• Title/Summary/Keyword: CoMSIA

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CoMFA and CoMSIA Analysis on the Selective Fungicidal Activity of N-phenyl-D-phenylthionocarbamate Analogues against Resistant and Sensitive Gray Mold (Botrytis cinerea) (저항성 및 감수성 잿빛곰팡이병균(Botrytis cinerea)에 대한 N-Phenyl-O-phenylthionocarbamate 유도체들의 선택적인 살균활성에 관한 CoMFA 및 CoMSIA 분석)

  • Soung, Min-Gyu;Sung, Nack-Do
    • The Korean Journal of Pesticide Science
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    • v.11 no.3
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    • pp.138-143
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    • 2007
  • The relationships between three dimensional quantitative structure and activity relationships (3D-QSARs) for the selective fungicidal function between N-phenyl substituents of N-phenyl-O-phenyl-thionocarbamate derivatives analogues and their the fungicidal activities against resistant (RBC) and sensitive (SBC) gray mold (Botrytis cinerea) were studied quantitatively using CoMFA and CoMSIA methods. The statistical values of optimized CoMSIA (M7) model were better ($r^2$ & $q^2=CoMSIA{\gg}CoMFA$) than that of CoMFA (M5) model. And the factor influencing of the selective between the fungicidal activity against RBC and SBC was dependent on electrostatic field of CoMFA (M5) model. Therefore, it is predicted that, from the CoMSIA contour maps of CoMSIA (M7) model, the selectivity will be improved by the H-bond donor that is with negatively charged favored group at meta-position on the N-phenyl ring.

CoMFA and CoMSIA Analysis on the Fungicidal Activity against Damping-off (Pythium ultimum) with N-phenylbenzenesulfonamide Analogues (N-phenylbenzenesulfonamide 유도체들에 의한 모잘록병균 (Pythium ultimum)의 살균활성에 관한 CoMFA 및 CoMSIA분석)

  • Jang, Seok-Chan;Kang, Kyu-Young;Sung, Nack-Do
    • The Korean Journal of Pesticide Science
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    • v.11 no.1
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    • pp.8-17
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    • 2007
  • Three-dimensional quantitative structure-activity relationships (3D-QSARs) on the fungicidal activity against damping-off (Pythium ultimum) with N-phenylbenzenesulfonamide and N-phenyl-2-thienylsulfonamide analogues (1-34) were studied quantitatively using CoMFA (comparative molecular field analysis) and CoMSIA (comparative molecular similarity indeces analysis) methodologies. On the whole, the statistical qualities of CoMSIA models with field fit alignment (FF1-FF5) were slightly higher than that of atom based fit alignment (AF1-AF5) but, the deviations of statistical quality between two alignments in case of CoMFA models were slightly lower. The statistical results of CoMFA and CoMSIA model showed that the optimized CoMSIA model (FF1: $r_{cv.}^2\;(q^2)=0.674$ & $r_{ncv.}^2=0.964$) for damping-off is better predictability and fitness for fungicidal activities than CoMFA model (AF5: $r_{cv.}^2\;(q^2)=0.616$ & $r_{ncv.}^2=0.930$). The fungicidal activities according to the information of the CoMSIA (FF1) model were dependence upon the electrostatic and hydrophobic field of the N-phenylbenzene sulfonamide analogues. Therefore, from the results of graphical analyses on the contour maps with CoMSIA (FF3) model, it is expected that the characters of R4-substituent on the N-phenyl ring as hydrophobic and hydrogen bond acceptor will be contributed to the fungicidal activity against damping-off.

3D-QSAR on the Herbicidal Activities of New 2-(4-(6-chloro-2-benzoxazolyloxy)phenoxy)-N-phenylpropionamide Derivatives (새로운 2-(4-(6-chloro-2-benzoxazolyloxy)phenoxy)-N-phenylpropionamide 유도체들의 제초활성에 관한 3차원적인 정량적 구조와 활성과의 관계)

  • Sung, Nack-Do;Jung, Hoon-Sung
    • Applied Biological Chemistry
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    • v.48 no.3
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    • pp.252-257
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    • 2005
  • Three-dimensional quantitative structure-activity relationships (3D-QSARs) for the herbicidal activities against pre-emergence barnyard grass (Echinochloa crus-galli) by new 2-(4-(6-chloro-2-benzoxazolyloxy)phenoxy)-N-phenylpropion amide derivatives were studied quantitatively using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) methodologies. The best CoMFA model (AI-2) and CoMSIA model (AII-4) were derived from an atom based fit alignment and a combination of CoMFA fields. The herbicidal activities from CoMFA and CoMSIA contour maps showed that the activity will be able to be increased according to the substituents variation on the N-phenyl ring.

3D-QSAR Analysis on the Fungicidal Activity of N-phenyl-O-phenylthionocarbamate Analogues against Gray Mold (Botrytis cinerea) (잿빛곰팡이병균(Botrytis cinerea)에 대한 N-Phenyl-O-phenyl-thionocarbamate 유도체들의 살균활성에 관한 3D-QSAR 분석)

  • Sung, Nack-Do;Park, Kee-Han;Jang, Seok-Chan;Soung, Min-Kyu
    • The Korean Journal of Pesticide Science
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    • v.11 no.2
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    • pp.59-66
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    • 2007
  • Three dimensional quantitative structure-activity relationships (3D-QSARs) on the fungicidal activity of N-phenyl-O-phenylthionocarbamate analogues against resistant and sensitive gray mold (Botrytis cinerea) (RBC & SBC) were studied quantitatively using CoMFA and CoMSIA methods. The correlation coefficient and predict- ability of optimized CoMFA model with the atom based fit alignment were better ($r^2$ & $q^2=CoMFA{\gg}CoMSIA$) than that of CoMSIA model. And statistical values of the models on the fungicidal activity against SBC were showed higher ($r^2=SBC{\gg}RBC$) than that of RBC. In CoMFA models, steric field on the activity was more influenced than electrostatic field. And in case of CoMSIA models, the influence of CoMSIA field on the activity against RBC and SBC was differ from each other but the influence of H-bond donor field was same to the two fungi. It is revealed that the selectivity factor with CoMFA model on the fungicidal activity between the two fungi was caused on the difference of steric field. Therefore, it is predicted that the large steric field with meta- and para-substituents on the N-phenyl ring will be improved to the fungicidal activity with SBC.

CoMSIA Analysis on The Inhibition Activity of PTP-1B with 3${\beta}$-Hydroxy-12-oleanen-28-oic Acid Analogues (3${\beta}$-Hydroxy-12-oleanen-28-oic Acid 유도체들의 PTP-1B저해활성에 대한 CoMSIA분석)

  • Kim, Sang-Jin;Chung, Young-Ho;Kim, Se-Gon;Sung, Nack-Do
    • Applied Biological Chemistry
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    • v.51 no.3
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    • pp.171-176
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    • 2008
  • The comparative molecular similarity indices analysis (CoMSIA) models between 3${\beta}$-Hydroxy-12-oleanen-28-oic acid (1-30) analogues as substrate molecule and their inhibitory activities ($pI_{50}$) against protein tyrosine phosphatase (PTP)-1B were derived and discussed quantitatively. Listing in order, the CoMFA>CoMSIA${\geq}$HQSAR>2D-QSAR model, these QSAR models had the better statistical values. The optimized CoMSIA F1 model at grid 3.0${\AA}$ had the best predictability and fitness ($q^2$=0.754 and $r^2$=0.976) by field fit alignment. The order of contribution ratio (%) of CoMSIA fields concerning the inhibitory activities was a H-bond acceptor (48.9%), steric field (25.8%) and hydrophobic field (25.4%), respectively. Therefore, the inhibitory activities of substrate molecules against PTP-1B were dependent upon H-bond acceptor field (A) of $R_4$-group. From the analytical results of CoMSIA contour maps, oleanolic acid derivatives will have better inhibition activities if $R_1$ group has H-bond acceptor disfavor, $R_3$group has steric disfavor and $R_4$ group has steric, hydrophobic, H-bond favor.

Comparative Molecular Similarity Indices Analysis (CoMSIA) of 8-substituted-2-aryl-5-alkylaminoquinolines as Corticotropin-releasing factor-1 Receptor Antagonists

  • Nagarajan, Santhosh Kumar;Madhavan, Thirumurthy
    • Journal of the Chosun Natural Science
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    • v.9 no.4
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    • pp.241-248
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    • 2016
  • Corticotropin-releasing factor receptors (CRFRs) activate the hypothalamic-pituitary-adrenal axis, which is an integral part of the fight or flight response to stress. Increase in CRH level is observed in Alzheimer's disease and major depression and hypoglycemia. Here, we report on the relevant physicochemical parameters required for the CRFR inhibitors. Comparative molecular similarity indices analysis (CoMSIA) was performed with the derivatives of 8-substituted-2-aryl-5-alkylaminoquinolinesas CRFR inhibitors. The best predictions were obtained for the best CoMSIA model with a $q^2$ of 0.576 with 6 components and $r^2$ of 0.977. The statistical parameters from the generated CoMSIA models indicated that the data are well fitted and have high predictive ability. CoMSIA contour maps could be useful in the designing of more potent and novel CRFR derivatives.

Comparison of QSAR Methods (CoMFA, CoMSIA, HQSAR) of Anticancer 1-N-Substituted Imidazoquinoline-4,9-dione Derivatives

  • Suh, Myung-Eun;Park, So-Young;Lee, Hyun-Jung
    • Bulletin of the Korean Chemical Society
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    • v.23 no.3
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    • pp.417-422
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    • 2002
  • Comparison studies of the Quantitative Structure Activity Relationship (QSAR) methods with new imidazo-quinolinedione derivatives were conducted using Comparative Molecular Field Analysis (CoMFA), Comparative Molecular Similarity Indices Analysis (CoMSIA), and the Hologram Quantitative Structure Activity Relationship (HQSAR). When the CoMFA crossvalidation value, q2, was 0.625, the Pearson correlation coefficient, r2, was 0.973. In CoMSIA, q2 was 0.52 and r2 was 0.979. In the HQSAR, q2 was 0.501 and r2 was 0.924. The best result was obtained using the CoMSIA method according to a comparison of the calculated values with the real in vitro cytotoxic activities against human ovarian cancer cell lines.

The Influence of the Substituents on the Benzo Ring for Antioxidant Activity of 4-Methyl-2H-benzopyran-2-one Analogues (4-Methyl-2H-benzopyran-2-one 유도체들의 항산화 활성에 관한 Benzo 고리상 치환기들의 영향)

  • Choi, Won-Seok;Lee, Jae-Whang;Cho, Yun-Gi;Sung, Nack-Do
    • Journal of Applied Biological Chemistry
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    • v.53 no.2
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    • pp.99-104
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    • 2010
  • The influences on antioxidant activities of the substituents ($R_1-R_4$) on benzo ring in 4-Methyl-2H-benzopyran-2-one analogues (1-23) were discussed quantitatively using three dimensional quantitative structure-activity relationships (3D-QSARs: Comparative molecular field analyses (CoMFA) and Comparative molecular similarity indice analyses (CoMSIA)) methods. The statistical qualities of CoMSIA models were better than those of CoMFA models and the CoMSIA 2 model was optimized model ($q^2$=0.700 & $r^2$=0.979). Also, the contribution ratios (%) of the optimized CoMSIA 2 model were H-bond donor field 43.5%, electrostatic field 41.8% and steric field 14.7% so that the antioxidant activity exhibited a strong correlation with H-bond donor and electrostatic factor of molecules. From the analytical results of the CoMSIA contour maps, if the positive charge favor group and H-bond donor disfavor group were placed in the $R_1-R_4$ positions on the benzo ring, it was predicted that the groups would raised the antioxidant activity.

Comparative molecular similarity indices analyses (CoMSIA) and hologram quantitative structure activity relationship (HQSAR) on the fungicial activity of 2-N-benzyl-5-phenoxy-3-isothiazolone derivatives against phytophthora blight fungus (고추역병균에 대한 2-N-benzyl-5-Phenoxy-3-isothiazolone 유도체의 살균활성에 관한 비교분자 유사성 지수분석(CoMSIA)과 홀로그램 구조-활성 관계(HQSAR))

  • Sung, Nack-Do;Kim, Ki-Hyun
    • The Korean Journal of Pesticide Science
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    • v.6 no.3
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    • pp.209-217
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    • 2002
  • Two different QSAR methods, the comparative molecular similarity indices analyses (CoMSIA) and hologram quantitative structure activity relationship (HQSAR) are studied for the fungicidal activities ($pI_{50}$) of 2-N-benzyl-5-phenoxy-3-isothiazolone derivatives against sensitive (SPC: 95CC7105) and resisitive (RPC: 95CC7303) phytophthora blight fungus (Phytaphthora capsici). According to the findings from these QSAR investigation, the cross-validation value, $q^2$ and Pearson correlation coefficient, $r^2$ in the two methods were CoMSIA: RPC; $q^2=0.675,\;r^2=0.942$, SPC; $q^2=0.350,\;r^2=0.876$ and HQSAR: RPC; $q^2=0.519,\;r^2=0.869$, SPC; $q^2=0.483,\;r^2=0.990$, respectively. Therefore, the two models of comparative statistical significance were obtained. From the CoMSIA contour maps, the important factors for selective fungicidal activity against RPC are to be expected that the lower hydrophobic and not bulkiness substituent as hydrogen bonding acceptor have to introduce to meta and para-position (C1-C6) on the phenoxy moiety. And the results of prediction suggest that HQSAR method showed higher fungicidal activity than CoMSIA method.

3D-QSAR Analysis on the Insecticidal Activities of N-Substituents on Imidazol Ring in Imidacloprid Analogues (Imidacloprid 유도체 중 imidazol 고리상 N-치환체들의 살충활성에 대한 3D-QSAR 분석)

  • Soung, Min-Gyu;Kim, Se-Gon;Soog, Nack-Do
    • The Korean Journal of Pesticide Science
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    • v.11 no.3
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    • pp.131-137
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    • 2007
  • CoMFA and CoMSIA model were derived and reviewed on the insecticidal activities of N-substituents (X) on the imidazol ring in imidacloprid analogues at the different alignment condition. Regarding the predictability ($q^2$ or $r_{cv.}^2$) and fitness ($r_{ncv.}^2$) of the two optimized models, the atom based fit (A) alignments were better than that of the field fit (F) alignment and, on the other hand, CoMSIA (A10) model was better than CoMFA (A5) model. Also, from the most optimized CoMSIA (A10) model, the insecticidal activity by N-substituents (X) was dependence on the electrostatic field and H-bond acceptor field. It is predicted that, from the contour maps with optimized CoMSIA (A10) model, H-bond acceptors at ortho- and meta- position will contribute for improving of insecticidal activities and, as the functional groups of carbonyl oxygen atom are charged negatively and positively charged at the ortho- position of benzyl group, insecticidal activities will also be improved.