Abstract
The thiazole derivatives as important members of heterocyclic compounds have attracted much synthetic interest due to their different biological properties. In recent years, studies on the synthesis of morpholine compounds have increased because of the properties of this core. In particular, the hybrid structures in which the thiazole ring is linked to morpholine nuclei in one molecular frame have gained popularity. The presented review is an attempt to summarize a huge volume of data on morpholinothiazoles being a widely studied class of these molecules used in modern organic and medicinal chemistry. The manuscript covers the approaches to the synthesis of the morpholinothiazoles derivatives. The synthetic strategies of the target compounds depend on one-pot or multistage reactions or the transformation of other related heterocycles. Additionally, we covered the biological activities and other applications of certain morpholinothiazoles. The information on these compounds made special consideration of medicinal chemists to yield a combinatorial library and carry out thorough efforts in the search of morpholinothiazoles.
Graphical Abstract
[http://dx.doi.org/10.1038/nrd1523] [PMID: 15459676]
[http://dx.doi.org/10.1016/j.ejmech.2014.10.059] [PMID: 25462241]
[http://dx.doi.org/10.1016/j.cdc.2022.100883]
[http://dx.doi.org/10.3389/fmolb.2021.775013] [PMID: 35111810]
[http://dx.doi.org/10.1080/00397911.2017.1399422]
[http://dx.doi.org/10.3390/molecules24030539] [PMID: 30717217]
[http://dx.doi.org/10.2174/1389557518666180816112151] [PMID: 30112994]
[http://dx.doi.org/10.2174/1570193X15666180412152743]
[http://dx.doi.org/10.1134/S1070428013060018]
[http://dx.doi.org/10.1038/s41598-019-56463-2] [PMID: 31882733]
[http://dx.doi.org/10.1021/jm901415x] [PMID: 19916508]
[http://dx.doi.org/10.1007/s11172-015-0980-9]
[http://dx.doi.org/10.1016/j.ijbiomac.2020.09.043] [PMID: 32931834]
[http://dx.doi.org/10.1248/cpb.c12-00498] [PMID: 22976330]
[http://dx.doi.org/10.1016/j.bmcl.2008.06.076] [PMID: 18625552]
[http://dx.doi.org/10.1016/j.jphotochem.2016.10.009]
[http://dx.doi.org/10.1016/j.saa.2016.07.054] [PMID: 27673496]
[http://dx.doi.org/10.2174/22113525113119990119]
[http://dx.doi.org/10.1016/j.bmcl.2014.02.004] [PMID: 24560540]
[http://dx.doi.org/10.1016/j.optmat.2018.03.024]
[http://dx.doi.org/10.1016/j.molstruc.2021.131476]
[http://dx.doi.org/10.34117/bjdv6n2-225]
[http://dx.doi.org/10.1002/ardp.19933261107]
[http://dx.doi.org/10.1134/S1070428020030148]
[http://dx.doi.org/10.5155/eurjchem.7.3.271-279.1427]
[http://dx.doi.org/10.2174/18756638MTA2aNjkk1] [PMID: 32416682]
[http://dx.doi.org/10.1080/00397911.2021.1970774]
[http://dx.doi.org/10.1007/s00044-012-0318-1] [PMID: 23807823]
[http://dx.doi.org/10.1016/j.ejmech.2016.04.028] [PMID: 27131068]
[PMID: 17225562]
[http://dx.doi.org/10.1002/jhet.838]
[http://dx.doi.org/10.1002/ardp.201100001] [PMID: 21932255]
[http://dx.doi.org/10.1111/cbdd.13744] [PMID: 32543026]
[http://dx.doi.org/10.1016/j.ejmech.2018.01.061] [PMID: 29407963]
[http://dx.doi.org/10.1007/s11164-017-2945-0]
[http://dx.doi.org/10.5560/znb.2014-4081]
[http://dx.doi.org/10.5562/cca3279]
[http://dx.doi.org/10.1016/j.tetlet.2013.02.045]
[http://dx.doi.org/10.2174/22133356114019990002]
[PMID: 13320273]
[http://dx.doi.org/10.3998/ark.5550190.0007.a01]
[http://dx.doi.org/10.1135/cccc19810436]
[http://dx.doi.org/10.1002/prac.19733150204]
[http://dx.doi.org/10.1063/5.0018081]
[http://dx.doi.org/10.1016/j.jscs.2022.101431]
[http://dx.doi.org/10.3109/14756366.2011.594047] [PMID: 21740103]
[http://dx.doi.org/10.1515/hc.2011.016]
[http://dx.doi.org/10.1016/j.bioorg.2020.104426] [PMID: 33161255]
[http://dx.doi.org/10.1134/S1070363208040221]
[http://dx.doi.org/10.1186/s13065-021-00756-z] [PMID: 33906691]
[http://dx.doi.org/10.1021/acs.jafc.9b03891] [PMID: 31596575]
[http://dx.doi.org/10.1021/ja01546a064]
[http://dx.doi.org/10.1007/s11172-007-0254-2]
[http://dx.doi.org/10.3184/174751916X14519928918516]
[http://dx.doi.org/10.1002/adsc.201901670]
[http://dx.doi.org/10.1080/10426500490257131]
[http://dx.doi.org/10.1016/j.bioorg.2019.102998] [PMID: 31128819]
[http://dx.doi.org/10.4274/tjps.galenos.2018.82612] [PMID: 32454740]
[http://dx.doi.org/10.1002/jhet.5570450339]
[http://dx.doi.org/10.1021/acs.orglett.7b01594] [PMID: 28678513]
[http://dx.doi.org/10.1080/10426500490468092]
[http://dx.doi.org/10.1007/s11094-016-1416-z]
[http://dx.doi.org/10.1016/j.bioorg.2021.105151] [PMID: 34333424]