Abstract
The dithiobisbenzamides 1–4 were synthesized using 2,2′-dithiosalicylic acid with ammonia/ethylamine/benzylamine and 1,2-diaminopropane under different reaction conditions such as grinding, microwave irradiation and conventional heating which yielded the same products but in different yields. The synthesized compounds were subjected to antibacterial screening against both Gram-Positive (S. aureus, B. cereus, E. faecalis) and Gram-Negative (E.coli, S.typhi, P.aeruginosa, Klebshiella pneumoniae, Shigella) bacteria. The acyclic amides 1–3 showed activity against gram-positive bacteria while no activity was observed for Gram-negative bacteria. On the other hand cyclic amide, 4 was completely inactive against both types of bacteria. The synthesised benzamides were also screened for their anti-HIV activity.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Koz’minykh VO (2006) Synthesis and biological activity of substituted amides and hydrazides of 1,4-dicarboxylic acids (a review). Pharmaceut Chem J 40(1):8–17
Negwer M, Scharnow HG (2001) Organic-chemical drugs and their synonyms, 8th edn. Wiley-VCH, Weinheim, 4254
Mishra A, Kaushik NK, Verma AK, Gupta R (2008) Synthesis, characterization and antibacterial activity of cobalt(III) complexes with pyridine-amide ligands. Eur J Med Chem 43(10):2189–2196
Patel NB, Patel SD, Patel JN, Patel JC, Gorgamwala YS (2011) Synthesis and antibacterial activity of thioureido amide of fluoroquinolone. Int J Biochem 5(1):37–45
Xy L, Farthing AK, Dropinski JF, Meinke PT, Mccallum C, Leavitt E (2009) Nocathiacin analogs: synthesis and antibacterial activity of novel water-soluble amides. Bioorg Med Chem Lett 19(13):3531–3535
Husain A, Ahmad A, Mujeeb M, Akhter M (2010) New amides of sulphonamides: synthesis and biological evaluation. J Chil Chem 55(1):74–77
Medou M, Priem G, Rocheblave L, Pepe G, Meyer M, Chermann JC, Kraus JL (1999) Synthesis and anti-HIV activity of alpha-thiophenoxy-hydroxyethylamide derivatives. Eur J Med 34(7–8):625–638
Domagal JM, Bader JP, Gogliotti RD, Sanchez JP, Stier MA, Song Y, Va JVN (1997) A new class of anti-HIV agents targeted toward the nucleocapsid protein NCp7: the 2,2′-dithiobisbenzamides. Bioorg Med Chem 5(3):569–579
Comerford JW, Clark JH, Macquarrie DJ, Breeden SW (2009) Clean, reusable and low cost heterogeneous catalyst for amide synthesis. Chem Commun 2562–2564
Uppiah DJN, Bhowon MG, Jhaumeer-Laulloo S (2009) Solventless synthesis of imines derived from diphenyldisulphide diamine or p-vanillin. E J Chem 6(S1):S195–S200
Ancker TRV, Cave GWV, Raston CL (2006) Benign approaches for the synthesis of bis-imine Schiff bases. Green Chem 8:50–53
Perreux L, Loupy A, Volatron F (2002) Solvent-free preparation of amides from acids and primary amines under microwave irradiation. Tetrahedron 58:2155–2162
Gopalakrishnan M, Sureshkumar P, Kanagarajan V, Thanusu J, Govindaraju R (2006) A simplified green chemistry approaches to organic synthesis in solid media. Activated fly ash, an industrial waste (pollutant) as an efficient and novel catalyst for some selected organic reactions in solvent free conditions under microwave irradiation. ARKIVOC 2006:130–141
Nomura E, Hosoda A, Mori H, Taniguchi H (2005) Rapid base-catalyzed gecarboxylation and amide-forming reaction of substituted cinnamic acids via microwave heating. Green Chem 7:863–866
Bhowon MG, Jhaumeer-Laulloo S, Rungasami P (2003) Synthesis and characterization of some transition metal chelates of 2,2;-dithiobenzoic acid. Asian J Chem 15(2):1008–1012
Witrouw M, Balzarini J, Pannecouque C, Jhaumeer-Laulloo S, Este JA, Schols D, Chereanov P, Schmit JC, Debyser Z, Vandamme AM, Desmyter J, Ramadas SR, De Clercq E (1997) SRR-SB3, a disulphide-containing macrolide that inhibits a late stage of the replicative cycle of human immunodeficiency virus. Antimicrob Agents Chemother 41:262–268
Jhaumeer-Laulloo BS, Ramadas SR (1999) Synthesis and anti-HIV activity of macrocyclic dilactams containing disulphide bridge. Indian J Heterocycl Chem 9:01–06
Acknowledgements
The authors thank Prof De Clerq of Leuven University for anti-HIV activity and the Victoria Hospital, Candos, Mauritius for providing the strains of bacteria.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2012 Springer Science+Business Media B.V.
About this chapter
Cite this chapter
Gungah, R., Moosun, S., Jhaumeer-Laulloo, S., Bhowon, M.G. (2012). Synthesis and Biological Activity of Derivatives of 2,2′-Dithiobisbenzamides. In: Gupta Bhowon, M., Jhaumeer-Laulloo, S., Li Kam Wah, H., Ramasami, P. (eds) Chemistry for Sustainable Development. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-8650-1_26
Download citation
DOI: https://doi.org/10.1007/978-90-481-8650-1_26
Published:
Publisher Name: Springer, Dordrecht
Print ISBN: 978-90-481-8649-5
Online ISBN: 978-90-481-8650-1
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)