Table 9.

Structures and activity of the vitamin C derivatives against hyaluronidase.⁶⁵

	Compound	Substituent			${IC}_{50}$ (µM) or % inhibitiona, pH 5.0
		${\mathrm{R}}_1$	${\mathrm{R}}_2$	${\mathrm{R}}_3$	SagHyal4755	BTH
	1	H	H	H	6100	Inactive
	6	Me	Me	H	Inactive	Inactive
	7	Bn	Bn	H	355	Inactive
	8	${\mathrm{CH}}_2{\mathrm{CH}}_2$		H	24% (2000)	Inactive
	9	Me	Me	$\mathrm{CO}({{\mathrm{CH}}_2)}_{14}{\mathrm{CH}}_3$	5% (160)	Inactive
	10	Bn	Bn	$\mathrm{CO}({{\mathrm{CH}}_2)}_{14}{\mathrm{CH}}_3$	Inactive	Inactive
	11	${\mathrm{CH}}_2{\mathrm{CH}}_2$		$\mathrm{CO}({{\mathrm{CH}}_2)}_{14}{\mathrm{CH}}_3$	32% (190)	Inactive
	13a	H	H	$\mathrm{COC}({{\mathrm{CH}}_3)}_3$	43% (1100)	Inactive
	13b	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_4{\mathrm{CH}}_3$	475	Inactive
	13c	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_6{\mathrm{CH}}_3$	772	Inactive
	13d	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_8{\mathrm{CH}}_3$	102	1380
	13e	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_9{\mathrm{CH}}_3$	72	580
	13f	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_{10}{\mathrm{CH}}_3$	47	208
	13g	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_{11}{\mathrm{CH}}_3$	14.3	96
	13h	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_{12}{\mathrm{CH}}_3$	8.4	71
	13i	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_{14}{\mathrm{CH}}_3$	4.2	57
	13j	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_{16}{\mathrm{CH}}_3$	0.9	39
	13k	H	H	$\mathrm{CO}-\mathrm{Ph}$	132	33% (1430)
	13l	H	H	$\mathrm{CO}{\mathrm{CH}}_2-\mathrm{p}{\mathrm{C}}_6{\mathrm{H}}_4-\mathrm{Ph}$	358	2006
	13m	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_5\mathrm{O}-\mathrm{Ph}$	717	Inactive
	13n	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_5\mathrm{O}{\mathrm{CH}}_2\mathrm{P}\mathrm{h}$	437	Inactive
	13o	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_5\mathrm{O}-\mathrm{p}-{\mathrm{C}}_6{\mathrm{H}}_4-\mathrm{Ph}$	61	188
	13p	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_5\mathrm{O}{\mathrm{CH}}_2-\mathrm{p}{\mathrm{C}}_6{\mathrm{H}}_4-\mathrm{Ph}$	102	543
	13q	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_5\mathrm{O}-\mathrm{p}{\mathrm{C}}_6{\mathrm{H}}_4-{\mathrm{C}}_2{\mathrm{H}}_5$	280	Inactive
	13r	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_5\mathrm{O}-\mathrm{p}{\mathrm{C}}_6{\mathrm{H}}_4-\mathrm{O}{\mathrm{CH}}_2-\mathrm{Ph}$	76	210
	13s	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_{10}\mathrm{O}-\mathrm{Ph}$	31	105
	13t	H	H	$\mathrm{CO}({{\mathrm{CH}}_2)}_{10}\mathrm{p}{\mathrm{C}}_6{\mathrm{H}}_4-\mathrm{Ph}$	7.5	37

Bn: benzyl group.