Abstract
In the present work, the photooxygenation of N-(2-thiazolyl) sulfanilamide, 2-(4-thiazolyl) benzimidazole and thiacetazone in presence of methyl orange as a sensitizer under 125 W mercury vapour lamp has been reported under different conditions (acidic, neutral, and alkaline). Structures of the products have been established by spectral and elemental analysis.
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Bermudez LE, Reynolds R, Kolonoski P, Aralar P, Inderlied CB (2003) Thiosemicarbazole (thiacetazone-like) compound with activity against Myco bacterium avium in mice. Antimicrob Agents Chemother 47:2685–2687
Dover LG, Alahari A, Gratraud P, Gomes JM, Bhowruth V (2007) EthA, a common activator of thiocarbamide-containing drugs acting on different mycobacterial targets. Antimicrob Agents Chemother 51:1055–1066
Shubha J, Amitbodh U, Binitha K (2003) pH dependent phototransformation of atropine. Int J Chem Sci 1(2):107–110
Hubert-Brierre Y, Herlem D, Khuong- Hu F (1975) Oxidation photochimique d’amines tertiaries et d’alcaloids comportant unheterocyl N-methyl anabasine, ajmaline. Tetrahedron 31:3049–3054
Qian L, Ortiz de Montellano PR (2006) Oxidative activation of Thiacetazone mycobacterium tuberculosis flavin monooxygenase EtaA and human FM01 and FM03. Chem Res Toxicol 19:443–449
Chawada SS, Bokadia MM, Shubha J (2002) Laser versus lamp photolysis: a comparative account of the photolysis of papavarine by laser and UV lamp. Indian J Chem (41B)4:865–867
Chandan S, Nitin G, Sunil Puri K (2002) Photo-oxygenation of geraniol: synthesis of a novel series of hydroxy functionalized anti-malarial 1,2,4-trioxanes. Bioorg Med Chem Lett 12:1913–1916
Exel G, Tamer T, Bartoschek A (2005) Photo oxygenation in polymer matrices: en route to highly active antimalarial peroxides. Pure Appl Chem 77:1059–1074
Shubha J, Nagavanshi R (2009) Photooxygenation of pyrozoline by singlet molecular oxygen. Oxid Commun 32:330–334
Baric R, Bhattacharya K, Das P, George MV (1986) Photochemical transformations of 1-imidazolyl-1,2-benzoylalke-nes, steady-state and lase flash photolysis investigations. J Org Chem 51:3420–3428
Iqbal J, Hussain A, Anamika G (2005) Sensitized photooxygenation of tinosponone, a clerodane diterpene from Tinospora cordifolia. Acta Chim Slov 52:455–459
Shubha J, Archana K, Pradeep KP, Neelaiah Babu G (2010) Photooxygenation of adenosine by singlet molecular oxygen in different conditions. Asian J Res Chem 3:110–112
Ahamad MG, Samir AR, Mahmoud A, Farouk S (2002) Deoxyartemisinin derivatives from photooxygenation of anhydrodeoxydihydroartemisinin and their cytotoxic evaluation. J Nat Prod 65:184–188
Geeta G, Pradeep Singh ND, Kasinath V (2002) Photooxygenation of niminol, a tetra nortriterpenoid from Azadirachta indica A. Juss. Molecules 7:112–118
Humphries KA, Robert W (1991) Triplet sensitized photooxygenation of therapeutic retinoids. Pharm Res 8:826–831
Mahran MR, Sidky MM, Wamhoff H (1983) Photoreactions of 2-(4-thiazolyl)-1H-benzimidazole (thiabendazole) in the presence of singlet oxygen. Chemosphere 12(11–12):1611
Matsumoto M (1985) In: Frimer AA (ed) Singlet oxygen, vol II. CRC Press, Boca Raton, pp 205–263
Wasserman HH, McCarthy KE, Prowse KS (1986) Oxazoles in carboxylate protection and activation. Chem Rev 86:845–856
George MV, Bhat V (1979) Photooxygenations of nitrogen heterocycles. Chem Rev 79:447–478
Straight RC, Spikes JD (1985) In: Frimer AA (ed) Singlet oxygen, vol IV. CRC Press, Boca Raton, pp 91–143
Albini A, Fasani E (1998) Drugs: photochemistry and photostability. The Royal Society of Chemistry, Cambridge
Burrows HD, Canle ML, Santaballa JA, Steenken SJ (2002) Reaction pathways and mechanisms of photodegradation of pesticides. Photochem Photobiol B 67:71–108
Akasaka T, Ando W (1992) In: Ando W (ed) Organic peroxides. Wiley, New York, pp 599–659
Saito I, Matsuura T, Nagakawa M, Hino T (1977) Photooxidic intermediates in photosensitized oxygenation of tryptophan derivatives. Acc Chem Res 10:346–352
Michale K (2000) Advanced biology. Oxford University Press, Oxford, p 46
Wright JB (1951) The chemistry of benzimidazoles. Chem Rev 48:397–541
Dorman SE, Chaisson RE (2007) The rise of extensively drug-resistant tuberculosis. Nat Med 13:295–298
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The authors are thankful to the authorities at RSIC, CDRI Lucknow for providing spectral and elemental analysis data.
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Jain, S., Chourey, M. & Jetti, S.R. Photooxygenation of N-(2-Thiazolyl) sulfanilamide, 2-(4-Thiazolyl) benzimidazole and Thiacetazone. Proc. Natl. Acad. Sci., India, Sect. A Phys. Sci. 82, 291–294 (2012). https://doi.org/10.1007/s40010-012-0033-9
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DOI: https://doi.org/10.1007/s40010-012-0033-9