Synthesis of Certain New Morpholine Derivatives Bearing a Thiazole Moiety

Year 2019, , 554 - 558, 01.08.2019

Nurcan Berber

https://doi.org/10.16984/saufenbilder.414310

Cited By: 2

Abstract

Morpholine
is a synthetic simple heterocyclic organic compound having characteristic
functional groups of amine and ether. Feasible physicochemical properties
(polarity and solubility), low cost and wide availability make it a suitable
candidate for the synthesis of many potent drugs. In our work, we were
synthesized a new series of thiazole substituted morpholine derivatives in two
steps. In the first stage, thiourea was synthesized and the formation of
thiazole ring at the other stage was ensured.

Keywords

Morpholine, Thiourea, Thiazole

References

• 1. Review of morpholine and its derivatives, Merck Index, 12th ed. published by Merck & co, Whitehouse Station, NJ, 1996; 1074-5.
• 2. Pushpak, M.; Bekington, M.; Synthesis of substituted 4-(3-alkyl-1,2,4-oxadiazol-5ylmethyl)-3,4-dihydro-2H-1,4-benzoxazinesand 4-(1H-benzimidazol-2-ylmethyl)-3,4-dihydro-2H-1,4benzoxazines. Tetrahedron Lett. 2006; 47(44):7823-7826.
• 3. Zhou, G.; Zorn, N.; Ting, P.; et.al.; Cook John. Development of Novel benzomorpholine class of diacylglycerol acyltransferase I inhibitors. Med. Chem. Lett. 2014; 5(5): 544-549.
• 4. Achari, B.; Sukhendu, B. M.; Dutta, P.; et.al.; Perspectives on 1, 4-benzodioxions,1, 4-benzoxazines and their 2, 3- dihydro derivatives. Synlett. 2004; 14:2449-2467.
• 5. Surendra Kumar R.; Moydeen M.; Al-Deyab S.S.; et.al.; Synthesis of new morpholine-connected pyrazolidine derivatives and their antimicrobial, antioxidant, and cytotoxic activities. Bioorg Med Chem Lett., 2017; 27:66–71.
• 6. Doan P.; Karjalainen A.; Chandraseelan J.G.; et al. Synthesis and biological screening for cytotoxic activity of N-substituted indolines and morpholines. Eur J Med Chem, 2016;120:296–303.
• 7. Gadekar P.K.; Roychowdhury A.; Kharkar P.S.; et al. Design, synthesis and biological evaluation of novel azaspiro analogs of linezolid as antibacterial and antitubercular agents. Eur J Med Chem, 2016;122:475–87.
• 8. Micheli F.; Cremonesi S.; Semeraro T.; et al. Novel morpholine scaffolds as selective dopamine DA. D3 receptor antagonists. Bioorganic Med Chem Lett 2016; 26:1329–32.
• 9. Zhao Z.; Pissarnitski D.A.; Josien H.B.; et al. Substituted 4-morpholine N-arylsulfonamides as ɣ-secretase inhibitors. Eur J Med Chem, 2016; 124:36–48.
• 10. Desai N.C.; Rajpara K.M.; Joshi V.V.; Microwave induced synthesis of fluorobenzamides containing thiazole and thiazolidine as promising antimicrobial analogs. J Fluor Chem, 2013;145:102–11.
• 11. Pattan S.R.; Dighe N.S.; Nirmal S.A.; et al. Synthesis and biological evaluation of some new substituted amino thiazole derivatives. Asian J Res Chem. 2009; 2:196–201.
• 12. Argyropoulou I.; Geronikaki A.; Vicini P.; et al. Synthesis and biological evaluationof sulfonamide thiazole and benzothiazole derivatives as antimicrobial agents. Arkivoc. 2009; VI:89–102.
• 13. Sharma R.N.; Xavier F.P.; Vasu K.K.; et al. Synthesis of 4-benzyl-1,3-thiazole derivatives as potential anti-inflammatory agents: an analogue-based drug design approach. J Enzyme Inhib Med Chem. 2009 ;24:890–897.
• 14. TrautmanH.D.; Longe L.M.; The synthesis of 2,3-disubstituted-4-thiazolidones. J AmChem Soc. 1948; 70:3436–3439.
• 15. Surray A.R.; 4-Thiazolidones.IV. The preparation of some 3-alkylaminoalkyl-2-aryl derivatives. J Am Chem Soc. 1949; 71:3354–3356.
• 16. Bhattacharya P.; Leonard, J.T.; Roy K;. Exploring QSAR of thiazole and thiadiazole derivatives as potent and selective human adenosine A3 receptor antagonists using FA and GFA techniques. Bioorg Med Chem. 2005; 13:1159–1165.
• 17. Karade H.N.; Acharya B.N.;, Sathe M.; et al. Design, synthesis, and antimalarial evaluation of thiazole-derived amino acids. Med Chem Res. 2008; 17:19–29.
• 18. Berber, N., Arslan, M., Yavuz, E., et. al., ‟Synthesis and evaluation of new phthalazine urea and thiourea derivatives as carbonic anhydrase inhibitors.ˮ ID 742178, p.p. 8, Hindawi, 2013.
• 19. Güleç, Ö., Arslan, M., Gencer,N., et. al., ‟Synthesis and carbonic anhydrase inhibitory properties of new spiroindoline-substituted sulphonamide compounds.ˮ Arch. Physiol. Biochem., 2017; 123(5):306-312.