Table 1.

The calculated lipophilicities (log P/Clog P), electronic σ parameters and IC₅₀ [μmol/L] values related to PET inhibition in spinach chloroplasts of quinoline-2-carboxamides 1–19c in comparison with 3-(3,4-dichlorophenyl)-1,1-dimethylurea (DCMU) standard. NF = not found in literature, ND = not determined due to precipitation during the experiment or interaction with 2,6-dichlorophenol-indophenol (DCIPP).

Comp.	R1	R2	PET inhibition IC50 [μmol/L]	log P ACD/Log P	σ [35]
1	i-Pr	H	ND	2.02 ± 0.34	−0.19 [36]
2	–C12H25	H	573	6.98 ± 0.32	NF
3	–(CH2)4–		1598	1.15 ± 0.26	NF
4	–(CH2)5–		ND	1.72 ± 0.26	NF
5	c-Pn	H	762	2.63 ± 0.33	−0.20 [36]
6	c-Hx	H	1041	3.20 ± 0.33	−0.15 [36]
7	c-Hp	H	ND	3.76 ± 0.33	NF
8	c-Oc	H	415	4.33 ± 0.33	NF
9	Ph	H	85.1	2.90 ± 0.34	0.60 [36]/0
10	Bn	H	59.4	2.91 ± 0.35	0.22 [36]
11	–C2H4Ph	H	ND	3.33 ± 0.33	0.08 [36]
12a	2-OH-Ph	H	16.3	2.54 ± 0.36	−0.09
12b	3-OH-Ph	H	ND	2.55 ± 0.36	0.12
12c	4-OH-Ph	H	ND	2.15 ± 0.35	−0.37
13a	2-OCH3-Ph	H	ND	2.80 ± 0.36	−0.39 [37]
13b	3-OCH3-Ph	H	ND	3.06 ± 0.36	0.12
13c	4-OCH3-Ph	H	ND	2.85 ± 0.36	−0.27
14a	2-CH3-Ph	H	142.9	3.36 ± 0.34	NF
14b	3-CH3-Ph	H	100.6	3.36 ± 0.34	−0.07
14c	4-CH3-Ph	H	ND	3.36 ± 0.34	−0.17
15a	2-F-Ph	H	98.1	2.86 ± 0.44	0.24 [38]
15b	3-F-Ph	H	86.9	3.38 ± 0.44	0.34
15c	4-F-Ph	H	75.3	3.34 ± 0.44	0.06
16a	2-Cl-Ph	H	56.3	3.41 ± 0.36	0.20 [38]
16b	3-Cl-Ph	H	91.9	3.93 ± 0.37	0.37
16c	4-Cl-Ph	H	147.6	3.89 ± 0.36	0.23
17a	2-Br-Ph	H	92.2	3.58 ± 0.44	0.21 [38]
17b	3-Br-Ph	H	409.0	4.10 ± 0.44	0.39
17c	4-Br-Ph	H	307.9	4.06 ± 0.44	0.23
18a	2-CF3-Ph	H	109.4	4.09 ± 0.42	NF
18b	3-CF3-Ph	H	329.5	4.25 ± 0.42	0.43
18c	4-CF3-Ph	H	ND	3.91 ± 0.41	0.74
19a	2-NO2-Ph	H	ND	3.15 ± 0.38	0.80 [38]
19b	3-NO2-Ph	H	ND	3.28 ± 0.38	0.71
19c	4-NO2-Ph	H	ND	3.36 ± 0.38	1.26
DCMU	–	–	1.9	–	–