Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols including natural products

被引:44
作者
Balaydin, Halis Turker [1 ,2 ]
Soyut, Hakan [1 ,3 ]
Ekinci, Deniz [4 ]
Goksu, Suleyman [1 ]
Beydemir, Sukru [1 ,5 ]
Menzek, Abdullah [1 ]
Sahin, Ertan [1 ]
机构
[1] Ataturk Univ, Fac Sci, Dept Chem, TR-25240 Erzurum, Turkey
[2] Artvin Coruh Univ, Fac Educ, Dept Elementary Sci Educ, Artvin, Turkey
[3] Bayburt Univ, Fac Educ, Dept Elementary Sci Educ, Bayburt, Turkey
[4] Ondokuz Mayis Univ, Fac Agr, Dept Agr Biotechnol, Samsun, Turkey
[5] Ataturk Univ, Biotechnol Applicat & Res Ctr, TR-25240 Erzurum, Turkey
关键词
Bromophenols; diphenylmethane; carbonic anhydrase; glaucoma; enzyme inhibition; IN-VITRO; THERAPEUTIC APPLICATIONS; PHENOLS; PATTERNS; METALS; SERIES;
D O I
10.3109/14756366.2011.574131
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
(2-Bromo-3,4-dimethoxyphenyl) (3,4-dimethoxyphenyl) methanone (10) and its derivatives with Br, one dibromide and isomeric three tribromides, were synthesized. Demethylation of these compounds afforded a series of new bromophenols. Inhibition of human cytosolic carbonic anhydrase II (hCA II) isozyme by these new bromophenols and naturally occurring 3,4,6-tribromo-5-(2,5-dibromo-3,4-dihydroxybenzyl) benzene-1,2-diol (3), and 5,5'-methylenebis(3,4,6-tribromo-benzene-1,2-diol) (4) was investigated. The synthesized compounds showed carbonic anhydrase inhibitory capacities with IC50 values in the range of 0.7-372 mu M against hCA II. Some bromophenols investigated here showed effective hCA II inhibitory activity and might be used as leads for generating novel carbonic anhydrase inhibitors which are valuable drug candidates for the treatment of glaucoma, epilepsy, gastric and duodenal ulcers, neurological disorders, or osteoporosis.
引用
收藏
页码:43 / 50
页数:8
相关论文
共 42 条
  • [1] Total Synthesis of the Biologically Active, Naturally Occurring 3,4-Dibromo-5-[2-bromo-3,4-dihydroxy-6-(methoxymethyl)benzyl]benzene-1,2-diol and Regioselective O-Demethylation of Aryl Methyl Ethers
    Akbaba, Yusuf
    Balaydin, Halis Tuerker
    Goksu, Sueleyman
    Sahin, Ertan
    Menzek, Abdullah
    [J]. HELVETICA CHIMICA ACTA, 2010, 93 (06) : 1127 - 1135
  • [2] Intravenous anesthetics inhibit human paraoxonase-1 (PON1) activity in vitro and in vivo
    Alici, Haci Ahmed
    Ekinci, Deniz
    Beydemir, Suekrue
    [J]. CLINICAL BIOCHEMISTRY, 2008, 41 (16-17) : 1384 - 1390
  • [3] First and short syntheses of biologically active, naturally occurring brominated mono- and dibenzyl phenols
    Balaydin, Halis T.
    Akbaba, Yusuf
    Menzek, Abdullah
    Sahin, Ertan
    Goksu, Suleyman
    [J]. ARKIVOC, 2009, : 75 - 87
  • [4] Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product
    Balaydin, Halis Turker
    Gulcin, Ilhami
    Menzek, Abdullah
    Goksu, Suleyman
    Sahin, Ertan
    [J]. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2010, 25 (05) : 685 - 695
  • [5] In vitro inhibition of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II
    Bayram, Esra
    Senturk, Murat
    Kufrevioglu, O. Irfan
    Supuran, Claudiu T.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (20) : 9101 - 9105
  • [6] BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3
  • [7] An analysis of expression patterns of genes encoding proteins with catalytic activities
    Cankaya, Murat
    Hernandez, Ana Martinez
    Ciftci, Mehmet
    Beydemir, Sukru
    Ozdemir, Hasan
    Budak, Harun
    Gulcin, Ilhami
    Comakli, Veysel
    Emircupani, Tufan
    Ekinci, Deniz
    Kuzu, Muslum
    Jiang, Qiuhong
    Eichele, Gregor
    Kufrevioglu, Omer Irfan
    [J]. BMC GENOMICS, 2007, 8 (1)
  • [8] Sildenafil is a strong activator of mammalian carbonic anhydrase isoforms I-XIV
    Coban, T. Abduelkadir
    Beydemir, Suekrue
    Gucin, Ilhami
    Ekinci, Deniz
    Innocenti, Alessio
    Vullo, Daniela
    Supuran, Claudiu T.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (16) : 5791 - 5795
  • [9] Çoban TA, 2008, J ENZYM INHIB MED CH, V23, P266, DOI [10.1080/14756360701474780 , 10.1080/14756360701474780]
  • [10] Highly brominated mono- and bis-phenols from the marine red alga Symphyocladia latiuscula with radical-scavenging activity
    Duan, Xiao-Juan
    Li, Xiao-Ming
    Wang, Bin-Gui
    [J]. JOURNAL OF NATURAL PRODUCTS, 2007, 70 (07): : 1210 - 1213