Aromatic substituent constants for structure-activity correlations

Hansch, Corwin; Leo, Albert J.; Unger, Stefan; Kim, Ki Hwai; Nikaitani, D.; Lien, Eric J.

doi:10.1021/jm00269a003

Cited by 1,283 publications

(690 citation statements)

References 1 publication

Supporting

Mentioning

657

Contrasting

Unclassified

Order By: Relevance

“…26 Biological activity data determined as MIC values were first transformed to pMIC on molar basis, which was used as dependent variable in QSAR study. These were correlated with different molecular descriptors like log of octanol-water partition coefficient (logP), molar refractivity (MR), Kier's molecular connectivity ( 0 χ v ) and shape (κ 1 ,κα  ) topological indices, Randic topological index (R), Balban topological index (J), Wiener topological index (W), Total energy (Te), energies of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO), dipole moment (µ), electronic energy (Ele.E) and nuclear energy (Nu.E) [26][27][28][29][30][31][32][33] . The values of selected descriptors used in regression analysis are presented in Table 3.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, antimicrobial and QSAR studies of substituted anilides

Narasimhan¹,

Narang²,

Judge³

et al. 2007

Arkivoc

View full text Add to dashboard Cite

A series of substituted anilides were synthesized and tested in vitro for antibacterial activity against Gram positive B. subtilis, S. aureus and Gram negative E.coli and as well as for antifungal activity against C. albicans and A. niger. The compounds having a nitro group showed better activity among different substituted anilides. QSAR investigation with linear regression analysis was applied to find correlation between various physicochemical parameters and antimicrobial activity. The QSAR results showed that antibacterial as well as antifungal activity could be modeled using molecular connectivity indices (

show abstract

Section: Resultsmentioning

confidence: 99%

“…36 The description of these descriptors are available in the literature [26][27][28][29][30][31][32][33] and therefore they are not described again here.…”

Section: Qsar Analysismentioning

confidence: 99%

Synthesis, antimicrobial and QSAR studies of substituted anilides

Narasimhan¹,

Narang²,

Judge³

et al. 2007

Arkivoc

View full text Add to dashboard Cite

show abstract

“…Substituent constants for electronic (Opar.) and steric (MR) effects were from Hansch et al [21] or were calculated by Driebergen [9].…”

Section: Methodsmentioning

confidence: 99%

Microsomal superoxide anion production and NADPH-oxidation in a series of 22 aziridinylbenzoquinones

Prins

Koster

Verboom

et al. 1989

Biochemical Pharmacology

View full text Add to dashboard Cite

Abstract--Several 2,5-bis(1-aziridinyl)-1,4-benzoquinones (BABQs) can be activated to alkylating species by reduction of the quinone moiety. On the other hand, cytotoxicity of these compounds can be induced by redox cycling. A series of BABQs and their methylated analogues (BMABQs) with different substituents at the 3-and 6-position was synthesized in order to investigate the influence of the substituents on the reduction of the quinone moiety and on the generation of superoxide anion radicals with rat liver microsomes. Superoxide anion production (SAP) ranged from 3.7 -+ 0.1 to 742 -+ 74 nmoles/min/mg protein with quinone concentrations of 10 nmoles/ml. NADPH-oxidation was measured under the same conditions and it correlated well (r = 0.88, P < 0.001) with SAP. It ranged from 1.4 ---0.2 to 494-+ 60nmoles/min/mg protein. SAP for 22 B(M)ABQs showed a good correlation with the summated electronic substituent constant O'para.total (F = 0.86, P < 0.001). It can be concluded that superoxide anion production by 22 B(M)ABQs in rat liver microsomes can be predicted from structural features of the compounds.

show abstract

“…On the basis of intercorrelation between the independent variables and also their individual correlation with antimicrobial activity The different physicochemical parameters, viz., topological, electronic, thermodynamic, and spatial [45][46][47][48][49][50][51], were quantified using TSAR 3.3 software (2000) for synthesized derivatives are summarized in Table 3.…”

Section: Development Of Ot-qsar Modelsmentioning

confidence: 99%

Synthesis, Molecular Modeling, and Quantitative Structure–activity Relationship Studies of Undec-10-Enehydrazide Derivatives as Antimicrobial Agents

Kumari

Narang

Nayak

et al. 2017

Asian J Pharm Clin Res

View full text Add to dashboard Cite

Objective: In recent years, an increasing frequency and severity of antimicrobial resistance to different antimicrobial agents, demands new remedies for the treatment of infections. Therefore, in this study, a series of undec-10-enehydrazide derivatives were synthesized and screened for in vitro activity against selected pathogenic microbial strains. Methods:The synthesis of the intermediate and target compounds was performed by standard procedure. Synthesized compounds were screened for antimicrobial activity by tube dilution method. Molecular docking study of synthesized derivatives was also performed to find out their interaction with the target site of β-ketoacyl-acyl carrier protein synthase III, (FabH; pdb id:3IL7) by docking technique. Quantitative structure-activity relationship (QSAR) studies were also performed to correlate antimicrobial activity with structural properties of synthesized molecules.Results: Antimicrobial screening results showed that compound 8 having benzylidine moiety with methoxy groups at meta and para position and compound 16 having 3-chloro-2-(3-flourophenyl)-4-oxoazetidine moiety was found to be most potent. QSAR studies revealed the importance of Randic topology parameter (R) in describing the antimicrobial activity of synthesized derivatives. Molecular docking study indicated hydrophobic interaction of deeply inserted aliphatic side chain of the ligand with FabH. The N-atoms of hydrazide moiety interacts with Ala246 and Asn247 through H-bonding. The m-and p-methoxy groups form H-bond with water and side chain of Arg36, respectively. Conclusion:Compound 8 having benzylidine moiety with methoxy groups at meta and para position and compound 16 having 3-chloro-2-(3-flourophenyl)-4-oxoazetidine moiety was found to most potent antibacterial and antifungal compounds, respectively.

show abstract

Aromatic substituent constants for structure-activity correlations

Cited by 1,283 publications

References 1 publication

Synthesis, antimicrobial and QSAR studies of substituted anilides

Synthesis, antimicrobial and QSAR studies of substituted anilides

Microsomal superoxide anion production and NADPH-oxidation in a series of 22 aziridinylbenzoquinones

Synthesis, Molecular Modeling, and Quantitative Structure–activity Relationship Studies of Undec-10-Enehydrazide Derivatives as Antimicrobial Agents

Contact Info

Product

Resources

About