Design, synthesis, and biological evaluation of 3-benzenesulfonamide-linked 3-hydrazinoisatin derivatives as carbonic anhydrase inhibitors

被引:2
|
作者
Swain, Baijayantimala [1 ,5 ]
Marde, Vaibhav S. [1 ]
Singh, Priti [1 ]
Angeli, Andrea [2 ]
Khan, Abrar [1 ]
Yaddanapudi, Venkata M. [3 ]
Ullah, Qasim [4 ]
Supuran, Claudiu T. [2 ]
Arifuddin, Mohammed [1 ,6 ]
机构
[1] Natl Inst Pharmaceut Educ & Res NIPER, Dept Med Chem, Hyderabad 500037, Telangana, India
[2] Univ Firenze, Neurofarba Dept, Sez Sci Farmaceut & Nutraceut, Via Ugo Schiff 6, I-50019 Florence, Italy
[3] Natl Inst Pharmaceut Educ & Res NIPER, Dept Chem Sci, Proc Chem Proc Technol, Hyderabad, Telangana, India
[4] Maulana Azad Natl Urdu Univ MANUU, Sch Sci, Phys Sci Sect, Hyderabad, Telangana, India
[5] Bharat Inst Technol Pharm, Ibrahimpatnam 501510, Telangana, India
[6] Maulana Azad Natl Urdu Univ MANUU, Hyderabad, Telangana, India
关键词
cancer; carbonic anhydrase; isatin; isoform selectivity; sulfonamide; ISOFORMS IX; SULFONAMIDES; SELECTIVITY; ISATIN; DISCOVERY; VB;
D O I
10.1002/ardp.202300718
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new series of isatin-linked benzenesulfonamide derivatives (9a-w) were synthesized using the tail approach and assayed for their inhibitory potency against four different human carbonic anhydrase (hCA) isoforms, hCA I, II, IX, and XII. Most of these synthesized compounds exhibited interesting inhibition potency against isoforms hCA I, IX, and XII in the nanomolar range and by taking the standard drug acetazolamide. The most potent compounds in the case of hCA I were 9c (435.8 nM) and 9s (956.4 nM), for hCA IX, 9a (60.5 nM), 9d (95.6 nM), 9g (92.1 nM), and 9k (75.4 nM), and for hCA XII, 9p (84.5 nM). However, these compounds showed more selectivity toward hCA IX over hCA I, II, and XII. Thus, these compounds can be further developed as potential lead molecules for the development of isoform-selective hCA IX inhibitors with further structural modifications. A new series of 3-hydrazinoisatin-linked 3-benzenesulfonamide derivatives 9a-w were synthesized and subjected to screening against the human carbonic anhydrase (hCA; EC 4.2.1.1) isoforms hCA I, II, IX, and XII. Most of them displayed good potency and selectivity against the isoform hCA IX. image
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页数:9
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