Abstract
The NMR elucidation of five novel SQ109 analogues including SQ109 is reported herein. These derivatives were synthesized as potential anti-tuberculosis candidates. One-dimensional NMR (1H and 13C) techniques show a series of overlapping signals from the methine and methylene groups of these compounds, thereby making it extremely difficult to assign all NMR signals. Two-dimensional (2D) NMR techniques were instrumental in overcoming these challenges. This paper appears to be a rare report on the complete structure elucidation of mono-substituted adamantane moieties.
Similar content being viewed by others
References
Dabur R, Chhillar AK, Yadav V, Kamal PK, Gupta J, Sharma GL (2005) J Med Microbiol 54:549–552
Orzeszko A, Gralewska R, Starosciak BJ, Kazimierczuk Z (2000) Acta Biochim Pol 47:87–94
Orzeszko A, Kaminska B, Orzeszko G, Starosciak BJ (2000) Farmaco 55:619–623
Orzeszko A, Kaminska B, Starosciak BJ (2002) Farmaco 57:619–624
Kolocouris A, Dimas K, Pannecouque C, Witvrouw M, Foscolos GB, Stamatiou G, Fytas G, Zoidis G, Kolocouris N, Andrei G, Snoeck R, De Clercq E (2002) Bioorg Med Chem Lett 12:723–727
Geldenhuys WJ, Malan SF, Bloomquist JR, Marchand AP, Van der Schyf CJ (2005) Med Res Rev 25:21–48
Nagasawa HT, Elberling JA, Shirota FN (1973) J Med Chem 16:823–826
Nagasawa HT, Elberling JA, Shirota FN (1975) J Med Chem 18:826–830
Zah J, Terre’Blanche G, Erasmus E, Malan SF (2003) Bioorg Med Chem 11:3569–3578
Jia L, Tomaszewski JE, Hanrahan C, Coward L, Noker P, Gorman G, Nikonenko B, Protopopova M (2005) Br J Pharmacol 144:80–87
Smith JP, Riley TR, Devenyi A, Bingaman SI, Kunselman A (2004) J Gen Internal Med 19:662–668
Davies WL, Hoffmann CE, Paulshock M, Wood TR, Haff RF, Grunert RR, Watts JC, Hermann EC, Neumayer EM, McGahen JW (1964) Science 144:862
Stanicova J, Miskovsky P, Sutiak V (2001) Vet Med 46:244–256
Toggas SM, Masliah E, Mucke L (1996) Brain Res 706:303–307
Parsons CG, Danysz W, Quack G (1999) Neuropharmacology 38:735–767
McKeage K (2009) CNS Drugs 23:881–897
Lee RE, Protopopova M, Crooks E, Slayden RA, Terrot M, Barry CE (2003) J Combin Chem 5:172–187
Protopopova M, Hanrahan C, Nikonenko B, Samala R, Chen P, Gearhart J, Einck L, Nacy CA (2005) J Antimicrob Chemother 56:968–974
Chen P, Gearhart J, Protopopova M, Einck L, Nacy CA (2006) J Antimicrob Chemother 58:332–337
Anderson JE, de Meijere A, Kozhushkov SI, Lunazzi L, Mazzanti A (2003) J Org Chem 68:8494–8499
Ganguly B, Singh A, Basaric N, Matkovic M, Mlinaric-Majerski K (2008) J Mol Struct 888:238–243
Mikhova B, Stamboliyska B, Koch A, Duddeck H, Kleinpeter E (2008) Magn Resonance Chem 46:1153–1157
Vikic-Topic D, Pejov L (2000) Croat Chem Acta 73:1057–1075
Vikic-Topic D, Pejov L (2001) J Chem Inf Comput Sci 41:1478–1487
Govender T, Kruger HG, Raasch T (2005) Struct Chem 16:129–134
Kruger HG, Mdluli PS (2006) Struct Chem 17:121–125
Kruger HG, Ramdhani R (2006) Magn Resonance Chem 44:1058–1062
Kruger HG, Ramdhani R (2006) S Afr J Chem 59:U28–U71
Boyle GA, Kruger HG, Maguire GEM, Singh A (2007) Struct Chem 18:633–639
Boyle GA, Govender T, Kruger HG, Maguire GEM, Naicker T (2008) Magn Resonance Chem 46:1089–1095
Boyle GA, Govender T, Kruger HG, Maguire GEM, Naicker T (2008) Struct Chem 19:429–434
Onajole OK, Govender P, Govender T, Maguire GEM, Kruger HG (2009) Struct Chem 20:1067–1076
Onajole OK, Makatini MM, Govender P, Govender T, Maguire GEM, Kruger HG (2010) Magn Resonance Chem 48:249–255
Fourie L, Govender T, Hariprakasha HK, Kruger HG, Raasch T (2004) Magn Resonance Chem 42:617–623
Kruger HG, Mdluli P, Power TD, Raasch T, Singh A (2006) J Mol Struct Theochem 771:165–170
Altaib MS, Arvidson PI, Govender T, Maguire GEM, Makatini M, Onajole OK, Kruger HG (2010) Magn Resonance Chem 48:435–442
Govender T, Kruger HG, Makatini M, Onajole OK (2008) Struct Chem 19:719–726
Onajole OK, Govender T, Makatini M, Kruger HG (2008) Magn Resonance Chem 46:1007–1014
Onajole OK, Govender K, Govender P, Van Helden P, Kruger HG, Maguire GEM, Muthusamy K, Pillay M, Wiid I, Govender T (2009) Eur J Med Chem 44:4297–4305
Onajole OK, Govender P, Van Helden P, Kruger HG, Maguire GEM, Wiid I, Govender T (2010) Eur J Med Chem 45:2075–2079
Bohlmann F, Zeisberg R, Klein E (1975) Org Magn Resonance 7:426–432
Acknowledgment
This study was supported by Grants from the National Research Foundation, GUN 2073251, Aspen Pharmacare and the University of KwaZulu-Natal.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Onajole, O.K., Govender, P., Govender, T. et al. NMR elucidation of novel SQ109 derivatives. Struct Chem 21, 1203–1209 (2010). https://doi.org/10.1007/s11224-010-9661-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11224-010-9661-3