Skip to content
Research Article Open access CC BY 3.0

A Theoretical Study of the Relationships between Electronic Structure and Anti-inflammatory and Anti-cancer Activities of a Series of 6,7-substituted-5,8-Quinolinequinones

Juan S. Gómez-Jeria

International Research Journal of Pure and Applied Chemistry · pp. 270–291 · Published 16 Jan 2014

10.9734/IRJPAC/2014/7876

Abstract

We report the results of the search of quantum-chemical model-based relationships between electronic structure and anti-inflammatory and antiproliferative activity against HL60 and T-cells of a group of 6,7-substituted-5,8-quinolinequinones. The wave functions and local atomic reactivity indices were obtained at the ab initio Hartree-Fock 6-311G (d,p) level of theory. We found and discussed several significant relationships explaining the variation of anti-inflammatory and anti-proliferative activity in terms of the variation of very definite and distinct sets of local atomic reactivity indices belonging to specific atoms of a common molecular skeleton. The variation of anti-inflammatory and anti-cancer activities seems to occur through very different mechanisms. It is shown that σ molecular orbitals localized on certain atoms could play an important function in controlling biological activity. The working hypothesis stating that a model built for in vitro drug-receptor interactions is useful for the study of other biological activities is supported by the results presented here.  

6,7-substituted-5 8-quinolinequinones QSAR local atomic reactivity indices anti-cancer activity anti-inflammatory activity anti-proliferative activity Quantum Chemistry

References (52)

  1. 1 Chemical reactivity and the concept of charge- and frontier-controlled reactions [DOI]
  2. 2 Quinolines and structurally related heterocycles as antimalarials [DOI]
  3. 3 Quinoline as a Privileged Scaffold in Cancer Drug Discovery [DOI]
  4. 4 Quinolone Antimicrobial Agents [DOI]
  5. 5 Streptonigrin. 1. Structure-activity relationships among simple bicyclic analogs. Rate dependence of DNA degradation on quinone reduction potential [DOI]
  6. 6 Structure determination of lavendamycin- a new antitumor antibiotic from streptomyces lavendulae [DOI]
  7. 7 Anti-inflammatory Thiazine Alkaloids Isolated from the New Zealand AscidianAplidiumsp.: Inhibitors of the Neutrophil Respiratory Burst in a Model of Gouty Arthritis [DOI]
  8. 8 The anti-cancer, anti-inflammatory and tuberculostatic activities of a series of 6,7-substituted-5,8-quinolinequinones [DOI]
  9. 9 Synthesis, cytotoxic activities and structure–activity relationships of topoisomerase I inhibitors: Indolizinoquinoline-5,12-dione derivatives [DOI]
  10. 10 Modeling the Drug-Receptor Interaction in Quantum Pharmacology [DOI]
  11. 11 Polyelectronic perturbation treatment of chemical reactivity [DOI]
  12. 12 Isolation of lavendamycin. A new antibiotic from Streptomyces lavendulae. [DOI]
  13. 13 Novel quinolinequinone antitumor agents: structure-metabolism studies with NAD(P)H:quinone oxidoreductase (NQO1) [DOI]
  14. 14 Synthesis and anti-inflammatory structure–activity relationships of thiazine–quinoline–quinones: Inhibitors of the neutrophil respiratory burst in a model of acute gouty arthritis [DOI]
  15. 15 Synthesis and antifungal activity of 1H-pyrrolo[3,2-g]quinoline-4,9-diones and 4,9-dioxo-4,9-dihydro-1H-benzo[f]indoles [DOI]
  16. 16 AN EMPIRICAL WAY TO CORRECT SOME DRAWBACKS OF MULLIKEN POPULATION ANALYSIS [DOI]
  17. 17 On some problems in quantum pharmacology I. The partition functions [DOI]
  18. 18 Quantum Chemical Approach to the Relationship Between Molecular Structure and Serotonin Receptor Binding Affinity [DOI]
  19. 19 Electronic Structure and Serotonin Receptor Binding Affinity of 7‐Substituted Tryptamines QSAR of 7‐Substituted Tryptamines [DOI]
  20. 20 Quantum‐chemical study of the relation between electronic structure and pA2 in a series of 5‐substituted tryptamines [DOI]
  21. 21 Quantum chemical study of electronic structure and receptor binding in opiates. [DOI]
  22. 22 Quantum-chemical Structure-Activity Relationships in carbamate insecticides [DOI]
  23. 23 A THEORETICAL STRUCTURE-AFFINITY RELATIONSHIP STUDY OF SOME CANNABINOID DERIVATIVES [DOI]
  24. 24 A STRUCTURE-AFFINITY STUDY OF THE OPIOID BINDING OF SOME 3-SUBSTITUTED MORPHINANS [DOI]
  25. 25 A THEORETICAL STUDY OF THE INHIBITION OF WILD-TYPE AND DRUG-RESISTANT HTV-1 REVERSE TRANSCRIPTASE BY SOME THIAZOLIDENEBENZENESULFONAMIDE DERIVATIVES [DOI]
  26. 26 PARAMETRIZATION OF THE ORIENTATIONAL EFFECTS IN THE DRUG-RECEPTOR INTERACTION [DOI]
  27. 27 A ZINDO/1 STUDY OF THE CANNABINOID-MEDIATED INHIBITION OF ADENYLYL CYCLASE
  28. 28 A general perturbation treatment of chemical reactivity [DOI]
  29. 29 Streptonigrin, an antitumor substance. I. Isolation and characterization.
  30. 30 Novel quinolinequinone antitumor agents: Structure-metabolism studies with NAD(P)H:quinone oxidoreductase (NQO1) [DOI]
  31. 31 Electronic representation of the lipophilic parameter .pi. [DOI]
  32. 32 A DFT and Semiempirical Model-Based Study of Opioid Receptor Affinity and Selectivity in a Group of Molecules with a Morphine Structural Core [DOI]
  33. 33 Quantum-chemical structure-affinity studies on kynurenic acid derivatives as Gly/NMDA receptor ligands [DOI]
  34. 34 MODEL-BASED QUANTUM-CHEMICAL STUDY OF THE UPTAKE OF SOME POLYCHLORINATED POLLUTANT COMPOUNDS BY ZUCCHINI SUBSPECIES [DOI]
  35. 35 A Theoretical Study of the Relationships between Electronic Structure and CB1 and CB2 Cannabinoid Receptor Binding Affinity in a Group of 1-Aryl-5-(1-H-pyrrol-1-yl)-1-H-pyrazole-3-carboxamides [DOI]
  36. 36 THEORETICAL STUDY OF THE OPIOID RECEPTOR SELECTIVITY OF SOME 7-ARYLIDENENALTREXONES [DOI]
  37. 37 QUANTUM CHEMICAL STUDY OF THE RELATIONSHIPS BETWEEN ELECTRONIC STRUCTURE AND PHARMACOKINETIC PROFILE, INHIBITORY STRENGTH TOWARD HEPATITIS C VIRUS NS5B POLYMERASE AND HCV REPLICONS OF INDOLE-BASED COMPOUNDS [DOI]
  38. 38 A DFT STUDY OF THE RELATIONSHIPS BETWEEN ELECTRONIC STRUCTURE AND PERIPHERAL BENZODIAZEPINE RECEPTOR AFFINITY IN A GROUP OF N,N-DIALKYL-2-PHENYLINDOL-3-YLGLYOXYLAMIDES [DOI]
  39. 39 Studies related to antitumor antibiotics. Part VII. Synthesis of streptonigrin analogues and their single strand scission of DNA [DOI]
  40. 40 Superdelocalizability and charge density. A correlation with partition coefficients [DOI]
  41. 41 A molecular orbital description of the partitioning of aromatic compounds between polar and nonpolar phases [DOI]
  42. 42 Coenzyme Q. 139. Synthesis of new alkylamino- and alkylaminomethyl-5,8-quinolinequinones as inhibitors of coenzyme Q and as antimalarials [DOI]
  43. 43 A quantum-chemical and experimental study of the hallucinogen (±)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON) [DOI]
  44. 44 Antituberculosis activity of 6 cyclo-octylamino-5,8-oquinolinequinone (CQQ) [DOI]
  45. 45 Quinone natural products: streptonigrin (NSC-45383) and lapachol (NSC-11905) structure-activity relationships.
  46. 46 New quinolinequinone inhibitors of mitochondrial reductase systems and reversal by coenzyme Q [DOI]
  47. 47 Coenzyme Q. 136. Synthesis of new 5,8-quinolinequinones as inhibitors of coenzyme Q and as antimalarials [DOI]
  48. 48 Coenzyme Q. 151. Antimetabolites of coenzyme Q. 14. Quinolinequinone analogs which inhibit mitochondrial DPNH-oxidase and succinoxidase [DOI]
  49. 49 Ueber einige Abkömmlinge des Orthooxychinolins [DOI]
  50. 50 ChemInform Abstract: SYNTHETIC APPROACHES TO STREPTONIGRIN AND BIOLOGICAL ACTIVITIES ON THE QUINOLINEQUINONE SYSTEMS [DOI]
  51. 51 Frontier Orbitals and Reaction Paths - Selected Papers of Kenichi Fukui [DOI]
  52. 52 The Structure of Streptonigrin [DOI]

Cited by 5

New Aryl Derivatives of Quinolinedione and Related Heterocyclic Compounds

Samuel Attah Egu, Uchechukwu Chris Okoro, Efeturi Abraham Onoabedje · Journal of Heterocyclic Chemistry · 2016

Showing 2 of 5 known citations — external sources report more than can currently be individually listed.

Article metrics

Real usage data collected on this platform.

68

Page views

0

PDF downloads

32

Outbound clicks

5

Citations

Views over time

Views by country

Approximate, from request IP at view time — not citizenship or institution. Countries with fewer than 5 views are grouped as "Other".

Traffic sources

Referring site, by host.

Views and downloads exclude known bots/crawlers. Citations combines this platform's own DOI-resolved index with each external source's own reported total — see Cited by above for individually listed citing works. Last refreshed 0 seconds ago.