Synthesis and Biological Activity of Novel Imidazo[2,1-b][1,3,4]thiadiazole Derivatives†

doi:10.7503/cjcu20130659

Abstract

Abstract:

To develop new β2-AR antagonists, eighteen novel 2,6-disubstituted imidazo[2,1-b][1,3,4]thiadiazole derivatives containing 2-benzoxazolinone/benzothiazolinone moiety, 2-[(2-benzoxazolinone/benzothiazolinone-3-yl)methyl]-6-aryl-imidazo[2,1-b][1,3,4]thiadiazoles(5a—5i'), were synthesized by the condensation of compounds 4a and 4a' with α-bromoarylketones under reflux in dry ethanol. Their structures of the newly synthesized compounds were confirmed by IR, ¹H NMR and elemental analysis. The target compounds were screened as β2-adrenergic receptor antagonist. The result indicated that some of them display obvious antagonistic effects to β2-AR, and compound 5c' shows the highest antagonistic effect(70%). They can be considered as potential candidates as novel β2-AR antagonists.

Key words: 2-Benzoxazolinone/Benzothiazolinone, Imidazo[2,1-b][1,3,4]thiadiazole, β2-Adrenergic receptor antagonist

CLC Number:

O626

TrendMD:

LI Yingjun, LI Chunyan, JIN Kun, SHAO Xin, ZHOU Xiaoxia, LI Lina, ZHAO Nan, YU Yang, LUO Tongchuan. Synthesis and Biological Activity of Novel Imidazo[2,1-b][1,3,4]thiadiazole Derivatives^†[J]. Chem. J. Chinese Universities, 2014, 35(3): 531.

Figures/Tables 2

References 25

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Compd.	X	Ar	Response^b(%)	Compd.	X	Ar	Response^b(%)
5a	O	C₆H₅	49.64±38.06	5a'	S	C₆H₅	69.37±33.14
5b	O	4-CH₃OC₆H₄	42.68±36.56	5b'	S	4-CH₃OC₆H₄	49.77±31.05
5c	O	4-BrC₆H₄	94.94±15.95	5c'	S	4-BrC₆H₄	29.23±9.46
5d	O	4-ClC₆H₄	87.54±8.47	5d'	S	4-ClC₆H₄	73.34±23.58
5e	O	4-FC₆H₄	75.73±24.03	5e'	S	4-FC₆H₄	85.03±18.02
5f	O	3-O₂NC₆H₄	79.76±13.04	5f'	S	3-O₂NC₆H₄	94.26±8.60
5g	O	4-O₂NC₆H₄	90.60±16.56	5g'	S	4-O₂NC₆H₄	105.16±4.92
5h	O	2-C₁₀H₇	96.93±5.00	5h'	S	2-C₁₀H₇	92.77±13.59
5i	O	4-Ph-C₆H₄	107.87±8.98	5i'	S	4-Ph-C₆H₄	89.59±13.50

Compd.	X	Ar	Response^b(%)	Compd.	X	Ar	Response^b(%)
5a	O	C₆H₅	49.64±38.06	5a'	S	C₆H₅	69.37±33.14
5b	O	4-CH₃OC₆H₄	42.68±36.56	5b'	S	4-CH₃OC₆H₄	49.77±31.05
5c	O	4-BrC₆H₄	94.94±15.95	5c'	S	4-BrC₆H₄	29.23±9.46
5d	O	4-ClC₆H₄	87.54±8.47	5d'	S	4-ClC₆H₄	73.34±23.58
5e	O	4-FC₆H₄	75.73±24.03	5e'	S	4-FC₆H₄	85.03±18.02
5f	O	3-O₂NC₆H₄	79.76±13.04	5f'	S	3-O₂NC₆H₄	94.26±8.60
5g	O	4-O₂NC₆H₄	90.60±16.56	5g'	S	4-O₂NC₆H₄	105.16±4.92
5h	O	2-C₁₀H₇	96.93±5.00	5h'	S	2-C₁₀H₇	92.77±13.59
5i	O	4-Ph-C₆H₄	107.87±8.98	5i'	S	4-Ph-C₆H₄	89.59±13.50