. 2023 Apr 15;254:115376. doi: 10.1016/j.ejmech.2023.115376

Table 1.

IC₅₀ and CC₅₀ values of compounds 1 c-g and 2c/d-17c/d against SARS-CoV-2 3CL^pro and MERS-CoV 3CL^pro, and EC₅₀ values of selected compounds against SARS-CoV-2.

General Structure (I) of inhibitors for 1 c-g, 2c/d – 7c/d, 10c/d – 16c/d
Compound Code	R	X	Y	Z	IC₅₀ (μM)^a		EC₅₀ (μM)^a^,^b	CC₅₀ (μM)
Compound Code	R	X	Y	Z	SARS-CoV-2	MERS-CoV	SARS-CoV-2	CC₅₀ (μM)
1c	H	S	H	-CHO	0.07 ± 0.02	0.08 ± 0.02	0.012 ± 0.01	>50
1d				-CH(OH)SO₃Na	0.09 ± 0.01	0.09 ± 0.02	0.010 ± 0.02	>50
1e					0.21 ± 0.02	0.04 ± 0.01	0.05 ± 0.03	>50
1f					0.45 ± 0.05	0.18 ± 0.06	0.07 ± 0.05	>50
1g				-CN	0.49 ± 0.05	0.41 ± 0.08	0.06 ± 0.06	>50
2c	H	S	D	-CHO	0.20 ± 0.02	0.06 ± 0.01	0.011 ± 0.02	>50
2d	H	S	D	-CH(OH)SO₃Na	0.31 ± 0.03	0.04 ± 0.01	0.012 ± 0.03	>50
3c^d	H		H	-CHO	0.33 ± 0.01	0.19 ± 0.07	NT	>50
3d^d	H		H	-CH(OH)SO₃Na	0.35 ± 0.10	0.25 ± 0.09	NT	>50
4c	H		H	-CHO	0.19 ± 0.05	0.26 ± 0.01	NT	>50
4d	H		H	-CH(OH)SO₃Na	0.20 ± 0.01	0.28 ± 0.01	NT	>50
5c	m-F	S	H	-CHO	0.14 ± 0.02	0.10 ± 0.02	0.009 ± 0.02	>50
5d	m-F	S	H	-CH(OH)SO₃Na	0.13 ± 0.01	0.13 ± 0.03	0.010 ± 0.02	>50
6c	p-F	S	H	-CHO	0.17 ± 0.03	0.19 ± 0.07	NT	>50
6d	p-F	S	H	-CH(OH)SO₃Na	0.27 ± 0.02	0.15 ± 0.01	NT	>50
7c	m-Cl	S	H	-CHO	0.15 ± 0.01	0.11 ± 0.04	0.010 ± 0.01	>50
7d	m-Cl	S	H	-CH(OH)SO₃Na	0.17 ± 0.03	0.10 ± 0.02	0.011 ± 0.01	>50
8c				-CHO	0.32 ± 0.03	0.14 ± 0.04	NT	>50
8d				-CH(OH)SO₃Na	0.31 ± 0.02	0.14 ± 0.05	NT	>50
9c				-CHO	0.30 ± 0.02	0.12 ± 0.04	NT	>50
9d				-CH(OH)SO₃Na	0.31 ± 0.09	0.21 ± 0.10	NT	>50
*10c*	H	O	H	-CHO	0.31 ± 0.05	0.04 ± 0.01	NT	>50
*10d*	H	O	H	-CH(OH)SO₃Na	0.24 ± 0.05	0.02 ± 0.02	NT	>50
*11c*	p-Cl	O	H	-CHO	0.46 ± 0.11	0.02 ± 0.01	NT	>50
*11d*	p-Cl	O	H	-CH(OH)SO₃Na	0.34 ± 0.03	0.11 ± 0.05	NT	>50
*12c*	p-Cl	O	D	-CHO	0.17 ± 0.05	0.04 ± 0.01	0.015 ± 0.05	>50
*12d*	p-Cl	O	D	-CH(OH)SO₃Na	0.17 ± 0.02	0.02 ± 0.02	0.012 ± 0.03	>50
*13c*	m-Cl	O	H	-CHO	0.19 ± 0.02	0.02 ± 0.02	0.013 ± 0.01	>50
*13d*	m-Cl	O	H	-CH(OH)SO₃Na	0.21 ± 0.03	0.02 ± 0.02	0.014 ± 0.01	>50
*14c*	m-Cl	O	D	-CHO	0.30 ± 0.08	0.04 ± 0.03	NT	>50
*14d*	m-Cl	O	D	-CH(OH)SO₃Na	0.28 ± 0.07	0.07 ± 0.02	NT	>50
*15c*	p-F	O	H	-CHO	0.22 ± 0.03	0.03 ± 0.02	NT	>50
*15d*	p-F	O	H	-CH(OH)SO₃Na	0.23 ± 0.01	0.04 ± 0.02	NT	>50
*16c*	m-F	O	H	-CHO	0.20 ± 0.01	0.05 ± 0.02	NT	>50
*16d*	m-F	O	H	-CH(OH)SO₃Na	0.12 ± 0.02	0.04 ± 0.02	NT	>50
*17c*^d				-CHO	0.29 ± 0.02	0.12 ± 0.01	0.025 ± 0.07	>50
*17d*^d				-CH(OH)SO₃Na	0.32 ± 0.12	0.10 ± 0.01	0.025 ± 0.01	>50
*GC373*^e				-CHO	0.38 ± 0.09	0.28 ± 0.05	0.031 ± 0.02	>100
*GC376*^e				-CH(OH)SO₃Na	0.41 ± 0.07	0.25 ± 0.10	0.027 ± 0.01	>100

cNT = Not Tested;

Mean ± SD for IC₅₀ and EC₅₀;

Determined using SARS-CoV-2 replicon system [44], (h).

Mixture of diastereomers;

Previously reported^28(h),(i)