Table 1. Benzothiophene Analogues: Structures, Considered Tautomers and Species, and MK2 Inhibition IC₅₀ Values (M).^28,29.

						considered		log(1/IC50)
ligand no.	X	R1	R2	R3	R4	tautomers	species	exp	calcd
1	NH	H	H	OCH3	H	T1,T2	S1,S5,S7	6.745	6.739
2	NH	CH3	H	OCH3	H	T1,T2	S1,S5,S7	7.398	7.635
3	NH	H	CH3	OCH3	H	T1,T2	S1,S5,S7	6.523	6.713
4	NH	(CH2)2CH3	H	OCH3	H	T1,T2	S1,S5,S7	5.818	5.486
5	NH	CH2OH	H	OCH3	H	T1,T2,T5	S1,S5,S7,S11	7.854	7.446
6	S	H	H	OCH3	H	T1,T3	S1,S9	5.963	5.547
7	CH2	H	H	OCH3	H	T1,T3	S1,S9	6.301	6.281
8	NH	CH2NH2	H	OCH3	H	T1,T2	S1,S2,S5,S6	8.301	8.436
9	NH	CH2NHCH2CH3	H	OCH3	H	T1,T2	S1,S2,S5,S6	6.244	6.021
10	NH	CH2NH(CH2)2CH3	H	OCH3	H	T1,T2	S1,S2,S5,S6	6.347	6.621
11	NH	CH2NHCH2Pha	H	OCH3	H	T1,T2,T5	S1,S2,S5,S6,S12	6.244	6.418
12	NH	CH2N(CH3)CH2Ph	H	OCH3	H	T1,T2,T5	S1,S2,S5–S7,S12	5.719	6.074
13	NH	CH3	H	OH	H	T1,T2	S1,S2,S5,S6–S8	6.721	6.944
14	NH	CH3	H	OCH2(3-OCH3-Ph)	H	T1,T2	S1,S5,S7	6.959	7.022
15	NH	CH3	H	OCH2-c-C3H5	H	T1,T2	S1,S5,S7	5.879	5.874
16	NH	CH3	H	O(CH2)2OCH3	H	T1,T2	S1,S5,S7	6.569	6.769
17	NH	CH3	H	OCH2CH(CH3)2	H	T1,T2	S1,S5,S7	6.398	6.238
18	NH	CH3	H	OCH2COOCH3	H	T1,T2	S1,S5,S7	7.523	7.212
19	NH	CH3	H	OCH2-c-C6H11	H	T1,T2	S1,S5,S7	5.463	5.593
20	NH	CH3	H	O–CH=CHb		T1,T2	S1,S5,S7	7.796	7.775
21	NH	CH3	H	O–CH2–CH2		T1,T2	S1,S5,S7	7.553	7.593
22	NH	CH3	H	N=CH–CH=CH		T1,T2,T4	S1,S5,S7,S10	9.000	8.549
23	NH	CH3	H	OC(Ph)=CH		T1,T2	S1,S5,S7	6.824	6.801
24	NH	CH3	H	N=C(Cl)-CH=CH		T1,T2,T4	S1,S5,S7,S10	8.699	8.474
25	NH	CH3	H	N=C(Ph)-CH=CH		T1,T2,T4	S1,S5,S7,S10	8.046	7.758
26	NH	CH3	H	N=C(4-Py)-CH=CHc		T1,T2,T4	S1,S5–S7,S10	7.854	7.967
27	NH	CH3	H	N=C(3-Py)-CH=CH		T1,T2,T4	S1,S5–S7,S10	8.301	7.705
28	NH	CH3	H	N=C(5-Pm)-CH=CHd		T1,T2,T4	S1,S5,S7,S10	7.638	7.356
29	NH	CH3	H	N=C(2-OCH3-Ph)-CH=CH		T1,T2	S1,S5,S7	7.699	7.517
30	NH	CH3	H	N=C(3-OCH3-Ph)-CH=CH		T1,T2,T4	S1,S5,S7,S10	7.387	7.199
31	NH	CH3	H	N=C(2-F-Ph)-CH=CH		T1,T2,T4	S1,S5,S7,S10	7.854	7.705
32	NH	CH3	H	N=C(2-CH3-Ph)-CH=CH		T1,T2,T4	S1,S5,S7,S10	7.523	7.771
33	NH	CH3	H	N=C(4-CH3-3-Py)-CH=CH		T1,T2,T4	S1,S2,S5–S7,S10	8.301	8.265
34	NH	CH2N-Tpe	H	OCH3	H	T1,T2	S1,S2,S5,S6	<4.699	4.879
35	NH	CH2N-Mof	H	OCH3	H	T1,T2,T5	S1,S2,S5,S7,S11	<4.699	4.812

^aPh: phenyl.

^bR3 and R4 join the phenyl ring to form cyclic derivatives in ligands 20–33.

^cPy: pyridyl.

^dPm: pyrimidinyl.

^eTp: tetrahydropyrrolyl.

^fMo: morpholinyl.