PMID- 17118494
OWN - NLM
STAT- MEDLINE
DCOM- 20070514
LR  - 20070312
IS  - 0223-5234 (Print)
IS  - 0223-5234 (Linking)
VI  - 42
IP  - 3
DP  - 2007 Mar
TI  - 3D-QSAR study of sulfonamide inhibitors of human carbonic anhydrase II.
PG  - 365-72
AB  - 3D-QSAR models of Comparative of Molecular Field Analysis (CoMFA) and Comparative 
      of Molecular Similarity Indices Analysis (CoMSIA) of 61 potent carbonic anhydrase 
      II (CAII) sulfonamide inhibitors were performed using two methods. The 
      conventional ligand-based 3D-QSAR studies were performed based on the lower 
      energy conformations employing database alignment rule. The receptor-based 
      3D-QSAR models were also derived using bioactive conformations obtained by 
      docking compounds to the active sites of CAII. The receptor-based model gave q(2) 
      values of 0.623 and 0.562, r(2) values of 0.986 and 0.987 for CoMFA and CoMSIA, 
      respectively, which were much better than those of ligand-based model (q(2) 
      values of 0.532 and 0.466). The predictive ability of the models was validated 
      using the test set of 10 compounds that were not included in the training set of 
      51 compounds. Results of CoMFA and CoMSIA suggested that heterocyclic 
      sulfonamides are more active than aromatic sulfonamides, in the latter 
      1,3,5-triazole group substituting one hydrogen atom of the amido is favored and 
      moderate groups in its 4- and 6-position are required. These results provided 
      further understanding of the relationship between the structural features of CAII 
      and its activities, which should be applicable to design and find new potential 
      CAII inhibitors.
FAU - Huang, Huoqiang
AU  - Huang H
AD  - State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming 
      Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan 650204, China.
FAU - Pan, Xulin
AU  - Pan X
FAU - Tan, Ninghua
AU  - Tan N
FAU - Zeng, Guangzhi
AU  - Zeng G
FAU - Ji, Changjiu
AU  - Ji C
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20061121
PL  - France
TA  - Eur J Med Chem
JT  - European journal of medicinal chemistry
JID - 0420510
RN  - 0 (Carbonic Anhydrase Inhibitors)
RN  - 0 (Sulfonamides)
RN  - EC 4.2.1.- (Carbonic Anhydrase II)
SB  - IM
MH  - Carbonic Anhydrase II/*antagonists & inhibitors
MH  - Carbonic Anhydrase Inhibitors/*chemical synthesis/chemistry/*pharmacology
MH  - Humans
MH  - Hydrogen Bonding
MH  - Least-Squares Analysis
MH  - Models, Molecular
MH  - Quantitative Structure-Activity Relationship
MH  - Reproducibility of Results
MH  - Substrate Specificity
MH  - Sulfonamides/*chemical synthesis/chemistry/*pharmacology
EDAT- 2006/11/23 09:00
MHDA- 2007/05/15 09:00
CRDT- 2006/11/23 09:00
PHST- 2006/06/12 00:00 [received]
PHST- 2006/07/21 00:00 [revised]
PHST- 2006/09/21 00:00 [accepted]
PHST- 2006/11/23 09:00 [pubmed]
PHST- 2007/05/15 09:00 [medline]
PHST- 2006/11/23 09:00 [entrez]
AID - S0223-5234(06)00355-2 [pii]
AID - 10.1016/j.ejmech.2006.09.022 [doi]
PST - ppublish
SO  - Eur J Med Chem. 2007 Mar;42(3):365-72. doi: 10.1016/j.ejmech.2006.09.022. Epub 
      2006 Nov 21.