Abstract
Various 2-aminothiazole and 2-aminothiadiazole derivatives viz N-[4-(2-Chloro-4-fluoro-phenyl)-thiazol-2-yl]-2-substituted acetamides (3a, 4a, 5a) and N-[5-(4-substituted aryl)-[1,3,4]thiadiazol-2-yl]-2-acetamides (3b, 3c, 4b, 4c, 5b, 5c) were synthesized from their corresponding properly substituted 2-aminothiazoles and 2-aminothiadiazoles. Structures of all the newly synthesized compounds were established by analytical and spectral data. Synthesized compounds were screened for their local anaesthetic activity using the rat sciatic nerve model.
Graphical Abstract
Various 2-aminothiazole and 2-aminothiadiazole derivatives viz N-[4-(2-Chloro-4-fluoro-phenyl)-thiazol-2-yl]-2-substituted acetamides (3a, 4a, 5a) and N-[5-(4-substituted aryl)-[1,3,4]thiadiazol-2-yl]-2-acetamides (3b, 3c, 4b, 4c, 5b, 5c) were synthesized from their corresponding properly substituted 2-aminothiazoles and 2-aminothiadiazoles. Structures of all the newly synthesized compounds were established by analytical and spectral data. Synthesized compounds were screened for their local anaesthetic activity using the rat sciatic nerve model.
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References
Bhargava PN, Chaurasia MR (1969) New local anesthetics. Derivatives of 5-diethylaminoacetamido-2-arylimino-3-aryl-4-thiazolidones. J Pharm Sci 58:896–898
Bhargava PN, Singh PR (1960) Synthesis of new local anaesthetics II. J Indian Chem Soc 37:241–243
Bhargava PN, Prakash S, Singh HD (1978) Synthesis of 2-N,N-dialkyl(oralkylaryl)aminoacetamido-(substituted)-benzothiazoles or -thiazoles as local anaesthetics. J Indian Chem Soc 55(7):726–729
Caliendoa G, Fiorinoa F, Griecoa P, Perissuttia E, Santagadaa V, Melib R, Mattace G, Angelina Zanescoc R, De Nuccic G (1999) Preparation and local anaesthetic activity of benzotriazinone and benzoyltriazole derivatives. Eur J Med Chem 34:1043–1051
Caliendol G, Di Carloz R, Grecol G, Griecol P, Meli R, Novellinol E, Perissuttil E, Santagada V (1995) Synthesis, local anesthetic activity and QSAR studies for a set of N-[2-(alkylamino)ethyl]benzotriazol-x-y1 acetamides. Eur J Med Chem 30:603–608
Catterall W, Mackie K (2001) Local anaesthetics. In: Hardman JG, Limbird LE, Gilman AG (eds) Goodman and Gilman’s the pharmacological basis of therapeutics, 10th edn. McGraw-Hill, New York, pp 687–731
Giri S, Singh H (1964) Thiadiazoles. I. Synthesis of substituted sulfathiadiazoles and related compounds. J Indian Chem Soc 41:295–298
Lakhan R, Rai BJ (1986) Local anaesthetics. IV. Synthesis and activity of 2-(N-substituted or N,N disubstituted aminoacetamido)-4- or -4-5-substituted thiazoles. Farmaco Sci 41(10):788–793
Lofgren N (1948) Studies on local anaesthetics: xylocaine a new synthetic drug. Hoegsstroms, Stockholm
Mattocks AM, Hutchinson ON (1948) Local anesthetics; N-dialkylaminoalkylimides of naphthalic and diphenylmaleic acids. J Am Chem Soc 70:3474–3475
Renuka J, Shipra (1997) Synthesis, spectral studies and antimicrobial activity of some fluorinecontaining 2-amino-4-arylthiazoles. J Indian Chem Soc 74:54–55
Srivastava PN, Rai SK (1980) Some derivatives of 2-aminothiazole as potent local anaesthetic. Eur J Med Chem Chim Ther 15:274
Takman BH, Camougis G, Lofgren NM (1969) Studies on local anaesthetics. Hydroxyalkylamioacylanilines as local anaesthetics. Acta Pharm Suec 6(1):25–32
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Badiger, N.P., Khan, A., Kalashetti, M.B. et al. Synthesis and local anaesthetic activities of 2-aminothiazole/thiadiazole analogues of lidocaine. Med Chem Res 21, 1544–1549 (2012). https://doi.org/10.1007/s00044-011-9659-4
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DOI: https://doi.org/10.1007/s00044-011-9659-4