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. 2023 Jan 9;66(2):1583–1600. doi: 10.1021/acs.jmedchem.2c01830

Table 1. SAR of Aromatic Substitution, h/rTRPA1 IC50 [nM] Potency, for Compounds 15, 16, and 24ah.

graphic file with name jm2c01830_0009.jpg

compounda R1 R2 R3 hTRPA1 IC50 [nM] rTRPA1 IC50 [nM]
15 H H NO2 14 1370
(rac)-16 H H F 36 1560
eutomer 16a H H F 33 860
16b H H F >25 000 >25 000
24a H H Cl 340 11 500
24b H H CN 390 7570
24c H H Me 1270 >12 500
24d H H OMe >125 00 >12 500
24e H H –C(O)NHEt >12 500 >12 500
24f H F H 750 3800
24g H CN H 5550 13 000
24h F H F 1000 >10 000
a

Compounds are diastereomeric mixtures unless stated otherwise (#4, ratio >10:1 cis/trans).