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5-(4-Aminophenyl)-2-thiol-1,3,4-oxadiazole (3) was synthesized via the reaction of carbon disulfide with 4-aminobenzoyl hydrazide in presence of potassium hydroxide in absolute ethanol. Compound 3 was converted to the corresponding diazonium salt which was introduced in coupling reaction with alkaline solution of 2-hydroxybenzaldehyde as coupling reagent to give azooxadiazole derivative (4) containing aldehyde group. The resulting aldehyde (4) was then introduced in condensation reactions with the aromatic Thiophenol derivatives including using microwave irradiation technique in absolute ethanol to produce ten 2-amino-4-(2-hydroxy-5-((4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl)diazenyl)phenyl)-6-(phenylthio)pyridine-3,5-dicarbonitrile derivatives (5a-j), respectively in vitro Antibacterial activity of the target compounds were investigated using two types of bacteria, Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative). The results indicated that the newly synthesized 2-amino-4-(2-hydroxy-5-((4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl) diazenyl)phenyl)-6-(phenylthio)pyridine-3,5-dicarbonitrile derivatives (compounds 5d and 5f) showed enhanced activity against Gram-negative bacteria when compared with that of the control drug (gentamycin).
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221-227
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- Chemical Research Laboratory, Department of Chemistry, Saurashtra University, Rajkot - 360005, Gujarat, India
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- Chemical Research Laboratory, Department of Chemistry, Saurashtra University, Rajkot - 360005, Gujarat, India
References
- [1] Ugi, I., A. Dömling; W. Hörl; 1994. Multicomponent Reactions in Organic Chemistry, Endeavour. J. Zhu., HBienayme; Multicomponent Reactions; Wiley-VCH: Weinheim, 2005, 18, 115.
- [2] Abdulkarim M. A. Al-Kadasi and G. M. Nazeruddin. J. Chem. Pharm. Res. 2010, 2(3): 536.
- [3] S. Jayakumar and T. K. Shabeer. J. Chem. Pharm. Res. 2011, 3(6): 1089
- [4] H. Chen; W. Zhang; R. Tam; A. K. Raney;. PCT Int. Appl, 2005. WO, 058315 A1 20050630
- [5] V. Perrier; A. C. Wallace; K. Kaneko; J. Safar; S. B. Prusiner; F. E. Cohen; Natl. Acad. Sci. U.S.A. 2000, 97, 6073.
- [6] Yogesh Bhola, Ashutosh Naliapara, Jigna Modi, Yogesh Naliapara, World Scientific News 117 (2019) 29-43.
- [7] D. R. Anderson; N. W. Stehle; S. A. Kolodziej; E. J. Reinhard. PCT Int. Appl. 2004, WO 055015 A120040701.
- [8] H. Harada; S. Watanuki; T. Takuwa; K. Kawaguch; T. Okazaki; Y. Hirano; C. Saitoh; PCT Int. Appl. 2002, WO, 006237 A1 20020124.
- [9] M. W. Beukers; L. C. W. Chang; J. K. Frijtag Drabbe Künzel; T. Mulder-Krieger; R. F.Spanjersberg; J. Brussee; A. P. Ijzerman. J. Med. Chem. 2004, 47, 3707.
- [10] B. B. Fredholm; A. P. Ijzerman; K. A. Jacobson; K.N.Klotz; Linden. J. Pharmacol. Rev. 2001, 53, 527,899.
- [11] N. M. Evdokimov; I. V. Magedov; A. S. Kireev; A. Kornienko, Org. Lett. 2006, 8, 899.
- [12] N. M. Evdokimov; S.A.Kireev; A. A. Yakovenko; M. Y. Antipin; I.V. Magedov; A. Kornienko. J. Org. Chem. 2007, 72, 3443.
- [13] B.C Ranu; R. Jana; S. Sowmiah. J. Org. Chem. 2007, 72, 3152.
- [14] R. Mamgain; R. Singh; D. S. Rawat. J. Heterocycl. Chem. 2009, 46, 69.
- [15] M. Sridhar; B. C. Ramanaiah; C. Narsaiah; B. Mahesh; M. Kumaraswamy; K. K. R. Mallu; V. M. Ankathi; P.S. Rao; Tetrahedron Lett. 2009, 50, 3897.
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short_communication
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bwmeta1.element.psjd-8e919c30-d0a7-4891-90f1-e150048b54d5