- Synthesis, characterization and antitumor activities of some novel thiazinones and thiosemicarbazones derivatives
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Two series of thiazinone and thiosemicarbazone derivatives (1-12) were synthesized using 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones (ABNs) and 3–alkyl–2,6–diarylpiperidin–4–ones as the starting materials. The structures of newly synthesized compounds were established on the basis of FT–IR, NMR spectroscopy and mass spectrometry. From the spectroscopic data, we identified that the cyclization reaction of thioamide with dialkyl acetylenedicarboxylate selectively gives six membered methyl 2-(2-(2,4-disubstituted-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazinyl)-4-oxo-4H-1,3-thiazine-6-carboxylates (1-6). In order to investigate the antitumor activities of the synthesized compounds, in?vitro cytotoxicity studies were carried out using human prostate cancer cell lines. Tested compounds showed good/moderate activities against cancer cell lines and further investigation carried out by live/dead assay.
- Anand, Selvam Athavan Alias,George, Kiran,Thomas, Nisha Susan,Kabilan, Senthamaraikannan
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p. 821 - 829
(2020/05/22)
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- Antimicrobial evaluation of a set of heterobicyclic methylthiadiazole hydrazones: Synthesis, characterization, and SAR studies
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To exploit the potential antimicrobial activities of azabicyclic skeleton based compounds, a set of 2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-one-4-methyl- 1,2,3-thiadazole-5-carbonyl hydrazones were synthesized. Unambiguous structural elucidation has been
- Kodisundaram, Paulrasu,Amirthaganesan, Shanmugasundaram,Balasankar, Thirunavukkarasu
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p. 11952 - 11956
(2014/01/06)
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- Synthesis, stereochemistry and in vitro antimicrobial evaluation of novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-4-phenyl-2, 3-dihydrothiazoles
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2-[(2,4-Diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-4-phenyl-2, 3-dihydrothiazoles (3a-3k) have been synthesized by the cyclization of 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones with phenacyl bromide and characterized by ana
- Ramachandran, Rajamanickam,Parthiban, Paramasivam,Rani, Mannangatty,Jayanthi, Sampathkumar,Kabilan, Senthamaraikannan,Jeong, Yeon Tae
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scheme or table
p. 6301 - 6304
(2011/12/02)
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- Synthesis and antimicrobial studies of novel 2,4-diaryl-3-azabicyclo[3.3.1] nonan-9-one 4′-phenylthiosemicarbazones
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New series of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one 4′-phenylthiosemicarbazones (compounds 9-16) was obtained from the corresponding 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones. The synthesized compounds have been characterized by their elemental, anal
- Umamatheswari, Seeman,Kabilan, Senthamaraikannan
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experimental part
p. 430 - 439
(2012/01/06)
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- Synthesis, complete NMR spectral assignments, and antifungal screening of new 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one oxime derivatives
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A series of differently substituted 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9- one oximes have been synthesized and their 1H and 13C NMR chemical shifts have been unambiguously assigned using H,H-COSY, NOESY, HSQC, and HMBC spectral data
- Parthiban, Paramasivam,Rathika, Paramasivam,Park, Keun Soo,Jeong, Yeon Tae
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experimental part
p. 79 - 93
(2010/07/10)
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- Efficient synthesis of novel 2,4-[diaryl-3-azabicyclo[3.3.1]nonan-9-yl]-5- spiro-4-acetyl-2-(acetylamino)-δ2-1,3,4-thiadiazolines
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2,4-[Diaryl-3-azabicyclo[3.3.1]nonan-9-yl]-5-spiro-4-acetyl-2-(acetylamino) -2-1,3,4-thiadiazoline derivatives (3a-h) have been synthesized by the cyclization of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones (2a-h) under acetylating condition. The synthesized compounds were characterized by analytical and spectral (infrared, 1H NMR, and 13C NMR) studies. Copyright
- Rani,Ramachandran,Kabilan
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scheme or table
p. 1694 - 1700
(2010/07/17)
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- Synthesis, structure and conformational analysis of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones and semicarbazones
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A series of thiosemicarbazones and semicarbazones have been synthesized and characterized by one and two dimensional NMR spectroscopy. The possible ring conformations of both the hydrazones are discussed. The chemical shifts and coupling constants suggest that the reported hydrazones adopt twin-chair conformations with equatorial orientation of the aryl substituents. Besides, the proposed conformations are further confirmed by single crystal X-ray diffraction analysis and molecular optimization geometry method. Crown Copyright
- Ramachandran,Rani,Kabilan
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scheme or table
p. 42 - 50
(2010/09/06)
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- Efficient synthesis, spectral analysis and antimicrobial studies of nitrogen and sulfur containing spiro heterocycles from 2,4-diaryl-3- azabicyclo[3.3.1]nonan-9-ones
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Acetyl and propionyl group substituted thiadiazole derivatives (4a-4h, 5a-5h, 6a, 6b, 7a and 7b) have been synthesized by the cyclization of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones (2a-2h, 3a and 3b) with acetic anhydride/propionic anhydride and were characterized by Elemental analysis, IR, 1H NMR and 13C NMR spectral analysis. Single crystal X-ray diffraction has also been recorded for compounds 4c and 5a. From the NMR and Single crystal X-ray diffraction analysis, compounds 4b-4d, 4f-4h, 5b, 5c, 5f-5h, 6a, 7a and 7b were found to adopt twin-chair conformations whereas compounds 4a, 4e, 5a, 5d, 5e and 6b adopt chair and boat conformation of cyclohexane and piperidine rings, respectively. Besides, the synthesized compounds were screened for antibacterial and antifungal activities using serial dilution method. The microbiological analysis showed that the electron withdrawing function substituted phenyl group at C-2 and C-4 of azabicyclononane based thiadiazoles 4c/4h and 5c/5h exposed significant antimicrobial activity against Salmonella typhi, Escherichia coli, Klebsiella pneumoniae, Aspergillus flavus, Aspergillus niger and Candida albicans at MIC of 6.25 μg/ml.
- Rani,Ramachandran,Kabilan
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supporting information; experimental part
p. 6637 - 6643
(2010/12/19)
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- Design, synthesis and biological evaluation of novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-1,3-thiazolidin-4-ones as a new class of antimicrobial agents
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New series of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones (9-16) obtained from the corresponding 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones (1-8) upon cyclization with ethylbromoacetate in the presence of sodium acetate-acetic acid buffer afforded novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-1,3-thiazolidin-4-ones (17-24). The synthesized compounds have been characterized by their elemental, analytical and spectral studies. Besides, the reported compounds were screened for their antibacterial and antifungal activities against a spectrum of microbial organisms. These studies proved that compounds 11/18/20/23 against Staphylococcus aureus, 19/20/24 against Salmonella typhi show maximum inhibition potency at low concentration (6.25 μg/ml) whereas 18/19 against Candida albicans and 19/20/21 against Rhizopus sp. showed beneficial antifungal activity at minimum concentration.
- Ramachandran,Rani,Kabilan
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supporting information; scheme or table
p. 2819 - 2823
(2009/12/31)
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