. Author manuscript; available in PMC: 2012 Aug 11.

Published in final edited form as: J Med Chem. 2011 Jul 18;54(15):5522–5531. doi: 10.1021/jm2005767

Table 1.

Inhibition of Human α-Thrombin by Sulfated Benzofuran Monomers.^a

	R	R′	log IC₅₀ (M)	IC₅₀ (μM)	ΔY
5a	—OCH₂CH₃	—CH₃	nd^b	>2500^c	-
5b	—OCH₃	—CH₃	nd	>3000^c	-
5c	—OC(CH₃)₃	—CH₃	nd	>3000^c	-
5d	—OCH₂ CH₂OCH₃	—CH₃	nd	>2000^c	-
5e	—OCH₂CH₃	—CH₂CH₃	−1.7±0.2^d	20560±8500	0.60
5f	—OCH₂CH₃	—CH(CH₃)₂	−1.9±0.3	13650±10400	0.75
5g	—OCH₂CH₃	—CH₂OCH₃	nd	>16000^c	-
5h	—OCH₂CH₃	Morpholine-4-carbonyl	nd	>25,000^c	-
5i	—OCH₂CH₃	Benzoyl-p-methoxy	−3.3±0.2	520±280	0.54
5j	—OCH₂CH=CH₂	—CH₃	nd	>3000	-
9a	N-morpholino	—CH₃	nd	>2000^c	-
9b	N-piperidino	—CH₃	nd	>2000^c	-
10^e	—CH₂CH₃	—CH₃	nd	>7000^c	-

Thrombin inhibition was measured in spectrophotometric assay through initial rate of Spectrozyme TH hydrolysis as described in Experimental section.

Not determined due to incomplete and/or poor inhibition.

Estimates on the basis of the highest concentration used in experiment.

standard error shown is ±1 S.E.

10 contains a morpholine group at the allylic position (instead of a –CH₃ group). See Figure 2 for the full structure.