A series of new 1,3-diaryltriazene sulfonamides was synthesised by reaction of diazonium salt of metanilamide (3-aminobenzene sulfonamide) with substituted aromatic amines. The obtained new compounds were assayed as inhibitors of four physiologically and pharmacologically relevant human (h) isoforms of carbonic anhydrases (CA, EC 4.2.1.1), specifically, hCA I, hCA II, and hCA VII (cytosolic isoforms), as well as the tumour-associated membrane-bound isoform hCA IX. All isoforms investigated here were inhibited by the newly synthesised 1,3-diaryltriazene sulfonamide derivatives from the micromolar to the nanomolar range. The cytosolic isoforms were inhibited with K(i)s in the range of 92.3-8371.1 nM (hCA I), 4.3-9194.0 nM (hCA II), and 15.6- 9477.8 nM (hCA VII), respectively. For the membrane-bound tumour-associated isoform hCA IX, the KI-s ranged between 50.8 and 9268.5 nM. The structure-activity relationship (SAR) with these newly synthesised metanilamide derivatives are discussed in detail.
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Temple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Temple Univ, Sch Pharm, Molder Ctr Drug Discovery Res, 3307 N Broad St, Philadelphia, PA 19140 USA
Adiyaman Univ, Fac Pharm, Dept Pharmaceut Chem, TR-02040 Adiyaman, TurkeyTemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Akocak, Suleyman
;
Alam, M. Raqibul
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Temple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Temple Univ, Sch Pharm, Molder Ctr Drug Discovery Res, 3307 N Broad St, Philadelphia, PA 19140 USATemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Alam, M. Raqibul
;
Shabana, Ahmed M.
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Temple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Temple Univ, Sch Pharm, Molder Ctr Drug Discovery Res, 3307 N Broad St, Philadelphia, PA 19140 USATemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Shabana, Ahmed M.
;
Sanku, Rajesh Kishore Kumar
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Temple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Temple Univ, Sch Pharm, Molder Ctr Drug Discovery Res, 3307 N Broad St, Philadelphia, PA 19140 USATemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Sanku, Rajesh Kishore Kumar
;
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Vullo, Daniela
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Thompson, Harry
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Temple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Temple Univ, Sch Pharm, Molder Ctr Drug Discovery Res, 3307 N Broad St, Philadelphia, PA 19140 USATemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Thompson, Harry
;
Swenson, Erik R.
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Univ Washington, VA Puget Sound Hlth Care Syst, Med Serv, Seattle, WA 98195 USATemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Swenson, Erik R.
;
Supuran, Claudiu T.
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Univ Florence, Neurofarba Dept, Pharmaceut Sci Sect, Polo Sci, Via Ugo Schiff 6, I-50019 Florence, ItalyTemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Supuran, Claudiu T.
;
Hies, Marc A.
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Temple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Temple Univ, Sch Pharm, Molder Ctr Drug Discovery Res, 3307 N Broad St, Philadelphia, PA 19140 USATemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
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Ferencvaros Hlth Ctr, Dept Gastroenterol, Mester Utca 45, H-1095 Budapest, HungaryFerencvaros Hlth Ctr, Dept Gastroenterol, Mester Utca 45, H-1095 Budapest, Hungary
Buzas, Gyorgy M.
;
Supuran, Claudiu T.
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Univ Firenze, Sez Sci Farmaceut, Polo Sci, Neurofarba Dept, Florence, ItalyFerencvaros Hlth Ctr, Dept Gastroenterol, Mester Utca 45, H-1095 Budapest, Hungary
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Temple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Temple Univ, Sch Pharm, Molder Ctr Drug Discovery Res, 3307 N Broad St, Philadelphia, PA 19140 USA
Adiyaman Univ, Fac Pharm, Dept Pharmaceut Chem, TR-02040 Adiyaman, TurkeyTemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Akocak, Suleyman
;
Alam, M. Raqibul
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Temple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Temple Univ, Sch Pharm, Molder Ctr Drug Discovery Res, 3307 N Broad St, Philadelphia, PA 19140 USATemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Alam, M. Raqibul
;
Shabana, Ahmed M.
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Temple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Temple Univ, Sch Pharm, Molder Ctr Drug Discovery Res, 3307 N Broad St, Philadelphia, PA 19140 USATemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Shabana, Ahmed M.
;
Sanku, Rajesh Kishore Kumar
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Temple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Temple Univ, Sch Pharm, Molder Ctr Drug Discovery Res, 3307 N Broad St, Philadelphia, PA 19140 USATemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Sanku, Rajesh Kishore Kumar
;
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Vullo, Daniela
;
Thompson, Harry
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Temple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Temple Univ, Sch Pharm, Molder Ctr Drug Discovery Res, 3307 N Broad St, Philadelphia, PA 19140 USATemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Thompson, Harry
;
Swenson, Erik R.
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Univ Washington, VA Puget Sound Hlth Care Syst, Med Serv, Seattle, WA 98195 USATemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Swenson, Erik R.
;
Supuran, Claudiu T.
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Univ Florence, Neurofarba Dept, Pharmaceut Sci Sect, Polo Sci, Via Ugo Schiff 6, I-50019 Florence, ItalyTemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Supuran, Claudiu T.
;
Hies, Marc A.
论文数: 0引用数: 0
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机构:
Temple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
Temple Univ, Sch Pharm, Molder Ctr Drug Discovery Res, 3307 N Broad St, Philadelphia, PA 19140 USATemple Univ, Sch Pharm, Dept Pharmaceut Sci, 3307 N Broad St, Philadelphia, PA 19140 USA
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Ferencvaros Hlth Ctr, Dept Gastroenterol, Mester Utca 45, H-1095 Budapest, HungaryFerencvaros Hlth Ctr, Dept Gastroenterol, Mester Utca 45, H-1095 Budapest, Hungary
Buzas, Gyorgy M.
;
Supuran, Claudiu T.
论文数: 0引用数: 0
h-index: 0
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Univ Firenze, Sez Sci Farmaceut, Polo Sci, Neurofarba Dept, Florence, ItalyFerencvaros Hlth Ctr, Dept Gastroenterol, Mester Utca 45, H-1095 Budapest, Hungary