Synthesis of 4-(2-substituted hydrazinyl)benzenesulfonamides and their carbonic anhydrase inhibitory effects

Figures & data

Table 1. The physical data of the compounds S1–S11.

Compounds	Ketone	Melting point (°C)	Crystallization solvent	Melting point (°C)	Crystallization solvent	HRMS [MH]^+ Calc. Mass	HRMS [MH]^+ Found Mass
S1		257–259	Ethanol	247–248†	DMF:H2O†	290.0963	290.0958
S2		234–235	Ethanol	224–226†	Ethanol†	304.1120	304.1111
S3		237–238	DMF:H2O	221–222†	DMF:H2O†	324.0574	324.0562
S4		210–212	Ethanol	210–212‡	Ethanol‡	308.0869	308.0866
S5		241–243	Ethanol	210–212†	Ethanol†	368.0068	368.0058
S6		215–217	Ethanol	230–232‡	Ethanol‡	320.1069	320.1056
S7		266–268	Ethanol	254–255†	DMF:H2O†	335.0814	335.0813
S8		217–218	Ethanol	230–232‡	Ethanol‡	296.0527	296.0518
S9		249–251	Ethanol	–	–	280.0756	280.0753
S10		247–249	DMF:H2O	–	–	302.0963	302.0945
S11		214–216	DMF:H2O	–	–	302.0970	302.0962

†Synthesis of some pyrazolyl benzenesulfonamide derivatives as dual anti-inflammatory antimicrobial agents23.

‡Synthesis and biological evaluation of some 4-functionalized-pyrazoles as antimicrobial agents46.

Scheme 1. Synthesis of the compounds S1–S9.

Scheme 2. Synthesis of the compounds S10 and S11.

Table 2. Human carbonic anhydrase isoenzymes (hCA I and II) inhibition values with 4-(2-substituted hydrazinyl)benzenesulfonamide derivatives (S1–S11) using esterase assay.

	Ki (nM)
Compounds	hCA I	hCA II
S1	2.23 ± 0.14	8.02 ± 3.04
S2	2.42 ± 0.51	6.93 ± 2.51
S3	2.15 ± 0.42	7.91 ± 3.30
S4	2.67 ± 0.30	9.12 ± 4.42
S5	1.97 ± 0.23	11.64 ± 5.21
S6	2.73 ± 0.48	6.34 ± 2.64
S7	1.90 ± 0.43	1.97 ± 0.40
S8	2.73 ± 0.08	10.69 ± 4.73
S9	2.52 ± 0.38	9.43 ± 1.94
S10	2.06 ± 0.66	6.73 ± 2.18
S11	1.79 ± 0.22	1.72 ± 0.58
AZA*	5.41 ± 1.28	6.82 ± 1.59

*Acetazolamide (AZA) was used as a standard inhibitor for all hCA.

Akıncıoğlu A, Topal M, Gülçin İ, Göksu S. Novel sulfamides and sulfonamides incorporating tetralin scaffold as carbonic anhydrase and acetylcholine esterase inhibitors. Arch Pharm 2014;347:68–76

 PubMed Web of Science ®Google Scholar

Bekhit AA, Ashour HMA, Abdel-Rahman HM, et al. Synthesis of some pyrazolyl benzenesulfonamide derivatives as dual anti-inflammatory antimicrobial agents. J Enzyme Inhib Med Chem 2009;24:296–309

 PubMed Web of Science ®Google Scholar