximes [18][19][20][21][22][23] have been shown to exist largely in chair conformation with equatorial orientation of the substituents. In the past two decades, a broad range of biological effects including antiviral, antitumor, bactericidal, fungicidal and antinflammatory activities have been described for these compounds [24][25][26][27][28]. Rajarajan et al have investigated the crystal [29] and theoretical studies of compound 3t-pentyl-2r, 6c-diphenylpiperidin-4-one [30] (1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectral and Structure Activity Relationship Studies of Substituted 3t-pentyl-2r, 6c–diarylpiperidin-4-ones and their Corresponding Oxime Derivatives

2014

Can Chem Trans

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Five 3t-pentyl-2r, 6c-diarylpiperidin-4-ones (1-5) and their oxime derivatives (6-10) (aryl = C 6 H 5 , p-FC 6 H 4, p-NO 2 C 6 H 4 , p-CH 3 OC 6 H 4 , p-ClC 6 H 4 ) have been synthesized by condensing 2-octanone with the appropriate substituted benzaldehydes and ammonium acetate. For all these compounds, 1 H and 13 C NMR spectra have been recorded and for certain compounds HOMOCOSY, HSQC, HMBC and Mass spectra have also been recorded. The spectral data suggest that the compounds exist in chair conformation with equatorial orientation of the bulky substituents. Long range coupling is observed between H(5) ax and H(6) (ax) in all the cases suggesting that H(5) ax is anti to C(6)-C(5) bond. To study the structure activity relationship, these compounds were assayed for their antibacterial and antifungal activities via screening them against Staphylococcus aureus, Escherichia coli, Solmonella typhi, Psedomonas aeruginosa and Candida albicans, Aspergillus niger, Mucor, Rhizopus sp respectively. Among the synthesized compounds p-fluoro and p-methoxy substituted compounds exhibit better activity against E.coli, S.typhi and A.niger.

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Synthesis, stereochemistry and antimicrobial studies of novel oxime ethers of aza/diazabicycles

Cited by 51 publications

References 17 publications

Crystal structure of (E)-2-(4-methoxystyryl)-2,3-dihydro-1H-perimidine acetonitrile monosolvate

Crystal structure of (E)-2-(4-methoxystyryl)-2,3-dihydro-1H-perimidine acetonitrile monosolvate

Antioxidant Potential of Piperidine Containing Compounds-a Short Review

Synthesis, Spectral and Structure Activity Relationship Studies of Substituted 3t-pentyl-2r, 6c–diarylpiperidin-4-ones and their Corresponding Oxime Derivatives

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