PMID- 24682061
OWN - NLM
STAT- MEDLINE
DCOM- 20141209
LR  - 20140424
IS  - 1873-3557 (Electronic)
IS  - 1386-1425 (Linking)
VI  - 128
DP  - 2014 Jul 15
TI  - New aromatic/heteroaromatic propanesulfonylhydrazone compounds: synthesis, 
      physical properties and inhibition studies against carbonic anhydrase II (CAII) 
      enzyme.
PG  - 452-60
LID - S1386-1425(14)00236-4 [pii]
LID - 10.1016/j.saa.2014.02.049 [doi]
AB  - Some new aromatic/heteroaromatic propanesulfonylhydrazone derivatives (1-8) were 
      synthesized and characterized by elemental analyses, FT-IR, (1)H NMR, (13)C NMR, 
      LC/MS techniques. The geometry optimizations and spectral calculations were 
      performed by using DFT/B3LYP/6-311G(d,p) basis set in Gaussian 09 program. The 
      inhibition activities of the synthesized compounds on carbonic anhydrase II 
      (CAII) isoenzyme have been investigated by comparing IC50 values. Acetazolamide 
      (5-acetamido-1,3,4-thiadiazole-2-sulfonamide) AAZ, a clinically used in CAII 
      inhibition has also been investigated as standard inhibitor. The best 
      aromatic/heteroaromatic propanesulfonylhydrazone inhibitors of this isoform were 
      o-aminobenzaldehydepropanesulfonylhydrazone (1) and thiophenecarboxyaldehyde 
      propanesulfonylhydrazone (5) having the same IC50 (0.55 mM) value. The molecular 
      descriptors for propanesulfonylhydrazones were obtained to develop structure 
      activity relationship (SAR) model between experimental IC50 values and the 
      molecular descriptors calculated by PM3-based SAR models in Hyperchem 8, 
      respectively. The obtained models confirm the good carbonic anhydrase II (CAII) 
      inhibition activity of the propanesulfonylhydrazone derivatives. The selected 
      descriptors are sensitive both to the imine (CH=N) and NH2 groups that are 
      responsible from higher activities of (1) and (5) in their series.
CI  - Copyright (c) 2014 Elsevier B.V. All rights reserved.
FAU - Ozmen Ozdemir, Ummuhan
AU  - Ozmen Ozdemir U
AD  - Department of Chemistry, Faculty of Science, Gazi University, Ankara 06500, 
      Turkey. Electronic address: ummuhan@gazi.edu.tr.
FAU - Altuntas, Aysegul
AU  - Altuntas A
AD  - Department of Chemistry, Faculty of Science, Gazi University, Ankara 06500, 
      Turkey.
FAU - Gunduzalp, Ayla Balaban
AU  - Gunduzalp AB
AD  - Department of Chemistry, Faculty of Science, Gazi University, Ankara 06500, 
      Turkey.
FAU - Arslan, Fatma
AU  - Arslan F
AD  - Department of Chemistry, Faculty of Science, Gazi University, Ankara 06500, 
      Turkey.
FAU - Hamurcu, Fatma
AU  - Hamurcu F
AD  - Department of Molecular Biology and Genetics, Faculty of Science, Bartin 
      University, Bartin 74100, Turkey.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20140225
PL  - England
TA  - Spectrochim Acta A Mol Biomol Spectrosc
JT  - Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy
JID - 9602533
RN  - 0 (Enzyme Inhibitors)
RN  - 0 (Hydrazones)
RN  - EC 4.2.1.- (Carbonic Anhydrase II)
SB  - IM
MH  - Carbonic Anhydrase II/*antagonists & inhibitors/*chemistry
MH  - Enzyme Inhibitors/chemical synthesis/*chemistry
MH  - Hydrazones/chemical synthesis/*chemistry
MH  - *Models, Chemical
OTO - NOTNLM
OT  - Aromatic/heteroaromatic propanesulfonylhydrazone derivatives
OT  - Carbonic anhydrase II (CAII) inhibition
OT  - SAR
EDAT- 2014/04/01 06:00
MHDA- 2014/12/15 06:00
CRDT- 2014/04/01 06:00
PHST- 2013/12/27 00:00 [received]
PHST- 2014/02/13 00:00 [revised]
PHST- 2014/02/16 00:00 [accepted]
PHST- 2014/04/01 06:00 [entrez]
PHST- 2014/04/01 06:00 [pubmed]
PHST- 2014/12/15 06:00 [medline]
AID - S1386-1425(14)00236-4 [pii]
AID - 10.1016/j.saa.2014.02.049 [doi]
PST - ppublish
SO  - Spectrochim Acta A Mol Biomol Spectrosc. 2014 Jul 15;128:452-60. doi: 
      10.1016/j.saa.2014.02.049. Epub 2014 Feb 25.