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• W2056761490 abstract "first_page settings Order Article Reprints Font Type: Arial Georgia Verdana Font Size: Aa Aa Aa Line Spacing:    Column Width:    Background: Open AccessShort Note Synthesis of (2-Chloropyridine-3-yl)-(4-nitrobenzylidene) amine and its antibacterial activity by A. A. Jarrahpour 1,*, M. Motamedifar 2, H. Mousavipour 1, N. Hadi 2 and M. Zarei 1 1 Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran 2 Department of Bacteriology & Virology, Shiraz Medical School, Shiraz University Medical Science, Shiraz 71345, Iran * Author to whom correspondence should be addressed. Molbank 2004, 2004(1), M364; https://doi.org/10.3390/M364 Received: 24 October 2003 / Accepted: 11 February 2004 / Published: 24 February 2004 Download Download PDF Download PDF with Cover Download XML Download Epub Download Supplementary Material Browse Figure Versions Notes Schiff bases are reported to show a variety of biological activities such as antibacterial [1,2,3], antifungal [4,5], anticancer [6,7] and herbicidal [8] activities . Pyridinium compounds have biological activities [9] such as antifungal [10] and antibacterial [10,11] activities. The presence of a chloro moiety in different types of compounds causes them to exhibit pesticidal activity8. Based on these facts , we synthesized 2-chloro pyridin-3-yl–(4-nitrobenzylidene) amine 3. According to ab initio calculations at the HF/6-31G (d,p) level, Schiff base 3 at dihedral angel of 42.9 o is about 15.70 kj/mol more stable than the coplanar pyridine and nitrophenyl rings (Figure 1). The titled compound was tested against S. aureus, B. subtilis, K. pneumonia and P. aeruginosa by the disk diffiusion method and was not active at the level of 200 μg/disk. A mixture of 3-amino-2-chloropyridine 1(1.28 g, 10.00 mmol), 4-nitrobenzaldehyde 2 (1.51 g, 10.00 mmol) and anhydrous magnesium sulfate (4.00 g) in dry dichloromethane (40.00 mL) was stirred at room temperature for four hours. The suspension was filtered and washed with dichloromethane.The solvent was evaporated under reduced pressure and Schiff base 3 was formed as a yellow solidwhich was recrystalized from warm ethanol (2.23 g , 85% ). m.p.146-148 oC.IR (KBr) (cm-1): 1340.40 and 1517.90 (NO2), 1600.0 (N=CH), 1633.60 (C=N pyridine ring) .1H-NMR (CDCl3) (250 MHz)δ(ppm): 7.23-8.38 (m , 7 H, Ar-H), 8.54 (s, 1H, CH=N).13C- NMR (CDCl3) (62.90 MHz)δ(ppm): 123.65-147.18 (2 ph), 161.41 (CH=N).MS (m/z, %): 261 (M +, 64.90), 149 (NO2Ph-C=N, 36.00 ), 126(C5H3NClN, 15.00 ), 112 (C5H3NCl, 34.00), 92( C5H3N2, 29.00 ), 77 ( C5H3N, 31.20), 53 (N=CH-CH=CH, 35.00), 51 (N=C-C=CH, 100.00). Supplementary materialsSupplementary File 1Supplementary File 2Supplementary File 3Acknowledgment The authors thank the Shiraz University Research Council for financial support (Grant No. 81-SC-1495-C191).ReferencesShaikh kabeer, A.; Baseer, M.A.; Mote, N.A. Asian J. Chem. 2001, 13(2), 496–500.Pandeya, S.N.; Sriram, D.; Nath, G.; De Clercq, E. Il Farmaco 1999, 54, 624–628.El-masry, Afaf.H.; Fahmy, H.H.; Ali Abdelwahed, S.H. Molecules 2000, 5, 1429–1438.More, P.G.; Bhalvankar, R.B.; Pattar, S.C. J. Indian Chem. Soc. 2001, 78, 474–475.Singh, W.M.; Dash, B.C. Pesticides 1998, 22(11), 33–37.Desai, S.B.; Desai, P.B.; Desai, K.R. Heterocycl. Commun. 2001, 7(1), 83–90.Phatak, P.; Jolly, V.S.; Sharma, K.P. Orient. J. Chem. 2000, 16(3), 493–494.Samadhiya, S.; Halve, A. Orient. J. Chem. 2001, 17(1), 119–122.Sepcic, Kristina. J. Toxicol. , Toxin Rev. 2000, 19(2), 136–160.Sliwa, W.; Mianowska, B. Heterocycles 1989, 29(3), 557–595.Druta, I.; Dinica, R.; Bacu, E.; Anderi, M. Chem. Abstr. 2000, 132, 205326b.Sample Availability : Available from MDPI. Figure 1 : The minimum energy conformation of Schiff base 3. Figure 1 : The minimum energy conformation of Schiff base 3. © 2004 MDPI. All rights reserved. Share and Cite MDPI and ACS Style Jarrahpour, A.A.; Motamedifar, M.; Mousavipour, H.; Hadi, N.; Zarei, M. Synthesis of (2-Chloropyridine-3-yl)-(4-nitrobenzylidene) amine and its antibacterial activity. Molbank 2004, 2004, M364. https://doi.org/10.3390/M364 AMA Style Jarrahpour AA, Motamedifar M, Mousavipour H, Hadi N, Zarei M. Synthesis of (2-Chloropyridine-3-yl)-(4-nitrobenzylidene) amine and its antibacterial activity. Molbank. 2004; 2004(1):M364. https://doi.org/10.3390/M364 Chicago/Turabian Style Jarrahpour, A. A., M. Motamedifar, H. Mousavipour, N. Hadi, and M. Zarei. 2004. Synthesis of (2-Chloropyridine-3-yl)-(4-nitrobenzylidene) amine and its antibacterial activity Molbank 2004, no. 1: M364. https://doi.org/10.3390/M364 Find Other Styles Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here. Article Metrics No No Article Access Statistics For more information on the journal statistics, click here. Multiple requests from the same IP address are counted as one view." @default.
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